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At least 721 records · Page 40Linked to original sources
PubMed2003

Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.

The organic soluble extract from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory) showed in vitro activity against M. tuberculosis. Bioassay-guided fractionation of this extract resulted in the identification of two new resin glycosides (6, 7). Base-catalyzed hydrolysis of these glycosides gave operculinic acid (1) as the glycosidic acid component as well as trans-cinnamic acid, propanoic acid, and lauric acid. The complete structure elucidation was accomplished through derivatization, 1D and 2D NMR spectroscopy (TOCSY, ROESY, HSQC, HMBC), and MS/MS experiments on 6 and 7 as well as the permethylated derivative 8.

Antitubercular Agents↗
PubMed2004

Steroidal glycosides from the bulbs of Ornithogalum thyrsoides.

Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.

Antineoplastic Agents, Phytogenic↗
PubMed2006

Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea.

Bioassay-guided fractionation of the active n-BuOH extract of the sea cucumber Holothuria fuscocinerea resulted in the isolation of three new triterpene glycosides, fuscocinerosides A (1), B (2), and C (3), along with two known glycosides, pervicoside C (4) and holothurin A (5), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Compounds 1-5 possess the same tetrasaccharide moiety, 3-O-methyl-beta-D-glucopyranosyl-(1-->3)-beta-D- glucopyranosyl-(1-->4)-beta-D-quinovopyranosyl-(1-->2)-4-O-sodiumsulfato-beta-D-xylopyranosyl, linked to C-3 of holostane triterpene aglycones that differ in their side chains and 17-substituents. Their structures were elucidated by extensive spectral studies as well as chemical evidence. All the glycosides showed in vitro cytotoxicity against two human tumor cell lines.

Animals↗
PubMed2006

Profiling of the resin glycoside content of Mexican jalap roots with purgative activity.

Mexican Jalap roots, a prehispanic medicinal plant complex still considered to be a useful laxative, can be found as an ingredient in some over-the-counter products sold by herbalists in contemporary Mexico. The drug is prepared from the dried roots of several morning glories, all of which have been identified as members of the genus Ipomoea. Analysis of several commercial samples was assessed by generating HPLC and 13C NMR spectroscopic profiles of the glycosidic acids obtained through saponification of the resin glycoside contents. These profiles distinguish the three Mexican jalaps currently in frequent use and can serve as analytical tools for the authentication and quality control of these purgative herbal drugs. Ipomoea purga, the authentic "jalap root", yielded two new hexasaccharides of convolvulinic and jalapinolic acids, purgic acids A (1) and B (2), respectively. Scammonic acid A (3), a tetrasaccharide, was produced from Ipomoea orizabensis, the Mexican scammony or false jalap. Operculinic acid B (4), a pentasaccharide, was identified in Ipomoea stans. Semipreparative HPLC was performed to obtain pure samples of new compounds 1 and 2 in sufficient quantity to elucidate their structure by high-field NMR spectroscopy. Purgic acid A (1) was identified as (11S)-hydroxytetradecanoic acid 11-O-beta-D-quinovopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->3)-O-[beta-D-fucopyranosyl-(1-->4)]-O-alpha-L-rhamnopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-quinovopyranoside, while purgic acid B (2) was characterized with (11S)-hydroxyhexadecanoic acid as its aglycon but having the same glycosidation sequence in the oligosaccharide core.

Cathartics↗
PubMed2006

Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala.

Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11alpha,12alpha-epoxy-3beta-[(O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl)-oxy]olean-28,13-olide (2), and 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells.

Amaranthaceae↗
PubMedDate not supplied

TLC-spectrophotometric assay of the main glycosides of red squill, a specific rodenticide.

Red squill bulbs, with reported specific rodenticidal properties, have been assayed for their content of the two main glycosides, scilliroside and scillaren A, by a method depending on the separation of the glycosides from purified plant extracts by tlc followed by spectrophotometric (uv and visible) determination of the individual glycosides in the eluates. The method was found convenient for assessment of the potency of red squill bulbs.

Bufanolides↗
PubMed1998

Flavonol and chalcone ester glycosides from Bidens andicola.

Five new flavonol 7-O-glycosides (1-5), having quercetin or quercetin 3-methyl ether as their aglycons, and sugar chains made up of three or four sugars, including beta-D-glucopyranose, alpha-L-rhamnopyranose, and beta-D-xylopyranose, have been isolated from the aerial parts of Bidens andicola, along with a new chalcone ester glycoside (6) and five known chalcone ester glycosides. The structures of 1-6 were elucidated using a combination of spectroscopic techniques.

Carbohydrate Sequence↗
PubMed1998

Hovetrichosides C-G, five new glycosides of two auronols, two neolignans, and a phenylpropanoid from the bark of Hovenia trichocarea.

Two 2-hydroxy-2-benzylcoumaranone glycosides, 2,4, 6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-beta-D-glucopyranoside (maesopsin 4-O-glucoside) (1) and 2,4,6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-beta-D-glucopyranosido-4'-y l-alpha-L -rhamnopyranoside (maesopsin 4-O-glucosido 4'-O-rhamnoside) (2), two neolignan glycosides, 2R-(E)-2, 3-dihydro-2-(4'-hydroxy-3'-methoxylphenyl)-5-(3"-hydroxy-1"-pro pen yl) -7-methoxy-3-benzofuranmethanol-4'-yl-beta-D-glucopyranosyl-(1-->3 )-[ beta-D-glucopyranosyl-(l-->2)]-beta-d-glucopyranoside (3) and (threo) 1-(4'-hydroxy-3'-methoxy)-2-(4"-hydroxymethyl-2", 6"-dimethoxyphenoxy)-propane-1,3-diol-4'-yl-beta-d-glucopynosid e (4), and a phenylpropanoid glycoside, 3-methoxy-5-(2'-propenyl)-1, 2-benzenediol-1-yl-beta-D-apiofuranosyl-(1-->6)-beta-D- glucopyransodie (5) were isolated from the bark of Hovenia trichocarea. Compounds 1-5 were named hovetricosides C-G, respectively, and their structures were established by extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds acanthoside B, kelampayoside A, shashenoside I, and 3,4, 5-trimethoxyphenol-1-O-beta-D-xylopyranosyl-(1-->6)-beta-D- glucopyranoside.

Carbohydrate Sequence↗
PubMed2000

New cytotoxic sterol glycosides from the octocoral Carijoa (Telesto) riisei.

Two new steroidal glycosides, 3beta-O-(3'-O-acetyl-beta-D-arabinopyranosyl)-25xi-choles tan e-3beta, 5alpha,6beta,26-tetrol-26-acetate (riisein A, 2) and 3beta-O-(4'-O-acetyl-beta-D-arabinopyranosyl)-25xi-choles tan e-3beta, 5alpha,6beta,26-tetrol-26-acetate (riisein B, 3), were isolated from extracts of the Brazilian telestacean octocoral Carijoa (Telesto) riisei collected near Rio de Janeiro. The new glycosides co-occur with the polyhydroxy sterol, 25xi-cholestane-3beta,5alpha,6beta, 26-tetrol-26-acetate (1), an inseparable diastereomeric mixture previously reported from Telesto riisei collected in Micronesia. The structures of the new glycosides were assigned by spectroscopic methods and by comparison with spectral data for sterol 1. Riiseins A and B showed in vitro cytotoxicity toward HCT-116 human colon adenocarcinoma with IC(50) values of 2.0 microg/mL.

Animals↗
PubMed2004

One-pot chemo-, regio-, and stereoselective double-differential glycosidation mediated by lanthanide triflates.

Nuanced activation of n-pentenyl, thioglycoside, and trichloroacetimidate donors by lanthanide salts coupled with donor/acceptor matching can simplify oligosaccharide assembly. Thus, a one-pot, double-differential glycosidation process can be designed, in which an n-pentenyl acceptor-diol is chemo- and regioselectively glycosidated by using an n-pentenyl ortho ester under the agency of Yb(OTf)(3)/NIS followed by in situ addition of a 2-O-acylated trichloroacetimidate or ethyl thioglycoside to effect stereoselective glycosidation at the remaining OH.

Carbohydrate Conformation↗
PubMed1999

2-Deoxy-2-iodo- and 2-deoxy-2-bromo-alpha-glucopyranosyl trichloroacetimidates: highly reactive and stereoselective donors for the synthesis of 2-deoxy-beta-glycosides.

[formula: see text] 2-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-10 and 22 are extremely useful precursors of 2-deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at -78 degrees C with a range of glycosyl acceptors using TBS-OTf as the activating agent. beta-Glycosides are obtained with > or = 19:1 selectivity in six of the seven examples reported herein.

Acetamides↗
PubMed1997

Antifungal activity of a new triterpenoid glycoside from Pithecellobium racemosum (M.).

PURPOSE: In a continuation of our search for novel antifungal compounds from higher plants, the standard extract of the bark of Pithecellobium racemosum was found to have good activity against important AIDS-related opportunistic yeasts. METHODS: The extract was subjected to bioguided fractionation using silica gel column chromatography which led to purification of triterpene glycosides. The structures of these compounds were determined by a combination of spectroscopic (IR, NMR, HRMS) and chemical methods. RESULTS: Compound 1 is a new glycoside, 3-O[alpha-L-arabinopyranosyl (1-2)][alpha-L arabinopyranosyl (1-6)]2-acetoamido-2-deoxy-beta-D-glucopyranosyl oleanolic acid and Compound 2 was identified as the known compound 3-O-[alpha-L-arabinopyranosyl (1-2)]alpha-L-arabinopyranosyl (1-6)] 2-acetamido-2-deoxy-beta-D-glucopyranosyl echinocystic acid. CONCLUSIONS: Compound 1 is a new glycoside, 3-O-[alpha-L-arabinopyranosyl (1-2)]alpha-L-arabinopyranosyl (1-6)]-2-acetoamido-2-deoxy-beta-D-glucopyranosyl oleanolic acid and exhibits moderate antifungal activity against T. mentogrophytes, C. albicans and S. cerevisiae with MIC values of 6.25, 12.5 and 12.5 micrograms/ml respectively.

Antifungal Agents↗
PubMed1996

Synthesis and anti-proliferative activity of 2-hydroxy-1,2-dihydroacronycine glycosides.

PURPOSE: Combination of the acronycine pharmacophore with various sugar units appeared of interest, since numerous anticancer agents possess a sugar moiety, which strongly influence both their bioavailability and their selective toxicity towards tumor cells. METHODS: A series of 2-hydroxy-1,2-dihydroacronycine glycosides were synthetized, by condensation of the racemic aglycone with appropriate glycoside donors. Their effect on the inhibition of L1210 cell proliferation were evaluated. RESULTS: Compounds 6a, 6b, 11a, 11b, and 12a, 12b, including a halogenated sugar moiety displayed activities of the same order of magnitude as acronycine itself. Compounds 7a, 7b, and 8a, 8b, bearing a 2.3.6-trideoxy-3-azido-L-lyxo- and L-arabino-hexopyranose unit respectively, were significantly more potent than acronycine in inhibiting cell proliferation. CONCLUSIONS: The activity of 2-hydroxy-1,2-dihydroacronycine glycosides seems to be related to the lipophilicity of the sugar unit.

Acronine↗
PubMed2002

Effects of muramyl dipeptide glycosides on lymphocyte proliferation and production of interleukin-2.

We studied the effect of new muramyl dipeptide glycosides with different structure of aglycon and configuration glycoside bond on spontaneous and mitogen-induced proliferation of mouse splenocytes and production of interleukin-2 by these cells. Biological activity of muramyl dipeptide beta-glycosides with aliphatic, carbocyclic, adamantile, and phenol aglycons is higher than that of the original compound, while alpha-glycosylation decreases the immunostimulating effect of this glycopeptide.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMed2004

Seasonal variation in the content of hydrolyzable tannins, flavonoid glycosides, and proanthocyanidins in oak leaves.

Oaks have been one of the classic model systems in elucidating the role of polyphenols in plant-herbivore interactions. This study provides a comprehensive description of seasonal variation in the phenolic content of the English oak (Quercus robur). Seven different trees were followed over the full course of the growing season, and their foliage repeatedly sampled for gallic acid, 9 individual hydrolyzable tannins, and 14 flavonoid glycosides, as well as for total phenolics, total proanthocyanidins, carbon, and nitrogen. A rare dimeric ellagitannin, cocciferin D2, was detected for the first time in leaves of Q. robur, and relationships between the chemical structures of individual tannins were used to propose a biosynthetic pathway for its formation. Overall, hydrolyzable tannins were the dominant phenolic group in leaves of all ages. Nevertheless, young oak leaves were much richer in hydrolyzable tannins and flavonoid glycosides than old leaves, whereas the opposite pattern was observed for proanthocyanidins. However, when quantified as individual compounds, hydrolyzable tannins and flavonoid glycosides showed highly variable seasonal patterns. This large variation in temporal trends among compounds, and a generally weak correlation between the concentration of any individual compound and the total concentration of phenolics, as quantified by the Folin-Ciocalteau method, leads us to caution against the uncritical use of summary quantifications of composite phenolic fractions in ecological studies.

Carbon↗
PubMed2001

Biphasic effect of cardiac glycosides on action potential duration in isolated Purkinje fibers.

Despite the historical use of cardiac glycosides, the data describing the electrophysiological characteristics of this class of drug are not fully clear. The present study reported the biphasic effect of cardiac glycosides, digoxin (1.25 microM) and acetylstrophanthidin (0.15 microM), on action potential duration in isolated Purkinje fibers by the conventional glass microelectrode technique. At the cycle lengths of 990, 690 and 490 msec., action potential duration lengthened within 10 min. and shortened after 10 min. of digoxin and acetylstrophanthidin administration. The biphasic effect was observed at a concentration of 4.0 mM [K(+)]o. However, at a higher [K(+)]o concentration of 5.4 mM, only the shortening effect on action potential duration was recorded. These results suggest that the biphasic effect of cardiac glycosides on action potential duration is related to the concentration of extracellular potassium and is not related to the stimulating cycle lengths.

Action Potentials↗