- A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity
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A new secoiridoid glycoside, isopatrinioside (1) and a new sesquiterpenoid glycoside, valeriananoid F (2), together with nine known compounds, were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was an unusual monocyclic iridoid glycoside ring-opened between C-1 and C-2 produced by the cleavage of the pyran ring. Of the eleven isolates, compounds 1 and 4 exhibited moderate neuroprotective effects against CoCl2-induced neuronal cell death in PC12 cells.
- Tan, Yu-Zhu,Yong, Yan,Dong, Yan-Hong,Wang, Ru-Jing,Li, Hong-Xiang,Zhang, Hai,Guo, Da-Le,Zhang, Shi-Jin,Dong, Xiao-Ping,Xie, Xiao-Fang
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- Anthraquinone glycosides from Cassia roxburghii and evaluation of its free radical scavenging activity
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The methanolic extract of the leaves of Cassia roxburghii DC., was investigated for its anthraquinone glycosides and antioxidant activity. Two new anthraquinone glycosides named emodin 1-O-β-d-glucopyranosyl-(1→2)- glucopyranoside (1) and aloemodin 8-O-β-
- El-Toumy, Sayed A.,El Souda, Sahar S.,Mohamed, Tahia K.,Brouard, Inaki,Bermejo, Jame
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- A new triterpene glycoside from fruit of Phytolacca americana
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Glycosides H and I, the structures of which were established by modern physicochemical analytical methods (PMR, 13C NMR, COSY, TOCSY, HMBC, MS) and acid-base hydrolysis, were isolated from the purified total saponins from fruit of Phytolacca americana containing at least 10 triterpene glycosides by rechromatography of enriched fractions over a column of silica gel. Glycoside H was a bidesmoside of phytolaccageninic acid, which was isolated earlier from cell culture of Phytolacca acinosa. Glycoside I was 3-O-(β-D-xylopyranosyl- (1 → 3)-β-D-galactopyranosyl-(1 → 3-β-D-xylopyranosyl)-28-O- β-D-glucopyranosyl phytolaccagenin, which was isolated by us for the first time.
- Getiya,Gabelaya,Mshvildadze,Pichette,Lavoie,Dekanosidze
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- New phenolic glycosides from Polygonum cuspidatum
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Two new isobenzofuranone derivatives, polyphthaliside A (1) and polyphthaliside B (2), and a new isocoumarin derivative, polyisocoumarin (3), were isolated from Polygonum cuspidatum. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. The cytotoxicity activity and PTP1B inhibitory activity of compounds 1–3 were estimated and none of them exhibited activities at a concentration of 10 μM.
- Jiang, Jian-Shuang,Li, Fu-Shuang,Feng, Zi-Ming,Yang, Ya-Nan,Zhang, Pei-Cheng
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- Substrate control through per-O-methylation of cyclodextrin acids
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Per-O-methylated cyclodextrins containing a single 2-O-(2-acetate), 2-O-(3-propanoate) or a 6-carboxylate were investigated for glycosidase activity on p-nitrophenyl glycosides. The former two compounds displayed enzyme catalysis giving rate accelerations of 500-1000, while the latter compound gave marginal catalysis. These results show that per-O-methylated cyclodextrins direct substrate binding from the secondary face leading to better catalysis. The Royal Society of Chemistry.
- Fenger, Thomas H.,Bols, Mikael
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- Three new glycosides from Hylocereus undatus
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Three new glycosides, undatusides A-C (1-3), and 11 known compounds (4-14) were isolated from the flowers of Hylocereus undatus. Their structures were elucidated on the basis of spectroscopic data and chemical method.
- Wu, Xin,Wang, Ying,Huang, Xiao-Jun,Fan, Chun-Lin,Wang, Guo-Cai,Zhang, Xiao-Qi,Zhang, Qin-Wen,Ye, Wen-Cai
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- Polysciosides J and K, two new oleanane-type triterpenoid saponins from the leaves of Polyscias fruticosa (L.) harms. cultivating in An Giang Province, Viet Nam
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For the first time, the phytochemical constituents of the leaves of Polyscias fruticosa (L.) Harms. cultivating in An Giang Province, Viet Nam were investigated and led to purify two new oleanane-type triterpenoid saponins, named polyscioside J (1) and polyscioside K (2) together with two known saponins, ladyginoside A (3) and chikusetsusaponin IVa (4) using variously chromatographic methods. Saponin (4) was reported for the first time from this species. Their structures were verified by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and compared with previous literatures.
- Do, Van Mai,Tran, Cong Luan,Nguyen, Tan Phat
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- NMR-Based Investigation of Hydrogen Bonding in a Dihydroanthracen-1(4 H)one from Rubia philippinensis and Its Soluble Epoxide Hydrolase Inhibitory Potential
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Hydrogen bonding is a vital feature of a large ensemble of chemical structures. Soluble epoxide hydrolase (sEH) has been targeted for development of the treatment for inflammation-associated diseases. Compounds 1 and 2 were purified from Rubia philippinensis, and their structures were established via physical data analysis. Compound 1 possesses intramolecular hydrogen bonding, sufficiently robust to transfer heteronuclear magnetization via a nonbonded interaction. The bonding strength was assessed using the 1H NMR chemical shift temperature coefficients (-1.8 ppb/K), and the heteronuclear coupling constants were measured. The stereochemical details were investigated using interproton distance analysis and ECD. Purified compounds displayed moderate sEH-inhibitory activity.
- Oh, Joonseok,Quan, Khong Trong,Lee, Ji Sun,Park, Inwha,Kim, Chung Sub,Ferreira, Daneel,Thuong, Phuong Thien,Kim, Young Ho,Na, Minkyun
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- A membrane-bound trehalase from Chironomus riparius larvae: Purification and sensitivity to inhibition
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A preparation of a membrane-bound trehalase from the larvae of the midge Chironomus riparius (Diptera: Chironomidae) was obtained by detergent solubilization, ion-exchange chromatography and concanavalin A affinity chromatography. Trehalase was purified 1080-fold to a specific activity of 75 U mg-1. The initial rate of trehalase activity followed Henri-Michaelis-Menten kinetics with a Km of 0.48 ± 0.04 mM. Catalytic efficiency was maximal at pH 6.5. The activity was highly inhibited by mono-and bicyclic iminosugar alkaloids such as (in order of potency) casuarine (IC50 = 0.25 ± 0.03 μM), deoxynojirimycin (IC50 = 2.83 ± 0.34 μM) and castanospermine (IC50 = 12.7 ± 1.4 μM). Increasing substrate concentration reduced the inhibition. However, in the presence of deoxynojirimycin, Lineweaver-Burk plots were curvilinear upward. Linear plots were obtained with porcine trehalase. Here, we propose that deoxynojirimycin inhibits the activity of trehalase from C. riparius according to a ligand exclusion model. Inhibition was further characterized by measuring enzyme activity in the presence of a series of casuarine and deoxynojirimycin derivatives. For comparison, inhibition studies were also performed with porcine trehalase. Results indicate substantial differences between midge trehalase and mammalian trehalase suggesting that, in principle, inhibitors against insect pests having trehalase as biochemical targets can be developed.
- Forcella, Matilde,Cardona, Francesca,Goti, Andrea,Parmeggiani, Camilla,Cipolla, Laura,Gregori, Maria,Schirone, Raffaella,Fusi, Paola,Parenti, Paolo
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- New cycloartane glycosides from the rhizomes of Cyperus rotundus and their antidepressant activity
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Two new cycloartane glycosides, cyprotusides A (1) and B (2), were isolated from the rhizomes of Cyperus rotundus. Their chemical structures were elucidated on the basis of IR, MS, NMR spectroscopic analyses coupled with chemical degradation. The potential antidepressant activity of the two compounds was evaluated. In the despair mice models, compounds 1 and 2 showed significant antidepressant activity.
- Zhou, Zhong-Liu,Lin, San-Qing,Yin, Wen-Qing
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- New grayanol diterpenoid and new phenolic glucoside from the flowers of Pieris formosa
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A new grayanol diterpenoid, grayanotoxin XXII (1), and a new phenolic glucoside, benzyl 2-hydroxy-4-O-[-xylopyranosyl(1″→6′)-β- glucopyranosyl]-benzoate (2), were isolated from the flowers of Pieris formosa. Their structures were determined on the basis of spectroscopic analysis and chemical methods.
- Wang, Wei-Guang,Li, Hong-Mei,Li, Hai-Zhou,Wu, Zhao-Yuan,Li, Rong-Tao
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- Acridone alkaloids from the rhizomes of Luvunga scandens (Roxb.) Buch. Ham.
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The ethyl acetate extract of the rhizomes of Luvunga scandens (Roxb.) Buch. - Ham. ex Wight & Arn (Rutaceae) delivered one new acridone alkaloid named Luvungaside A (1) together with three known acridone alkaloids, namely 1,3-dihydroxy-2-methoxy-10-methyl-9-acridone (2), arborinine (3) and 1-hydroxy-3-methoxy-10-methyl-9-acridone (4). Compounds were reported for the first time from the species L. scandens applying various chromatography methods. Chemical structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D & 2D experiments and comparison with the literature. The cytotoxicity and hepatoprotective activity of compounds 1–4 in human hepatoma cell line HepG2 was measured by MTT assay. At 10–100 μM, compounds expressed significant hepatoprotective effect with prevention percentage ranging from 81.1% to 194.3%, compared to the positive control quercetin displaying 49.0%.
- Tran, Nguyen Minh An,Do, Thi Hong Tuoi,Truong, Luu Hong,Le, Dung Tien,Phan, Minh Nhat,Pham, Nguyen Kim Tuyen,Mai, Dinh Tri,Nguyen, Tan Phat
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- Three new phenol compounds from Iris dichotoma PALL
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Three new phenolic compounds, irisdichototins D, E, and F (1 - 3, resp.) were isolated from the stems of Iris dichotoma. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D-NMR techniques.
- Huang, Long,Ma, Wenhui,Liu, Yanze,Peng, Yong,Xiao, Peigen
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- Antidiabetic ellagitannins from pomegranate flowers: Inhibition of α-glucosidase and lipogenic gene expression
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Two new ellagitannins containing a rare 3-oxo-1,3,3a,8b-tetrahydrofuro[3,4- b]benzofuran moiety, namely punicatannins A (1) and B (2), were isolated from pomegranate (Punica granatum) flowers. Their structures with absolute configuration were determined by detailed analysis of spectroscopic data, electronic circular dichroism (ECD) calculation, and chemical hydrolysis. A plausible biogenetic route involving a key enzymatic 1,4-Michael addition is proposed. Punicatannin A showed potent inhibition of α-glucosidase and lipogenic gene expression.
- Yuan, Tao,Ding, Yuanqing,Wan, Chunpeng,Li, Liya,Xu, Jialin,Liu, Ke,Slitt, Angela,Ferreira, Daneel,Khan, Ikhlas A.,Seeram, Navindra P.
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- New dammarane-type triterpenoid glycosides from Gynostemma burmanicum
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The chemical composition of Gynostemma burmanicum King ex Chakrav. was investigated for the first time in this study. Nine dammarane glycosides (1?9) were isolated from the EtOH extract of the aerial parts of G. burmanicum. Their structures were elucidate
- Nguyen Phuong, Thao,Nguyen Tien, Dat,Pham, Thanh Binh,Pham, Thanh Ky,Than, Thi Kieu My
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- Three new lignan glycosides from the Firmiana simplex
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In our quest for structurally intriguing compounds from Korean medicinal plant sources, chromatographic separation of the 80% MeOH extract from Firmiana simplex resulted in the isolation and identification of three new lignan glycosides (1-3), together with six known lignan glycosides (4-9). The structures of 1-3 were determined on the basis of spectroscopic analyses, including extensive 2D-NMR and enzyme hydrolysis. Nitric oxide (NO) production was evaluated in the lipopolysaccharide-Activated microglial cell line, BV-2 to investigate the anti-neuroinflammatory effects of the isolated compounds (1-9). Compound 7 marginally inhibited NO levels with IC50 values of 59.83 μM.
- Woo, Kyeong Wan,Park, Jong Eel,Cha, Joon Min,Subedi, Lalita,Kim, Sun Yeou,Lee, Kang Ro
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- Isolation and Some Properties of Sorbitol Oxidase from Streptomyces sp. H-7775
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A sorbitol oxidase (SOX) was found in the cell-free extract of a strain isolated from soil. The strain was classified and designated as Streptomyces sp. H-7775. SOX is constitutively expressed in the cell. The molecular weight of SOX that purified from the cell-free extract was 45,000. The optimum pH and the Km for sorbitol were 6.5-7.5 and 0.26 mM, respectively. The prosthetic group was a covalently bound FAD. SOX catalyzed oxidation of D-sorbitol to glucose and hydrogen peroxide without any requirements of exogenous cofactors. SOX did not react with glucose, a reaction product of D-sorbitol. This feature is useful in its application for diagnosis.
- Hiraga, Kazumi,Kitazawa, Mitsunori,Kaneko, Norihisa,Oda, Kohei
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- Six new ergostane-type steroids from king trumpet mushroom (Pleurotus eryngii) and their inhibitory effects on nitric oxide production
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Six new ergostane-type steroids; (22E)-3β,5α,6α,11-tetrahydroxy-9(11)-seco-ergosta-7,22-dien-9-one (1), (22E)-8,14-epoxyergosta-6,22-diene-3β,5α,9α-triol (2), (22E)-4α,5α-epoxyergosta-7,22-diene-3β,6β-diol (3), (22E)-3β,4β,5α-trihydroxyergosta-7,22-dien-6-one (4), (22E)-ergosta-7,22-diene-3β,5β,6α-triol (5), and (22E)-6β-methoxyergosta-7,22-diene-3β,5α-diol 3-O-β-D-glucopyranoside (6) were isolated from the fruiting bodies of king trumpet mushroom (Pleurotus eryngii), along with fourteen known compounds (7–20). All isolated compounds were evaluated for their inhibitory effects on macrophage activation using a nitric oxide production inhibition assay.
- Kikuchi, Takashi,Maekawa, Yukina,Tomio, Arisa,Masumoto, Yuki,Yamamoto, Taishi,In, Yasuko,Yamada, Takeshi,Tanaka, Reiko
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- A grayanotox-9(11)-ene derivative from Rhododendron brachycarpum and its structural assignment via a protocol combining NMR and DP4 plus application
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A growing body of evidence points to the useful roles of computational approaches in the structural characterization of natural products. Rhododendron brachycarpum has been traditionally used for the control of diabetes, hepatitis, hypertension, and rheumatoid arthritis and classified as an endangered species in Korea. A grayanotox-9(11)-ene derivative along with five known diterpenoids, were isolated from the MeOH extract of R.?brachycarpum. Extensive 1D and 2D NMR experiments were conducted to establish the 2D structure and relative configuration of the grayanotox-9(11)-ene derivative. Comparison of simulated and experimental ECD spectra resulted in an inconclusive outcome to assign its absolute configuration. Alternatively, gauge-including atomic orbitals (GIAO) NMR chemical shift calculations, with support by the advanced statistical method DP4 plus, and acid hydrolysis were employed to establish its absolute configuration. This work exemplifies how NMR analysis, combined with quantum mechanics calculations, is a viable approach to accomplish structural assignment of minor abundance molecules in lieu of X-ray crystallography or chiroptical approaches.
- Tuan, Nguyen Quoc,Oh, Joonseok,Park, Hyun Bong,Ferreira, Daneel,Choe, Sanggil,Lee, Juseon,Na, MinKyun
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- A new chromene glycoside from tithonia diversifolia
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A new chromene glycoside, 6-acetyl-2,2-dimethylchromene-8-O-β-D- glucoside, together with four known compounds were isolated from the aerial parts of Tithonia diversifolia. Their structures were established by 1H, 13C NMR, and HMQC together with the other physical and chemical investigations.
- Zhai, Hong-Li,Zhao, Gui-Jun,Yang, Gen-Jin,Sun, He,Yi, Bo,Sun, Lian-Na,Chen, Wan-Sheng,Zheng, Shui-Qing
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- Cordycepamides A?E and cordyglycoside A, new alkaloidal and glycoside metabolites from the entomopathogenic fungus Cordyceps sp.
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Five new alkaloidal metabolites cordycepamides A?E (1?5), and one glycoside metabolite cordyglycoside A (6), together with six known compounds (7?12) were isolated from the entomopathogenic fungus Cordyceps sp. (LB1.18060004) from unidentified insect collected in Baoshan City, Yunnan Province, People's Republic of China. The structures were characterized by NMR and HRESIMS spectroscopic analyses. Cordycepamides A and B (1 and 2) were mixtures of two isomers in 5:4 ratio by integration of 1H NMR spectra. In additional, the structure of cordycepamide A (1) was further confirmed by X-ray crystallography as a pair of enantiomers. Absolute configurations of sugar moiety of cordyglycoside A (6) was confirmed by the acid hydrolysis and subsequent HPLC analysis. The isolated metabolites were evaluated for antimicrobial, cytotoxicity, and the DPPH scavenging assay, only 4 showed modest antioxidant effects in the DPPH scavenging assay (IC50 = 51.42 ± 3.08 μM).
- Fan, Wenwen,Li, Erwei,Liu, Xingzhong,Ren, Jinwei,Wang, Wenzhao,Zhang, Yongjie
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- New coumarins and monoterpene galloylglycoside from the stem bark of Sapium baccatum
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Sapium baccatum has been traditionally used as therapeutic remedies. To support its medicinal benefits, our current phytochemical investigation attempted to further discover novel bioactive compounds from S. baccatum. Eight new phenolic compounds, namely, seven coumarins (1–7) and one monoterpene galloylglycoside (8), together with 23 (9–31) known compounds were isolated. Their structures were determined by extensive spectroscopic methods and comparison with literatures. The three pairs of enantiomers of 1, 2 and 7 were confirmed on the basis of HPLC chiral analysis, electronic circular dichroism data and optical rotations. Two coumarins (1–2) were proven to be artifacts through HPLC analysis. The inhibitory effects on TNF-α secretion were examined biologically in LPS-induced BV2 microglia cells and all of the tested compounds exhibited significant inhibitory activity, especially new compound 1 possessed stronger inhibitory effects compared to the positive control quercetin. In addition, compounds 14 and 15 showed weak antifungal activity against Candida albicans SC5314 with MIC values both at 64 μg/mL. The results laid a solid foundation for additional research on S.baccatum related to its anti-inflammatory and antifungal medicinal value.
- Li, Ting,Wang, Shanshan,Fan, Peihong,Lou, Hongxiang
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- Three new sulfated triterpenoids from the roots of Gypsophila pacifica
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Three new sulfated triterpenoids (1-3), along with one known compound (4), were isolated from the roots of Gypsophila pacifica Kom. The structures of the new compounds were established as 3β-O-sulfate gypsogenin 28-O-β-d-glucopyranosyl ester (1), 3β-O-sulfate gypsogenin (2), and 3β-O-sulfate quillaic acid (3) on the basis of 1D, 2D NMR, and HR-ESI-MS methods.
- Luo, Jian-Guang,Nie, Wei,Kong, Ling-Yi
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- 2β-D-GLUCOPYRANOSYLOXY-2-METHYLPROPANOL IN ACACIA SIEBERANA VAR. WOODII
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A new diol glucoside, 2-β-D-glucopyranosyloxy-2-methylpropanol, the first reported naturally occurring monoglucoside of an aliphatic dihydric alcohol, was isolated from pods of Acacia sieberana var. woodii.Structure eucdation was based on 1H and 13C NMR spectroscopy, and anzymatic analyses.The compound was hydrolysed very slowly by almond β-glucosidase, but cleaved by a β-glucuronidase enzyme complex from Helix pomatia.Key Word Index - Acacia sieberana var. woodii; Mimosoideae; glycoside; novel diol glucoside; 2-methyl-1,2-propanediol aglycone; dihydric alcohol; glycol; diol lipids.
- Brimer, Leon,Christensen, S. Broegger,Nartey, Frederick
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- Structural characterization of cholestane rhamnosides from ornithogalum saundersiae bulbs and their cytotoxic activity against cultured tumor cells
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Previous phytochemical studies of the bulbs of Ornithogalum saundersiae, an ornamental perennial plant native to South Africa, resulted in the isolation of 29 new cholestane glycosides, some of which were structurally unique and showed potent cytotoxic activity against cultured tumor cell lines. Therefore, we aimed to perform further phytochemical examinations of methanolic extracts obtained from Ornithogalum saundersiae bulbs, isolating 12 new cholestane rhamnosides (1-12) and seven known compounds (13-19). The structures of the new compounds (1-12) were identified via NMR-based structural characterization methods, and through a sequence of chemical transformations followed by spectroscopic and chromatographic analysis. The cytotoxic activity of the isolated compounds (1-19) and the derivatives (1a and 6a) against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells was evaluated. Compounds 10-12, 16, and 17 showed cytotoxicity against both HL-60 and A549 cells. Compound 11 showed potent cytotoxicity with an IC50 value of 0.16 μM against HL-60 cells and induced apoptotic cell death via a mitochondrion-independent pathway.
- Iguchi, Tomoki,Kuroda, Minpei,Naito, Rei,Watanabe, Tomoyuki,Matsuo, Yukiko,Yokosuka, Akihito,Mimaki, Yoshihiro
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- Four New Diterpene Glucosides from Perovskia atriplicifolia
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Four new diterpene glucosides, namely perovskiaditerpenosides A?–?D (1?–?4), were isolated from the BuOH extract of Perovskia atriplicifolia. Their structures were well elucidated by chemical methods and comprehensive spectroscopic analyses including MS, IR, and NMR (1D and 2D). The newly isolated compounds were screened for their cytotoxic activity against HepG2, NB4, HeLa, K562, MCF7, PC3, and HL60. The obtained results indicated that the new compounds possessed considerable cytotoxic activity.
- Gao, Lu,Zhou, Jun,Zhu, Le-Yu,Zhang, Juan-Rong,Jing, Yu-Xing,Zhao, Jia-Wen,Huang, Xiang-Zhong,Li, Gan-Peng,Jiang, Zhi-Yong,Xue, Da-Yuan
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- New Glycosides of Eriodictyol from Dracocephalum palmatum
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Two new glycosides of eriodictyol were isolated from the aerial part of Dracocephalum palmatum and identified using UV, NMR, and CD spectroscopy and mass spectrometry as (S)-eriodictyol-7-O-(6′′-O-malonyl)-β-Dglucopyranoside (pyracanthoside-6′′ -O-malonat
- Olennikov,Chirikova,Kim, Eungyoung,Kim, Sang Woo,Zul’fugarov
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- Three new monoterpene glycosides from Sibiraea laevigata (L.) Maxim
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Three new compounds, 3,7-dimethy-7-methoxy-3-octene-5-one-1-O-β-D-glucopyranoside (1), 3,7-dimethy-7-methoxy-3(Z)-octene-5-one-1-O-β-D-glucopyranoside (2) and 3,7-dimethy-3-hydroxy-6-octene-5-one-1-O-β-D-glucopyranoside (3), together with fourteen known c
- Mei, Li-Juan,Shao, Yun,Shi, Yan-Ping,Tao, Yan-Duo,Wang, Qi-Lan,Wang, Yan-Ming,Zhao, Jian-Qiang
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- Medicinal flowers. XXXX.1) Structures of dihydroisocoumarin glycosides and inhibitory effects on aldose reducatase from the flowers of Hydrangea macrophylla var. thunbergii
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Six dihydroisocoumarin glycosides, florahydrosides I and II, thunberginol G 8-O-β-D-glucopyranoside, thunberginol C 8-O-β-D-glucopyranoside, 4-hydroxythunberginol G 3′-O-β-D-glucopyranoside, and thunberginol D 3′-O-β-D-glucopyranoside, have been isolated from the flowers of Hydrangea macrophylla SERINGE var. thunbergii MAKINO (Saxifragaceae) together with 20 known compounds. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, acylated quinic acid analog, neochlorogenic acid, was shown to substantially inhibit aldose reductase [IC50=5.6 μM]. In addition, the inhibitory effects on aldose reductase of several caffeoylquinic acid analogs were examined for structure-activity relationship study. As the results, 4,5-O-trans-p-dicaffeoyl-D-quinic acid was found to exhibit a potent inhibitory effect [IC50=0.29 μM].
- Liu, Jiang,Nakamura, Seikou,Zhuang, Yan,Yoshikawa, Masayuki,Hussein, Ghazi Mohamed Eisa,Matsuo, Kyohei,Matsuda, Hisashi
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- Caragiside D, a new isoflavone glucoside from caragana conferta
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Caragiside D (1), a new isoflavone glucoside, has been isolated from the n-BuOH soluble subfraction of the MeOH soluble extract of the whole plant of Caragana conferta along with one known isoflavone glucoside, caragiside A (2), and two lignan glucosides, pinoresinol 4-O-glucoside (3) and syringaresinol 4-O-glucoside (4). The structures of these compounds were elucidated through spectroscopic techniques including MS and 2D NMR. The purity of compound 1 was confirmed by HPLC.
- Perveen, Shagufta,Al-Taweel, Areej Mohammad,Khan, Afsar,Fawzy, Ghada Ahmed,Malik, Abdul
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- The bioassay-guided isolation of antifungal saponins from Hosta plantaginea leaves
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Four new steroidal saponins hostaside Ⅰ (1), hostaside Ⅱ (2), hostaside Ⅲ (3), and hostaside Ⅳ (4), together with five known steroidal saponins (5–9), were isolated by the bioassay-guided fractionation from the leaves of Hosta plantaginea (Lam.) Aschers, a worldwide well-known ornamental plant. Hostasides Ⅰ and Ⅱ showed significant antifungal activities, and they could inhibit the growth of Candida albicans and Fusarium oxysporium with MIC values as low as 4?μg/ml.
- Wang, Meng-Yue,Peng, Ying,Peng, Chong-Sheng,Qu, Jiang-Yuan,Li, Xiao-Bo
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- A new flavonoid glycoside and four other chemical constituents from viscum coloratum and their antioxidant activity
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A new flavonoid glycoside, identified as rhamnazin-3-β-D-(6″- β- hydroxy-β-methylglutaryl)-β-D-glucoside-4′-β-D- glucoside (1), along with four known compounds, shikimic acid (2), quebrachitol (3), abscisic acid (4), 3,5-dihydroxy-1,7-bis(4-hydroxyphenyl)heptane (5), were isolated from the branches and leaves of Viscum coloratum. Their structures were elucidated on the basis of MS, 1D NMR, and 2D NMR techniques. All compounds were isolated in the family Loranthaceae for the first time. This paper describes the isolation, structural elucidation as well as in vitro antioxidant activity of these isolates.
- Fan, Ronghua,Ma, Yuying,Yuan, Hongxia,Zhang, Yongzhi,Wei, Binbin,Zhao, Yunli,Yu, Zhiguo
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- Isolation, identification and antioxidative capacity of water-soluble phenylpropanoid compounds from Rhodiola crenulata
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Six water-soluble phenylpropanoid compounds obtained from Rhodiola crenulata (R. crenulata) were fractionated by high-speed counter-current chromatography (HSCCC), and purified by semi-preparative high-performance liquid chromatography (Semi-prep HPLC). The purities of the six compounds were all above 98.0% and their structures were identified by spectroscopic methods. Among them, a new compound, 2-(4-hydroxyphenyl)-ethyl-O-β-d-glucopyranosyl-6-O- β-d-glucopyranoside (1), together with two known phenylpropanoids, p-hydroxyphenacyl-β-d-glucopyranoside (3) and picein (4) were isolated from R. crenulata for the first time. Meanwhile, the contents of six isolated ingredients from the crude extract of R. crenulata had been simultaneously detected, with satisfactory results. Furthermore, the antioxidant activities of the six compounds were accessed by measuring the radical scavenging activity against 2,2-diphenyl-1-picrylhydrazy (DPPH), and four compounds exhibited potent antioxidative activity.
- Chen, Danjun,Fan, Junting,Wang, Peng,Zhu, Lanying,Jin, Yang,Peng, Yan,Du, Shuhu
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- Enzymatic and structural characterization of hydrolysis of gibberellin A4 glucosyl ester by a rice β-D-glucosidase
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In order to identify a rice gibberellin ester b-D-glucosidase, gibberellin A4 β-D-glucosyl ester (GA4-GE) was synthesized and used to screen rice β-Glucosidases. Os3BGlu6 was found to have the highest hydrolysis activity to GA4-GE among five recombinantly expressed rice glycoside hydrolase family GH1 enzymes from different phylogenic clusters. The kinetic parameters of Os3BGlu6 and its mutants E178Q, E178A, E394D, E394Q and M251N for hydrolysis of p-nitrophenyl b-D-glucopyranoside (pNPGlc) and GA 4-GE confirmed the roles of the catalytic acid/base and nucleophile for hydrolysis of both substrates and suggested M251 contributes to binding hydrophobic aglycones. The activities of the Os3BGlu6 E178Q and E178A acid/base mutants were rescued by azide, which they transglucosylate to produce b-D-glucopyranosyl azide, in a pH-dependent manner, while acetate also rescued Os3BGlu6 E178A at low pH. High concentrations of sodium azide (200-400 mM) inhibited Os3BGlu6 E178Q but not Os3BGlu6 E178A. The structures of Os3BGlu6 E178Q crystallized with either GA4-GE or pNPGlc had a native a-D-glucosyl moiety covalently linked to the catalytic nucleophile, E394, which showed the hydrogen bonding to the 2-hydroxyl in the covalent intermediate. These data suggest that a GH1 β-Glucosidase uses the same retaining catalytic mechanism to hydrolyze 1-O-acyl glucose ester and glucoside.
- Hua, Yanling,Sansenya, Sompong,Saetang, Chiraporn,Wakuta, Shinji,Cairns, James R. Ketudat
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- Four new cytotoxic oligosaccharidic derivatives of 12-oleanene from Lysimachia heterogenea Klatt
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Cytotoxicity-guided phytochemical analysis on the extract of Lysimachia heterogenea Klatt led to the isolation of 3β,16β-12-oleanene-3,16,23,28-tetrol (1) and its four new oligosaccharidic derivatives heterogenosides A, B, C, and D (2-5). Their structural
- Huang, Xin-an,Liang, Yong-ju,Cai, Xiao-ling,Feng, Xiao-quan,Zhang, Chuan-hai,Fu, Li-wu,Deng, Wen-di
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- Novel monoterpenoid indole alkaloids from Melodinus yunnanensis
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Five monoterpenoid indole alkaloids, namely meloyines A-B (1–2), meloyines II-III (3–4), and 10-O-glucosyl-scandine (5) together with thirty-four known alkaloids were isolated from leaves and twigs of Melodinus yunnanensis. Alkaloid 1 was characterized as an unprecedented skeleton with a 6/5/5/6/6/4 ring system, and alkaloids 3–4 were dimeric monoterpenoid quinolone alkaloids. Their structures were elucidated based on 1D and 2D- NMR, FTIR, UV, and MS spectroscopic data. The cytotoxic activity of new alkaloids were evaluated against three human cancer cell lines.
- Zhang, Bing-Jie,Liu, Cheng,Bao, Mei-Fen,Zhong, Xiu-Hong,Ni, Ling,Wu, Jing,Cai, Xiang-Hai
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- Two new sesquiterpenoid glycosides from the stems of Zanthoxylum armatum DC
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Two new sesquiterpenoid glycosides as dihydrophaseic acid 4′-O-[6″-O-(4″′-hydroxy-3″′, 5″′-dimethoxy) benzoyl)]-β-D-glucopyranoside (1) and dihydrophaseic acid 4′-O-[6″-O-(3″′-methoxy- 4″′-hydroxy) benzoyl)]-β-D-glucopyranoside (2), were isolated from the stems of Zanthoxylum armatum in the study. The compound 1 and 2 showed moderate scavenging activity in DPPH free radical assay with IC50 values of 241 and 264 μM, respectively.
- Liu, Ya-Lin,Gao, Liang-Liang,Song, Tong-Tong,Guo, Tao,Chang, Jun
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- Micellar catalysis on pentavalent vanadium ion oxidation of D-sorbitol in aqueous acid media: A kinetic study
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Vanadium(V) oxidation of D-sorbitol shows a first-order dependency on the concentrations of D-sorbitol, vanadium(V), H+ and HSO4 - . These observations remain unaltered in the presence of externally added surfactants. The effects of the cationic surfactant (i.e., CPC), anionic surfactant (i.e., SDS) and neutral surfactant (i.e., TX-100) have been studied. CPC inhibits the reactions whereas SDS and TX-100 accelerate the reaction to different extents. SDS and TX-100 can be used as catalysts in the production of D-glucose from D-sorbitol.
- Saha, Bidyut,Chowdhury, Kiran M.,Mandal, Jayashree
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- Depolymerization of cellulosic feedstocks using magnetically separable functionalized graphene oxide
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Hydrolysis of cellulose into saccharides using a magnetically separable functionalized graphene is reported for potential applications in the environmentally benign saccharification of cellulose. Crystalline pure cellulose is hydrolyzed by graphene bearing -SO3H, -COOH and -OH functional groups in combination with iron nanoparticles. We observed nearly complete hydrolysis of cellulose into glucose and small (4-5 unit size) oligomers using low (1:1) catalyst to cellulose ratio. The apparent activation energy for the hydrolysis of cellulose into glucose using these catalysts is estimated to be 12 kJ mol-1, several times smaller than that for sulfuric acid under optimal conditions (170 kJ mol-1). The catalyst can be readily magnetically separated from the saccharide solution after the reaction for reuse in the reaction without loss of activity. Nearly complete hydrolysis of sugarcane bagasse into water soluble saccharides with repeated recycling was also possible. The catalytic performance of the graphene-based catalyst is attributed to the ability of the water soluble nanostructured material with a large concentration of polar groups (-OH, -COOH) which readily adsorb cellulose, while providing a large concentration of acidic functionality to hydrolyze the cellulose.
- Verma, Deepak,Tiwari, Rashmi,Sinha, Anil Kumar
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- Xanthone glycosides from swertia bimaculata with α -glucosidase inhibitory activity
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Seven new xanthone glycosides (1-7) were isolated from the n-butanol extract of Swertia bimaculata, together with six known compounds (8-13). Their structures were elucidated on the basis of extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, a
- Yue, Yao-Dong,Zhang, Yu-Tang,Liu, Zhao-Xia,Min, Qiu-Xia,Wan, Luo-Sheng,Wang, Yong-Long,Xiao, Zuo-Qi,Chen, Jia-Chun
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- New ecdysteroid and ecdysteroid glycosides from the roots of Serratula chinensis
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Three new ecdysteroid glycosides (1–3) and one new ecdysteroid (4), were isolated from the roots of Serratula chinensis. Their structures were established on the basis of extensive spectroscopic analysis and chemical methods.
- Zhang, Zi-Yue,Yang, Wei-Qun,Fan, Chun-Lin,Zhao, Hui-Nan,Huang, Xiao-Jun,Wang, Ying,Ye, Wen-Cai
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- The study of factors influencing the depolymerisation of cellulose using a solid catalyst in ionic liquids
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Cellulose is the most abundant biomass in the world and constitutes a large fraction of plant biomass. The tight hydrogen-bonding network and van der Waals interactions greatly stabilise cellulose, making it notoriously resistant to hydrolysis. Hence, more efficient pre-treatment procedures are required for the conversion of cellulose to monosaccharides. In this study, the depolymerisation of cellulose and wood in ILs using a solid catalyst is performed successfully. Depolymerisation produces three types of substances: total reducing sugar (TRS), glucose and ethanol. With Avicel, yields of TRS, glucose and ethanol are 76.3% (w/w), 17.2% (w/w) and 4.2% (w/w), respectively. With wood, yields of TRS, glucose and ethanol are 25.6% (w/w), 11.5% (w/w) and 7.7% (w/w), respectively. The time courses of product yields indicates that the depolymerisation of cellulose in [C4mim]Cl, using Dowex, is similar to the depolymerisation with concentrated H2SO4.
- Watanabe, Hisanori
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- Complete assignments of 1H and 13C NMR spectroscopic data for three new stigmastane glycosides from Vernonia cumingiana
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Three new steroidal saponins, Vernoniosides S1 (1), Vernoniosides S2 (2) and Vernoniosides S3 (3) were isolated from the stem of Vernonia cumingian. Their chemical structures were elucidated on the basis of MS, NMR spectroscopic and chemical analysis. Com
- Suo, Maorong,Yang, Junshan
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- Three new secoiridoid glycosides from the rhizomes and roots of Gentiana scabra and their anti-inflammatory activities
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Three new (1-3) and 17 known (4-20) iridoid and secoiridoid glycosides were isolated from a methanol extract of the rhizomes and roots of Gentiana scabra. Their chemical structures were elucidated from 1D and 2D NMR, IR absorption, and HR-ESI-MS spectra, as well as comparisons of these data with reported values. The effects of the isolated compounds on lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells were investigated. Compounds 6, 10 and 20 exhibited significant inhibitory effects on LPS-induced IL-12 p40 and IL-6 production with IC50 values of 1.62-14.29 M. Compound 10 also showed a strong inhibitory effect on the LPS-stimulated production of TNF- with an IC50 value of 10.45 M.
- Li, Wei,Zhou, Wei,Kim, Sohyun,Koo, Jung-Eun,Kim, Yuna,Koh, Young-Sang,Shim, Sang Hee,Ma, Jin Yeul,Ho Kim, Young
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- Use of electrospray ionization ion-trap tandem mass spectrometry and principal component analysis to directly distinguish monosaccharides
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RATIONALE Carbohydrates are good source of drugs and play important roles in metabolism processes and cellular interactions in organisms. Distinguishing monosaccharide isomers in saccharide derivates is an important and elementary work in investigating saccharides. It is important to develop a fast, simple and direct method for this purpose, which is described in this study. METHODS Stock solutions of monosaccharide with a concentration of 400 μM and sodium chloride at a concentration of 10 μM were made in water/methanol (50:50, v/v). The samples were subjected to electrospray ionization ion-trap tandem mass spectrometry (ESI-MS) and the detected [2M + Na - H2O]+ ions were further investigated by tandem mass spectrometry (MS/MS), followed by applying principal component analysis (PCA) on the obtained MS/MS data sets. RESULTS The MS/MS spectra of the [2M + Na - H2O]+ ions at m/z 365 for hexoses and m/z 305 for pentoses yielded unambiguous fragment patterns, while rhamnose can be directly identified by its ESI-MS [M + Na] + ion at m/z 187. PCA showed clustering of MS/MS data of identical monosaccharide samples obtained from different experiments. By using this method, the monosaccharide in daucosterol hydrolysate was successfully identified. CONCLUSIONS A new strategy was developed for differentiation of the monosaccharides using ESI-MS/MS and PCA. In MS/MS spectra, the [2M + Na - H 2O]+ ions yielded unambiguous distinction. PCA of the archived MS/MS data sets was applied to demonstrate the spatial resolution of the studied samples. This method presented a simple and reliable way for distinguishing monosaccharides by ESI-MS/MS. Copyright
- Xia, Bing,Zhou, Yan,Liu, Xin,Xiao, Juan,Liu, Qing,Gu, Yucheng,Ding, Lisheng
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- Three new lignan glycosides with IL-6 inhibitory activity from Akebia quinata
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Three new lignan glycosides, akeqintoside A [(7S,8S)-7,8-dihydro-8- hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1′-benzofuranpropanol 2′-O-β-D-glucopyranoside] (1), akeqintoside B [(7R,8R)-7,8-di-hydro- 8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1′-(9′-methoxy- 7′-propenyl) benzofuran 2′-O-β-D-glucopyranoside] (2), and akequintoside C [7R*,8R*-dihydroxy-7-(4-hydroxy-3-methoxyphenyl)- glycerol 9-O-β-D-(6′-O-caffeoyl)-glucopyranoside] (3) were isolated from Akebia quinata along with five known compounds, syringin (4), vanilloloside (5), salidroside (6), 3,4-dihydroxyphenylethyl alcohol 8-O-β-D- glucopyranoside (7), and calceolarioside B (8). The structures of the compounds were identified based on one dimensional (1D)- and 2D-NMR, including 1H-1H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser effect spectroscopy (NOESY) spectroscopic analyses. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in tumor necrosis factor-alpha (TNF-α) stimulated MG-63 cells was also examined.
- Jin, Hong-Guang,Kim, A. Ryun,Ko, Hae Ju,Lee, Sang Kook,Woo, Eun-Rhan
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- Flavonoids and terpenoids with PTP-1B inhibitory properties from the infusion of salvia amarissima ortega
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An infusion prepared from the aerial parts of Salvia amarissima Ortega inhibited the enzyme protein tyrosine phosphatase 1B (PTP-1B) (IC50~88 and 33 μg/mL, respectively). Phytochemical analysis of the infusion yielded amarisolide (1), 5,6,40-trihydroxy-7,30-dimethoxyflavone (2), 6-hydroxyluteolin (3), rutin (4), rosmarinic acid (5), isoquercitrin (6), pedalitin (7) and a new neo-clerodane type diterpenoid glucoside, named amarisolide G (8a,b). Compound 8a,b is a new natural product, and 2–6 are reported for the first time for the species. All compounds were tested for their inhibitory activity against PTP-1B; their IC50 values ranged from 62.0 to 514.2 μM. The activity was compared to that of ursolic acid (IC50 = 29.14 μM). The most active compound was pedalitin (7). Docking analysis predicted that compound 7 has higher affinity for the allosteric site of the enzyme. Gas chromatography coupled to mass spectrometry analyses of the essential oils prepared from dried and fresh materials revealed that germacrene D (15) and β-selinene (16), followed by β-caryophyllene (13) and spathulenol (17) were their major components. An ultra-high performance liquid chromatography coupled to mass spectrometry method was developed and validated to quantify amarisolide (1) in the ethyl acetate soluble fraction of the infusion of S. amarissima.
- González-Andrade, Martín,Mata, Rachel,Pérez-Vásquez, Araceli,Rangel-Grimaldo, Manuel,Rivero-Cruz, Isabel,Salinas-Arellano, Eric,Torres-Colin, Rafael
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- Purification and characterization of a novel GH1 beta-glucosidase from Jeotgalibacillus malaysiensis
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Beta-glucosidase (BGL) is an important industrial enzyme for food, waste and biofuel processing. Jeotgalibacillus is an understudied halophilic genus, and no beta-glucosidase from this genus has been reported. A novel beta-glucosidase gene (1344 bp) from J. malaysiensis DSM 28777T was cloned and expressed in E. coli. The recombinant protein, referred to as BglD5, consists of a total 447 amino acids. BglD5 purified using a Ni-NTA column has an apparent molecular mass of 52 kDa. It achieved the highest activity at pH 7 and 65 °C. The activity and stability were increased when CaCl2 was supplemented to the enzyme. The enzyme efficiently hydrolyzed salicin and (1 → 4)-beta-glycosidic linkages such as in cellobiose, cellotriose, cellotetraose, cellopentose, and cellohexanose. Similar to many BGLs, BglD5 was not active towards polysaccharides such as Avicel, carboxymethyl cellulose, Sigmacell cellulose 101, alpha-cellulose and xylan. When BglD5 blended with Cellic Ctec2, the total sugars saccharified from oil palm empty fruit bunches (OPEFB) was enhanced by 4.5%. Based on sequence signatures and tree analyses, BglD5 belongs to the Glycoside Hydrolase family 1. This enzyme is a novel beta-glucosidase attributable to its relatively low sequence similarity with currently known beta-glucosidases, where the closest characterized enzyme is the DT-Bgl from Anoxybacillus sp. DT3-1.
- Liew, Kok Jun,Lim, Lily,Woo, Hui Ying,Chan, Kok-Gan,Shamsir, Mohd Shahir,Goh, Kian Mau
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- A new megastigmane diglycoside from litsea glutinosa (Lour.) C. B. Rob.
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Phytochemical study on the leaves and twigs of afforded the new megastigmane diglycoside (6S, 7E, 9R)-6, 9-dihydroxy-4, 7-megastigmadien-3-one- 9-O-[α-L-arabinofuranosyl-(l→6)]-β-D-glucopyranoside (1), along with glycosides (6S, 7E, 9R)-roseoside (2), (7'R, 8'R)-3, 5'-dimethoxy-9, 9'-dihydroxy-4, 7'-epoxylignan 4'-β-D-glucopyranoside (3), (7'R, 8'S)-dihydrodehydrodiconifenyl alcohol 9'-O-β-D-xylopyranoside (4) and pinoresinol 3-O-β-D-glucopyranoside (5). Their structures were established on the basis of extensive spectroscopic and chemical methods. Compounds 2-5 were reported for the first time in this species. Compound 1 was evaluated for cytotoxic activities against human tumor cell lines (myeloid leukemia HL-60, hepatocellular carcinoma SMMC-7721, lung cancer A-549, breast cancer MCF-7 and colon cancer SW480 cells), for which it was proved to be inactive (IC 50 > 40 μM).
- Wang, Yun-Song,Liao, Zhen,Li, Yan,Huang, Rong,Zhang, Hong-Bing,Yang, Jing-Hua
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- Two new dammarane-type triterpenoid saponins from notoginseng medicinal fungal substance
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Two new dammarane-type triterpenoid saponins, namely ginsenoside Rk6(1) and ginsenoside-Rh22(2), were isolated from notoginseng medicinal fungal substance. The structures of 1 and 2 were established as 3β,6α,12β,26-tetrahydroxydammar
- Xu, Wei,Liu, Xin,Liu, Xiao-Li,Jia, Ai-Ling,Wang, Xin-Wen,Qiu, Zhi-Dong
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- Two new glycosides from Dianella ensifolia (L.) DC
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The Dianella genus includes approximately 20 species in all over the world. So far, only the chemical constituents of the lipophilic extract from Dianella ensifolia have been investigated. However, there have been no reports of its aqueous extract. In thi
- Fan, Miao-Yin,Liu, Bing-Rui,Yang, Fan,Zhang, Pu-Zhao
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- Parisvaniosides A–E, five new steroidal saponins from Paris vaniotii
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The species of Paris genus is a prolific source of structurally diverse steroidal saponins responsible for multivarious biological properties. The first phytochemical investigation on the steroidal saponin constituents from the rhizomes of Paris vaniotii Lévl. led to the discovery and structural characterization of four new spirostanol saponins, named parisvaniosides A-D (1–4), and one new furostanol glycoside, named parisvanioside E (5), along with eleven known analogues (6–16). Their structures were unambiguously established on the basis of extensive spectroscopic analysis and comparison with the reported spectroscopic data. Compound 1 is a rare spirostanol saponin sharing with a C-9/C-11 double bond and a peroxy group located between C-5 and C-8 of the aglycone, whereas 3 and 4 are unusual C-27 steroidal sapoins with hydroxyl/methoxyl at both C-5 and C-6. Furthermore, 5 is the first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B. All isolated saponins were evaluated for their anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW 264.7 macrophages.
- Ji, Yun-Heng,Liu, Hai-Yang,Ni, Wei,Xiao, Long-Gao,Yan, Huan,Yu, Ling-Ling
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- Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica
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Six undescribed long-chain fatty acid esters of isoflavone glycosides were obtained from the rhizomes of Iris domestica (L.). Their structures were elucidated by comprehensive spectroscopic data, alkaline hydrolysis, and acid hydrolysis. This is the first report of the long-chain (C14–C18) fatty acid derivatives of isoflavone glycosides from natural products. Belamcandnoate B and D exhibited moderate cytotoxic activities against HCT-116, HepG2, and BGC823 cell lines with IC50 values of 1.69–6.86 μM. Belamcandnoate B and E exhibited 72.27 and 58.98% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 μM.
- Li, Jiayuan,Liu, Yanfei,Ni, Gang,Wang, Renzhong,Yu, Dequan
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- New glycosides from the leaves and rattan stems of Schisandra chinensis
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Two new glycosides, vanillic acid 4-O-β-D-(6′-O-(Z)-2′'-methylbut-2′'-enoate)glucopyranoside (1), p-methoxycarvacrol-6-O-β-D-glucopyranoside (2), along with two known analogues (3-4), were isolated from the leaves and rattan stems of Schisandra chinensis.
- Bao, TeRiGen,Fu, ChunWang,Jia, JingMing,Liu, LuQi,Wang, AnHua,Yang, YongCheng
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- Iridoid glucosides from the leaves of Vitex negundo var. cannabifolia
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Five new iridoid glucosides, cannabifolisides A–E (1 – 5), together with nine analogues (6 – 14), were isolated from the leaves of Vitex negundo var. cannabifolia. Their structures were elucidated by spectroscopic data (NMR, UV, IR, and MS) analyses and comparison of their spectroscopic and physical data with the literature values. The protective effect of isolated compounds on human gastric epithelial cells were evaluated by measuring the enhanced cell viability of GES-1 cell insulted by TCA. Among these, compounds 4, 6, 8, 10, 12, and 14 remarkably increased the cell viability in a concentration-depend manner.
- Huo, Huixia,Li, Jun,Li, Manman,Liang, Naiyun,Ma, Jiale,Song, Yuelin,Sun, Jing,Tu, Pengfei,Wang, Rongye,Zhao, Yunfang,Zheng, Jiao
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- Four new prenylflavonol glycosides from the leaves of Cyclocarya paliurus
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Four new prenylflavonol glycosides (1–4) along with two known analogues (5–6) were isolated from the leaves of Cyclocarya paliurus for the first time. The structures of these compounds were characterized by comprehensive analysis of 1 D, 2 D NMR, HRESIMS,
- Ye, Zi-Jun,Sun, Hui-Hui,Chen, Zu-Hui,Wu, Jian-Ping,Li, Jing,Zhu, Hui,Huang, Lu-Lu,Chang, Xi-Wen,Ou, Sai-Yu,Wang, Wen-Xuan,He, Xiao-Ai,Zhu, Gang-Zhi,Xu, Kang-Ping
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p. 772 - 779
(2020/08/10)
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- Steroidal alkaloids and their glycosides from the bulbs of Fritillaria unibracteata
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Seven undescribed steroidal alkaloids, including two jervine-type steroidal alkaloids, fritiunibras A-B (1–2), and five cevanine-type steroidal alkaloid glycosides, fritiunibras C-G (3–7), along with six known cevanine-type steroidal alkaloids and their glycosides (8–13) were isolated from the bulbs of Fritillaria unibracteata Hsiao et K. C. Hsia. Their structures were determined by interpretation of comprehensive spectroscopic and single-crystal X-ray diffraction analysis. The absolute configurations of sugar moieties were determined by HPLC analysis and compared with standards after hydrolysis and derivatization. Furthermore, their inhibitory effects on NO production and cytotoxic activities were evaluated.
- Dong, Hui-Wen,Kathy TSE, Wai-Gaun,Liang, Hong,Tu, Peng-Fei,Wang, Shu-Hui,Wang, Yu-Qi,Yang, Tie-Chui,Zeng, Ke-Wu,Zhang, Yun-Hu
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- Isolation, structural elucidation and molecular docking studies against SARS-CoV-2 main protease of new stigmastane-type steroidal glucosides isolated from the whole plants of Vernonia gratiosa
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Phytochemical investigation of the whole plants of Vernonia gratiosa Hance. led in the isolation and identification of two new stigmastane-type steroidal glucosides (1–2), namely vernogratiosides A (1), and B (2). Their chemical structures were fully elucidated based on 1 D/2D NMR spectroscopic, HR-ESI-MS data analyses, and by producing derivatives by chemical reactions. The binding potential of the isolated compounds to replicase protein ? main protease of SARS-CoV-2 were examined using the molecular docking simulations. Our results show that the isolated steroidal glucosides (1–2) bind to the substrate‐binding site of SARS-CoV-2 main protease with binding affinities of ?7.2 and ?7.6 kcal/mol, respectively, as well as binding abilities equivalent to N3 inhibitor that has already been reported (–7.5 kcal/mol).
- Anh, Hoang Le Tuan,Anh, Le Tuan,Lee, Ki Yong,Phong, Nguyen Viet,Quang Minh, Bui,Trang, Nguyen Minh,Trung, Nguyen Quang,Van Cong, Pham,Van Dan, Nguyen,Viet Duc, Ngo,Vinh, Le Ba
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supporting information
(2022/02/22)
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- Chemical Components in Hedera rhombea Leaves and Their Cytotoxicity
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Two novel triterpene glycosides (1 and 2), 17 known triterpene glycosides (3-19), two known flavonoid glycosides (20 and 21), and two known norsesquiterpene glucosides (22 and 23) were isolated from Hedera rhombea (Araliaceae) leaves. The structures of 1
- Mimaki, Yoshihiro,Miyake, Katsunori,Oguro, Airi,Shimomura, Tatsuya,Yokogawa, Shohei,Yokosuka, Akihito
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p. 175 - 181
(2022/02/05)
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- Xanthosaponins A and B, two unusual steroidal saponins with an unprecedented 16,17-: Seco -cholestane skeleton from Solanum xanthocarpum and their cytotoxic activities
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Xanthosaponins A (1) and B (2), two unusual steroidal saponins with a new 16,17-seco-cholestane carbon skeleton were isolated from the fruits of Solanum xanthocarpum. The structures of all isolated compounds were determined using 1D and 2D NMR experiments and MS analyses. Xanthosaponin A (1) exhibited significant cytotoxic activity against MGC803, LN229, and SMMC7721 cells. This journal is
- Jiang, Peng,Jiang, Yi-Kai,Kuang, Hai-Xue,Li, Xiao-Mao,Liu, Yan,Pan, Juan,Wang, Si-Yi,Xu, Zhen-Peng,Yang, Bing-You
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p. 1815 - 1820
(2022/01/31)
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- Chain conformations and steady-shear viscosity properties of pectic polysaccharides from apple and tomato
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In this study, apple pectin (AP) and tomato pectin (TP) were demonstrated to be a high-ester (74.8%) polysaccharide with the weight-average molecular weight (Mw) of ～ 243 kDa and a low-ester (45.9%) polysaccharide with the Mw of ～ 19 kDa, respectively. The semi-rigid chain conformations of pectic polysaccharides in NaNO3 aqueous solution were deduced according to the Smidsr?d “B values” of AP (0.025) and TP (0.029), while AP and TP exhibited higher stiffness in water due to the electric repulsion of carboxyl groups, which was visually observed by AFM images. Under steady shear, the shear-thickening behaviors of AP and TP in NaNO3 aqueous solutions were observed in the shear rate range of ?1, which were attributed to the disruption of the ordered arrangement induced by semi-rigid pectin chains into randomly entangled structure by weak shear force. AP exhibited stronger shear-thickening behavior due to the formation of more entanglements resulted from the higher Mw and longer side chains highly branched at rhamngalacturonan region. This study provides the scientific basis for the construction of the relationship of steady-shear property with chain conformation and molecular weight of pectin.
- Hu, Shihao,Nie, Shaoping,Wang, Junqiao,Wang, Qiang,Xu, Xiaojuan
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- Three new compounds from the twigs and leaves of Nageia fleuryi Hickel
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Two new diterpenoids, 12,15-di-O-acetylhypargenin B (1) and taiwanin F-12-O-β-D-glucopyranoside (2), one new monoterpenoid, (S)-7-methyl-3-methyleneoct-6-ene-1,2-diyl diacetate (3), together with eight known compounds (4?11), were obtained from the twigs
- Chen, Lu-Zhou,Liu, Yu-Nan,Lou, Hong-Xiang,Ren, Dong-Mei,Shen, Tao,Wang, Xiao-Ning,Xiang, Lan,Xu, Jia-Xin,Yang, Hu
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supporting information
(2022/03/31)
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- Structurally diverse isoquinoline and amide alkaloids with dopamine D2 receptor antagonism from Corydalis bungeana
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Four new isoquinoline alkaloids including a benzophenanthridine alkaloid (1), a morphine derivative (2), a narceine-type alkaloid (3) and a simple isoquinoline alkaloid (4), a new amide alkaloid (5) and a new phthalic acid derivative (6), together with eleven known alkaloids (7–17) were obtained from the whole herbs extract of Corydalis bungeana Turcz. Their structures and absolute configurations were elucidated by extensive spectroscopic data analysis including HRESIMS, NMR and electronic circular dichroism (ECD) and ECD calculation. Compounds 1–17 were evaluated for dopamine D2 receptor activity in CHO-D2 cells. Among them, 16 showed the highest antagonistic activity on the D2 receptor with an IC50 value of 2.04 ± 0.01 μM. Compounds 14 and 15 exhibited moderate antagonism with IC50 values of 13.66 ± 2.28 and 31.72 ± 2.52 μM, respectively.
- Cheng, Jun-Xiang,Feng, Jia-Tao,Guo, Zhi-Mou,Han, Yang,Hou, Tao,Liang, Xin-Miao,Liu, Yan-Fang,Wang, Ji-Xia,Wang, Yao-Dong,Zhang, Zi-Hui,Zhou, Han
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- Two new isoflavones from the barks of Dalbergia hancei Benth
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Two new isoflavone compounds, Dalhancei A (1) and Dalhancei B (2), along with a known compound epicatechin (3) were isolated from 80% methanol extract of the barks of Dalbergia hancei Benth. The structures of compounds 1–3 were elucidated by comparison with the literature and physical data analysis, including optical rotation, MS, 1D and 2D NMR spectra. Compounds 1 and 2 showed weak inhibitory activity against tyrosinase at 16.22 mmol/L, with inhibition rates of 42.23 ± 0.18% and 45.68 ± 0.17%, respectively; compound 1 exhibited weak inhibitory activity against α-glucosidase with the inhibition rate of 43.72 ± 0.22% at 5.41 mmol/L, compounds 2 and 3 had better α-glucosidase inhibitory activity than compound 1 with IC50 values of 0.90 ± 0.18 and 0.41 ± 0.17 mmol/L, respectively.
- Ge, Li,He, Rui-Jie,Huang, Yong-Lin,Li, Xiao-Mei,Pang, Nao,Wang, Ya-Feng,Yang, Bing-Yuan,Yang, Ke-Di
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supporting information
(2022/03/27)
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- Four cucurbitane glycosides taimordisins A–D with novel furopyranone skeletons isolated from the fruits of Momordica charantia
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Four novel triterpene glycosides, taimordisins A–D (1–4), were discovered from fresh fruits of Taiwanese Momordica charantia. The chemical framework and relative stereochemistry of these four natural products were isolated, purified, and determined by using various separation and spectroscopy techniques. Each of them features a unique bicyclic-fused or trifuso-centro-fused ring system. Notably, 1 and 2 are cucurbitane-based compounds possessing a new C-24 and C-2″ carbon–carbon linkage with 5-hydroxy-2-(hydroxymethyl)tetrahydro-4H-pyran-4-one and 6-(hydroxymethyl)tetrahydro-4H-pyran-3,4,4-triol units, respectively, and represented an unprecedented molecular skeleton. In terms of biosynthesis, they all originate from a common precursor 3-hydroxycucurbita-5,24-dien-19-al-7,23-di-O-β-glucopyranoside. Of two sugar moieties, the one at 23-O-β-glucopyranoside grants each individual congener uniqueness likely through microbial symbiont-mediated intramolecular transformation into two major types of furo[2,3-b]pyranone and furo[3,2-c]pyranone derivatives. These new products possess desirable anti-inflammatory biological activities in addition to being generally regarded as safe.
- Hsiao, Pin-Chun,Huang, Hung-Tse,Kuo, Yao-Haur,Li, Tsung-Lin,Liaw, Chia-Ching,Lin, Yu-Chi,Lo, I-Wen,Zhang, Li-Jie
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- Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells
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The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of s
- Fukaya, Haruhiko,Kuroda, Minpei,Matsuo, Yukiko,Mimaki, Yoshihiro,Takatori, Kazuhiro,Tsuchihashi, Hiroko
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- Undescribed C -Glycosylflavones from Corn Silk and Potential Anti-inflammatory Activity Evaluation of Isolates #
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Phytochemical investigation of corn silk resulted in isolation and characterization of four flavone C-glycosides, chrysoeriol 6- C - β -oliopyranosyl-7- O - β -D-glucopyranoside (1), 3′-methoxycassiaoccidentalin A (2), chrysoeriol 6- C - β -boivinopyranosyl-7- O - β -D-glucopyranoside (3), and ax-4″-OH-3′-methoxymaysin (4), a triterpenoid, friedelin (5), two sterols, (22 E)-5 α,8 α -epidioxyergosta-6,22-dien-3 β -ol (6) and 6 β -hydroxystigmasta-4,22-diene-3-one (7), and a mixture of β -sitosterol and stigmasterol. Compounds 1 and 2 were previously undescribed. Structure elucidation of the isolated compounds was attained using spectral data including 1D and 2D NMR and HRESIMS. Compounds 1, 2, 5, and 6 inhibited iNOS activity in LPS-induced macrophages and decreased nitrite levels by 68.64 ± 4.46, 65.67 ± 6.47, 88.50 ± 0.50, and 94.00 ± 4.00%, respectively, at 50 μM. Compound 5 also showed inhibition of NF- κ B (51.00 ± 1.50%). Compounds 1 and 2 induced NAG-1 activity in chondrocytes by 1.80 ± 0.05 and 2.00 ± 0.13 fold, respectively. The extract of corn silk, however, did not exhibit inhibition of iNOS or NF- κ B but induced NAG-1 by 1.80 ± 0.51 fold.
- Ali, Zulfiqar,Khan, Ikhlas A.,Khan, Shabana I.,Radhakrishnan, Srivedavyasasri,Sarfare, Satish,Zulfiqar, Fazila
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- MS/MS-based molecular networking accelerated discovery of germacrane-type sesquiterpene lactones from Elephantopus scaber L
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Assisted by an MS/MS-based molecular networking guided strategy, six undescribed germacrane-type sesquiterpene lactones, namely scaberxones A-F, along with a known analog were obtained and characterized from Elephantopus scaber L. Their structures were unequivocally assigned by detailed spectroscopic analyses, NMR and ECD spectral calculations, and computer-assisted structure elucidation (CASE), complemented with single-crystal X-ray diffraction. All compounds were measured for their production of nitric oxide (NO) levels in lipopolysaccharide (LPS)-induced BV-2 microglial cells to assess their anti-neuroinflammatory activity. Scaberxone F showed the most potent inhibition of NO production at a concentration of 10 μM.
- Bai, Ming,Huang, Xiao-Xiao,Li, Qian,Lin, Bin,Liu, De-Feng,Lv, Tian-Ming,Qin, Shu-Yan,Song, Shao-Jiang,Xu, Wei
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- Two new steroidal alkaloids from the mature fruits of Solanum nigrum
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Two previously undescribed steroidal alkaloids, compounds 1–2, were isolated from the ripe fruits of Solanum nigrum, along with seven known metabolites (3–9). Based on spectroscopic and chemical evidence, including IR, NMR, and HR-ESI-MS analyses, the structures of the isolated compounds were elucidated as 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)]-β-D-galacopyranoside and 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside. Four steroidal alkaloids (compounds 1–2 and 4–5) were tested for their anti-proliferative effects against the HT-29, A549, and Lewis cell lines. Both of the previously isolated compounds inhibited the proliferation of these three cell lines in a dose-dependent manner, with the most significant effect being in the A549 cells, but neither reached IC50 at 50 μM. These results revealed that S. nigrum had weak cytotoxicity, indicating its clinical safety as a traditional anti-tumor herbal medicine.
- Lin, Li,Liu, LiangYu,Wang, JianNong,Wang, WenYi,Wu, Tong,Yang, YuKe
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- Phenylpropanoids from Brachybotrys paridiformis Maxim. ex Oliv. and their anti-HBV activities
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Using chemical and spectroscopic data, this study on Brachybotrys paridiformis Maxim. ex Oliv. identified four undescribed phenylpropanoids, brachin A–C and brachoside A, together with nine other known compounds. The isolated compounds were tested for anti-hepatitis B virus activities in the HepG2.2.15 cell line. Among them, caffeic anhydride showed the most potent activity.
- Ma, Chun-Liu,Qiu, He-Qin,Wang, Guang-Shu,Wang, Yi-Xiao,Wu, Si-Tong,Yu, Bai-Hong
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- PTP1B and α-glucosidase inhibitory activities of the chemical constituents from Hedera rhombea fruits: Kinetic analysis and molecular docking simulation
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In this study, we present the first investigation of Hedera rhombea Bean fruit, which led to the isolation of six undescribed compounds including two megastigmane glucosides, two rare 1,4-dioxane neolignanes, and two quinic acid derivatives, together with 26 known compounds. Their structures and absolute configurations were elucidated by extensive analysis of NMR spectroscopic data, HRMS, and ECD calculations. This is the first report on the isolation of methyl 3-O-caffeoyl-5-O-p-coumaroylquinate from a natural source. Among the isolated compounds, falcarindiol and caffeoyltryptophan showed significant PTP1B inhibition with IC50 values of 7.32 and 16.99 μM, respectively, compared to those of the positive controls [sodium orthovanadate (IC50 = 17.96 μM) and ursolic acid (IC50 = 4.53 μM)]. These two compounds along with several other compounds displayed significant α-glucosidase inhibitions with IC50 values ranging from 12.88 to 91.89 μM, stronger than that of the positive control (acarbose, IC50 = 298.07 μM). Enzyme kinetic analysis indicated that caffeoyltryptophan and falcarindiol displayed competitive and mixed-type PTP1B inhibition, respectively, whereas the α-glucosidase inhibition type was mixed-type for caffeoyltryptophan and uncompetitive (rarely reported for a-glucosidase inhibitors) for falcarindiol. In addition, molecular docking results showed that these active compounds exhibited good binding affinities toward both PTP1B and α-glucosidase with negative binding energies. The results of the present study demonstrate that these active compounds might be beneficial in the treatment of type 2 diabetes.
- Choi, Jae Sue,Ha, Manh Tuan,Kim, Chung Sub,Kim, Jeong Ah,Lee, Tae Hyun,Min, Byung Sun,Prajapati, Ritu
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- Photothermal strategy for the highly efficient conversion of glucose into lactic acid at low temperatures over a hybrid multifunctional multi-walled carbon nanotube/layered double hydroxide catalyst
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The conversion of carbohydrates into lactic acid has attracted increasing attention owing to the broad applications of lactic acid. However, the current methods of thermochemical conversion commonly suffer from limited selectivity or the need for harsh conditions. Herein, a light-driven system of highly selective conversion of glucose into lactic acid at low temperatures was developed. By constructing a hybrid multifunctional multi-walled carbon nanotube/layered double hydroxide composite catalyst (CNT/LDHs), the highest lactic acid yield of 88.6% with 90.0% selectivity was achieved. The performance of CNT/LDHs for lactic acid production from glucose is attributed to the following factors: (i) CNTs generate a strong heating center under irradiation, providing heat for converting glucose into lactic acid; (ii) LDHs catalyze glucose isomerization, in which the photoinduced OVs (Lewis acid) in LDHs under irradiation further improve the catalytic activity; and (iii) in a heterogeneous-homogeneous synergistically catalytic system (LDHs-OH-), OH- ions are concentrated in LDHs, forming strong base sites to catalyze subsequent cascade reactions.
- Duo, Jia,Jin, Binbin,Jin, Fangming,Shi, Xiaoyu,Wang, Tianfu,Ye, Xin,Zhong, Heng
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p. 813 - 822
(2022/02/09)
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- Structurally diverse glycosides of secoiridoid, bisiridoid, and triterpene-bisiridoid conjugates from the flower buds of two Caprifoliaceae plants and their ATP-citrate lyase inhibitory activities
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The ethanolic extracts of the dried flower buds of two Caprifoliaceae plants, Lonicera japonica and Abelia × grandiflora, showed considerable inhibitory activities against adenosine triphosphate (ATP)-citrate lyase (ACL), a new promising drug target for the treatment of metabolic disorders. Bioassay-guided purification in conjunction with HPLC-PDA profiling led to the isolation and characterization of thirty-five (1–35) and fourteen (1′?14′) structurally diverse compounds from the above two plant extracts, respectively. Compounds 1–9 and 1′?6′ are previously undescribed glycosides. Their structures were elucidated on the basis of spectroscopic data, electronic circular dichroism (ECD), and single crystal X-ray diffraction analyses. In particular, lonicejaposide A (1) has an unprecedented skeleton generated through the coupling of C-7 in secologanin with C-2′′ in phenylacetaldehyde via an aldol condensation. Abeliflorosides A (1′) and B (2′) are hitherto unknown glycosides of triterpene and bisiridoid conjugates constructed through the formation of a 1,3-dioxane moiety. All the isolates were evaluated for their inhibitory activities against ACL. Compounds 9, 25–28, 31, 1′, 2′, and 14′ displayed significant inhibitory effects, with IC50 values ranging from 0.1 to 14.2 μM. The interactions of selected compounds possessing different structure features (e.g., 9, 25, 31, and 2′) with ACL were thereafter performed by employing molecular docking studies. In addition, compound 2′, the most complex triterpene-bisiridoid conjugate glycoside reported herein, also inhibited acetyl-CoA carboxylase 1 (ACC1), with an IC50 value of 7.9 μM. The dried material of the flower buds of L. japonica (honeysuckle) is a well-known traditional oriental medicine (i.e., Flos Lonicerae Japonicae, FLJ) and has long been used in large quantities. The above findings not only provide new insights for the development of multipurpose utilization of FLJ in healthcare community, but also provide profitable clues indicating that the flower buds of A. × grandiflora might be a potential alternative to FLJ in the traditional Chinese medicine market.
- Wan, Jiang,Jiang, Chun-Xiao,Tang, Yu,Ma, Guang-Lei,Tong, Ying-Peng,Jin, Ze-Xin,Zang, Yi,E.A. Osman, Ezzat,Li, Jia,Xiong, Juan,Hu, Jin-Feng
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- Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions
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Sargassum fusiforme polysaccharides (SFPs), including SFP-3-40, SFP-3-60, SFP-3-80, SFP-7-40, SFP-7-60, SFP-7-80, SFP-10-40, SFP-10-60, and SFP-10-80, were extracted at different pH (3, 7, and 10), and then precipitated with graded precipitation of 40%, 60% and 80% (v/v) ethanol solution, respectively. Their physicochemical properties and α-glucosidase inhibitory activity were determined. Results showed that SFPs significantly differed in the contents of total sugar, protein, uronic acid, sulfate, the zeta potential, and molecular weight distribution. SFPs, including SFP-10-40, SFP-10-60, and SFP-10-80, had bigger absolute zeta potential value and higher respective average molecular weight in the same ethanol concentration precipitate. All samples were mainly composed of fucose, glucuronic acid, and mannose with different molar ratios. The extraction pH and precipitation ethanol solution concentration caused little changes in functional groups, but significantly altered surface morphology of SFPs. Congo red test revealed that all polysaccharides were not helical polysaccharides. Rheological measurements indicated that SFPs were pseudoplastic fluids and showed elastic behavior of the gel. Except SFP-3-40 and SFP-3-60, all other samples had a stronger α-glucosidase inhibitory activity than that of acarbose. The inhibition type of SFPs against α-glucosidase varied owing to different extraction pH and precipitation ethyl concentration. This study shows that extraction pH can significantly affect the structure and hypoglycemic activity of SFPs and provide a data support for the scientific use of Sargassum fusiforme in industrial production.
- Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen
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p. 602 - 610
(2021/11/30)
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- Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity
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As one of raw materials, the rhizome of Imperata cylindrica var. major (Nees) C.E. Hubb. is used in kinds of preparations curing inflammation related diseases, while its effective substances are not yet clear. In this paper, its chemical constituents and their anti-inflammatory activities were investigated. As results, ten compounds, named as imperphenoside A (1), imperphenols B (2) and C (3), imperphenosides D–F (4–6), and imperlignanosides A–D (7–10), along with previously reported thirty-seven known ones (11–47) were obtained from it. Their structures were ascertained basing on the extensive spectroscopic methods and electronic circular dichroism data analysis. Meanwhile, compounds 4, 11, 12, 24, 27, 31, 32, 37, 43, 45, and 47 exhibited nitric oxide inhibitory effects in concentration dependent at 3, 10, and 30 μM on lipopolysaccharides induced RAW 264.7 cells. Moreover, the western blot analysis indicated that compounds 4, 11, 43, and 47 could restrain the phosphorylation of nuclear factor kappa-B kinase to down-regulate the protein expression of inflammatory cytokines such as inducible nitric oxide synthase, interleukin-6 and tumor necrosis factor-α. In conclusion, they might play the anti-inflammatory effects through regulating NF-κB signaling pathway.
- Cao, Hui-Na,Han, Yu,Hao, Mi-Mi,Jiang, Hong-Yu,Li, Hui-Min,Ruan, Jing-Ya,Wang, Tao,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- Glucansucrases from lactic acid bacteria as biocatalysts for multi-ring catechol glucosylation
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Catechins are the major group of bioactive flavanols in green tea and cacao. 17 glucansucrase-active strains were identified from a set of 41 lactic acid bacteria, which were able to glucosylate (+)-catechin in a non-natural acceptor reaction. In total cell free extracts of 12 Leuconostoc and 5 Weissella strains were active on catechin and also 8 cell fractions exhibited catechin glucosylation activity. Six enzymes were selected for further evaluation and enriched up to 37 fold in yields of at least 40%. Glucansucrase of L. citreum DSM 5577 was the most efficient biocatalyst for (+)-catechin transformation with conversions of >40% after 24 h. NMR analysis of the major reaction product confirmed the (+)-catechin-4′-O-α-d-glucoside. Only L. kimchi B-65337 produced a second catechin monoglucoside. Four out of six glucansucrases glucosylated esculetin and all enzymes were active on haematoxylin. Glucansucrases of L. citreum DSM 5577, L. kimchi B-65337 and W. beninensis DSM 22752 were the best suited biocatalysts with conversions of >30% for esculetin and >60% for haematoxylin. W. beninensis DSM 22752 glucansucrase produced 89% haematoxylin glucosides without process optimization. L. kimchi B-65337 and W. beninensis DSM 22752 synthesized >40% diglucosides with the bifunctional haematoxylin. NMR analysis of the purified esculetin products confirmed formation of the 6-O-α-d- and 7-O-α-d-glucosides. Also two haematoxylin monoglucosides were identified as the 9-O-α-d- and 3-O-α-d-glucosides.
- Nolte, Johannes,Kempa, Alexander,Hochgürtel, Matthias,Sch?rken, Ulrich
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- An Efficient Method for the Isolation of Toxins from Pteridium aquilinum and Evaluation of Ptaquiloside against Cancer and Non-cancer Cells#
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The common fern, bracken (Pteridium aquilinum), is well known for its toxic effects on livestock due principally to the carcinogenic constituent ptaquiloside (1), although other toxins are present including the cyanogenic glycoside, prunasin (2). Here, we report an improved and relatively green process for the isolation of 1 and 2 from fresh bracken fronds and the evaluation of 1 for cytotoxicity against several cancer cell lines. The results indicate that 1 displays selective toxicity against cancer cells relative to noncancer retinal epithelial cells, and the improved method for the isolation of 1 is expected to facilitate further exploration of its pharmacological properties.
- Williams, Courtney,Allison, Simon J.,Phillips, Roger M.,Linley, Peter A.,Wright, Colin W.
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p. 892 - 895
(2021/06/06)
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- Autocatalyzed oxidation of d-glucitol by alkaline copper (III) periodate complex: A kinetic and mechanistic approach
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An autocatalyzed oxidation of d-glucitol (DG) by diperiodatocuprate (III) (DPC) in aqueous alkaline medium at a constant ionic strength of 0.06 mol dm?3 was studied spectrophotometrically. An autocatalysis was observed by one of the products formed, that is, Cu (II). A 1:2 stoichiometry (DG : DPC) exhibited reaction between the DG and DPC in an aqueous alkaline medium. The reaction was of first order in [DPC] when [DPC] ?] was less than unity, whereas periodate had retarding effect on the rate of reaction. Ionic strength had a negligible effect on the rate of reaction. The main reaction products were identified by the spot tests and spectroscopic analysis. The product, Cu (II), catalyzed the reaction with a fractional order. A composite mechanism involving uncatalyzed and autocatalyzed reaction paths was proposed. The activation parameters with respect to slow step of the mechanism and also the thermodynamic quantities were determined and discussed.
- Patil, Shreekant M.,Bagoji, Atmanand M.,Konnur, Santosh B.,Nandibewoor, Sharanappa T.
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supporting information
(2020/11/30)
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- Synthesis of 5-hydroxymethylfurfural from cassava (Manihot utilissima pohl) peels through dehydration reaction using deep eutectic solvent based on choline chloride/citric acid
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The high cellulose content in cassava peel has an opportunity to produce bio-based chemical products in 5-hydroxymethylfurfural (5-HMF) form. This study aimed to determine the optimum conditions of glucose dehydration reaction as a result of hydrolysis of the best cassava peel cellulose. The variables observed in this study were H2SO4 catalyst concentrations in the hydrolysis reaction, temperature and amount of deep eutectic solvents based on choline chloride/citric acid. The optimum dehydration reaction conditions in this study was the glucose:deep eutectic solvents mass ratio of 1:6 at the reaction temperature of 80 oC. The highest yield of 64.50% at an initial glucose concentration of 5.70% using a 1.5% H2SO4 catalyst during the hydrolysis of cassava peel cellulose. The results obtained in this study indicated that addition of choline chloride/citric acid as deep eutectic solvent can increase the yield of 5-HMF.
- Manurung,Silalahi,Winda,Siregar
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p. 1115 - 1119
(2021/05/10)
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- A new glucoside with a potent α-glucosidase inhibitory activity from Lycium schweinfurthii
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A new glucoside, 3-methoxy-4-O-β-D-glucopyranosyl-methyl benzoate, has been isolated from Lycium schweinfurthii along with five known compounds through bioactivity guided fractionation of the total plant methanolic extract towards α-glucosidase inhibitory activity. All the isolated compounds were tested for their inhibitory effect on α-glucosidase enzyme. As a result, four of them showed a potent inhibitory activity and thus constitute a therapeutic approach to decrease postprandial hyperglycemia in diabetic patients.
- Elbermawi, Ahmed,Halim, Ahmed F.,Mansour, El-Sayed S.,Ahmad, Kadria F.,Ashour, Ahmed,Amen, Yhiya,Shimizu, Kuniyoshi
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p. 976 - 983
(2019/06/10)
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- In vitro study on α-amylase and α-glucosidase inhibitory activities of a new stigmastane-type steroid saponin from the leaves of Vernonia amygdalina
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Using various chromatographic separations, four compounds, including one new steroid saponin named vernoamyoside E (1), were isolated from the leaves of the Vietnamese medicinal plant Vernonia amygdalina Delile (Asteraceae). Their structures were established by spectroscopic methods such as 1D- and 2D-NMR, HR-ESI-MS, and HPLC analysis. The inhibitory activities against α-glucosidase and α-amylase of the isolated compounds from V. amygdalina were reported for the first time. The results indicated that compound 1 significantly inhibited both against α-amylase and α-glucosidase activity.
- Anh, Hoang Le Tuan,Vinh, Le Ba,Lien, Le Thi,Cuong, Pham Viet,Arai, Masayoshi,Ha, Tran Phuong,Lin, Hoang Ngoc,Dat, Ton That Huu,Cuong, Le Canh Viet,Kim, Young Ho
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supporting information
p. 873 - 879
(2019/06/27)
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- Two new triterpenoid saponins: telephiifoliosides A and B from the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq
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The polar fraction of the MeOH extract of the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq. (Caryophyllaceae) was investigated for its constituents and two previously unreported monodesmosides triterpene saponins, telephiifoliosides A and B (1 and 2), along with the known bonushenricoside A (3) were isolated. Their structures were elucidated by combined spectroscopic and spectrometric techniques (1H NMR, 13C NMR, HSQC, 1H-1H COSY, HMBC, TOCSY, NOESY, HRESIMS) and chemical methods. The structures of the new saponins were established as; 3-O-α-L-arabinopyranosyljaligonic acid (1), and 3-O-α-L-arabinopyranosylphytolaccagenin ester (2). Upon evaluation of the antiproliferative activity on human malignant epithelial (HeLa) cells, none of the isolated compounds was efficient at the concentration of 33 μM. Highlights This is the first phytochemical study on Corrigiola litoralis subsp. telephiifolia. Two new saponins were isolated from the roots of Corrigiola litoralis subsp. telephiifolia. The isolated compounds were tested for their antiproliferative activity.
- Fouedjou, Romuald Tématio,Ponou, Beaudelaire Kemvoufo,Teponno, Rémy Bertrand,Melzig, Matthias,Tanaka, Chiaki,Miyamoto, Tomofumi,Tapondjou, Léon Azefack
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- New 23, 27-dihydroxy-oleanane-type triterpenoid saponins from Anemone Raddeana Regel
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Two new 23, 27-dihydroxy-oleanane-type triterpenoid saponins named Raddeanoside Rf and Raddeanoside Rg (1 and 2), along with thirteen known triterpenoid saponins (3–15) were isolated from the rhizome of Anemone raddeana Regel. Their structures were determined by chemical and spectral analysis, including 1 D, 2 D NMR data and HRESIMS. The type of aglycone 23, 27-dihydroxy oleanolic acid is extremely rare in natural products. In addition, the anti-cancer activity for all the compounds were evaluated. Compounds 9 and 10 exhibited significant cytotoxicity with IC50 values of 4.47 and 8.97 μM against human pancreatic cancer lines (PANC-1), while compound 6 with IC50 value of 8.19 μM against human lung lines (A549). The possible structure-activity relationships of these triterpenoid saponins were also tentatively discussed.
- Lv, Chongning,Zhao, Ying,Zhao, Bin,Han, Ling,Lu, Jincai
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p. 384 - 391
(2019/07/12)
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- Indole alkaloid glycosides from Isatis tinctoria roots
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Isatindigoside A and B (1 ? 2), two new indole alkaloid glycosides along with five known ones (3 ? 7) were obtained from the roots of I. tinctoria. Their structures were determined as isatindigoside A (1), isatindigoside B (2), isatindosulfonicacid A 3-O-β-D-glucopyranoside (3), indole-3-acetonitrile 6-O-β-D-glucopyranoside (4), isatindigobisindoloside A (5), isatindigobisindoloside B (6) isatindigobisindoloside F (7), by physicochemical properties and spectroscopic methods including 1 D, 2 D NMR, IR, HR-ESI-MS data. Nitric oxide (NO) inhibitory activities of all of the isolated compounds (1 ? 7) were also evaluated. Compounds 2 and 7 showed inhibitory effects against LPS-stimulated RAW 264.7 cells with IC50 values of 27.6 μM and 18.8 μM, respectively.
- Zhang, Dongdong,Du, Kang,Zhao, Yitian,Shi, Songshan,Wu, Yingchun,Jia, Qi,Chen, Kaixian,Li, Yiming,Wang, Rui
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p. 244 - 250
(2019/06/27)
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- Steroidal glycosides from the underground parts of Hosta ventricosa and their anti-inflammatory activities in mice
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Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities.
- Chu, Hong-Biao,Li, Nan-Nan,Zhang, Zong-Ping,Hu, Xiao-Yue,Yu, Cai-Yun,Hua, Lei
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p. 1766 - 1774
(2019/07/16)
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- A new isoflavone glycoside from flowers of Pueraria Montana var. lobata (Willd.) Sanjappa & Pradeep
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A new isoflavone glycoside, named 3’-hydroxytectorigenin-7-O-β-D-xylosyl-(1→6)-β-D-glucopyranoside (1) was isolated from the flowers of Pueraria montana var. lobata (Willd.) Sanjappa & Pradeep. The structure of compound 1 was characterised by HR-ESI-MS and NMR spectroscopic methods. In radical scavenging activity test using 2, 2-diphenyl-1-picrylhydrazyl (DPPH), compound 1 showed moderate activity with IC50 value of 42 ± 4.2 μg/mL.
- Ma, Yilong,Shang, Yafang,Zhong, Zhifeng,Zhang, Yingshuo,Yang, Yang,Feng, Jun,Wei, Zhaojun
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p. 1459 - 1464
(2019/08/26)
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- Two new 3-hexenol glycosides from the calyces of Physalis alkekengi var. franchetii
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Two new hexenol glycosides, (Z)-hex-3-en-1-ol O-β-d-xylcopyranosyl-(1-6)-β -d-glucopyranosyl-(1-2)-β-d-glucopyranoside (1) and (E)-hex-3-en-1-ol O-β-d-xylcopyranosyl-(1-6)-β-d-glucopyranosyl-(1-2)-β-d-glucopyranoside (2), were isolated from the 50% ethanol elution of macroporous resin of Physalis alkekengi var. franchetii. Their structures were established by detailed spectroscopic analysis, including extensive 2D-NMR data. This is the first time to report the (Z) and (E) 3-hexenol glycosides from Physalis alkekengi var. franchetii.
- Shu, Zunpeng,Tang, Yun,Yang, Yanni,Ding, Zihe,Zhong, Renxing,Xia, Tianyi,Li, Xinjia,Zheng, Cuiying,Wen, Zhixiong,Li, Wei,Wang, Yi
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p. 1274 - 1280
(2019/08/07)
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- Two novel flavonoids from the leaves of Rhododendron dauricum L. with their inhibition of TNF-α production in LPS-induced RAW 264.7 cells
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Two new flavonoids, (2S)-6,8-dimethyl-5,7,3′,4′-tetrahydroxyflavanone 4′-O-β-D-glucopyranoside (1) and quercetin 3-O-β-D-(6′′-p-methoxybenzoyl)-galactopyranoside (2), together with ten known flavonoids (3–12) were isolated from the leaves of Rhododendron dauricum L. The structures of the flavonoids were characterized from spectroscopic data (1D and 2D NMR and HR-ESI-MS). The isolated flavonoids were evaluated for their inhibitory effects on the production of tumour necrosis factor (TNF)-α in LPS-stimulated RAW 264.7 cells. Compound 11 exhibited inhibitory activity against TNF-α production with an IC50 value of 46.2 ± 1.2 μM.
- Ye, Chao,Jin, Mei,Jin, Chunshi,Wang, Rongshen,Wang, Jiaming,Zhang, Ying,Li, Sainan,Sun, Jinfeng,Zhou, Wei,Li, Gao
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p. 1331 - 1339
(2019/08/15)
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- A new chlorine-containing iridoid glycoside from Plantago maxima
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A phytochemical investigation on the whole plant of Plantago maxima Juss. ex Jacq led to the isolation of a new and rare chlorinated iridoid glycoside named plantomoside (1), along with three known compounds, geniposidic acid (2), 10-deoxygeniposidic acid (3), and viteoid II (4). The structure of 1 was determined through 1 D and 2 D NMR spectroscopic data analysis, HR-ESI-MS, and acid hydrolysis.
- Ma, Liang-Liang,Wang, Lu-Lu,Zhang, Yue-Feng,Jiang, Xiang-Fu,Zhu, Xin-Liu,Pan, Ke,Wan, Chuan-Xing,Zhou, Zhong-Bo
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p. 1491 - 1496
(2019/08/26)
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- Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer
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Three new phenolic glycosides, intermedia A–C (1–3), one new acyclic alcohol glycoside, intermedia D (4), together with 3 known glycosides (5–7), were isolated from the dried roots of Paeonia intermedia C. A. Meyer. Their structures were established by means of extensive spectroscopic analysis (HRESIMS, NMR). Compound 1 have a rare benzo[1,5]dioxepine skeleton. The bioassay results showed that compound 3 exhibited inhibitory activity against proinflammatory cytokines nitric oxide (NO) secretion in LPS-activated RAW264.7 cells with an IC50 value of 85.76 ± 1.36 μM.
- Yu, Liang,Zhu, Ling-Juan,Wang, An-Hua,Qin, Yu,Zhang, Xue,Jia, Jing-Ming,Yao, Xin-Sheng
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p. 1452 - 1458
(2019/08/30)
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- Pregnane glycosides from Gymnema inodorum and their α-glucosidase inhibitory activity
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Two new pregnane glycosides, gyminosides A and B (1 and 2) and three known, tinctoroside B (3), tinctoroside C (4), and gymnepregoside F (5) were isolated from the leaves of Gymnema inodorum (Lour.) Decne. Their structures were elucidated by physical and chemical methods and comparing with those reported in the literature. All these compounds were evaluated for α-glucosidase assay. Compound 5 exhibited the most anti α-glucosidase activity with inhibitory percentage of 63.7 ± 3.9% at the concentration of 200 μM. Compounds 1–4 showed moderate anti α-glucosidase activity with inhibitory percentage ranging from 40.0 to 52.1%.
- Trang, Do Thi,Yen, Duong Thi Hai,Cuong, Nguyen The,Anh, Luu The,Hoai, Nguyen Thi,Tai, Bui Huu,Doan, Vu Van,Yen, Pham Hai,Quang, Tran Hong,Nhiem, Nguyen Xuan,Minh, Chau Van,Kiem, Phan Van
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p. 2157 - 2163
(2019/11/03)
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- Steroidal constituents isolated from the seeds of Withania somnifera
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A new withanolide glycoside (1), two new ergostanol glycosides (2 and 3), and a new furostanol glycoside (4), along with nine known steroidal derivatives (5–12) were isolated from the seeds of Withania somnifera. The structures of the new compounds were determined using spectroscopic analysis and hydrolysis. The cytotoxic activities of the isolated compounds were evaluated against Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, and HL-60 human promyelocytic leukemia cells. Only 12 exhibited cytotoxic activity against these cell lines with IC50 values of 0.38, 0.54, and 1.5 μM, respectively.
- Iguchi, Tomoki,Kuroda, Minpei,Ishihara, Mai,Sakagami, Hiroshi,Mimaki, Yoshihiro
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supporting information
p. 2205 - 2210
(2019/11/03)
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- Two new pregnane steroidal glycosides from Cynanchum taihangense
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As our ongoing chemical investigation, two new pregnane steroidal glycosides, cynataihosides G (1), with a new aglycone, and H (2) were isolated from the 95% ethanol extract of Cynanchum taihangense. Their structures were elucidated on the basis of 1 D and 2 D NMR spectral data, HR-ESI-MS analysis and qualitative chemical methods. The compounds were subjected to detect the cytotoxicity against three human tumor cell lines (HL-60, THP-1 and PC-3). The compounds displayed no significant cytotoxicity. Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2019.1672682.
- Wang, Yu-Bo,Su, Shan-Shan,Tang, Ming-Xu,Zhao, Dan,Chen, Gang,Chen, Shao-Fei,Wang, Hai-Feng,Pei, Yue-Hu
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p. 2308 - 2314
(2019/11/03)
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- Neuroprotective triterpene saponins from the leaves of Panax notoginseng
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Two new triterpene saponins, namely notoginsenoside Ng5 (1) and notoginsenoside Ng6 (2) were isolated from the leaves of Panax notoginseng, along with five known ones. Their structures were determined by chemical methods, NMR and X-ray experiments. The absolute configuration of compound 3 with four sugar units was confirmed by single crystal X-ray analysis. Compounds 2–4 and 6 inhibited PC12 cell damage induced by serum deprivation, and increased cell viability from 58.7 ± 6.7% to 66.7 ± 4.5%, 76.1 ± 6.1%, 64.7 ± 5.2% and 67.2 ± 5.0% at 10 μM, respectively.
- Huang, Ji-Wu,Du, Yi-Qian,Li, Chuang-Jun,Yang, Jing-Zhi,Ma, Jie,Zang, Ying-Da,Chen, Nai-Hong,Zhang, Dong-Ming
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supporting information
p. 2388 - 2394
(2019/11/13)
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- Isolation and structure elucidation of a new flavonol glycoside from Sabia Parviflora
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A new flavonol glycoside named Sabiapside A (1), along with four known compounds, quercetin-3-O-gentiobioside (2), camellianoside (3), isobariclisin-3-O- rutinoside (4), tsubakioside A (5), was isolated from Sabia parviflora. Their structures were elucidated by extensive spectroscopic analysis including MS, UV, IR and NMR data. The antioxidant activities of these glycosides evaluated by ABTS+ and DPPH radical scavenging reaction was higher than that of vitamin C used as the reference antioxidant.
- Sun, Qingwen,Pan, Guoji,Xu, Wenfen,Lu, Xian,Bai, Caihong,Liu, Mengge,Chen, Yinrui
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p. 2408 - 2413
(2019/11/14)
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- Six new anthraquinone glycosides from Lasianthus acuminatissimus Merr.
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Six new anthraquinones named lasianthuoside F (1), G (2), H (3), I (4), J (5), K (6) were isolated from an acetone extract of the root of Lasianthus acuminatissimus. Their structures were elucidated by physical and chemical evidence and spectral analysis.
- Liu, Xingxing,Li, Taoan,Liu, Yong,Liu, Hongdong,Chen, Xiaotian,Ming, Jianxin,Lai, Xuewen,Li, Bin
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p. 2535 - 2543
(2019/11/16)
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- Two new phenylpropanoids and a new dihydrostilbenoid from the flower buds of Magnolia biondii pamp and their acetylcholinesterase inhibitory activities
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Two new phenylpropanoids, named (2'R*,3'R*)-2',3'-dihydroxy-4'-methoxy-caffeoyl butyrate (1), 9-acetoxy syringin (2), and a new dihydrostilbene, named (8'R)-4',5-dihydroxy-4,8'-dimethoxy-2-hydroxyethyl diphenylethane (3), together with five analogues (4–8), were isolated from the flower buds of Magnolia biondii Pamp. Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. The absolute configurations were deduced by comparison of experimental and calculated gauge-independent atomic orbital (GIAO) 1 D NMR data. Moreover, the isolated compounds (1–8) were evaluated in?vitro for their acetylcholinesterase (AChE) inhibitory activities.
- Cao, Yan-Gang,Li, Hong-Wei,Cao, Bing,Wang, Jian-Chao,Zhang, Yan-Li,Zhao, Xuan,Zheng, Xiao-Ke,Feng, Wei-Sheng
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p. 3233 - 3240
(2019/11/25)
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- New lupane-type and ursane-type triterpene saponins from the leaves of Trevesia palmata
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Three new triterpene saponins including two lupane-types and an ursane-type were isolated from the leaves of Trevesia palmata. Their structures were determined as 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-α-L-arabinopyranoside (1), 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl] ester (2), and 2α,3β,23-trihydroxyurs-12-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl] ester (3) by analysis of their HR-ESI-MS, 1D and 2D NMR spectra. The 2α,3β,23-trioxygenated pentacyclic triterpenes were uncommonly found in the nature. At concentration of 100 μM, compounds 1–3 inhibited NO production in LPS activated BV2 cells with inhibitory rates of 17.4 ± 1.8%, 33.1 ± 1.2%, and 11.7 ± 2.2%, respectively. But, they did not significantly inhibit yeast α-glucosidase activity.
- Yen, Pham Hai,Doan, Vu Van,Lien, Giang Thi Kim,Chuong, Nguyen Th? Hong,Thanh, Nguyen Thi Viet,Trang, Do Thi,Dung, Duong Thi,Nhiem, Nguyen Xuan,Tai, Bui Huu,Minh, Chau Van,Kiem, Phan Van
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supporting information
p. 3285 - 3292
(2019/12/11)
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- Chemical constituents of Trillium tschonoskii Maxim.
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A new fatty acid-spirostan steroid glycoside ester, a new cholestane glycoside and a new stilbene trimer, along with three known steroidal saponins, were isolated from the 70% EtOH extract of the roots and rhizomes of Trillium tschonoskii Maxim. The structure of isolated compounds was elucidated by spectroscopic analysis. Compound 1–6 were assessed for their cytotoxicity against cancer cell lines (MCF-7, HCT-116, DU-145, SGC-7901, MCF-7/ADR, K562/ADR), and the result showed that compound 4 was highly toxic to six human tumor cell lines.
- Yan, Ting,Wang, Anhua,Hu, Gaosheng,Jia, Jingming
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p. 3351 - 3359
(2020/01/22)
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- A new and 23 known cardenolide glycosides from Thevetia neriifolia seeds and their cytotoxic activities against human oral carcinoma cell lines
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Phytochemical analysis of Thevetia neriifolia seeds resulted in the isolation of one new (1) and 23 known (2－24) cardenolide glycosides. The structure of 1 was determined based on one- and two-dimensional NMR spectroscopic analysis and acid hydrolytic cleavage reaction. The effect of the cytotoxic activity of 1－24 on three human oral carcinoma cell lines was assessed. The cell lines included Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, HSC-4 human tongue carcinoma cells, and HGF human gingival fibroblast cells. The isolated compounds had a cytotoxic effect on the carcinoma cells with IC50 values ranging from 0.004 μM to 64.9 μM. The structure-activity relationship is also discussed.
- Tatsuno, Satoru,Iguchi, Tomoki,Kuroda, Minpei,Ishihara, Mai,Sakagami, Hiroshi,Mimaki, Yoshihiro
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supporting information
p. 4388 - 4393
(2020/01/31)
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