Triterpene glycosides ofScabiosa soongorica

Partial syntheses of glycosides of oleanolic acid — the 3-0--D-xylopyranoside (songoroside A), the 3,28-bis-0--D-xylopyranoside, and the 28-0--gentiobioside-3-0--D-xylopyranoside — and also the formation of 3-0--D-xylopyranosyloleanolic acid 13,28-lactone are described.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Institute of the Physiology and Experimental Pathology of High Mountain Regions of the Academy of Sciences of the KirgSSR, Frunze. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 668–673, September–October, 1979.     

Triterpene glycosides ofAstragalus and their genins. XXII. Cycloorbicoside A fromAstragalus orbiculatus

The quantitatively main glycoside — cycloorbicoside A — has been isolated from the epigeal parts of the plantAstragalus orbiculatus, 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 3-0--D-xylopyranoside.Institute of the Chemistry of Plant Substances Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 719–726, November–December, 1986.     

Tripenoid glycosides of alfalfa. VII. Medicosides E and F

Two hederagenin glycosides — medicosides E and F — have been isolated from the roots ofMedicago sativa L. (Leguminosae). Medicoside E has the structure of hederagenin 28-O--D-glucopyranoside 3-O-[O--G-glucopyranosyl-(13)--D-xylopyranoside]. Medicoside F has the structure of hederagenin 28-O--D-glucopyranoside 3-O-[O--D-glucopyranosyl-(12)--L-arabinopyranoside].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Institute of Organic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii. No. 5, pp. 701–705, September–October, 1993.     

Triterpene saponins fromThalictrum minus. V. Structure of thalicoside B

The epigeal part ofThalictrum minus L. has yielded a new bidesmoside — thalicoside B — which has the structure of oleanolic acid 28-O--D-glucopyranoside 3-O-[O--L-rhamnopyranosyl-(1 2)-O--D-glucopyranosyl-(1 3)--L-arabinopyranoside].Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR; A. A. Zhdanov Irkutsk State University; and Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 670–676, September–October, 1985.     

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.     

Triterpene glycosides ofAstragalus and their genins XLV. The chemical transformation of cycloartanes 1. Synthesis of 25-norglycosides

Literature information is given on the current state of the study of the chemical transformation of cycloartane triterpenoids. A method has been developed for the transformation of the genin part of glycosides of 20,24-epoxycycloartan-25-ols with retention of the carbohydrate constituents. Three 25-norglycosides have been synthesized from natural cyclosieversigenin glycosides, namely 16-acetoxy-3,6-dihydroxy-20R,25-norcycloartan-20,24-olide 3-O-[O--L-arabinopyranosyl-(12)--D-xylopyranoside] 6-O--D-xylopyranoside (VIII), sodium 3,6,16,20-tetrahydroxy-20R,25-norcycloartan-24-oate 6-O--D-glucopyranoside 3-O--D-xylopyranoside (XII), and 20R,25-norcycloartane-3,6,16,20,24-pentaol 6-O--D-glucopyranoside 3-O--D-xylopyranoside (XIII).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 710–718, September–October, 1993.     

Steroid saponins and sapogenins ofAllium IX. The structure of aginoside

Summary From a methanolic extract of the skins of the bulbs ofAllium giganteum Rgl, a new steroid glycoside has been isolated — aginoside, which is (25R)-5-spirostan-2, 3, 6-triol 3-0-{[0--D-xylopyranosyl-(13)-]-[0--D-glucopyranosyl-(12)]-0--D-glucopyranosyl-(14)-0--D-galactopyranoside}.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 480–486, July–August, 1976.     

Triterpene glycosides of Astragalus and of their genins. X. Cyclogalegigenin from Astragalus galegiformis

The flowers of the plantAstragalus galegiformis L. have yielded a new isoprenoid — cyclogalegigenin — the structure of which has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol.I. G. Kutateladze Institute of Pharmacochemistry, Academy of Sciences of the Georgian SSR, Tbilisi. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 332–339, May–June, 1983.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-0--L-rhamnopyranoside 3-0--D-xylopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

Triterpene glycosides ofAstragalus and their genins. XV. Cyclosiversiosides B and D fromAstragalus basineri

Two new glycosides have been isolated from the roots of the plantAstragalus basineri Trautv. — cyclosiversiosides B and D. It has been shown that cyclosiversioside B is cyclosiversigenin 3-O-(2,3-di-O-acetyl--D-xylopyranoside)-6-O--D-glucopyranoside. Cyclosiversioside D is cyclosiversigenin 3-O-(2-O-acetyl--D-xylopyranoside)-6-O--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 188–191, March–April, 1984.     

Triterpene glycosides ofAstragalus and their genins. VIII. Askendoside C fromAstragalus taschkendicus

A new glycoside of the cycloartane series — askendoside C — has been isolated from the roots of the plantAstragalus taschkendicus Bge., and its structure has been established on the basis of chemical transformations and spectral characteristics as 24R-cycloartane-3,6,16,24,25-pentaol 3-[0--L-arabinopyranosyl-(12)--D-xylopyranoside].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 173–180, March–April, 1983.     

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. 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.     

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 of Astragalus and their genins. XXVII. X-ray structural investigation of cyclogalegigenin

It has been shown by x-ray structural analysis that cyclogalegigenin has the 20S,24R stereochemistry and, consequently, is 20S,24R-epoxycycloartane-3,6,16,25-tetraol. Cyclosieversigenin is 20R,24S-epoxycycloartane-3,6,16,-25-tetraol.Institute of Applied Physics, Acadmy of Sciences of the Moldavian SSR, Kishinev. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 541–546, July–August, 1988.     

Pulchellin C and inuchinenolide C from Inula caspica

The pseudoguaianolide inuchinenolide C and the eudesmanolide pulchellin C have been isolated for the first time from the flower heads and leaves ofInula caspica Blume, and their spatial structures have been established by an x-ray structural experiment as 2,6-diacetoxy-6-hydroxy-1,7(H),8,10(H)-pseudoguai-11(13)-en-8,12-olide and 2,3-dihydroxy-5,7,8(H)-eudesma-4(15),11(13)-dien-8,12-olide, respectively.Institute of Organic Synthesis and Coal Chemistry, Academy of Sciences of the Kazakh SSR, Karaganda. A. N. Nesmeyanov Institute of Organometallic Compounds, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 748–757, November–December, 1990.     

Polysaccharides ofUngernia. VI. A mannan from the bulbs ofUngernia vvedenskyi

The results of a study of the structure of ungeromannan-V fromUngernia vvedenskii Khamidkh by oxidation with chromic oxide and with sodium periodate and by methylation have shown that the monosaccharide residues in it are linked by -1 4 glycosidic bonds. The macromolecule of ungeromannan-V has slight branching.Deceased.Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 770–775, November–December, 1980.     

Triterpene glycosides ofAstragalus and their genins. III. Cycloasgenin a fromAstragalus taschkendicus

The new isoprenoid cycloasgenin A has been isolated from the roots of the plantAstragalus taschkendicus C. Bge., and its structure has been established on the basis of chemical transformations and spectral characteristics as 6,11,16, 25-tetrahydroxy-20(S), 24(R)-epoxycycloartan-3-one.Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 572–581, September–October, 1981.     

Withasteroids ofPhysalis. V. A study of the1H and13C NMR spectra of the withasteroids visconolide and 28-hydroxywithaperuvin C

The PMR and¹³C NMR spectra of new withasteroids — visconolide and 28-hydroxywithaperuvin C, isolated fromPhysalis viscosa L. — have been investigated. A detailed analysis of the spectral characteristics obtained is given. For visconolide is proposed the structure of 4,12,17,28-pentahydroxy-1-oxo-5, 6-epoxy-22R-witha-2,24-dienolide, and for 28-hydroxywithaperuvin C that of 6,14,17,20R, 28-pentahydroxy-l-oxo-22R-witha-2, 4, 24-trienolide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 657–663, September–October, 1985.