Triterpene glycosides of Astragalus and their genins XXXVII. Cycloaraloside F from Astragalus amarus and Astragalus villosissimus

The glycosides of the plantAstragalus villosissimus Bunge have been studied. Four glycosides have been isolated from the roots of this plant, and two of them have been identified as -sitosterol -D-glucopyranoside and cycloaraloside C. The most polar glycoside, which has also been isolated from the roots ofAstragalus amarus Pall., proved to be a new triterpene glycoside of the cycloartane series and has been called cycloaraloside F. It is a trioside of cyclosieversigenin containing two molecules of D-glucose and one molecule of D-apiose. On the basis of chemical transformations and spectral characteristics, the structure of cycloaraloside F has been established as 20R, 24S-epoxycycloartane-3,6,16,25-tetraol 3-0-[O-D-apio--D-furanosyl-(12)--D-glucopyranoside] 25-O--D-glucopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 374–377, May–June, 1991.     

Triterpene Glycosides of Astragalus and Their Genins. LXI. Occurrence of Cycloartane 6-O-Monodesmosides

Cyclosiversigenin 6-O--L-rhamnopyranoside and 6-O--D-glucopyranoside were isolated fromAstragalus coluteocarpusBoiss. (Leguminosae) andAstragalus dissectusB. Fedtsch. et N. Ivanova, respectively. Cyclosiversigenin 5-O--L-rhamnopyranoside was shown to be an artifact forAstragalus coluteocarpus.Thus, the cyclosiversigenin 6-O--D-glucopyranoside that was isolated from certainAstragalusspecies is hypothesized also to be an artifact. Glycosylation of the 6 -hydroxyl group of cycloartanes by D-glucose and D-xylose, in contrast with other substituents, does not change the low-field position of the PMR signal of the 4-CH ₃ group (1.65 2.01 ppm) that is caused by the influence of deuteropyridine directly on the 6 -hydroxyl. Obviously one of the hydroxyls of the -D-glucopyranoside or -D-xylopyranoside residues has the same effect in this instance.     

Triterpene glycosides of Astragalus and their genins. XXIII. Cyclocanthogenin from Astragalus tragacantha

The epigeal part of the plantAstragalus tragantha Habl. (Leguminosea) has yielded (in addition to cyclosieversigenin, cyclocyclosiversioside F, and -sitosterol -D-glucopyranoside) a new methylsteroid of the cycloartane series — cyclocanthogenin — the structure of which has been established on the basis of chemical transformations and spectral characteristics, and also of a chemical correlation with the structure of cycloasgenin C, as 24S-cycloartane-3,6,16,24,25-pentaol.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 817–824, November–December, 1987.     

Iriterpene glycosides of Astragalus and their genins XLIII. Cycloaraloside B from Astragalus amarus

The structure of a new cycloartane glycoside, cycloaraloside B, isolated from the roots ofAstragalus amarus Pall. (Leguminosae) has been established on the basis of chemical transformations and spectral characteristics: it is 20R,24S-epoxycycloartane-3,6,16,25-tetraol 3-O-[O--L-rhamnopyranosyl-(12)-(6-O-acetyl--D-glucopyranoside)].Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 528–531, September–October, 1992.     

Triterpene Glycosides from Plants of the Astragalus Genus. Structure of Cyclounifolioside A from Astragalus unifoliolatus

The known compound oleanolic acid (1) and a new cycloartane glycoside cyclounifolioside A (2), which has the structure 6,16-di-O-acetyl-24R-cycloartan-6,16,24,25-pentaol 3-O--D-glucopyranoside, were isolated from Astragalus unifoliolatus Bunge. The structures of the isolated compounds were established using chemical transformations and two-dimensional spectra (TOCSY, ROESY, HMBC, HSQC, COSY).     

Triterpeneglycosides of Astragalus and their genins. XXV. Cyclocanthoside D from Astragalus tragacantha

The epigeal part of the plant ofAstragalus tragacantha Habl. (Leguminosae) has yielded, together with cyclosieversigenin 3-O--D-xylopyranoside, a new glycoside of the cycloartane series — cyclocanthoside D, the structure of which has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,6,16,24,25-pentaol 16-O--D-glucopyranoside 3-O--D-xylopyranoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 73–76, January–February, 1988.     

Triterpene glycosides of Astragalus and their genins XL. Cyclocarposide B from Astragalus coluteocarpus

In addition to cyclosieversigenin, -sitosterol -D-glucopyranoside, and cyclocarposide, we have isolated another three glycosides of triterpene nature from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). On the basis of chemical transformations and spectral characteristics, the structure of one of the new glycosides, which we have called cyclocarposide B, has been established as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-O--L-(2-O-acetylrhamnopyranoside) 3-O--D-xylopyranoside.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 227–231, March–April, 1992.     

Triterpene glycosides of Astragalus and their genins XLII. Cycloartanes of Astragalus tragacantha

Another six components ofAstragalus tragacantha Habl. have been identified on the basis of spectral characteristics and chemical transformations. We have previously described cyclocanthagenin and its 3-0--D-xylopyranoside — cyclocanthoside A — as products of the acid hydrolysis of cyclocanthoside D. Cyclocanthosides B, C, E, and G are here described for the first time and are (24S)-cycloartane-3,6,16,24,25-pentol 3-O-(4-O-acetyl--D-xylopyranoside) 6-O--D-glucopyranoside, (24S)-cycloartane-3,6,16,24,25-pentol 6-O-(6-O-acetyl--D-glucopyranoside) 3-O--D-xylopyranoside, (24S)-cycloartane-3,6, 16,24,25-pentol 6-O--D-glucopyranoside, and (24S)-cycloartane-3, 6, 16, 24, 25-pentol 6-O--D-glucopyranoside 3-O-[O--D-glucopyranosyl-(12)--D-xylopyranoside], respectively.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Institute of Ecological Genetics, Moldavian Academy of Sciences, Kishenev. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 360–367, May–August, 1992.     

Triterpene glycosides ofClimacoptera transoxana. III. The structures of copterosides E and F

New triterpene glycosides have been isolated from the epigeal part ofClimacoptera transoxana (Iljin) Botsch. — copterosides E and F. According to chemical transformations and physicochemical characteristics, copteroside E has the structure of oleanolic acid 28-O--D-glucopyranoside 3-O-{[O--D-xylopyranosyl-(12)]-[O--D-xylopyranosyl-(14)]--D-glucuronopyranoside} and copteroside F that that of hederagenin 28-O--D-glucopyranoside 3-O-{[O--D-xylopyranosyl-(12)]-[O--D-xylopyranosyl-(14)]--D-glucopyranoside}.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 596–601, September–October, 1983.     

IR spectra of certain methyl -d-glucopyranoside nitrates

Conclusions A study has been made of the IR spectra of methyl--D-glucopyranoside 2-and 3-nitrates, methyl--D-glucopyranoside 6-nitrate, and methyl-4-O-methyl--D-glucopyranoside 2,3-and 3,6-dinitrates and 2,3,6-trinitrate.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1763–1765, August, 1987.     

Triterpene glycosides of Astragalus and their genins. XXIV. Cycloorbicoside G from Astragalus orbiculatus

A bisdesmosidic glycoside — cycloorbicoside G — has been isolated from the epigeal parts of the plantAstragalus orbiculatus Ledeb. (Leguminosae), and on the basis of chemical transformations and spectral characteristics its structure has been established as (23R,24S)-16,23;16,24-diepoxycycloartane-3,7,25-triol 25-O--D-glucopyranoside 3-O--D-xylopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 837–842, November–December, 1987.     

Cardiac glycosides of Cheiranthus allioni. V

Conclusions Two additional cardiac glycosides, glucoerysimoside and glucoerysimosol, have been isolated from the seeds ofCheiranthus allioni Hort. Glucoerysimoside is strophanthidin 3-[O--D-digitoxopyranosyl-(4 1)-O--D-glucopyranosyl-(4 1)--D-glucopyranoside]. Glucoerysimosol is a new cardenolide having the same carbohydrate component, but its aglycone is strophanthidol. From these glycosides a new trisaccharide has been obtained which has been characterized as 4-O--cellobiosyl-D-digitoxose.Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 566–571, September–October, 1970.     

Triterpene Glycosides of Astragalus and Their Genins. LXVI. Cycloorbicoside C, a New Bisdesmoside

The new triterpene glycoside cycloorbicoside C was isolated from the aerial parts of Astragalus orbiculatus Ledeb. (Leguminosae) and was identified as (23R,24S)-16,23;16,24-diepoxycycloartan-3,25-diol 3-O--D-xylopyranoside 25-O--D-glucopyranoside.     

Structure of Cyclogaleginoside E from Astragalus galegiformis

The new cycloartane glycoside cyclogaleginoside E, 20S,24R-cycloartan-3,6,16,25-tetraol-3-O--D-xylopyranoside-25-O--D-glucopyranoside, was isolated from stems of Astragalus galegiformis L. Its structure was established using enzymatic and total acid hydrolysis, mass spectrometry, and PMR and ¹³C NMR.     

Triterpene glycosides ofHedera taurica XV. Structures of glycosides St-I3, St-I4a, St-I4b, and St-I5 from the stems of Crimean ivy

From the stems of Crimean ivyHedera taurica Carr. (fam. Araliaceae) we have isolated the new triterpene glycosides St-I₃, St-I₅, and St-I_4a, which are, respectively, the 3–0--D-glucopyranoside 28-O-[O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosides] of oleanolic acid and of hederagenin and the 3-O--D-glucopyranuronoside 28-O--gentiobioside of oleanolic acid, and also the previously known 3-O-[O--D-galactopyranosyl-(12)--D-glucopyranuronoside 28-O--D-glucopyranoside] of oleanolic acid (glycoside Rb-4).Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 404–410, May–June, 1997.     

Steroid glycosides ofNicotiana tabacum seeds I. The structures of nicotianosides A, B, and E

Two steroid glycosides of the spirostan series — nicotianosides A and B — and one glycoside of the furostan series — nicotianoside E — have been isolated from the seeds ofNicotiana tabacum L. Nicotianoside A is (25S)-5-spirostan-3-ol 3-O--D-glucopyranoside, nicotianoside B is (25S)-5-spirostan-3-ol 3-O-[O--L-rhamnopyranosyl-(12)-gb-D-glucopyranoside], and nicotianoside E is (25S)-5-furostan-3,22,26-triol 26-O--glucopyranoside 3-O-[O--L-rhamnopyranosyl-(12)--D-glucopyranoside].Institute of Genetics, Academy of Sciences of the Republic of Moldava, Kishinev, ul. Lesnaya, 20. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 737–742, November–December, 1994.     

Triterpene Glycosides of Plants of the Astragalus Genus. IV. Structure of Cyclounifolioside D from Astragalus unifoliolatus

The new cycloartane glycoside cyclounifolioside D (1) was isolated from roots of Astragalus unifoliolatus Bunge. The structure of 16-O-acetyl-24R-cycloartan-3,6,16,24,25-pentaol 3-O--D-glucopyranoside was established using chemical transformations and spectral data.     

Triterpene Glycosides from Astragalus. Structure of Cyclounifolioside B from Astragalus unifoliolatus

The previously known astrailienin A and the new cycloartane glycoside cyclounifolioside B with structure cyclosiversigenin 3-O-[-D-glucopyranosyl(1-2)]--D-glucopyranoside were isolated from Astragalus unifoliolatus Bunge. The structures of these compounds were established using chemical transformations and two-dimensional spectra (ROESY, HMBC, HSQC, TOCSY, COSY).     

Transformed steroids

Conclusions A synthesis was carried out for the 3-acetate of 16,23-oxido-21,24-dinorchol-5-en-3,17-diol-20-one and acetates of 16,23-oxido-21,24-dinorchol-5-en-3,17,20-triol, which are new polyhydrosteroids with an additional D-series E ring.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1156–1159, May, 1982.