- Expression, purification and characterization of a bifunctional α-L-arabinofuranosidase/β-D-xylosidase from Trichoderma koningii G-39
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A gene of α-L-arabinofuranosidase (Abf) from Trichoderma koningii G-39 was successfully expressed in Pichia pastoris. The recombinant enzyme was purified to > 90% homogeneity by a cation-exchanged chromatography. The purified enzyme exhibits both α-L-arabinofuranosidase and β-D-xylosidase (Xyl) activities with p-nitrophenyl-α-L- arabionfuranoside (pNPAF) and 2,4-dinitrophenyl-β-D-xylopyanoside (2,4-DNPX) as substrate, respectively. The stability and the catalytic feature of the bifunctional enzyme were characterized. The enzyme was stable for at least 2 h at pH values between 2 and 8.3 at room temperature when assayed for Abf and Xyl activities. Enzyme activity decreased dramatically when the pH exceeded 9.5 or dropped below 1.5. The enzyme lost 35% of Abf activity after incubation at 55 °C for 2 h, but retained 95% of Xyl activity, with 2,4-DNXP as substrate, under the same conditions. Further investigation of the active site topology of both enzymatic functions was performed with the inhibition study of enzyme activities. The results revealed that methyl-α-L- arabinofuranoside inhibition is noncompetitive towards 2,4-DNPX as substrate but competitive towards pNPAF. Based on the thermal stability and the inhibition studies, we suggest that the enzymatic reactions of Abf and Xyl are performed at distinct catalytic sites. The recombinant enzyme possesses both the retaining transarabinofuranosyl and transxylopyranosyl activities, indicating both enzymatic reactions proceed through a two-step, double displacement mechanism.
- Wan, Chin-Feng,Chen, Cheng-Ta,Huang, Lina,Li, Yaw-Kuen
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- Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans
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Chemical investigation of the Australian plant Haemodorum simulans (Haemodoraceae) resulted in the isolation of two new phenylphenalenones, haemoxiphidone and haemodordioxolane from the bulbs together with the first report of an oxabenzochrysenone glycoside, haemodoroxychrysenose from the aerial parts of the plant. Also isolated were two previously described phenylphenalenones 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione and haemodorone and two oxabenzochrysenones 5-hydroxyl-2-methoxy-1H-naphtho[2,1, 8-mna]xanthen-1-one and 5-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one. The X-ray structure of the phenylphenalenone 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd] pyran-1,3-dione was secured for the first time. All compounds were deduced by detailed spectroscopic analyses. HPLC-NMR chemical profiling of an enriched fraction containing a mixture of haemodordioxolane and 5,6-dimethoxy-7-phenyl- 1H,3H-naphtho[1,8-cd]pyran-1,3-dione facilitated the partial identification of these secondary metabolites. The structure previously assigned as xiphidone in our initial studies of this plant was re-assigned as the new isomer haemoxiphidone.
- Urban, Sylvia,Timmers, Michael A.,Brklja?a, Robert,White, Jonathan M.
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- Insight into Aluminum Sulfate-Catalyzed Xylan Conversion into Furfural in a Γ-Valerolactone/Water Biphasic Solvent under Microwave Conditions
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A simple and efficient biphasic system with an earth-abundant metal salt catalyst was used to produce furfural from xylan with a high yield of up to 87.8 % under microwave conditions. Strikingly, the metal salt Al2(SO4)3 e
- Yang, Tao,Zhou, Yi-Han,Zhu, Sheng-Zhen,Pan, Hui,Huang, Yao-Bing
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- New onoceranoid xyloside from Lansium parasiticum
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A novel onoceranoid triterpene xyloside named methyl lansioside C (1) together with two known glycosides (2 and 3) were isolated from polar fraction of the fruit peels of Lansium parasiticum. The structure and absolute configuration of the new compound we
- Ramadhan, Rico,Worawalai, Wisuttaya,Phuwapraisirisan, Preecha
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- A solid-acid-based process for the conversion of hemicellulose
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We describe a solid-acid-catalyzed conversion of hemicellulose (a component of lignocellulosic material) into xylose, arabinose and furfural in aqueous media.
- Dhepe, Paresh Laxmikant,Sahu, Ramakanta
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- Hederagenin glycosides from the fruits of Blighia unijugata
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A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester and 3-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester. These results revealed the existence of several conserved structural features that could be used as chemotaxonomic markers for the Blighia genus such as the glycosidic sequence 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl, the occurrence of 3-O-acetylated β-D-glucopyranosyl units and the systematic presence of hederagenin as aglycone.
- Petit, Bastien,Mitaine-Offer, Anne-Claire,Delaude, Clément,Miyamoto, Tomofumi,Tanaka, Chiaki,Lacaille-Dubois, Marie-Aleth
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- New monoterpenoids from fruits of Gardenia jasminoides var. radicans
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One new lactone, cyclopentanepyrone A (1), and two new monoterpenoids, gardeterpenone A (2) and jasminoside V (3), were isolated from the fruits of Gardenia jasminoides var. radicans, along with four known monoterpenoids, 4-7, which were isolated from this plant for the first time. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D- and 2D-NMR, ESI-MS, HR-ESI-MS, and CD experiments.
- Yu, Shao-Fu,Huang, Xiao-Jun,Fu, Shu-Na,Wu, Chun,Ye, Wen-Cai,Zhou, Guang-Xiong
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- Antihyperlipidemic glycosides from the root bark of Lycium chinense
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Three new glycosides (1–3), together with six known ones (4–9), were isolated from the root bark of Lycium chinense. Their structures were elucidated on the basis of MS and NMR spectroscopic data. Five compounds (3, 5, 6, 8, and 9) exhibited potent antihyperlipidemic activities in HepG2 cells as assessed by Oil Red O staining and significant inhibition of intracellular triglyceride (TG) levels, whereas two compounds (5 and 9) significantly reduced total cholesterol (TC) levels.
- Chen, Hui,Li, Yu-Jie,Sun, Yan-Jun,Li, Xiao-Kun,Jian-Hong, Gong,Wu, Ya,Su, Fang-Yi,Du, Kun,Zhang, Yan-Li,Feng, Wei-Sheng
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- Triterpenoid saponins from the roots of Clematis uncinata
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Eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), along with eleven known ones (9-19), were isolated from the roots of Clematis uncinata. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the isolated saponins were tested for their cytotoxic activities on human caski cervical cancer (Caski) cells, and compounds 13, 17 and 19 exhibited inhibitory effect on Caski cells.
- Li, Shuo-Guo,Huang, Xiao-Jun,Li, Man-Mei,Wang, Mei,Feng, Rui-Bing,Zhang, Wei,Li, Yao-Lan,Wang, Ying,Ye, Wen-Cai
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- Caspicaosides E-K, triterpenoid saponins and cytotoxic acylated saponins from fruits of Gleditsia caspica Desf.
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Seven bisdesmosidic triterpenoid saponins named caspicaosides E-K, were isolated from the methanolic fruit extract of Gleditsia caspica Desf. Their structures were determined by 1D and 2D NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised echinocystic acid or oleanolic acid as the aglycone and saccharide moieties at C-3 and C-28. Like most Gleditsia saponins, the oligosaccharide moiety at C-3 was identified as β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl- (1→6)-β-d-glucopyranosyl. The common oligosaccharide moiety linked to C-28 was determined as β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl- (1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl with the presence of additional β-d-galactopyranose unit and/or another α-l-rhamnopyranose moiety. The C-28 saccharide moiety was acylated with a monoterpenic acid unit or a monoterpenic acid linked to a monoterpene- arabinoside unit at the ester-β-d-glucopyranose C-6. Esterification of C-2 and C-3 hydroxyl groups of the terminal α-l-rhamnopyranose unit with a monoterpenic acid and epoxy-monoterpenic acid units, respectively, or with two identical monoterpenic acid units, was also shown. The acylated saponins caspicaosides G-K were assayed for their in vitro cytotoxicities against the three cell lines HCT116, HepG2 and MCF7. The tested saponins showed moderate to strong activities.
- Melek,Kassem,Miyase, Toshio,Fayad, Walid
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- Phenolic metabolites from the stems and leaves of sophora flavescens
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Two new compounds, (-)-(6aR,11aR)-4-methoxy-8,9-(methylenedioxy)pterocarpan 3-O-β-D-glucopyranoside (1) and 5-hydroxy-7-methoxyisoflavone 4′-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (2), were isolated, together with 30 known compounds from the stems and leaves of Sophora flavescens Aition. Their structures were elucidated by extensive spectroscopic analysis, including HRESI-MS data. A preliminary comparison of phenolic metabolite profiles, based on the qualitative HPLC analysis, indicated that the composition of the roots and the aerial parts were significantly different.
- Zhang, Chi,Wang, Yan-Min,Zhao, Feng-Chun,Chen, Liang-Mian,Zhang, Qi-Wei,Gao, Hui-Min,Wang, Zhi-Min
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- Stryphnosides G–P, 10 new triterpene glycosides from the pericarps of Stryphnodendron fissuratum
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Ten new triterpene glycosides, stryphnosides G–P (1–10), were isolated from the pericarps of Stryphnodendron fissuratum (Legminosae). The structures of 1–10 were determined based on spectroscopic analyses, including various two-dimensional NMR spectroscopic techniques, and the results of hydrolytic cleavage. The sugar moiety attached to C-3 of the aglycone of 4, 5, and 7–10 is composed of five or six monosaccharides, of which the terminal α-L-arabinosyl unit has a1C4conformation. Compounds 2 and 5 differ from the other isolates in having an α-L-rhamnosyl unit at the C-21 hydroxy group. The cytotoxic activity of 1–10, stryphnosides A–F (11–16), and their aglycones (1a, 11a, 14a, and 16a) against HL-60?cells was also examined.
- Yokosuka, Akihito,Okabe, Genki,Tatsuno, Satoru,Mimaki, Yoshihiro
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- Triterpenoids in Gypsophila trichotoma Wend.
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A new triterpeniod saponin 3-O-β-arabinopyranosyl-(1 → 3)-[β-galactopyranosyl-(1 → 2)]-β-glucuronopyranosyl gypsogenin (1), together with the known saponin 3-O-β-xylopyranosyl-(1 → 3)-[β-galactopyranosyl-(1 → 2)]-β-glucuronopyranosyl gypsogenin (2), and three known triterpenes gypsogenic acid (3), quillaic acid (4) and gypsogenin (5) were isolated from the roots of Gypsophila trichotoma Wend. (Caryophyllaceae). Their structures were elucidated by chemical and spectral methods. Cytotoxic activity of compounds 1 and 2 were tested against seven human cancer cell lines. Compound 1 showed cytotoxic activity against all of them, while compound 2 only against two cell lines.
- Yotova, Maya,Krasteva, Ilina,Jenett-Siems, Kristina,Zdraveva, Petranka,Nikolov, Stefan
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- New flavonoid glycosides from Xanthium strumarium with their protein tyrosine phosphatase 1B inhibitory activity
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Two new flavonoid glycosides named 6-hydroxy-3-methoxy-apigenin 7-O-α-?-rhamnopyranoside (1) and 3-hydroxyl-apigenin 8-C-β-?-xylopyranoside (2), along with five known compounds (3-7), were isolated from Xanthium strumarium. Their structures were elucidate
- Jiang, Pei-Jing,Lu, Mei-Jiao,Xi, Yi-Yuan,Chen, Jun,Zheng, Ju-Jia,Xu, Xiang-Wei
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- New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight
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As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The s
- Toukea, Daniel Djou,Kamto, Eutrophe Le Doux,Simo, Line Made,Mbing, Joséphine Ngo,Antheaume, Cyril,Haddad, Mohamed,Noté, Olivier Placide,Pegnyemb, Dieudonné Emmanuel
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p. 780 - 788
(2020/08/19)
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- Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.
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The methanol extract from the leaves of Ilex paraguariensis A. St.-Hil. (Aquifoliaceae), popularly known as mate, maté, or yerba maté, inhibits the intracellular triglyceride accumulation in HepG2 cells and suppresses the plasma triglyceride elevation in olive oil-treated mice. Three new triterpene saponins, termed mateosides I (1), II (2), and III (3), were isolated from the extract along with 29 known compounds. The structures of 1–3 were elucidated based on chemical and spectroscopic evidence. Among the isolates, principal saponin constituents, 2 and matesaponins 1 (7) and 2 (9), potently inhibited the triglyceride accumulation in HepG2 cells simultaneously treated with oleic acid and high glucose. In vivo assay of the methanol extract of I. paraguariensis revealed that 7 and 9 showed anti-hyperlipidemic activities in olive oil-treated mice. These results suggested that the saponin constituents of I. paraguariensis could be valuable bioactive marker for the anti-obesogenic activity. Graphical abstract: [Figure not available: see fulltext.]
- Inoue, Naoki,Konno, Takuya,Manse, Yoshiaki,Morikawa, Toshio,Muraoka, Osamu,Nagatomo, Akifumi,Ninomiya, Kiyofumi,Sakamoto, Chinatsu,Shibasaka, Aya,Sone, Mayuko,Xu, Yin,Yoshikawa, Masayuki
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- Exopolysaccharide Produced by Probiotic Bacillus albus DM-15 Isolated From Ayurvedic Fermented Dasamoolarishta: Characterization, Antioxidant, and Anticancer Activities
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An exopolysaccharide (EPS) was purified from the probiotic bacterium Bacillus albus DM-15, isolated from the Indian Ayurvedic traditional medicine Dasamoolarishta. Gas chromatography-mass spectrophotometry and nuclear magnetic resonance (NMR) analyses revealed the heteropolymeric nature of the purified EPS with monosaccharide units of glucose, galactose, xylose, and rhamnose. Size-exclusion chromatography had shown the molecular weight of the purified EPS as around 240 kDa. X-ray powder diffraction analysis confirmed the non-crystalline amorphous nature of the EPS. Furthermore, the purified EPS showed the maximum flocculation activity (72.80%) with kaolin clay and emulsification activity (67.04%) with xylene. In addition, the EPS exhibits significant antioxidant activities on DPPH (58.17 ± 0.054%), ABTS (70.47 ± 0.854%) and nitric oxide (58.92 ± 0.744%) radicals in a concentration-dependent way. Moreover, the EPS showed promising cytotoxic activity (20 ± 0.97 μg mL–1) against the lung carcinoma cells (A549), and subsequent cellular staining revealed apoptotic necrotic characters in damaged A549 cells. The EPS purified from the probiotic strain B. albus DM-15 can be further studied and exploited as a potential carbohydrate polymer in food, cosmetic, pharmaceutical, and biomedical applications.
- Kalimuthu, Palanisamy,Ma, Yongkun,Mathivanan, Krishnamurthy,Rai, Amit Kumar,Saravanan, Kandasamy,Sathiyanarayanan, Ganesan,Sekar, Soundarapandian,Sudharsan, Kumaresan,Vinothkanna, Annadurai
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- A new triterpenoid saponin from Glinus oppositifolius
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From the ethanol extract of Glinus oppositifolius, collected at Phu Yen province, Viet Nam, one new triterpenoid saponin (1) and four known compounds (2–5) were isolated. By means of NMR and HR-ESI-MS analyses, their structure was elucidated as 3-O-(β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl)spergulagenin A or glinusopposide V (1), glinusopposide L (2), spergulin B (3), vitexin (4) and astralagin (5). Two compounds (1–2) showed weak inhibitory activity against α-glucosidase.
- Phan, Thuy Thanh,Do, Lien T. M.,Phung, Trung Van,Nguyen, Thu Thi Hoai,Huynh, Vinh N.,Ngo, Duong Thi Thuy,Nguyen, Kim Phi Phung,Nguyen, Tuyet Thi Anh
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p. 171 - 176
(2020/07/03)
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- Protective effects of four new saponins from Gynostemma pentaphyllum against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells
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Gynostemma pentaphyllum has been used as a medicine-food homologious health product in China for a long time. This research aimed to isolate and identify its active compounds with protective effects against hydrogen peroxide induced SH-SY5Y cell death. Four new dammarane-type saponins were isolated from G. pentaphyllum using various chromatographic methods. They were identified as gypenoside S1 (1), gypenoside S3 (2), gypenoside S2 (3) and gypenoside S4 (4), respectively by HRESIMS and NMR spectra. Their cytotoxic activity was evaluated against three human cancer cell lines, A549 (lung), HepG2 (liver), SH-SY5Y (nerve), by MTT method. They showed low cytotoxicities with the IC50 values of more than 100 μM on three cancer cell lines. However, they appeared protective effects against hydrogen peroxide induced SH-SY5Y cell death in a dose-dependent manner. They recovered cell viability more than 69% at the concentration of 20 μM from 66%, while as vitamin C to 67%. Compound 3 and 4 recovered more than 79% at 100 μM. The present study suggests that G. pentaphyllum has antioxidative potential and the saponins from G. pentaphyllum are considered as the active compounds with safe and neuroprotecitve effect.
- Zhai, Xin-Fang,Zu, Ma-Li,Wang, Yu-Rong,Cui, Wei-Ye,Duan, Yu,Yang, Ce,Piao, Xiang-Lan
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- Isolation and structural characterization of four diastereomeric lignan glycosides from Abies holophylla and their neuroprotective activity
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Diastereomers are a type of a stereoisomer and they are often isolated as a mixture due to their similar physical properties. Through HPLC technique, we isolated four stereoisomeric lignan glycosides, holophyllosides A–D (1–4), from the trunk of Abies holophylla Maxim. which were first isolated as a mixture 25 years ago. The planar structures of 1–4 were characterized by conventional 1D and 2D NMR data analysis and their stereochemistry was determined via empirical comparison of their 13C NMR chemical shifts and 3JH-H coupling constants with the reported values, enzymatic hydrolysis followed by LC-MS analysis, and ECD experiment. Of the four stereoisomers isolated, only compounds 1, 3, and 4 showed moderate neuroprotective activity by inducing NGF secretion in C6 cells whereas 2 did not. This study highlights again the stereochemical importance of molecules in their biological and pharmaceutical application.
- Cha, Joon Min,Lee, Tae Hyun,Subedi, Lalita,Ha, Young Jun,Kim, Hye Ryeong,Kim, Sun Yeou,Choi, Sang Un,Kim, Chung Sub
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- Arenarosides A-G, Polyhydroxylated Oleanane-Type Saponins from Polycarpaea arenaria and their Cytotoxic and Antiangiogenic Activities
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Seven new polyhydroxylated oleanane-type triterpene saponins, arenarosides A-G (1-7), together with four known compounds, were isolated from an ethanol extract of the aerial parts of the Vietnamese plant Polycarpaea arenaria. The chemical structures of the newly isolated oleanane saponins were elucidated on the basis of spectroscopic and spectrometric analysis, especially 2D NMR and HRMS. Biological evaluation revealed that 3, 4, 6, and 7 showed moderate activities against four human cancer cell lines (A549, HTC116, PC3, and RT112) with IC50 values of 6.0-9.9 μM, and 3, 4, 5, and 7 also displayed promising antiangiogenesis effects with IC50 values 5 μM in the test system used. Among the isolates, arenaroside D (4) exhibited the most potent inhibitory effects, not only in cancer cell proliferation but also in angiogenic activities. Preliminary SAR studies revealed that the presence of an acetyl group at C-22 in oleanane-type triterpene saponins increases these bioactivities.
- Nguyen, Nham-Linh,Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Lu, Mei-Kuang,Cheng, Jing-Jy,Chen, Mei-Chuan,Kuo, Yao-Haur
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p. 259 - 267
(2021/02/06)
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- Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities
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Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, r
- Han, Qinghua,Qian, Yi,Wang, Xuda,Zhang, Qingying,Cui, Jingrong,Tu, Pengfei,Liang, Hong
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- Polythosides A and B, two new triterpenoid saponins from the roots of Acacia polyacantha Willd. (Mimosaceae)
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Two new oleanane-type triterpene saponins, named polythosides A and B (1 and 2), together with a known compound, silphioside E (3), were isolated from the roots of Acacia polyacantha. Their structures were elucidated by analysis of 1D and 2D-NMR experiments, and mass spectrometry (HR-ESITOF-MS) as oleanolic acid 3-O-β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranoside (1), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl] oleanolic acid-28-O-β-D-glucopyranosyl ester (2) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (3). The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. The results show that none of the compounds (assayed at 100 μM) showed cytotoxicity against H4IIE cells.
- Tchoukoua, Abdou,Tomfeun Nganou, Sandrine Carole,Dabole, Bernard,Yoshida, Jun,Ito, Yoshiaki,Ngadjui, Bonaventure Tchaleu,Shiono, Yoshihito
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p. 190 - 195
(2021/05/03)
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- Stilbene dimer xylosides and flavanols from the roots of Lysidice rhodostegia and their antioxidant activities
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Eight new stilbene dimer xylosides (1–8) and one new flavanol (9), along with seven known ones (10–16) were isolated from the roots of Lysidice rhodostegia. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HR-ESI-MS, 1D and 2D NMR), ECD calculations and acid hydrolysis. Compounds 1–16 were evaluated for their antioxidant activities using DPPH radical-scavenging assay. Especially, compounds 9 and 10 exhibited stronger antioxidant effects than the positive control (vitamin E), with IC50 values of 9.57 ± 1.30 and 13.60 ± 1.47 μM, respectively.
- Li, Yao-Lan,Li, Ying-Ying,Tang, Qing,Wang, Guo-Cai,Wang, Wen-Zhi,Wu, Zhong-Nan,Zhan, Zhao-Chun,Zhang, Sheng-Yuan,Zhang, Yu-Bo
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- Mimonoside D: a new triterpenoid saponin from Mimosa diplotricha Sauvalle (Fabaceae)
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A new triterpenoid saponin (Mimonoside D: 3-O-α-L-arabinopyranosyl-3β-hydroxyolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1→2)-β-D- glucopyranoside ester (1)) was isolated from the aerial parts of Mimosa diplotricha Sauvalle together with nine known compounds: 7,4′-dihydroxyflavone (2), kaempferol (3), lupeol (4), betulinic acid (5), β-sitosterol (6), β-sitosterol-3-O-β-D-glucopyranoside (7), lutein (8), 5,2′-dihydroxy-7,4′,5′-trimethoxyflavone (9) and vitexin (10). Their structures were elucidated on the basis of spectroscopic (1D and 2D nuclear magnetic resonance) and high-resolution mass spectrometric data as well as by comparison of their spectral data with those of related compounds. Compounds 2, 7 and 8 had already been isolated from M. diplotricha, while compounds 3, 4, 5 and 6 have been isolated from other Mimosa species. Compound 2 moderately inhibited Proteus mirabilis (MIC = 32μg/mL), weakly inhibited Pseudomonas aeruginosa (MIC = 64μg/mL) and very weakly inhibited Staphylococcus aureus (MIC = 128μg/mL) and Enterococus faecalis (MIC = 128μg/mL).
- Dzoyem, Jean Paul,Kemkuignou, Blondelle Matio,Kenmogne, Claudie Fokou,Opatz, Till,Ponou, Beaudelaire Kemvoufo,Tchuenguem, Roland T.,Kühlborn, Jonas,Tapondjou, Léon Azefack,Teponno, Rémy Bertrand
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- Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source
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The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The reaction conditions are also suitable for the formation of nitriles from various types of hydrophobic aldehyde substrates. Furthermore, cyanide can be eliminated from cyanohydrins, analogous to the Wohl degradation, by utilizing a readily-removed weakly basic resin as a promoter.
- Cheewawisuttichai, Thamrongsak,Hurst, Robert D.,Brichacek, Matthew
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- Acylated pelargonidin and cyanidin 3-sambubiosides from the flowers of Aeschynanthus species and cultivars
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Thirteen anthocyanins were isolated from the flowers of two Aeschynanthus species, A. fulgens and A. pulcher, and six cultivars, ‘Mahligai’, ‘Mona Lisa’, ‘SoeKa’, ‘Redona’, ‘Freshya’ and ‘Bravera’, and identified as pelargonidin and cyanidin 3-O-sambubiosides and their malonates, succinates, p-coumarates and caffeates, and pelargonidin 3-O-glucoside by acid hydrolysis, HR-MS and NMR. Of their anthocyanins, pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-malonylglucoside)] (2), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (3), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-p-coumaroylglucoside)] (4), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-Z-p-coumaroylglucoside)] (5), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-caffeoylglucoside)] (6) and cyanidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (9) were reported in nature for the first time.
- Iwashina, Tsukasa,Mizuno, Takayuki,Rahayu, Sri,Sugahara, Kohtaro,Tsutsumi, Chie,Widyatmoko, Didik
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- Bioactive oleanane-type saponins from Hylomecon Japonica
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Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.
- Li, Fei,Ma, Chun-Liu,Qu, Ming-Hui,Wang, Guang-Shu,Wang, Yi-Xiao,Wu, Si-Tong,Yu, Bai-Hong
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- Isolation and identification of two new sargentodoxosides from Sargentodoxa cuneata and their agonistic effects against FXR
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Sargentodoxa cuneata (Oliv.) Rehd. et Wils is a traditional Chinese medicine to treat acute appendicitis, rheumarthritis, abdominal pain, and painful menstruation for a long history. The investigation of S. cuneata led to the isolation and identification of twenty-three secondary metabolites, including two new compounds, sargentodoxosides A (1) and B (2), and twenty-one known ones (3-23). Their structural characterization was conducted by HRESIMS, 1 D and 2 D NMR spectra. All the isolated compounds were assayed for their agonistic activities against the farnesoid X receptor (FXR). Nine of the isolated compounds displayed significant agonistic effects against FXR at 0.1 μM, suggesting that they could be served as potential agents for the development of FXR agonists.
- Zhang, Wen,Sun, Cheng-Peng,Peng, Yu-Lin,Zhao, Wen-Yu,Wang, Zheng-Yue,Ning, Jing,Lv, Xia,Yu, Zhen-Long,Zhou, Shuang,Peng, Wei,Fang, Bang-Jiang,Ma, Xiao-Chi
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- Cycloartane triterpene glycosides from rhizomes of Cimicifuga foetida L. with lipid-lowering activity on 3T3-L1 adipocytes
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Six previously undescribed cycloartane triterpenes glycosides, cimimanols A–F (1–6), together with thirteen known analogues (7–19) were isolated from the rhizomes of Cimicifuga foetida. Among them, cimimanol A (1) was the first example of cycloartane triterpene glycoside featuring a unique cyclic carbonate, and cimimanol B (2) was a rare trinortriterpene glycoside. The chemical structures and absolute configurations of new compounds were determined on the basis of comprehensive spectroscopic analysis, chemical method, and X-ray crystal diffraction, as well as quantum chemistry calculations. Finally, all these compounds were evaluated for their lipid-lowering effect on 3T3-L1 adipocytes. Compounds 1–3, 6–10, 12–16, 18–19 could significantly reduce the fat accumulation in 3T3-L1 adipocytes, especially compounds 8, 9, 14, and 15 exhibited strong lipid-lowering effect at the concentration of 10 μM, with inhibition rates ranging from 8.35% to 12.07%.
- Li, Dashan,Lu, Jing,Lu, Shuangyang,Qiu, Minghua,Shi, Qiangqiang,Zhou, Lin
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- Five new phenylpropanoid glycosides from the flowers of Paulownia fortunei and their antioxidant activities
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In this study, we focused on the antioxidant activities in NRK52e cells, a rat renal proximal tubular cell line, of five new phenylpropanoid glycosides, paulowninosides B–F (Compounds 1–5), which were isolated from the n-BuOH soluble part of the 50 % acetone-H2O extract of the flowers of Paulownia fortunei. The structures of the compounds were determined by extensive spectroscopic analyses (UV and IR spectroscopy, HR-ESI-MS, 1D-, 2D-NMR). The levels of antioxidant activities of the compounds were determined by real-time cell analysis (RTCA) of NRK52e cells that underwent H2O2-induced oxidative injury. Compounds 1, 3 and 5 exhibited excellent antioxidant activities compared with control group.
- Zhang, Jingke,Li, Meng,Zhang, Beibei,Lv, Jinjin,Hao, Zhiyou,Zheng, Xiaoke,Feng, Weisheng
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p. 176 - 180
(2020/11/20)
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- Degradation of unprotected aldohexonic acids to aldopentoses promoted by light and oxygen
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Herein reported is a photoredox-catalyzed oxidative degradation reaction of unprotected aldohexonic acids, which are shortened by one-carbon to the corresponding aldopentoses. Oxygen including aerial oxygen is used as a terminal oxidant. The mild reaction conditions permit even disaccharides to successfully undergo the degradation reaction with the glycosidic bond remaining intact. Quinic acid is also converted to a useful chiral synthetic intermediate.
- Ito, Misato,Masuda, Yusuke,Murakami, Masahiro
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supporting information
p. 1309 - 1311
(2020/11/18)
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- Identification of a key enzyme for the hydrolysis of β-(1→3)-xylosyl linkage in red alga dulse xylooligosaccharide from Bifidobacterium adolescentis
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Red alga dulse possesses a unique xylan, which is composed of a linear β-(1→3)/β-(1→4)xylosyl linkage. We previously prepared characteristic xylooligosaccharide (DX3, (β-(1→3)-xylosylxylobiose)) from dulse. In this study, we evaluated the prebiotic effect of DX3 on enteric bacterium. Although DX3 was utilized by Bacteroides sp. and Bifidobacterium adolescentis, Bacteroides Ksp. grew slowly as compared with β-(1→4)-xylotriose (X3) but B. adolescentis grew similar to X3. Therefore, we aimed to find the key DX3 hydrolysis enzymes in B. adolescentis. From bioinformatics analysis, two enzymes from the glycoside hydrolase family 43 (BAD0423: subfamily 12 and BAD0428: subfamily 11) were selected and expressed in Escherichia coli. BAD0423 hydrolyzed β-(1→3)-xylosyl linkage in DX3 with the specific activity of 2988 mU/mg producing xylose (X1) and xylobiose (X2), and showed low activity on X2 and X3. BAD0428 showed high activity on X2 and X3 producing X1, and the activity of BAD0428 on DX3 was 1298 mU/mg producing X1. Cooperative hydrolysis of DX3 was found in the combination of BAD0423 and BAD0428 producing X1 as the main product. From enzymatic character, hydrolysis of X3 was completed by one enzyme BAD0428, whereas hydrolysis of DX3 needed more than two enzymes.
- Kobayashi, Manami,Kumagai, Yuya,Yamamoto, Yohei,Yasui, Hajime,Kishimura, Hideki
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- Identification and occurrence of phenylethanoid and iridoid glycosides in six Polish broomrapes (Orobanche spp. and Phelipanche spp., Orobanchaceae)
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There are about 200 holoparasitic broomrapes (Orobanchaceae) known worldwide, however, only several species have been so far investigated phytochemically. Among Orobanche s.l. are both rare and endangered species, as well as onerous crop pests. This study aims to give a phytochemical description, both qualitative and quantitative, of six broomrape species (Orobanche and Phelipanche taxa) growing in Poland, including species that have not been tested in detail (O. caryophyllacea, O. lutea, O. picridis, and P. arenaria). Sixteen metabolites, including 14 phenylethanoid glycosides (PhGs) and 2 iridoid glycosides (IrGs), were isolated and identified using NMR spectroscopy and hydrolysis, revealing the presence of two previously undescribed PhGs in P. ramosa, named ramoside A and 2′-acetylramoside A. In addition, in the example of O. caryophyllacea, we have reported as the first occurrence of IrGs in broomrapes. Concentrations of phenylethanoids, the main constituents of broomrapes, in the studied plant material (flowering shoots with haustoria) were determined using the UHPLC-PDA method. It was found that P. ramosa has been the richest source of PhGs. In addition, the differences between broomrapes have been visualized using principal component and cluster analysis. The results of the antiradical DPPH test of 13 PhGs confirmed previous findings on the relation of the antioxidant potential with the structure of phenolic moieties – phenolic acid and phenylethanoid unit.
- Jedrejek, Dariusz,Pawelec, Sylwia,Piwowarczyk, Renata,Pecio, ?ukasz,Stochmal, Anna
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- Triterpenic saponins from Medicago marina L
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The saponin composition of leaves and roots from Medicago marina L., sea medic, was investigated by a combination of chromatographic, spectroscopic and spectrometric (GC, LC, ESI-MS/MS, NMR) methods. Several compounds were detected and quantified by HPLC using the external standard method. Saponins from this plant species consist of a mixture of high molecular weight bidesmosidic derivatives of medicagenic and zanhic acid, containing up to six sugars in the molecules. Six of the detected saponins were previously isolated and reported as constituents of other Medicago spp.; one saponin was previously described in other plant species; four saponins are undescribed compounds in Medicago and never reported before in other plant species. These are: 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[β-D-apiofuranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester and 3-O-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester. The specific saponins synthesized by M. marina may have a role in its tolerance to environment, representing a reservoir of osmolytic sugars.
- Accogli, Rita,Argentieri, Maria Pia,Avato, Pinarosa,Biazzi, Elisa,Doria, Filippo,Mella, Mariella,Ronga, Domenico,Tava, Aldo
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- New 12,23-epoxydammarane type saponins obtained from panax notoginseng leaves and their anti-inflammatory activity
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Two new 12,23-epoxydammarane-type saponins, notoginsenosides NL-I (1) and NL-J (2), were isolated and identified from Panax notoginseng leaves through the combination of various chromatographies and extensive spectroscopic methods, as well as chemical reactions. Among them, notoginsenoside NL-J (2) had a new skeleton. Furthermore, the lipopolysaccharide (LPS)-induced RAW 264.7 macrophage model was used to identify the in vitro anti-inflammatory activity and mechanisms of compounds 1 and 2. Both of them exerted strong inhibition on nitric oxide (NO) productions in a concentration-dependent manner at 1, 10, and 25 μM. Moreover, these two compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), interleukin 6 (IL-6), cyclooxygenase-2 (COX-2), nuclear factor kappa-B (NF-κB/p65), and nitric-oxide synthase (iNOS) in LPS-activated RAW 264.7 cells.
- Han, Lifeng,Ruan, Jingya,Sun, Fan,Wang, Tao,Wu, Lijie,Yu, Haiyang,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- Two new acylated triterpenoidal saponins from Gleditsia caspica Desf. and the effect of its saponin content on LPS-induced cognitive impairment in mice
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Two bisdismosidic triterpenoidal saponins, caspicaoside A1 (1) and caspicaoside B1 (2), were isolated from Gleditsia caspica fruit methanolic extract. The structures of 1 and 2 were determined using chemical and spectral techniques. Gleditsia caspica fruit methanolic extract (MEGC) and its saponin containing fraction (SFGC) at the two dose levels 45 and 90 mg/kg b.wt. were studied comparatively for their effect on LPS-induced cognitive impairment in mice using Ginkgo biloba (100 mg/kg b.wt.) as a standard drug. Neurobehavioral tests (Morris Water Maze and Novel Object Recognition tests) were conducted to prove that MEGC and SFGC at the two levels were able to significantly improve memory and learning in mice dose dependently. Also, the two test drugs were able to significantly decrease the levels of proinflammatory cytokines (Tumor necrosis factor alpha and Interleukin 1-beta) in addition to reducing the extra-cellular deposition of amyloid beta 42 in a dose dependent manner.
- Kassem, I. A. A.,Melek, F. R.,Nabil, Marian,Ragab, Mai F.
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- New dammarane-type triterpenoid saponins from Panax notoginseng leaves and their nitric oxide inhibitory activities
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Inflammation is a very common and important pathological process that can cause many diseases. The discovery of anti-inflammatory drugs and the treatment of inflammation are particularly essential. Dammarane-type triterpenoid saponins (PNS) were demonstrated to show anti-inflammatory effects in the leaves of Panax notoginseng. Chromatographies and spectral analysis methods were combined to isolate and identify PNS. Moreover, the nitric oxide (NO) inhibitory activities of all compounds were examined in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. As a result, eleven new dammarane-type triterpenoid saponins, notoginsenosides NL-A1-NL-A4 (1-4), NL-B1-NL-B3 (5-7), NL-C1-NL-C3 (8-10), and NL-D (11) were isolated, and their structures were identified by using various spectrometric techniques and chemical reactions. Among them, compounds 4 and 11 were characterized by the malonyl substitution at 3-position. The 3-malonyl substituted dammarane-type terpennoids were first obtained from natural products. In addition, compounds 1, 2, 5, 6, and 8-10 were found to play an important role in suppressing NO levels at 50 μM, without cytotoxicity. All inhibitory activities were found to be dose-dependent.
- Hao, Mimi,Ruan, Jingya,Sun, Fan,Wang, Tao,Wu, Lijie,Xiang, Guilin,Yan, Jiejing,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- Chemical Constituents from the Roots of Polygala arillata and Their Anti-Inflammatory Activities
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A new compound, named arillatanoside E, which was elucidated as 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1 - 3)-β-D-xylopyranosyl-(1 - 4)-α-L-rhamnopyranosyl-(1 - 2)-(4-O-acetyl)-β-D-fucopyranosyl ester, along with 11 known compounds was isolated from the ethanolic extract of the roots of Polygala arillata. The 11 known compounds were identified as oleanolic acid (2), 3′-E-3,4,5-trimethoxy cinnamoyl-6-benzoyl sucrose (3), trans-ferulic acid (4), trans-feruloyl-glucoside (5), feruloyl-glucoside (6), 2,4,6-trimethoxy-1-O-β-D-glycoside (7), 3-methoxy-4-hydroxybenzoic acid (8), monopentadecanoin (9), sinapic acid (10), p-hydroxybenzaldehyde (11), and palmitic acid (12). Among them, seven isolated compounds 1, 2, 4, 5, 7, 8, and 10 exhibited little cytotoxic activity on macrophage RAW 264.7 cells. Then, the inhibitory effects of 7 isolates on nitric oxide (NO) production in lipopolysaccharide-activated macrophages were evaluated. As a result, 3 compounds have significant anti-inflammatory activity, and they were arillatanoside E (1), oleanolic acid (2), and 2,4,6-trimethoxy-1-O-β-D-glycoside (7).
- Xiang, Wei,Zhang, Guo-Dong,Li, Fang-Yi,Wang, Teng-Long,Suo, Tong-Chuan,Wang, Chun-Hua,Li, Zheng,Zhu, Yan
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- Xylan deterioration approach: Purification and catalytic behavior optimization of a novel β-1,4-D-xylanohydrolase from Geobacillus stearothermophilus KIBGE-IB29
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The β-1,4-D-xylanohydrolase is an industry valuable catalytic protein and used to synthesize xylooligosaccharides and xylose. In the current study, β-1,4-D-xylanohydrolase from Geobacillus stearothermophilus KIBGE-IB29 was partially purified up to 9.5-fold with a recovery yield of 52%. It exhibited optimal catalytic activity at pH-7.0 and 50 °C within 5 min. Almost 50% activity retained at pH-4.0 to 9.0 however, 70% activity observed within the range of 40 °C to 70 °C. The β-1,4-D-xylanohydrolase showed a significant hydrolytic pattern with 48.7 kDa molecular mass. It was found that the enzymatic activity improved up to 160% with 1.0 mM ethanol. Moreover, the activity of enzyme drastically increased up to 2.3 and 1.5 fold when incubated with Tween 80 and Triton X-100 (1.0 mM), respectively. The β-1,4-D-xylanohydrolase also retained 72% activity at ?80 °C after 180 days. Such a remarkable biochemical properties of β-1,4-D-xylanohydrolase make it possible to forecast its potential use in textile and food industries.
- Bibi, Zainab,Ul Qader, Shah Ali,Aman, Afsheen,Ur Rehman, Haneef,Nawaz, Muhammad Asif,Karim, Asad,Us Salam, Irum,Waqas, Muhammad,Kamran, Aysha
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- New dammarane-type saponins from gynostemma pentaphyllum
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Six new dammarane-type saponins, gypenosides CP1-6 (1 6), along with 19 known compounds 7 25, were isolated and characterized from the aerial parts of Gynostemma pentaphyllum. Among these compounds, eight dammarane-type saponins, 2, 5, 6, 7, 11, 12, 13, and 15, exhibited the greatest antiproliferative effects against two human tumor cell lines (A549 and HepG2).
- Chen, Po-Yen,Chang, Chih-Chao,Huang, Hui-Chi,Zhang, Li-Jie,Liaw, Chia-Ching,Lin, Yu-Chi,Nguyen, Nham-Linh,Vo, Thanh-Hoa,Cheng, Yung-Yi,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung,Kuo, Yao-Haur
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- Structures of triterpenoids from the leaves of Lansium domesticum
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From the methanolic extract of the leaves of Lansium domesticum, three new onoceranoid-type triterpenoids, lansium acids X–XII and a new cycloartane-type triterpene, lansium acid XIII, were isolated. The chemical structures of the isolated new compounds were elucidated on the basis of chemical/physicochemical evidence. For new onoceranoid-type triterpenoids, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. The isolated onoceranoid-type triterpenoids showed antimutagenic effects in the Ames assay against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1).
- Matsumoto, Takahiro,Kitagawa, Takahiro,Ohta, Tomoe,Yoshida, Tatsusada,Imahori, Daisuke,Teo, Stephen,Ahmad, Haji Sapuan bin,Watanabe, Tetsushi
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p. 727 - 734
(2019/05/29)
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- Triterpenoids and their glycosides from Glinus oppositifolius with antifungal activities against Microsporum gypseum and Trichophyton rubrum
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Four new triterpenoids, 3β,12β,16β,21β,22-pentahydroxyhopane (1), 12β,16β,21β,22-tetrahydroxyhopan-3-one (2), 3-oxo-olean-12-ene-28,30-dioic acid (3), and 3β-hydroxyoleana-11,13(18)-diene-28,30-dioic acid 30-methyl ester (4); 21 new triterpenoid saponins, glinusopposides A–U (5–25); and 12 known compounds (26–37) were isolated from the whole plants of Glinus oppositifolius. The structures of the new compounds were elucidated based on the analysis of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry (MS) data. All compounds from the plants were measured for antifungal activities against Microsporum gypseum and Trichophyton rubrum. Glinusopposide B (6), glinusopposide Q (21), glinusopposide T (24), and glinusopposide U (25) showed strong inhibitory activities against M. gypseum (MIC50 7.1, 6.7, 6.8, and 11.1 μM, respectively) and T. rubrum (MIC50 14.3, 13.4, 11.9, and 13.0 μM, respectively). For those active compounds with an oleanane skeleton, glycosylation (21–26) or oxidation (3) of 3-OH was helpful in increasing the activity; replacement of the 30-methyl group (29) by a carboxymethyl group (26) enhanced the activity; the presence of 11,13(18) double bonds (20) decreased the activity.
- Zhang, Dongdong,Fu, Yao,Yang, Jun,Li, Xiao-Nian,San, Myint Myint,Oo, Thaung Naing,Wang, Yuehu,Yang, Xuefei
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- Cycloartane and oleanane glycosides from the tubers of Eranthis cilicica
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Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1-11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.
- Watanabe, Kazuki,Mimaki, Yoshihiro,Fukaya, Haruhiko,Matsuo, Yukiko
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- Preparation process for L-lyxose
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The invention belongs to the technical field of L-lyxose preparation, and relates in particular to a preparation process for L-lyxose. The preparation process comprises the following steps: synthesisofzing 1-methyl-D-ribose, synthesis of 2,3-propylidene-methyl-D-ribose, synthesis of 2,3-propylidene-methylsulfonyl-mthyl-D-ribose, and synthesis of 2,3-propylidene-methyl-L-lyxose and L-lyxose. Thepreparation process for the L-lyxose takes D-ribose as the raw material, and is used for synthesizing L-lyxose by methyl conversion, propylidene conversion, protective group (methylsulfonyl) conversion, and conversion de-protection, so that L-lyxose is prepared through D to L conversion and methyl and propylidene desorption. The whole preparation process is high in catalysisconversion efficiency,is relatively simple in process, adopts cheap and easily available raw materials, is simple and convenient to operate, and is safe; and the obtained product is high in purity.
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Paragraph 0024; 0030; 0031; 0037; 0038; 0044
(2019/02/25)
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- Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.
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A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C46H74O17, [M]+ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.
- Asati, Nidhi,Yadava
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p. 499 - 507
(2017/09/30)
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- Melanogenesis-Inhibitory and Cytotoxic Activities of Triterpene Glycoside Constituents from the Bark of Albizia procera
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Five oleanane-type triterpene glycosides including three new ones, proceraosides E-G (1-3), were isolated from a MeOH-soluble extract of Albizia procera bark. The structures of 1-3 were determined by use of NMR spectra, HRESIMS, and chemical methods. Compounds 1-5 exhibited inhibitory activities against the proliferation of the A549, SKBR3, AZ521, and HL60 human cancer cell lines (IC50 0.28-1.8 μM). Additionally, the apoptosis-inducing activity of compound 2 was evaluated by Hoechst 33342 staining and flow cytometry, while the effects of 2 on the activation of caspases-9, -8, and -3 in HL60 cells were revealed by Western blot analysis.
- Zhang, Jie,Akihisa, Toshihiro,Kurita, Masahiro,Kikuchi, Takashi,Zhu, Wan-Fang,Ye, Feng,Dong, Zhen-Huan,Liu, Wen-Yuan,Feng, Feng,Xu, Jian
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supporting information
p. 2612 - 2620
(2019/01/04)
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- Characterization of Two New Endo-β-1,4-xylanases from Eupenicillium parvum 4–14 and Their Applications for Production of Feruloylated Oligosaccharides
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Two new endo-1,4-beta-xylanases encoding genes EpXyn1 and EpXyn3 were isolated from mesophilic fungus Eupenicillium parvum 4–14. Based on analysis of catalytic domain and phylogenetic trees, the xylanases EpXYN1 (404 aa) and EpXYN3 (220 aa) belong to glycoside hydrolase (GH) family 10 and 11, respectively. Both EpXYN1 and EpXYN3 were successfully expressed in Pichia pastoris and the recombinant enzymes were characterized using beechwood xylan, birchwood xylan, or oat spelt xylan as substrates, respectively. The optimum temperatures and pH values were 75?°C and 5.5 for EpXYN1, and 55?°C and 5.0 for EpXYN3. EpXYN1 exhibited a high stability at high temperature (65?°C) or at pH values from 8 to 10. EpXYN3 kept over 80% enzymatic activity after treatment at pH values from 3 to 10. The specific activities of EpXYN1 and EpXYN3 were 384.42 and 214.20?U/mg?using beechwood xylan as substrate, respectively. EpXYN1 showed lower Km values and higher specific activities toward different xylans compared to EpXYN3. Thin-layer chromatography analysis indicated that the hydrolysis profiles of xylans or xylo-oligosacharides were different by EpXYN1and EpXYN3. EpXYN3 had a higher efficiency than EpXYN1 in production of feruloylated oligosaccharides (FOs) from de-starched wheat bran. The maximum levels of FOs released by EpXYN1 and EpXYN3 were 11.1 and 14.4?μmol/g, respectively. In conclusion, the two xylanases are potential candidates for various industrial applications.
- Long, Liangkun,Xu, Meijuan,Shi, Yuexin,Lin, Qunying,Wang, Jing,Ding, Shaojun
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p. 816 - 833
(2018/05/15)
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- Naphthalene glycosides in the Thai medicinal plant Diospyros mollis
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This study evaluated methanol extracts from the leaves and branches of the Thai medicinal plant Diospyros mollis (Ebenaceae). Seven triterpenes and 22 aromatic compounds, including five new compounds, were isolated, and their structures were determined. The new compounds had the following structures: diospyrol glycoside (makluoside A, 1), 8,8′-di-O-6-β-d-apiofuranosyl-β-d-glucopyranosyl-6,6′-dimethyl-2,3′-binaphthalene-1-ol-1′,4′- dione (makluoside B, 2), and 3-methyl-1,8- naphthalenediol glycosides (makluosides C-E, 3–5). Makluoside B is the first example of a naphthoquinone glycoside that has both a 3-methyl-1,8-naphthalenediol unit and a 5-hydroxy-7-methyl-1,4-naphthoquinone unit. The hyaluronidase inhibitory activity of the isolates was evaluated, revealing that one of the triterpene derivatives possessed moderate inhibitory activity.
- Suwama, Takaharu,Watanabe, Keisuke,Monthakantirat, Orawan,Luecha, Prathan,Noguchi, Hiroshi,Watanabe, Kenji,Umehara, Kaoru
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p. 220 - 229
(2017/10/17)
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- A new benzofuran derivative glycoside and a new coumarin glycoside from roots of Heracleum dissectum Ledeb
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Heracleum dissectum Ledeb. is an ethnic herb used by Oroqen people in Northeast China. The roots of this plant are usually used for treatment of several diseases. However, chemical constituents and pharmacological study were rarely reported. In this present study, phytochemical investigation of H. dissectum methanolic extract (HdME) led to the isolation of a new benzofuran derivative glycoside, 6-methoxycarbonylethyl-benzofuran-5-O-β-d-xylopyranosyl (1 → 2)-β-d-glucopyranoside (1) and a new coumarin glycoside, 6″-β-d-glucopyranosyl-apterin (2). Their structures were elucidated on the basis of physicochemical properties and the detailed interpretation of various spectroscopic data. Adipogenesis accumulating activity was assayed in 3T3-L1 cells. Compound 2 could potently accelerate the accumulation of triglycerides (TG) in 3T3-L1 adipocytes in which TG concentrations were 15.6 ± 2.3, 26.8 ± 1.8, and 35.6 ± 2.6% higher than those of the control group at the concentration of 3, 10, and 30 μM, respectively. In contrast, compound 1 exhibited comparatively weak activity on TG accumulation in adipocytes. This result denoted that the new compound 2 might possess antidiabetic activity in vivo.
- Mi, Jie,Peng, Yajie,Zhang, Haimin,Wang, Xinrui,Huo, Yayu,Wang, Zhigang,liu, Ying,Gao, Yang,Zhang, Hailong
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p. 470 - 475
(2017/10/07)
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- Rhamnellosides A and B, ω-phenylpentaene fatty acid amide diglycosides from the fruits of rhamnella franguloides
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Two new ω-phenylpentaene fatty acid amide diglycosides, rhamnellosides A (1) and B (2), were isolated from the fruits of Rhamnella franguloides (Rhamnaceae). These compounds were prioritized using LC-MS/MS molecular networking dereplication based on our p
- Kang, Kyo Bin,Gao, Ming,Kim, Geum Jin,Choi, Hyukjae,Sung, Sang Hyun
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- Structures and Antimutagenic Effects of Onoceranoid-Type Triterpenoids from the Leaves of Lansium domesticum
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A methanol extract of the dried leaves of Lansium domesticum showed antimutagenic effects against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) and 2-amino-1-methyl-6-phenylimidazo[4,5-bI]pyridine (PhIP) using the Ames assay. Nine new onoceranoid-type triterpenoids, lansium acids I-IX (1-9), and nine known compounds (10-16) were isolated from the extract. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. The absolute stereostructures of the new compounds were determined via their electronic circular dichroism spectra. Several isolated onoceranoid-type triterpeneoids showed antimutagenic effects in an in vitro Ames assay. Moreover, oral intake of a major constituent, lansionic acid (10), showed antimutagenic effects against PhIP in an in vivo micronucleus test.
- Matsumoto, Takahiro,Kitagawa, Takahiro,Teo, Stephen,Anai, Yuuka,Ikeda, Risa,Imahori, Daisuke,Ahmad, Haji Sapuan Bin,Watanabe, Tetsushi
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p. 2187 - 2194
(2018/10/25)
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- Triterpenoid saponins from anemone rivularis Var. Flore-minore and their anti-proliferative activity on HSC-T6 cells
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Five previously undescribed triterpenoid saponins (1–5), along with eight known ones (6–13), were isolated from the whole plants of Anemone rivularis var. flore-minore. Their structures were clarified by extensive spectroscopic data and chemical evidence.
- Wang, Xiao-Yang,Gao, Hui,Xie, Xiao-Jie,Jurhiin, Jirimubatu,Zhang, Mu-Zi-He,Zhou, Yan-Ping,Liu, Rui,Ning, Meng,Han, Jin,Tang, Hai-Feng
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- Dammarane-type saponins from the leaves of Panax notoginseng and their neuroprotective effects on damaged SH-SY5Y cells
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Seven dammarane-type saponins previously undescribed (notoginsenosides Fh1-Fh7) were isolated from the aqueous extract leaves of Panax notoginseng (Burk.) F.H.Chen (Araliaceae), together with eleven known saponins. Their structures of were elucidated by s
- Liu, Xin-Yi,Wang, Shan,Li, Chuang-Jun,Ma, Jie,Chen, Fang-You,Peng, Ying,Wang, Xiao-Liang,Zhang, Dong-Ming
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- A new flavonol glycoside and other flavonoids from the aerial parts of Taverniera aegyptiaca
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Isolation of flavonoids from the aerial parts of Taverniera aegyptiaca Bioss. (Fabaceae) led to identification of one new flavonol glycoside, isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (1), along with eleven compounds, which previously have not been isolated from this plant quercetin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (2), isorhamnetin-3-O-α-l-arabinopyranoside (3), quercetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (7), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (8), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside] (9), kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (10), isorhamnetin (11), 4,4′-dihydroxy-2′-methoxychalcone (12), formononetin (13) and calycosin (15)] and some compounds already known from this plant [quercetin-3-O-robinobioside (5), isorhamnetin-3-O-robinobioside (6), afrormosin (14) and odoratin (16)].
- Hassan, Ahmed R.,Amer, Khadiga F.,El-Toumy, Sayed A.,Nielsen, John,Christensen, S?ren Br?gger
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supporting information
p. 1 - 5
(2018/04/20)
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- Porous Tin-Organic Frameworks as Selective Epimerization Catalysts in Aqueous Solutions
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Epimerization of sugars is a carbon-efficient route not only to produce rare carbohydrates but also to extend the product scope for chemical production in future biorefineries. Industrially available catalysts for epimerization are limited mainly to soluble Mo(VI) species as well as substrate-specific epimerases. Here we report highly active and selective tin-organic frameworks (Sn-OF) as solid catalysts for the epimerization of aldoses at the C-2 position, such as the conversion of glucose to mannose. The reaction proceeds via a carbon skeleton rearrangement, that is, through breaking of a C-2/C-3 carbon bond and formation of a C-1/C-3 bond. Partially hydrolyzed Ph3Sn-OH sites were found to be the catalytically active centers. Our results suggest that the high catalytic activity of Sn-OFs for the epimerization is determined by (1) Lewis acidity of tin; (2) free Sn-OH groups; and (3) the high hydrophobicity of organic linkers applied in the aqueous solutions.
- Delidovich, Irina,Hoffmann, Andreas,Willms, Andrea,Rose, Marcus
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p. 3792 - 3798
(2017/06/19)
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- Cytotoxic steroidal saponins from Trillium kamtschaticum
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Eight new steroidal saponins, trillikamtosides K–R (1–8), along with three known analogues, were isolated from the whole plants of Trillium kamtschaticum. Their structures were unambiguously established by interpretation of spectroscopic data (MS and NMR) and chemical methods. Compound 1 had a rare aglycone featuring a skeleton of 16-oxaandrost-5-en-3-ol-17-one, which was reported for the first time. The isolated saponins were tested for cytotoxicities against HCT116 cells, and trillikamtoside R (8) was found to show the most cytotoxic effect with an IC50 value of 4.92?μM.
- Qin, Xu-Jie,Si, Yong-Ai,Chen, Yu,Liu, Hui,Ni, Wei,Yan, Huan,Shu, Tong,Ji, Yun-Heng,Liu, Hai-Yang
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supporting information
p. 2267 - 2273
(2017/05/10)
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- New triterpenoid saponins from the herb hylomecon japonica
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Background: Hylomecon japonica, a plant of the Papaveraceae family which is well-known for the alkaloids they produce, is a perennial plant widely distributed in the northeast, central and east regions of China. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, have been isolated from H. japonica, the investigation of saponins in H. japonica has not been reported until now. Methods: Various separation techniques, including polyporous resin column chromatography, silica gel column chromatography and hemi-preparative HPLC were applied to the isolation of triterpenoid saponins, and chemical methods such as acid hydrolysis and spectroscopic methods including HRESIMS and NMR were applied to their structure elucidation, and the XTT reduction method was used to assay cytotoxicity. Results: Two new triterpenoid saponins, named hylomeconoside A (1) and B (2) which were identified as 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl- (1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-quinovopyranoside (1) and 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl- (1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (2), and two known triterpenoid saponins identified as dubioside C (3) and lucyoside P (4) on the basis of spectroscopic and chemical evidence, were isolated from H. japonica. Compound 1 exhibited moderate cytotoxicity on MGC-803 and HL-60 cells, with IC50 values of 43.8 and 32.4 μg.mL-1, respectively. Conclusions: Compounds 1 and 2 are new saponins, and 1 is considered to be one of the antitumor principles in this plant. This is the first time that triterpenoid saponins have been isolated from plants of the Papaveraceae family.
- Qu, Yan-Fei,Gao, Jing-Yu,Wang, Jing,Geng, Yan-Mei,Zhou, Yu,Sun, Cheng-Xin,Li, Fei,Feng, Lei,Yu, Meng-Juan,Wang, Guang-Shu
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- New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)
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Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1–4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 μM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.
- Tchoukoua, Abdou,Tabopda, Turibio Kuiate,Usukhbayar, Narandulam,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Koseki, Takuya,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu
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p. 2261 - 2267
(2017/12/26)
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- Chemical constituents from the roots of Ampelopsis delavayana and their antibacterial activities
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Two new aromatic glycosides, 2-methylphenyl O-β-d-xylopyranosyl-(1→6)-O-β-d-glucopyranoside (1) and 2-methylphenyl O-α-arabinofuranosyl-(1→6)-O-β-glucopyranoside (2), together with eight known compounds were isolated from the roots of Ampelopsis delavayan
- Mei, Shuang-Xi,Li, Xu-Hong,Yang, Li-Guo,Li, Xiao-Hui,Xie, Jia-Ying,Yao, Qi,Su, Mei,Cui, Tao,Wang, Jing-Kun,Zhu, Zhao-Yun
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p. 190 - 195
(2016/11/29)
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