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At least 1,009 records · Page 56Linked to original sources
PubMed1992

Biologically active labdane-type diterpene glycosides from the root-stalks of Gleichenia japonica.

A glycoside showing a strong growth inhibition of lettuce was isolated from the root-stalks of Gleichenia japonica and its structure was established to be the 3-O-alpha-rhamnopyranosyl-(1----2)-beta-glucopyranoside of 13-O-alpha-rhamnopyranosyl-(+)-3 beta-hydroxymanool. In addition, two related glycosides were also isolated and they were characterized as the 3-O-beta-fucopyranosyl-(1----3)-alpha-rhamnopyranosyl-(1----2)-beta- glucopyranoside of 13-O-alpha-rhamnopyranosyl-(+)-3 beta-hydroxymanool and the 13-O-rhamnopyranoside of the same diterpene alcohol. The diterpene alcohol accelerated the growth of lettuce.

Carbohydrate Sequence↗
PubMed1992

Oleanane glycosides from Glycyrrhiza yunnanensis roots.

From the roots of Glycyrrhiza yunnanensis, collected in Yunnan, China, six new oleanane-type triterpene glycosides named yunganosides A1, B1, C1, D1, E2 and F2 were isolated together with hypaphorine. The structures of these glycosides were established by spectroscopic and chemical means.

Carbohydrate Sequence↗
PubMed1992

Scammonins VII and VIII, two resin glycosides from Convolvulus scammonia.

Two minor ether-soluble resin glycosides, scammonins VII and VIII, were isolated from Radix Scammoniae, the roots of Convolvulus scammonia. In addition to (2S)-2-methylbutyric acid and tiglic acid, they are composed, respectively, of orizabic acid A and a new glycosidic acid named scammonic acid B, with similar macrocyclic ester structures to those of the scammonic acid A-based scammonins I-VI. Isolation of genuine scammonins III-V, which were previously obtained as peracetates, is also described.

Carbohydrate Sequence↗
PubMed1992

Phenylpropanoid glycosides from Marrubium alysson.

From the aerial parts of Marrubium alysson a new phenylpropanoid glycoside, alyssonoside, and five known glycosides, verbascoside (= acteoside), leucosceptoside A, martynoside, forsythoside B and leucosceptoside B were isolated. On the basis of spectral data, the structure of the new compound was elucidated as beta-(3,4-dihydroxyphenyl)ethyl-O-[alpha-L-rhamnopyranosyl-(1-->3)]-O- [beta-D-apiopyranosyl-(1-->6)]-4-O-feruloyl-beta-D-glucopyra noside.

Carbohydrate Sequence↗
PubMed1993

Triterpenoid glycosides from Stauntonia hexaphylla.

From Stauntonia hexaphylla, two new 3,28-bisglycosidic triterpenoid glycosides named staunosides A and B, were isolated along with three known triterpenoid glycosides, one of which was isolated from nature of the first time, though it had previously been obtained from the acid hydrolysate of kizuta saponin K12. On the basis of chemical and physicochemical evidence, the structures of staunosides A and B were elucidated as 3-O-(beta-D-glucopyranosyl)-hederagenin-28-O-[beta-D- glucopyranosyl(1-->6)-beta-D-glucopyranosyl]ester and 28-O-[alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)- beta-D-glucopyranosyl]ester, respectively.

Carbohydrate Sequence↗
PubMed1993

Two phenethyl alcohol glycosides from Scutellaria orientalis subsp. pinnatifida.

Two new phenethyl alcohol glycosides, darendoside A and B (= deacyl martynoside) were isolated from the methanolic extract of the aerial parts of Scutellaria orientalis subsp. pinnatifida, along with four known glycosides, syringin, martynoside, leucosceptoside A and verbascoside. On the basis of chemical and spectral evidence the structures of darendoside A and B were determined as beta-(4-hydroxyphenyl)ethyl O-beta-D-apiofuranosyl-(1-->2)-O-beta-D-glucopyranoside and beta-(3-hydroxy-4-methoxyphenyl)ethyl O-alpha-L-rhamnopyranosyl-(1-->3)-O-beta-D-glucopyranoside (= deacyl martynoside), respectively.

Carbohydrate Sequence↗
PubMed1993

14-Decarboxyquinovic and quinovic acid glycosides from Zygophyllum album.

Further investigation of the leaves and stems of Zygophyllum album afforded four triterpene glycosides which were characterized as 14-decarboxyquinovic acid-3 beta-O-beta-D-quinovopyranosyl (1-->4)-quinovopyranoside, quinovic acid 28-O-beta-D-glucopyranosyl (2-->1)beta-D-glucopyranosyl ester, quinovic acid 27-O-beta-D-glucopyranosyl(2-->1)beta-D-glucopyranosyl ester and quinovic acid-3-beta-O-glucopyranosyl(2-->1)rhamnopyranoside. In addition, two flavonoid glycosides were isolated. The structures of the isolated compounds were established by GC, GC-MS, mass spectra, 1H and 13C NMR.

Carbohydrate Sequence↗
PubMed1995

Flavonol glycosides from Epimedium koreanum.

A novel flavonol glycoside named caohuoside-B was isolated from the aerial parts of Epimedium koreanum, along with a known flavonol glycoside, epimedokoreanoside-I. Their structures were established by spectroscopic methods. The new compound was elucidated as anhydroicaritin 3-O-beta-D-(4,6-O- diacetyl)glucopyranosyl-(1-->3)-alpha-L-(4"-O-acetylrhamnopyranoside+ ++)-7-O-beta- D-glucopyranoside.

Carbohydrate Conformation↗
PubMed1995

Fully acetylated carbamate and hypotensive thiocarbamate glycosides from Moringa oleifera.

Six new and three synthetically known glycosides have been isolated from the leaves of Moringa oleifera, employing a bioassay-directed isolation method on the ethanolic extract. Most of these compounds, bearing thiocarbamate, carbamate or nitrile groups, are fully acetylated glycosides, which are very rare in nature. Elucidation of the structures was made using chemical and spectroscopic methods, including 2D NMR techniques. Thiocarbamates showed hypotensive activity.

Acetylation↗
PubMed1995

Triterpenoid glycosides from Cephalaria transsylvanica.

On the basis of spectroscopic and chemical methods, the structures of two new triterpenoid glycosides, transsylvanoside E and F, isolated from Cephalaria transsylvanica have been established as 3-O-[beta-D-xylopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->2)-beta-D-xylopyranosyl]-3 beta,23- dihydroxy delta 12-oleanen-28-carboxylic acid and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-beta-D-xylopyranosyl]-28-O-[beta- D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl]-3 beta,23-dihydroxy delta 12-oleanen- 28-carboxylic acid, respectively. A new proglycoside was isolated from the cleavage of the ester-glycoside linkage and it's structure characterized as 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L- rhamnopyranosyl (1-->4)-beta-D-xylopyranosyl]-3 beta,23-dihydroxy delta 12-oleanen-28-carboxylic acid.

Carbohydrate Conformation↗
PubMed1995

Verbascoside derivatives and iridoid glycosides from Penstemon crandallii.

The new phenylethanoid glycosides 2-O-acetyl-3'''-O-methylverbascoside and 2,4"-di-O-acetyl-3'''-O-methylverbascoside were isolated and identified from Penstemon crandallii. The major iridoid glycoside was plantarenaloside and no aucubin type iridoids were found. This contrasted with a previous analysis of P. teucrioides, from the same Penstemon subsection, which was dominated by aucubin derivatives.

Carbohydrate Conformation↗
PubMed1995

Flavonol sinapoyl glycosides from leaves of Thevetia peruviana.

From the leaves of Thevetia peruviana four new flavonol glycosides, kaempferol 3-glucosyl(1 --> 4) [6"'-sinapoylglucosyl] (1 --> 2) galactoside and 3-[2""-sinapoylglucosyl](1 --> 4)[6"'-sinapoylglucosyl](1 --> 2)galactoside and kaempferol and quercetin 3-[6"'-sinapoylglucosyl](1 --> 2)galactoside were isolated, together with the known compounds, kaempferol and quercetin 3-glucosyl(1 --> 2)galactoside. The glycosides were characterized from FAB mass, 1H and 13C NMR and UV spectral data.

Carbohydrate Conformation↗
PubMed1996

Cholestane- and pregnane-type glycosides from the roots of Tribulus cistoides.

From the methanolic extract of the roots of Tribulus cistoides the cardioactive saponin-3, which is known to occur in the leaves, was isolated along with tribulosin, a pregnane-type glycoside and eight new cholestane glycosides. D-(+)-Pinitol and sucrose were major constituents. The structures were established by spectroscopic studies of the isolated compounds, their acetylated derivatives and their hydrolysation products. Chemical conversions revealed the configurations at C-22 and C-25, respectively.

Carbohydrate Sequence↗
PubMed1996

Aryl and triterpenic glycosides from Margyricarpus setosus.

Investigation of aerial parts of Margyricarpus setosus afforded three new aryl glycosides, beta-hydroxyphenylethyl-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside, benzyl-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside, 4-methoxybenzyl-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside, and three new triterpene glycosides, tormentic acid 3 beta-O-beta-D-quinovopyranoside, tormentic acid 3 beta-O-beta-D-fucopyranoside and tormentic acid 3 beta-O-alpha-L-rhamnopyranoside. Twelve known compounds were also found, among them beta-hydroxy-3',4'-dimethoxyphenylethyl glucoside and beta-hydroxy-3',4'-dimethoxyphenylethyl rutinoside, which were obtained previously by partial synthesis, were isolated for the first time from a natural source. The structures of the new compounds were elucidated on the basis of chemical and spectral data.

Carbohydrate Conformation↗
PubMed1996

A cyanogenic glycoside from Canthium schimperianum.

A new cyanogenic glycoside esterified with an iridoid glycoside, 2R-[(2-methoxybenzoylgenoposidyl)-5-O-beta-D-apiofuranosyl-( 1-->6)-beta-glucopyranosyloxy]-2-phenyl acetonitrile, was isolated from the seeds of Canthium schimperianum and identified from its spectroscopic data. The new compound showed weak growth retarding activity towards neonate larvae of Spodoptera littoralis (ED50 8580 ppm) compared to the co-occurring hydroxycinnamic acids, 3,4-dicaffeoylquinic acid (ED50 550 ppm) and 3,5-dicaffeoylquinic acid (ED50 520 ppm).

Animals↗
PubMed1996

Glycosides of megastigmane and of the simple alcohols from Alangium premnifolium.

From the water-soluble fraction of a methanol extract of leaves of Alangium premnifolium, two new megastigmane glycosides, alangionosides N and O, along with three known megastigmane glycosides, dendranthemoside A and alangionosides A and B, were isolated. Shimaurinosides A and B, xylopyranosyl(1-->6)glucopyranosides of simple alcohols were also found to be constituents of the water-soluble fraction. Structures were determined by spectroscopic analyses.

Alcohols↗
PubMed1996

Steroidal glycosides from the subterranean parts of Liriope spicata var. prolifera.

In a continuation of phytochemical studies on the underground organs of Liriope spicata var. prolifera, four new steroidal glycosides, lirioproliosides A-D, along with two known compounds, 25(S)-ruscogenin 1-O-[alpha-L-rhamnopyranosyl(1-->2)[beta-D-xylopyranosyl (1-->3)]-beta-D-fucopyranoside and ophiopogonin A, were identified. The structures of lirioproliosides A-D were established by a combination of spectroscopic and chemical methods as 25(S)-ruscogenin 1-O-[alpha-L-rhamnopyranosyl(1-->2)][beta-D-xylopyranosyl (1-->3)]-beta-D-fucopyranoside-3-O-alpha-L-rhamnopyranoside, 25(S)-ruscogenin 1-O-[3-O-acetyl-alpha-L-rhamnopyranosyl(1-->2)]-beta-D-fucopyranoside, 25(S)-ruscogenin (1-O-[2-O-acetyl-alpha-L-rhamnopyranosyl (1-->2)]-beta-D-fucopyranoside and ruscogenin (1-O-[2-O-acetyl-alpha-L-rhamnopyranosyl(1-->2)]-beta-D-fucopyranoside, respectively. Among these steroidal glycosides, ophiopogonin A and lirioprolioside B, and lirioproliosides C and D, were isolated as epimeric pairs.

Glycosides↗
PubMed1993

Synthesis and structure-activity relationships of 14 beta-hydroxy-5 alpha-pregnanes: pregnanes that bind to the cardiac glycoside receptor.

5 alpha-pregnane-3 beta,14 beta,20 beta-triol 3-alpha-L-rhamnopyranoside (8) and 3 beta-(alpha-L-rhamnopyranosyloxy)-5 alpha-pregn-14-en-20-one (14) were prepared from uzarigenin by ozonolysis followed by zinc and acetic acid reduction and glycosidation. During the glycosidation reaction leading to (8) the corresponding ortho ester (9) was also obtained. Uzarigenin alpha-L-rhamnopyranoside (15) also was prepared. Synthesis of 5 alpha-pregnane-3 beta,14 beta,20 beta-triol (20) is described. Structures were established by analysis of their NMR spectra. The binding affinity of 5 alpha and 5 beta cardenolide and pregnane derivatives as measured in a radioligand binding assay was determined and their structure-activity relationships compared. The receptor binding affinity of the 5 alpha derivatives is less than that of the corresponding 5 beta derivatives.

Acetates↗