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At least 1,261 records · Page 70Linked to original sources
PubMed2004

Determination of six major flavonoid glycosides in Saussurea mongolica by capillary electrophoresis.

A new capillary electrophoresis (CE) method was established for simultaneous assay of six flavonoid O-glycosides, asebotin (AS), kaempferol 3- O-beta- D-glucopyranoside (KG), kaempferol 3- O-alpha- L-rhamnopyranoside (KR), 7-methoxykaempferol 3- O-alpha- L-rhamnopyranoside (KMR), quercetin 3- O-beta- D-glucopyranoside (QG) and quercetin 3- O-alpha- L-rhamnopyranoside (QR) obtained from Chinese herbal plant extract of Saussurea mongolica. The optimum buffer system was 30 mmol/L borate buffer (Na2B4O7/HCl, pH 9.00) with 40 % (v/v) methanol. Voltage was 15 kV and detection at 270 nm. The application of this method for the separation and determination of the six flavonoid O-glycosides in S. mongolica is reported. The relative standard deviations of migration times and peak areas were < 2.61 and 4.41%, respectively. The contents of six natural products ranged from 0.043 to 0.60 mg/g and recoveries ranged from 92.4 to 104.4%. The effects of pH value, buffer concentration, surfactant, beta -cyclodextrin and organic modifier on the separation were investigated.

Electrophoresis, Capillary↗
PubMed2005

Anti-acetylcholinesterase and anti-amnesic activities of a pregnane glycoside, cynatroside B, from Cynanchum atratum.

We previously reported that seven pregnane glycosides including cynatroside B isolated from the roots of Cynanchum atratum significantly inhibited acetylcholinesterase (AChE) activity. In the present study, we have characterized the mode of AChE inhibition of cynatroside B, the most potent of these isolated pregnane glycoside inhibitors. We have also examined the anti-amnesic activity of cynatroside B. Cynatroside B inhibited AChE activity in a dose-dependent manner and its IC50 value was 3.6 microM. The mode of AChE inhibition by cynatroside B was reversible and non-competitive in nature. Moreover, cynatroside B (1.0 mg/kg body weight i.p.) significantly ameliorated memory impairments induced in mice by scopolamine (1.0 mg/kg body weight s.c.) as measured in the passive avoidance and the Morris water maze tests. We suggest, therefore, that cynatroside B has both anti-AChE and anti-amnesic activities that may ultimately hold significant therapeutic value in alleviating certain memory impairments observed in Alzheimer's disease.

Acetylcholinesterase↗
PubMed2005

Norsesquiterpenoid and sesquiterpenoid glycosides from Evodia austrosinensis.

Two new norsesquiterpenoid glycosides named austrosides A and B, together with four known glycosides, corchoionoside B, citroside A, icariside B1 and dihydrophaseic acid 4'- O-beta- D-glucopyranoside were isolated from Evodia austrosinensis. Their structures were elucidated by 1D and 2D NMR data. Austroside A showed antibacterial activity against the Staphylococcus aureus antibiotic resistant strain.

Anti-Bacterial Agents↗
PubMed2005

Two new non-glycosidic iridoids from the leaves of Campsis grandiflora.

Two new non-glycosidic iridoids, which were named cachinol (1) and 1-O-methyl cachinol (2), were isolated from the methanol extract of the leaves of Campsis grandiflora together with a known iridoid cachineside I (3). The structures of compounds 1 and 2 were determined on the basis of spectroscopic methods including two dimensional NMR and high resolution mass spectrometry. All of the isolated compounds showed mild inhibitory activities on rat platelet aggregation. Compounds 1 and 3 (IC50 : 246 and 219 microM, respectively) showed about 2-fold higher inhibitory effects than acetylsalicylic acid (ASA, IC50: 412 microM) on collagen-induced aggregation. Compounds 1 and 2 (IC50: 43.2 and 38.4 microM, respectively) were about 2-fold more inhibitory than ASA (IC50: 75.2 microM), and about 4-fold more effective than their glycoside 3 (IC50: 189 microM) on AA-induced aggregation.

Animals↗
PubMed2005

In vitro neuroprotective activities of phenylethanoid glycosides from Callicarpa dichotoma.

Ten phenylethanoid glycosides, forsythoside B, acteoside, 2'-acetylacteoside, poliumoside, brandioside, echinacoside, isoacteoside, cistanoside H and E-tubuloside E as well as a new compound, Z-tubuloside E, were isolated from the n-BuOH fraction of Callicarpa dichotoma Raeuschel (Verbenaceae) by bioactivity-guided fractionation using glutamate-injured primary cultures of rat cortical cells as a screening system. These phenylethanoid glycosides significantly attenuated glutamate-induced neurotoxicity at concentrations ranging from 0.1 to 10 microM.

Animals↗
PubMed2005

Five new oleanolic acid glycosides from Achyranthes bidentata with inhibitory activity on osteoclast formation.

Bioassay-directed fractionation of a butanol-soluble fraction of methanol extract of the root of Achyranthes bidentata resulted in the isolation of 5 new oleanolic acid glycosides 1-5, namely, 18-(beta-D-glucopyranosyloxy)-28-oxoolean-12-en-3beta-yl 3-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosiduronic acid methyl ester (1), achyranthoside C dimethyl ester (2), achyranthoside C butyl dimethyl ester (3), achyranthoside E dimethyl ester (4), and achyranthoside E butyl methyl ester (5), together with 10 known compounds. Their structures were established on the basis of spectroscopic interpretation and chemical methods. All the oleanolic acid glycosides inhibited the formation of osteoclast-like multinucleated cells (OCLs) induced by 1alpha,25(OH)2D3 in a co-culture assay system.

Achyranthes↗
PubMed2006

The inhibitory effect of triterpenoid glycosides originating from Sanguisorba officinalis on tissue factor activity and the production of TNF-alpha.

We examined the inhibitory effects of novel triterpene glycoside compounds [ziyu-glycoside II (ZY-II) and its methyl ester (ZYM-201)], which originated from the roots of sanguisorba officinalis L. (Rosaceae), on tissue factor (TF) activity and tumor necrosis factor (TNF)-alpha production. In in vitro TF activity tests, ZY-II but not ZYM-201 strongly blocked lung TF activity with an IC50 value of 0.46 microM. By contrast, only ZYM-201 dose-dependently inhibited in vivo TF activity with an ED50 value of 1.7 mg/kg, when orally administered. Furthermore, ZYM-201 diminished both in vitro and in vivo TNF-alpha production with IC50 or ED50 values of 69.4 microM and 87.4 mg/kg, respectively. Therefore, these results suggest either that ZYM-201 may be developed as a potent inhibitor of both TF- and TNF-alpha-mediated diseases such as atherosclerosis and septic shock, or it may be a lead compound to be derivatized for further improvement of its curative efficacy.

Administration, Oral↗
PubMed1994

New benzyl alcohol glycosides from Pyrus bourgaeana.

Two new aromatic glycosides, benzyl beta-D-glucopyranosyl-(1-->2)-[beta-D-apiofuranosyl-(1-->6)]-beta- D- glucopyranoside and p-[beta-D-apiofuranosyl-(1-->6)]-beta-D- glucopyranosyloxy-benzylic alcohol, have been isolated from the aerial parts of Pyrus bourgaeana (Rosaceae). The structures were elucidated by spectral analyses (including 2D-NMR spectral measurements) and chemical methods. Arbutin and four other aromatic glycosides have also been isolated and identified.

Carbohydrate Sequence↗
PubMed1989

New antihepatotoxic naphtho-pyrone glycosides from the seeds of Cassia tora.

Two new naphtho-pyrone glycosides, 9-[(beta-D-glucopyranosyl-(1----6)-O-beta-D-glucopyranosyl)oxy]-10- hydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1 -one (5) and 6-[(alpha-apiofuranosyl-(1----6)-O-beta-D-glucopyranosyl)oxy]- rubrofusarin (6), together with cassiaside (3) and rubrofusarin-6-beta-gentiobioside (4) were isolated from the seeds of Cassia tora L. Their structures were elucidated on the basis of chemical and spectral data. The naphtho-gamma-pyrone glycosides (3, 4, and 6) were found to have significant hepato-protective effects against galactosamine damage, which were higher than that of silybin from Silybum marianum.

Cassia↗
PubMed1989

New cucurbitacin glycosides from Picrorhiza kurrooa.

From the roots of Picrorhiza kurrooa Royle and Benth., seven cucurbitacin glycosides have been isolated and structurally elucidated mainly by NMR and mass spectroscopy. Four of them (4, 5, 6, 7) are new and two, the 2-O-glycoside of cucurbitacin B (25-acetoxy-2-beta-glucosyloxy-16,20-dihydroxy-9-methyl-19-norl anosta-5, 23-diene-3,11,22-trione) and the 2-O-glucoside of 23,24 didydrocucurbitacin B (25-acetoxy-2-beta-glucosyloxy-16,20-dihydroxy-9-methyl-19-norl anost-5-ene-3, 11-22-trione) were so far not reported as constituents of this plant. The four new cucurbitacins could be identified as 2-beta-glucosyloxy-3,16,20,25-tetrahydroxy-9-methyl-19-norlanos ta-5, 23-diene-22-one, 2-beta-glucosyloxy-3,16,20,25-tetrahydroxy-9-methyl-19-norlanos t-5-ene-22-one, the 2-O-glucoside of cucurbitacin Q (25-acetoxy-2-beta-glucosyloxy-3,16,20-trihydroxy-9-methyl-19-n orlanosta-5, 23-diene-11,22-dione), and the 2-O-glucoside of deacetoxycucurbitacin B (2-beta-glucosyloxy-16,20-dihydroxy-9-methyl-19-norlanosta-5 , 24-diene-3,11,22-trione).

Animals↗
PubMed1983

[Prescription habits in the long-term treatment with digitalis glycosides].

The feasibility of discontinuing digitalis-glycoside treatment was tested in 200 patients with various cardiovascular diseases who, on admission to hospital, were on maintenance digitalis. Among those with the main diagnosis of hypertension digitalis administration was discontinued without ill effect in 73%; among those with peripheral arterial obstructive disease in 64%; and among those with coronary heart disease in 33%. Discontinuing digitalis was less often justified in patients with valvar defects, cardiomyopathies, myocardial infarction or cerebrovascular insufficiency. Indications for digitalis-glycoside treatment should be more rigorously applied.

Adult↗
PubMed2002

Detailed kinetic analysis and identification of the nucleophile in alpha-L-arabinofuranosidase from Geobacillus stearothermophilus T-6, a family 51 glycoside hydrolase.

alpha-l-Arabinofuranosidases cleave the l-arabinofuranoside side chains of different hemicelluloses and are key enzymes in the complete degradation of the plant cell wall. The alpha-l-arabinofuranosidase from Geobacillus stearothermophilus T-6, a family 51 glycoside hydrolase, was subjected to a detailed mechanistic study. Aryl-alpha-l-arabinofuranosides with various leaving groups were synthesized and used to verify the catalytic mechanism and catalytic residues of the enzyme. The steady-state constants and the resulting Brønsted plots for the E175A mutant are consistent with the role of Glu-175 as the acid-base catalytic residue. The proposed nucleophile residue, Glu-294, was replaced to Ala by a double-base pairs substitution. The resulting E294A mutant, with 4-nitrophenyl alpha-l-arabinofuranoside as the substrate, exhibited eight orders of magnitude lower activity and a 10-fold higher K(m) value compared with the wild type enzyme. Sodium azide accelerated by more than 40-fold the rate of the hydrolysis of 2',4',6'-trichlorophenyl alpha-l-arabinofuranoside by the E294A mutant. The glycosyl-azide product formed during this reaction was isolated and characterized as beta-l-arabinofuranosyl-azide by (1)H NMR, (13)C NMR, mass spectrometry, and Fourier transform infrared analysis. The anomeric configuration of this product supports the assignment of Glu-294 as the catalytic nucleophile residue of the alpha-l-arabinofuranosidase T-6 and allows for the first time the unequivocal identification of this residue in glycoside hydrolases family 51.

Alanine↗
PubMed2004

Mechanism-based fluorescent labeling of beta-galactosidases. An efficient method in proteomics for glycoside hydrolases.

(4-N-5-Dimethylaminonaphthalene-1-sulfonyl-2-difluoromethylphenyl)-beta-d-galactopyranoside was synthesized and successfully tested on beta-galactosidases from Xanthomonas manihotis (Wong-Madden, S. T., and Landry, D. Glycobiology (1995) 5, 19-28 and Taron, C. H., Benner, J. S., Hornstra, L. J., and Guthrie, E. P. (1995) Glycobiology 5, 603-610), Escherichia coli (Jacobson, R. H., Zhang, X. J., DuBose, R. F., and Matthews, B. W. (1994) Nature 369, 761-766), and Bacillus circulans (Fujimoto, H., Miyasato, M., Ito, Y., Sasaki, T., and Ajisaka, K. (1988) Glycoconj. J. 15, 155-160) for the rapid identification of the catalytic site. Reaction of the irreversible inhibitor with enzymes proceeded to afford a fluorescence-labeled protein suitable for further high throughput characterization by using antidansyl antibody and matrix-assisted laser desorption ionization time-of-flight/time-of-flight (MALDI-TOF/TOF). Specific probing by a fluorescent aglycon greatly facilitated identification of the labeled peptide fragments from beta-galactosidases. It was demonstrated by using X. manihotis beta-galactosidase that the Arg-58 residue, which is located within a sequence of 56IPRAYWKD63, was labeled by nucleophilic attack of the guanidinyl group. This sequence including Arg-58 (Leu-46 to Tyr-194) was similar to that (Met-1 to Tyr-151) of Thermus thermophilus A4, which is the first known structure of glycoside hydrolases family 42 (Hidaka, M., Fushinobu, S., Ohtsu, N., Motoshima, H., Matsuzawa, H., Shoun, H., and Wakagi, T. (2002) J. Mol. Biol. 322, 79-91). A catalytic glutamic acid (Glu-537) of E. coli beta-galactosidase was proved to be labeled by the same procedure, suggesting that the modification site with this irreversible substrate might depend both on the nucleophilicity of the amino acids and their spatial arrangement in the individual catalytic cavity. Similarly, a Glu-259 in 257TLEE260 was selectively labeled using B. circulans beta-galactosidase, indicating that Glu-259 is one of the nucleophiles in the active site. The present method can be readily extended to other glycosidases and should greatly aid the high throughput proteomics of many glycoside hydrolases showing both retaining- and inverting-type mechanisms.

Amino Acid Sequence↗
PubMed2002

A new biologically active flavonol glycoside from the seeds of Abrus precatorius Linn.

A new flavonol glycoside m.f. C29H34O16, m.p. 260-262 degrees C, [M]+ 638 (EIMS) was separated from the chloroform soluble fraction of the concentrated 80% methanolic extract of the seeds of Abrus precatorius (Linn). It was characterised as a new biologically active flavonol glycoside 7,3',5'-trimethoxy-4'-hydroxy flavone-3-O-beta-D-galactosyl-(l --> 4)-alpha-L-xyloside (1) by several colour reactions, spectral analysis and chemical degradations.

Abrus↗
PubMed2003

A new biologically active flavone glycoside from the seeds of Cassia fistula (Linn.).

A new bioactive flavone glycoside 1 [mp 252-254 degrees C, C28H32O16, [M]+ 624 (EIMS)] was isolated from the acetone soluble fraction of the defatted seeds of Cassia fistula (Linn.). It was characterized as a new bioactive flavone glycoside 5,3',4'-tri-hydroxy-6-methoxy-7-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-beta-D-galactopyranoside by several colour reactions, spectral analysis and chemical degradations. Compound 1 showed anti-microbial activity.

Anti-Bacterial Agents↗
PubMed2003

New furostanol glycosides from the rhizomes of Dioscorea futschauensis R. Kunth.

Two new furostanol glycosides, 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-23(S)-methoxyl-25(R)-furosta-5,20(22)-dien-3-O-alpha-L-rhamnopyranosyl(1 --> 2)-[beta-D-glucopyranosyl(1 --> 3)]-beta-D-glucopyranoside (dioscoreside E, 1) and 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-25(R)-furosta-5,20(22)-dien-3-O-alpha-Lrhamnopyranosyl(1 --> 2)-[beta-D-glucopyranosyl (1 --> 3)]-beta-D-glucopyranoside (prtotogracillin, 2), together with 11 known furostanol glycosides were isolated from the rhizomes of Dioscorea futshauensis R. Kunth. Their structures were elucidated on the basis of spectroscopic analysis (NMR and FABMS). Their anti-fungal activity against the plant pathogenic fungus Pyricularia oryzae and cytotoxic activity on K562 cancer cell line were evaluated in vitro.

Antifungal Agents↗
PubMed2005

A new biologically active flavonol glycoside from Psoralea corylifolia (Linn.).

A new biologically active flavonol glycoside (1) mp 264-265 degrees C, C32H38O20, [M]+ 742 (EIMS) has been isolated from the methanol-soluble fraction of the defatted seeds of Psoralea corylifolia (Linn.). It was characterised as the new flavonol glycoside 3,5,3',4'-tetrahydroxy-7-methoxyflavone-3'-O-alpha-L-xylopyranosyl(1-->3)-O-alpha-L-arabinopyranosyl(1-->4)-O-beta-D-galactopyranoside by several colour reactions, spectral analysis and chemical degradations. Compound 1 showed anti-microbial activity against various bacteria and fungi.

Bacteria↗
PubMed2005

A new bioactive flavone glycoside from the seeds of Melilotus indica All.

Melilotus indica All. [Chopra, R.N., Nayar, S.L. and Chopra, I.C. (1956) Glossary Indian Med. Plants, 164 C.S.I.R. Publication New-Delhi; Kirtikar, K.R. and Basu, B.D. (1935) Indian Medicinal Plants, 2nd Ed., Vol. I, pp. 703-704 Lalit Mohan Basuan Co. Allahabad. The Wealth of India (1962) A Dictionary of Raw Materials and Industrial Products, Vol. VI, pp. 329-331 (C.S.I.R. Publication: New-Delhi)] belongs to family Leguminosae, which is commonly known as 'Banmethi' in Hindi. It is found in North India, extending into S. Persia, S. Europe and the Tropical zone of India. The seeds are used as an anthelmintic, an antipyretic, for curing heart diseases, bronchitis, leprosy, bowel complaints and infantile diarrhea. The plant has also been used as a discutient, emollient, and as a fomentation. It is also useful in a plaster for swelling. It is considered astringent and narcotic. Earlier workers have reported the presence of C-glycosides [Sayed, E.L., Ishak, M.S. and Mabry, T.J. (1997) Asian J. Chem., 9, 551], methylene-dioxypterocarpan (MIS6) [Saxena, V.K. and Nigam, S. (1997) Fitoterapia, 68, 343-345], pterocarpane (MIS2) [Saxena, V.K. and Nigam, S. (1996) J. Institution Chem. 68, 122-125] and prenylated pterocarpan [Saxena, V.K. and Nigam, S. (1997) Fitoterapia, 68, 403-407] from this plant. Here, we report the isolation of the new flavone glycoside 5,7,4'-trihydroxy-6,3'-dimethoxyflavone-7-O-alpha-L-arabinopyranosyl(1-->6)-O-beta-D-galactopyranoside (1) from the seeds of this plant.

Flavones↗