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Steroidal glycosides from the aerial part of Asclepias incarnata L. II.

Thirty new steroidal glycosides were obtained from the aerial part of Asclepias incarnata L. (Asclepiadaceae). These glycosides were confirmed to have lineolon, isolineolon, 12-O-acetyllineolon, 12-O-(Z)-cinnamoyllineolon, metaplexigenin, 15 beta-hydroxylineolon, 15 beta-hydroxyisolineolon, 16 alpha-hydroxyisolineolon, 12-O-tigloyl-16 alpha-hydroxyisolineolon as the aglycone and 2,6-dideoxyhexopyranose as the sugar sequence by spectroscopic methods and chemical evidence.

Glucose↗

An androstane bioside and 3'-thiazolidinone derivatives of doubly-linked cardenolide glycosides from the roots of Asclepias tuberosa.

Steroidal compounds in the roots of Asclepias tuberosa were investigated and 17alpha-hydroxyandrosta-4,6,15-trien-3-one 17-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside, termed ascandroside, was isolated from the CHCl3-soluble fraction. Among five doubly-linked cardenolide glycosides, two were identified as 3'-spiro-linked thiazolidinone (4) and S-oxythiazolidinone derivatives (5) of delta5-calotropin. The stereochemistry at the C-3' in these two cardenolides is discussed. 3'-O-beta-D-Glucopyranosyl-delta5-calotropin (3) was also isolated along with A5-calotropin and its 3'-acetate. Nine glycosides of uzarigenin, coroglaucigenin and corotoxigenin were identified.

Androstanes↗

Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity.

Further search for cytotoxic compounds contained in the bulbs of Galtonia candicans (Liliaceae) led to the isolation of four potent cytotoxic cholestane glycosides (1-4) based upon 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one, three of which (2-4) have not been reported previously. A new cholestane bisdesmoside (5) and a new rearranged cholestane glycoside (6) were also isolated. The structural assignment of the new constituents was carried out by spectroscopic analysis and a few chemical transformations.

Cholestanes↗

Myrsinionosides A-E: megastigmane glycosides from the leaves of Myrsine seguinii Lev.

Eight megastigmane glycosides were isolated from the leaves of Myrsine seguinii collected in Okinawa. Three of them were found to be known compounds, i.e., ampelopsisionoside, alangionoside J, and linarionoside A. The structures of the new megastigmane glycosides were elucidated from the spectroscopic data and their absolute stereochemistries were determined in detail using a modified Mosher's method.

Acetylation↗

Glycosides of benzyl and salicyl alcohols from Alangium chinense.

From the water-soluble fraction of the dried leaves of Alangium chinense, three new glycosides, benzyl alcohol beta-D-glucopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 6)]-beta-D-glucopyranoside, 2'-O-beta-D-glucopyranosylsalicin, and 2'-O-beta-D-glucopyranosyl-6'-O-beta-D-xylopyranosylsalicin were isolated along with seven known glycosides. The structures of the new compounds were determined by spectroscopic and chemical means.

Benzyl Alcohols↗

Three new glycosides from Sinopodophyllum emodi (Wall.) Ying.

Tow new aryltetralin-type lignan glycosides: methyl epipodophyllate 7'-O-beta-D-glucopyranoyl-(1-->6)-beta-D-glucopyranoside (1), 4-demethylepipodophyllotoxin 7'-O-beta-D-glucopyranoside (2), and a new phenyl ethanol glycoside: phenyl ethanol 4-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (3), along with three known compounds: junipetriolosides (4), 3,4-dihydroxy-phenyl ethanol (5), and 4-hydroxy-phenyl ethanol (6) were isolated and identified from the n-butanol extract of the roots and rhizomes of Sinopodophyllum emodi (Wall.) Ying. The structures of the above were established by means of spectral data and chemical methods.

Glycosides↗

Triterpene glycosides from the cultures of Phytolacca americana.

A new triterpene glycoside I was isolated together with the five known triterpene glycosides 2-6 from the cultures of Phytolacca americana. The structure of 1 was elucidated by analysis of spectroscopic data and comparison of its NMR data with those of 2-7 and chemical degradation.

Carbohydrate Conformation↗

Medicinal foodstuffs. XXI. Structures of new cucurbitane-type triterpene glycosides, goyaglycosides-a, -b, -c, -d, -e, -f, -g, and -h, and new oleanane-type triterpene saponins, goyasaponins I, II, and III, from the fresh fruit of Japanese Momordica charantia L.

Eight cucurbitane-type triterpene glycosides called goyaglycosides-a, -b, -c, -d, -e, -f, -g, and -h and three oleanane-type triterpene saponins termed goyasaponins I, II, and III were isolated from the fresh fruit of Japanese Momordica charantia L. (Cucurbitaceae) together with five known cucurbitane-type triterpene glycosides momordicosides A, C, F1, I, and K. The structures of goyaglycosides and goyasaponins were elucidated on the basis of chemical and physicochemical evidence.

Glycosides↗

Isoflavonoid glycosides from the rhizomes of Iris germanica.

Four isoflavone glycosides were isolated from the rhizomes of Iris germanica. Compounds 1 and 2 are new, while compounds 3 and 4 are known isoflavone glycosides. These compounds were identified as iriskashmirianin 4'-O-beta-D-glucoside (1), nigricin 4'-O-beta-D-glucoside (2), irilone 4'-O-beta-D-glucoside (3) and iridin (4). Their structures were determined with the help of spectroscopic methods.

Glycosides↗

New phenylethanoid glycosides from Bacopa monniera.

Three new phenylethanoid glycosides, viz. monnierasides I-III (1-3) along with the known analogue plantainoside B were isolated from the glycosidic fraction of Bacopa monniera. Their structures were elucidated mainly on the basis of two dimensional (2D) NMR spectral analyses.

Bacopa↗

Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra.

Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-0-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-0-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several diarylheptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.

Animals↗

Flavanone and flavonol glycosides from the leaves of Thevetia peruviana and their HIV-1 reverse transcriptase and HIV-1 integrase inhibitory activities.

Two new flavanone glucosides, (2R)- and (2S)-5-O-beta-D-glucopyranosyl-7,4'-dihydroxy-3',5'-dimethoxyflavanone[pervianoside I (3), peruvianoside II(4)] and a new flavonol glycoside, quercetin 3-O-[beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-galactopyranoside] (peruvianoside III, 13) were isolated from the leaves of Thevetia peruviana Schum., together with nine known flavonol glycosides and two known iridoid glucosides. The structures of all compounds were determined on the basis of chemical and spectroscopic methods. Their inhibitory effects against HIV-1 reverse transcriptase and HIV-1 integrase were also investigated.

Flavonoids↗

Lucidin type anthraquinone glycosides from Putoria calabrica.

Two new lucidin type anthraquinone glycosides, putorinoside A (1) and putorinoside B (2) were isolated from Putoria calabrica, in addition to two known anthraquinone glycosides, lucidin 3-O-beta-glucopyranoside (3) and lucidin 3-O-primeveroside (4). Based on spectroscopic data, putorinosides A and B were identified as 2-hydroxymethyl-1-methoxy-3,5,6-trihydroxyanthraquinone 3-O-beta-glucopyranoside and 2-hydroxymethyl-1-methoxy-3,6-dihydroxyanthraquinone 3-O-beta-glucopyranoside, respectively.

Anthraquinones↗

Two new acylated flavanone glycosides from the leaves and branches of Phyllanthus emblica.

Two new acylated flavanone glycosides, (S)-eriodictyol 7-O-(6"-O-trans-p-coumaroyl)-beta-D-glucopyranoside (1) and (S)-eriodictyol 7-O-(6"-O-galloyl)-beta-D-glucopyranoside (2) were isolated from the leaves and branches of Phyllanthus emblica together with a new phenolic glycoside, 2-(2-methylbutyryl)phloroglucinol 1-O-(6"-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside (3), as well as 22 known compounds. Their structures were determined by spectral and chemical methods.

Acylation↗

Acylated-oxypregnane glycosides from the roots of Araujia sericifera.

Twenty-three new acylated-oxypregnane glycosides were obtained from the roots of Araujia sericifera. (Asclepiadaceae). These glycosides were confirmed to be tetraglycosides possessing twelve known compounds, 12-O-benzoyllineolon, 12-O-benzoyldeacylmetaplexigenin, ikemagenin, kidjolanin, cynanchogenin, caudatin, rostratamine, penupogenin, 12-O-benzoylisolineolon, 12-O-tigloyldecylmetaplexigenin (incisagenin), 12-O-benzoyl-20-O-acetylsarcostin, 20-O-benzoyl-12-O-(E)-cinnamoyl-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptahydroxy-(20S)-pregn-6-ene and ten new acylated-oxypregnanes, 12-O-benzoyl-20S-hydroxyisolineolon, 12-O-tigloyllineolon, 12-O-salicyloyllineolon, 12-O-salicyloyldeacylmetplexigenin, 12-O-benzoyl-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta-hexahydroxypregn-6-en-20-one, 12-O-benzoyl-19-benzoyloxydeacylmetapleligenin, 12-O-benzoyl-19-benzoyloxy-20-O-acetylsarcostin, 12-O-benzoyl-19-salicyloyloxy-20-O-acetylsarcostin, 12-O-benzoyl-5 alpha,6 alpha-epoxydeacylmetaplexigenin, and 12-O-benzoyl-5 alpha,6 alpha-epoxylineolon as their aglycones, using both spectroscopic and chemical methods.

Apocynaceae↗

Glycosides of Atractylodes ovata.

A new coumarin glycoside and a new glycoside of an acetylene derivative were isolated from the water-soluble portion of the methanolic extract of Atractylodes ovata rhizome together with eight known compounds. Their structures were characterized as scopoletin beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside and (2E)-2-decene-4,6-diyne-1,8-diol 8-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, respectively, based on chemical and spectroscopic investigations. A comparison of the polar constituents among Atractylodes japonica, Atractylodes lancea, and A. ovata is led to the conclusion that A. ovata is distinguishable from A. lancea and A. japonica, as also shown by phylogenetic analysis.

Atractylodes↗