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Cas Database

50-99-7

50-99-7

Identification

  • Product Name:D(+)-Glucose

  • CAS Number: 50-99-7

  • EINECS:200-075-1

  • Molecular Weight:180.158

  • Molecular Formula: C6H12O6

  • HS Code:17023051

  • Mol File:50-99-7.mol

Synonyms:(+)-Glucose;Glucose;C*Dry GL 01934;CPC hydrate;Cartose;Cerelose;Cerelose2001;Clearsweet 95;Clintose L;Corn sugar;Dextropur;Dextrose;Dextrosol;Glucodin;Glucolin;D-Glucose;Glucosteril;Goldsugar;Grape sugar;Hi-Mesh;Maxim Energy Gel;Meritose;Meritose 200;Roclys C 30725;Roferose ST;Staleydex 111;Staleydex 130;Staleydex 333;Staleydex 95M;Sugar, grape;Tabfine 097(HS);Tackidex 30L75;Vadex;Dextrose Anhydrous Food Grade;Glucose anhydrouse;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, IrritantXi

  • Hazard Codes:Xi,Xn

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. No toxicity (USCG, 1999) Pancreatic beta cells are highly sensitive to oxidative stress, which might play an important role in beta cell death in diabetes. The protective effect of 6,6'-bieckol, a phlorotannin polyphenol compound purified from Ecklonia cava, against high glucose-induced glucotoxicity was investigated in rat insulinoma cells. High glucose (30 mM) treatment induced the death of rat insulinoma cells, but treatment with 10 or 50 ug/mL 6,6'-bieckol significantly inhibited the high glucose-induced glucotoxicity. Furthermore, treatment with 6,6'-bieckol dose-dependently reduced the level of thiobarbituric acid reactive substances, generation of intracellular reactive oxygen species, and the level of nitric oxide, all of which were increased by high glucose concentration. In addition, 6,6'-bieckol protected rat insulinoma cells from apoptosis under high-glucose conditions. These effects were associated with increased expression of the anti-apoptotic protein Bcl-2 and reduced expression of the pro-apoptotic protein Bax. These findings indicate that 6,6'-bieckol could be used as a potential nutraceutical agent offering protection against the glucotoxicity caused by hyperglycemia-induced oxidative stress associated with diabetes.

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Sweep spilled substance into covered containers. Wash away remainder with plenty of water. ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas; Environmental precautions: No special environmental precautions required; Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants. Well closed.Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Keep in a dry place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-(+) Glucose powder, BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, ≥99.5%
  • Packaging:10kg
  • Price:$ 212
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-(+) Glucose ACS reagent
  • Packaging:5kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-(+) Glucose tested according to Ph.Eur.
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dextrose
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-(+) Glucose anhydrous EMPROVE? EXPERT Ph Eur,BP,USP,ACS
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-(+) Glucose anhydrous EMPROVE? EXPERT Ph Eur,BP,USP,ACS
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-Glucose (Dextrose) NIST SRM 917C
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-Glucose (Dextrose) NIST?SRM?917C
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:D-(+) Glucose anhydrous EMPROVE? EXPERT Ph Eur,BP,USP,ACS
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Dextrose meets EP, BP, JP, USP testing specifications, anhydrous
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Relevant articles and documentsAll total 1758 Articles be found

A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity

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

, p. 177 - 180 (2016)

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.

Anthraquinone glycosides from Cassia roxburghii and evaluation of its free radical scavenging activity

El-Toumy, Sayed A.,El Souda, Sahar S.,Mohamed, Tahia K.,Brouard, Inaki,Bermejo, Jame

, p. 47 - 51 (2012)

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-

A new triterpene glycoside from fruit of Phytolacca americana

Getiya,Gabelaya,Mshvildadze,Pichette,Lavoie,Dekanosidze

, p. 764 - 766 (2011)

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.

New phenolic glycosides from Polygonum cuspidatum

Jiang, Jian-Shuang,Li, Fu-Shuang,Feng, Zi-Ming,Yang, Ya-Nan,Zhang, Pei-Cheng

, p. 17 - 23 (2020)

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.

Substrate control through per-O-methylation of cyclodextrin acids

Fenger, Thomas H.,Bols, Mikael

, p. 7769 - 7771 (2010)

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.

Three new glycosides from Hylocereus undatus

Wu, Xin,Wang, Ying,Huang, Xiao-Jun,Fan, Chun-Lin,Wang, Guo-Cai,Zhang, Xiao-Qi,Zhang, Qin-Wen,Ye, Wen-Cai

, p. 728 - 733 (2011)

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.

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

Do, Van Mai,Tran, Cong Luan,Nguyen, Tan Phat

, p. 1250 - 1255 (2020)

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.

NMR-Based Investigation of Hydrogen Bonding in a Dihydroanthracen-1(4 H)one from Rubia philippinensis and Its Soluble Epoxide Hydrolase Inhibitory Potential

Oh, Joonseok,Quan, Khong Trong,Lee, Ji Sun,Park, Inwha,Kim, Chung Sub,Ferreira, Daneel,Thuong, Phuong Thien,Kim, Young Ho,Na, Minkyun

, p. 2429 - 2435 (2018)

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.

A membrane-bound trehalase from Chironomus riparius larvae: Purification and sensitivity to inhibition

Forcella, Matilde,Cardona, Francesca,Goti, Andrea,Parmeggiani, Camilla,Cipolla, Laura,Gregori, Maria,Schirone, Raffaella,Fusi, Paola,Parenti, Paolo

, p. 1186 - 1195 (2010)

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.

New cycloartane glycosides from the rhizomes of Cyperus rotundus and their antidepressant activity

Zhou, Zhong-Liu,Lin, San-Qing,Yin, Wen-Qing

, p. 662 - 668 (2016)

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.

New grayanol diterpenoid and new phenolic glucoside from the flowers of Pieris formosa

Wang, Wei-Guang,Li, Hong-Mei,Li, Hai-Zhou,Wu, Zhao-Yuan,Li, Rong-Tao

, p. 70 - 75 (2010)

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.

Acridone alkaloids from the rhizomes of Luvunga scandens (Roxb.) Buch. Ham.

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

, p. 2176 - 2181 (2019)

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%.

Three new phenol compounds from Iris dichotoma PALL

Huang, Long,Ma, Wenhui,Liu, Yanze,Peng, Yong,Xiao, Peigen

, p. 1033 - 1036 (2012)

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.

Antidiabetic ellagitannins from pomegranate flowers: 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.

, p. 5358 - 5361 (2012)

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.

New dammarane-type triterpenoid glycosides from Gynostemma burmanicum

Nguyen Phuong, Thao,Nguyen Tien, Dat,Pham, Thanh Binh,Pham, Thanh Ky,Than, Thi Kieu My

, p. 217 - 224 (2020)

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

Three new lignan glycosides from the Firmiana simplex

Woo, Kyeong Wan,Park, Jong Eel,Cha, Joon Min,Subedi, Lalita,Kim, Sun Yeou,Lee, Kang Ro

, p. 18 - 22 (2019)

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.

Isolation and Some Properties of Sorbitol Oxidase from Streptomyces sp. H-7775

Hiraga, Kazumi,Kitazawa, Mitsunori,Kaneko, Norihisa,Oda, Kohei

, p. 1699 - 1704 (1997)

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.

Six new ergostane-type steroids from king trumpet mushroom (Pleurotus eryngii) and their inhibitory effects on nitric oxide production

Kikuchi, Takashi,Maekawa, Yukina,Tomio, Arisa,Masumoto, Yuki,Yamamoto, Taishi,In, Yasuko,Yamada, Takeshi,Tanaka, Reiko

, p. 9 - 17 (2016)

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.

A grayanotox-9(11)-ene derivative from Rhododendron brachycarpum and its structural assignment via a protocol combining NMR and DP4 plus application

Tuan, Nguyen Quoc,Oh, Joonseok,Park, Hyun Bong,Ferreira, Daneel,Choe, Sanggil,Lee, Juseon,Na, MinKyun

, p. 45 - 50 (2017)

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.

A new chromene glycoside from tithonia diversifolia

Zhai, Hong-Li,Zhao, Gui-Jun,Yang, Gen-Jin,Sun, He,Yi, Bo,Sun, Lian-Na,Chen, Wan-Sheng,Zheng, Shui-Qing

, p. 198 - 200 (2010)

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.

Cordycepamides A?E and cordyglycoside A, new alkaloidal and glycoside metabolites from the entomopathogenic fungus Cordyceps sp.

Fan, Wenwen,Li, Erwei,Liu, Xingzhong,Ren, Jinwei,Wang, Wenzhao,Zhang, Yongjie

, (2020)

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).

New coumarins and monoterpene galloylglycoside from the stem bark of Sapium baccatum

Li, Ting,Wang, Shanshan,Fan, Peihong,Lou, Hongxiang

, p. 435 - 442 (2019)

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.

Three new sulfated triterpenoids from the roots of Gypsophila pacifica

Luo, Jian-Guang,Nie, Wei,Kong, Ling-Yi

, p. 529 - 533 (2011)

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.

2β-D-GLUCOPYRANOSYLOXY-2-METHYLPROPANOL IN ACACIA SIEBERANA VAR. WOODII

Brimer, Leon,Christensen, S. Broegger,Nartey, Frederick

, p. 2005 - 2008 (1982)

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.

Structural characterization of cholestane rhamnosides from ornithogalum saundersiae bulbs and their cytotoxic activity against cultured tumor cells

Iguchi, Tomoki,Kuroda, Minpei,Naito, Rei,Watanabe, Tomoyuki,Matsuo, Yukiko,Yokosuka, Akihito,Mimaki, Yoshihiro

, (2017)

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.

Four New Diterpene Glucosides from Perovskia atriplicifolia

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

, (2017)

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.

New Glycosides of Eriodictyol from Dracocephalum palmatum

Olennikov,Chirikova,Kim, Eungyoung,Kim, Sang Woo,Zul’fugarov

, (2018)

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

Three new monoterpene glycosides from Sibiraea laevigata (L.) Maxim

Mei, Li-Juan,Shao, Yun,Shi, Yan-Ping,Tao, Yan-Duo,Wang, Qi-Lan,Wang, Yan-Ming,Zhao, Jian-Qiang

, p. 176 - 180 (2017)

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

Medicinal flowers. XXXX.1) Structures of dihydroisocoumarin glycosides and inhibitory effects on aldose reducatase from the flowers of Hydrangea macrophylla var. thunbergii

Liu, Jiang,Nakamura, Seikou,Zhuang, Yan,Yoshikawa, Masayuki,Hussein, Ghazi Mohamed Eisa,Matsuo, Kyohei,Matsuda, Hisashi

, p. 655 - 661 (2013)

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].

Caragiside D, a new isoflavone glucoside from caragana conferta

Perveen, Shagufta,Al-Taweel, Areej Mohammad,Khan, Afsar,Fawzy, Ghada Ahmed,Malik, Abdul

, p. 440 - 442 (2014)

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.

The bioassay-guided isolation of antifungal saponins from Hosta plantaginea leaves

Wang, Meng-Yue,Peng, Ying,Peng, Chong-Sheng,Qu, Jiang-Yuan,Li, Xiao-Bo

, p. 501 - 509 (2018)

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.

A new flavonoid glycoside and four other chemical constituents from viscum coloratum and their antioxidant activity

Fan, Ronghua,Ma, Yuying,Yuan, Hongxia,Zhang, Yongzhi,Wei, Binbin,Zhao, Yunli,Yu, Zhiguo

, p. 1455 - 1462 (2014)

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.

Isolation, identification and antioxidative capacity of water-soluble phenylpropanoid compounds from Rhodiola crenulata

Chen, Danjun,Fan, Junting,Wang, Peng,Zhu, Lanying,Jin, Yang,Peng, Yan,Du, Shuhu

, p. 2126 - 2133 (2012)

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.

Enzymatic and structural characterization of hydrolysis of gibberellin A4 glucosyl ester by a rice β-D-glucosidase

Hua, Yanling,Sansenya, Sompong,Saetang, Chiraporn,Wakuta, Shinji,Cairns, James R. Ketudat

, p. 39 - 48 (2013)

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.

Four new cytotoxic oligosaccharidic derivatives of 12-oleanene from Lysimachia heterogenea Klatt

Huang, Xin-an,Liang, Yong-ju,Cai, Xiao-ling,Feng, Xiao-quan,Zhang, Chuan-hai,Fu, Li-wu,Deng, Wen-di

, p. 6515 - 6518 (2009)

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

Novel monoterpenoid indole alkaloids from Melodinus yunnanensis

Zhang, Bing-Jie,Liu, Cheng,Bao, Mei-Fen,Zhong, Xiu-Hong,Ni, Ling,Wu, Jing,Cai, Xiang-Hai

, p. 5821 - 5826 (2017)

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.

Two new sesquiterpenoid glycosides from the stems of Zanthoxylum armatum DC

Liu, Ya-Lin,Gao, Liang-Liang,Song, Tong-Tong,Guo, Tao,Chang, Jun

, p. 3036 - 3041 (2020)

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.

Micellar catalysis on pentavalent vanadium ion oxidation of D-sorbitol in aqueous acid media: A kinetic study

Saha, Bidyut,Chowdhury, Kiran M.,Mandal, Jayashree

, p. 1321 - 1328 (2008)

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.

Depolymerization of cellulosic feedstocks using magnetically separable functionalized graphene oxide

Verma, Deepak,Tiwari, Rashmi,Sinha, Anil Kumar

, p. 13265 - 13272 (2013)

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.

Xanthone glycosides from swertia bimaculata with α -glucosidase inhibitory activity

Yue, Yao-Dong,Zhang, Yu-Tang,Liu, Zhao-Xia,Min, Qiu-Xia,Wan, Luo-Sheng,Wang, Yong-Long,Xiao, Zuo-Qi,Chen, Jia-Chun

, p. 502 - 508 (2014)

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

New ecdysteroid and ecdysteroid glycosides from the roots of Serratula chinensis

Zhang, Zi-Yue,Yang, Wei-Qun,Fan, Chun-Lin,Zhao, Hui-Nan,Huang, Xiao-Jun,Wang, Ying,Ye, Wen-Cai

, p. 208 - 214 (2017)

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.

The study of factors influencing the depolymerisation of cellulose using a solid catalyst in ionic liquids

Watanabe, Hisanori

, p. 1168 - 1171 (2010)

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.

Complete assignments of 1H and 13C NMR spectroscopic data for three new stigmastane glycosides from Vernonia cumingiana

Suo, Maorong,Yang, Junshan

, p. 179 - 183 (2009)

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

Three new secoiridoid glycosides from the rhizomes and roots of Gentiana scabra and their anti-inflammatory activities

Li, Wei,Zhou, Wei,Kim, Sohyun,Koo, Jung-Eun,Kim, Yuna,Koh, Young-Sang,Shim, Sang Hee,Ma, Jin Yeul,Ho Kim, Young

, p. 1920 - 1927 (2015)

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.

Use of electrospray ionization ion-trap tandem mass spectrometry and principal component analysis to directly distinguish monosaccharides

Xia, Bing,Zhou, Yan,Liu, Xin,Xiao, Juan,Liu, Qing,Gu, Yucheng,Ding, Lisheng

, p. 1259 - 1264 (2012)

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

Three new lignan glycosides with IL-6 inhibitory activity from Akebia quinata

Jin, Hong-Guang,Kim, A. Ryun,Ko, Hae Ju,Lee, Sang Kook,Woo, Eun-Rhan

, p. 288 - 293 (2014)

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.

Flavonoids and terpenoids with PTP-1B inhibitory properties from the infusion of salvia amarissima ortega

González-Andrade, Martín,Mata, Rachel,Pérez-Vásquez, Araceli,Rangel-Grimaldo, Manuel,Rivero-Cruz, Isabel,Salinas-Arellano, Eric,Torres-Colin, Rafael

, (2020)

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.

Purification and characterization of a novel GH1 beta-glucosidase from Jeotgalibacillus malaysiensis

Liew, Kok Jun,Lim, Lily,Woo, Hui Ying,Chan, Kok-Gan,Shamsir, Mohd Shahir,Goh, Kian Mau

, p. 1094 - 1102 (2018)

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.

A new megastigmane diglycoside from litsea glutinosa (Lour.) C. B. Rob.

Wang, Yun-Song,Liao, Zhen,Li, Yan,Huang, Rong,Zhang, Hong-Bing,Yang, Jing-Hua

, p. 2234 - 2238 (2011)

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).

Two new dammarane-type triterpenoid saponins from notoginseng medicinal fungal substance

Xu, Wei,Liu, Xin,Liu, Xiao-Li,Jia, Ai-Ling,Wang, Xin-Wen,Qiu, Zhi-Dong

, p. 1138 - 1142 (2016)

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

Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica

Li, Jiayuan,Liu, Yanfei,Ni, Gang,Wang, Renzhong,Yu, Dequan

, (2021/11/01)

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.

Two new glycosides from Dianella ensifolia (L.) DC

Fan, Miao-Yin,Liu, Bing-Rui,Yang, Fan,Zhang, Pu-Zhao

, p. 18 - 20 (2021/11/11)

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

Iridoid glucosides from the leaves of Vitex negundo var. cannabifolia

Huo, Huixia,Li, Jun,Li, Manman,Liang, Naiyun,Ma, Jiale,Song, Yuelin,Sun, Jing,Tu, Pengfei,Wang, Rongye,Zhao, Yunfang,Zheng, Jiao

, p. 56 - 62 (2021/11/30)

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.

New glycosides from the leaves and rattan stems of Schisandra chinensis

Bao, TeRiGen,Fu, ChunWang,Jia, JingMing,Liu, LuQi,Wang, AnHua,Yang, YongCheng

, p. 21 - 23 (2021/11/11)

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.

Parisvaniosides A–E, five new steroidal saponins from Paris vaniotii

Ji, Yun-Heng,Liu, Hai-Yang,Ni, Wei,Xiao, Long-Gao,Yan, Huan,Yu, Ling-Ling

, (2021/12/16)

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.

Process route upstream and downstream products

Process route

4-nitrophenyl-β-D-glucoside
2492-87-7

4-nitrophenyl-β-D-glucoside

D-glucose
50-99-7

D-glucose

Conditions
Conditions Yield
4-nitrophenyl-β-D-glucoside; With C15H27ClCuN3O6(1+)*ClO4(1-); dihydrogen peroxide; triethylamine; In water; at 60 ℃; for 2h; Inert atmosphere;
In water; Reagent/catalyst; Catalytic behavior; Kinetics; Inert atmosphere;
38.3%
With water; for 0.333333h; Rate constant; acetate buffer pH 5, β-D-glucosidase;
With β-D-glucopyranosidase; In water; at 40 ℃; for 1.5h; Product distribution; 0.1M acetate buffer (pH=4.2), mechanism of action of enzyme;
With sodium acetate buffer; β-D-glucan exohydrolase isoenzyme ExoI; at 37 ℃; Mechanism; rate of hydrolysis relative to various β-linked oligo-, polysaccharides and aryl β-D-glucosides, other reagents: β-D-glucan exohydrolase isoenzyme ExoII, Na citrate-Na3PO4 buffer, pH 5.25, other pH values, other temperature, various reaction time;
With sodium phosphate buffer; vanilla bean β-D-glucosidas; Vanilla planifolia Andrews; at 40 ℃; pH=7; Enzyme kinetics;
With Dalbergia cochinchinensis Pierre dalcochinase N189F mutant; sodium acetate; In water; at 30 ℃; for 0.0833333h; pH=5; Reagent/catalyst; Kinetics; Enzymatic reaction;
With β-glucosidase I from Prunus domestica seeds; citric acid; at 45 ℃; pH=5.5; Temperature; pH-value; Time; Reagent/catalyst; Kinetics; aq. phosphate buffer; Enzymatic reaction;
With C-terminally His6-tagged Oryza sativa L. β-glucosidase OsTAGG2; In aq. acetate buffer; at 37 ℃; for 0.166667h; pH=5; pH-value; Temperature; Reagent/catalyst; Kinetics; Catalytic behavior; Enzymatic reaction;
With Aspergillus niger ASKU28 glycoside hydrolase family 3 β-glucosidase D487A mutant; In aq. buffer; at 40 ℃; for 0.166667h; pH=4.0; Reagent/catalyst; Kinetics; Enzymatic reaction;
With disodium hydrogenphosphate; Aspergillus niger β-glucosidase; water; citric acid; at 50 ℃; for 0.166667h; pH=4.8; Reagent/catalyst; pH-value; Temperature; Kinetics; Enzymatic reaction;
With recombinant Solanum torvum GH3 β-glucosidase with a polyhistidine tag; at 37 ℃; pH=4.5 - 5; Kinetics; Enzymatic reaction;
With rice transglycosidase Os9BGlu31 (wild type); water; In aq. acetate buffer; at 30 ℃; for 0.5h; pH=4.5; Reagent/catalyst; Kinetics; Enzymatic reaction;
4-nitrophenyl-α-D-glucopyranoside
3767-28-0

4-nitrophenyl-α-D-glucopyranoside

D-glucose
50-99-7

D-glucose

Conditions
Conditions Yield
With MES buffer; 1,4-anhydro-4-seleno-D-arabinitol derived inhibitor; recombinant human maltase glucoamylase; at 37 ℃; for 0.583333h; pH=6.5; Further Variations:; Reagents; Enzyme kinetics;
With sodium acetate buffer; at 37 ℃; pH=5.0; Further Variations:; Reagents; Enzyme kinetics;
With McIlvaine buffer; at 60 ℃; pH=6.5; Further Variations:; Catalysts; Enzyme kinetics;
With glucoamylase of Rhizopus oryzae NBRC 4785 strain; water; at 30 ℃; for 0.5h; pH=5.0; aq. acetate buffer;
With Bacillus licheniformis TH4-2 type I α-glucosidase; at 45 ℃; for 0.166667h; pH=6; Concentration; Kinetics; aq. acetate buffer; Enzymatic reaction;
With baker’s yeast α-glucosidase EC 3.2.1.20; water; In aq. phosphate buffer; at 20 ℃; pH=7.0; Reagent/catalyst; Kinetics;
cyanidin 3,5-O-diglucopyranoside
20905-74-2

cyanidin 3,5-O-diglucopyranoside

cyanidin
13306-05-3

cyanidin

D-glucose
50-99-7

D-glucose

Conditions
Conditions Yield
Acidic aq. solution;
cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside]

cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside]

cyanidin
13306-05-3

cyanidin

L-arabinose
5328-37-0

L-arabinose

D-glucose
50-99-7

D-glucose

caffeic acid
331-39-5,501-16-6

caffeic acid

Conditions
Conditions Yield
Acidic conditions;
TREHALOSE
99-20-7

TREHALOSE

UDP-glucose
133-89-1

UDP-glucose

D-glucose
50-99-7

D-glucose

Conditions
Conditions Yield
With Pyrococcus horikoshii trehalose synthase; at 60 ℃; for 24h; pH=6; Time; Kinetics; aq. acetate buffer; Enzymatic reaction;
cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]

cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]

3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6,537-98-4

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

D-xylose
58-86-6

D-xylose

cyanidin
13306-05-3

cyanidin

D-glucose
50-99-7

D-glucose

malonic acid
141-82-2

malonic acid

para-coumaric acid
7400-08-0,50940-26-6

para-coumaric acid

Conditions
Conditions Yield
With hydrogenchloride; water; at 100 ℃; for 2h;
cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-pcoumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]

cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-pcoumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]

3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6,537-98-4

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

D-xylose
58-86-6

D-xylose

cyanidin
13306-05-3

cyanidin

D-glucose
50-99-7

D-glucose

malonic acid
141-82-2

malonic acid

para-coumaric acid
7400-08-0,50940-26-6

para-coumaric acid

Conditions
Conditions Yield
With hydrogenchloride; water; at 100 ℃; for 2h;
cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumar-oyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]

cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumar-oyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]

3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6,537-98-4

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

D-xylose
58-86-6

D-xylose

cyanidin
13306-05-3

cyanidin

D-glucose
50-99-7

D-glucose

malonic acid
141-82-2

malonic acid

para-coumaric acid
7400-08-0,50940-26-6

para-coumaric acid

Conditions
Conditions Yield
With hydrogenchloride; water; at 100 ℃; for 2h;

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