Triterpene glycosides of Astragalus and their genins XXXV. Cycloaraloside C from Astragalus amarus

A new triterpene glycoside of the cycloartane series (cycloaraloside C) has been isolated from the roots of the plantAstragalus amarus Pall. (Leguminosae). Cycloaraloside C is a bioside of cyclosieversigenin including one D-glucose residue and one D-apiose residue. The structure of the glycoside has been shown on the basis of the chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 3-O-[O-(D-apio--D-furanosyl)-(1 2)--D-glucopyranoside]. This is the first time that D-apiose has been found among cycloartane glycosides.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 783–787, November–December, 1990.     

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 XXXIV. Cycloaraloside E from Astragalus amarus

Five compounds of glycosidic nature, designated 5–9 have been isolated from the roots of the plantAstragalus amarus Pall. (Leguminosae). The structure of substance 8, which has been called cycloaraloside E, has been shown on the basis of chemical transformations and spectral characteristics. Cycloaraloside E is 20R, 24S-epoxycycloartane-3,6,16,25-tetraol 3,25-di-0--D-glucopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 656–659, September–October, 1990.     

Coronillobiosidol — A cardenolide glycoside from seeds of Coronilla scorpioides

The seeds ofCoronilla scorpioides have yielded a new cardenolidic bioside, which has been called coronillobiosidol and has the structure of 3-O-[O--D-glucopyranosyl-(1 4)--D-glucopyranosyl]-14, 19-dihydroxy-5-card-20(22)-enolide.Khar'kov State Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 726–728, September–October, 1988.     

Triterpene glycosides of the holothurian Eupentacta pseudoquinquisemita

The holothurianEupentacta pseudoquinquisemita Deichmann collected in Kraternaya Bay, Ushishir Islands has yielded two triterpene pentaosides — the previously known cucumarioside C₂, and cucumarioside H, which is a new glycoside. With the aid of¹³C NMR spectroscopy and solvolytic desulfation its structure has been determined as 6-acetoxy-3-([3-O-methyl--D-xylopyranosyl-(1 3)--D-glucopyranosyl-(1 4)] [-D-xylopyranosyl-(1 4)] [-D-xylopyranosyl-(1 2)]--D-quinovopy-ranosyl-(1 2)-(4-O-sulfato--D-xylopyranosyloxy)holosta-7,22,24(trans)-triene. Cucumarioside H was also identified inEupentacta (=Cucumaria)fraudatrix from Posyet Bay, Sea of Japan.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 221–225, March–April, 1988.     

Two new triterpene glycosides from the holothurian Duasmodactyla kurilensis

Two new glycosides have been isolated from the total triterpene glycosides of the holothurianDuasmodactyla kurilensis: kurilosides A (III) and C (IV). It has been established that (III) is 16-acetoxy-3-{[O--D-glucopyranosyl-(1 4)-O--D-quinovopyranosyl-(1 2)]-[O-(3-O-methyl--D-glucopyranosyl)-(1 3)-O-(6-O-(sodium sulfato)--D-glucopyranosyl)-(1 4)]--D-xylopyranosyloxy}-4,4,14-trimethylpregen-9(11)-en-20-one, while the minor glycoside (IV) is 16-acetoxy-3-{O--D-quinovopyranosyl-(1 2)-[O-(3-O-methyl--D-glucopyranosyl-(1 3)-O-(6-O-(sodium sulfato)--D-glucopyranosyl)-(1 4)]--D-xylopyranosyloxy}-4,4,14-trimethylpregn-9(11)-en-20-one.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 221–226, March–April, 1991.     

Triterpene glycosides of Astragalus and their genins XXX. Cycloaraloside A from Astragalus amarus

In addition to -sitosterol, cyclosieversigenin, and -sitosterol -D-glucopyranoside, the roots of the plantAstragalus amarus Pall. (Leguminosae) have yielded a new triterpene glycoside of the cycloartane series — cycloaraloside A, which has the structure of 2OR,24S-epoxycycloartane-3,6,16,25-tetraol 3-O--D-glucopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–809, November–December, 1989.     

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.     

Phytoecdysteroids ofSilene nutans. III. Nusilsterone

A new ecdysteroid — nusilsterone — has been insolated from the whole plantSilene nutans L. It has been shown that it is 1,2,3,14,20R,22R,24,25-octahydroxy-5--cholest-7-en-6-one.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii. No. 4, pp. 522–525, July–August, 1985.     

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.     

New polyhydroxysteroids from the far-eastern starfish Henricia sp.

From the far-eastern starfishHenricia sp. we have isolated and characterized the new polyhydroxysteroid (24S)-5-cholestane-3,4,6,8,15,24-hexaol and three new glycosides: (24S)-5-cholestane-3,4,6,8,15,24-hexaol 3-O-(2,4-di-O-methyl--D-xylopyranoside) (henricioside H₁), 24-methyl-5-cholesta-4,22E-diene-3,6,8,15,16,26-hexaol 3-O-(2,3-di-O-methyl--D-xylopyranoside) (henricioside H₂), and the 22,23-dihydro derivative of henricioside H₂ (henricioside H₃).Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 249–253, March–April, 1993.     

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 ofSophora japonica seeds

We have isolated from the seeds of Sophora japonica the known soyasaponogenol B-3-[O--D-glucopyranosyl-(12)-O--D-glucopyranuronoside] (adzukisaponin II), soyasapogenol B [3-O--galactopyranosyl-(12)-O--L-glucopyranuronoside] (soyasaponin III), soyasapogenol B 3-(O--L-rhamnopyranosyl-(12)-O--L-glucopyranosyl-(12)-O--D-glucopyranuronoside] (adzukisaponin V), soyasapogenol B 3-(O--D-rhamnopyranosyl-(12)-O--D-galactopyranosyl-(12)-O--D-glucopyranuronoside] (soyasaponin I), and the new glycoside (1) — soyasapogenol B 3-[O--D-glucopyranuronoside]. The structure of this glycoside has been established on the basis of the results of enzymatic, complete, and partial hydrolyses and¹³C NMR spectra.Simferopol' State University and Kursk State Medical Institute, Kursk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 709–713, September–October, 1995. Original submitted March 3, 1995.     

Radiation-induced reactions of cholesterol in an aqueous medium

⁶⁰Co -ray radiolysis of cholesterol /3-hydroxy-5-cholestene/ /I/ in the two-phase system /water-ethyl acetate/ and in the presence of air has been studied using TLC and GC methods. The following products were observed in the irradiated mixture: 3, 7-dihydroxy-5-cholestene /II/, G O. 36, 3-hydroxy-7-keto-5-cholestene /III/, G 1.48, 3-hydroxy-7-keto-5-cholestane /IV/, G 0.22, 3,5,6-trihydroxy-5-cholestane /V/, G 0.83, 5,6-epoxy-3-hydroxy-5-cholestane /VIa/, G 0.26, 5,6-epoxy-3-hydroxy-5-cholestane /VIb/, G 0.24, and 2, 3-dihydroxy-5-cholestene /VII/, G 0.22. The dose dependence of the formation of these products shows that the cholesterol derivatives substituted in the position 7 /II–IV/ are formed from a common precursor — the radical Ia. On the other hand, the products of the 5–C=C double bond reactions /V and VI/ are formed independently. Also the product VII is formed independently. A reaction scheme that is in agreement with these results is proposed.     

Triterpene glycosides of Astragalus and their genins XLIV. Structure of cyclocarposides A and C

The structures of two new cycloartane glycosides — cyclocarposides A and C, isolated from the herbAstragalus coluteocarpus Boiss. — have been established on the basis of spectral characteristics and chemical transformations. Cyclocarposides A and C are: 204R,24S-epoxycycloartane-3,6,17,25-tetraol 3-O-(2-O-acetyl--D-xylopyranoside)6-O-(2-O-acetyl--L-rhamnopyranoside) and 20R,24S-epoxycyloartane-3,6,16,25-tetraol 3-O-(2-O-acetyl--D-xylopyranoside) 6-O--L-rhamnopyranoside, respectively.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Pamir Biological Institute, Tadzhikistan Academy of Sciences, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 694–698, November–December, 1992.     

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 Hedera taurica. IV. Structure of hederosides A1, A2, D1, and D2 from the berries of Crimean ivy

New triterpene glycosides have been isolated from the berries of Crimean ivyHedera taurica Carr. (family Araliaceae) — hederoside A₁ (methyl ester of 3-O--D-glucopyranosylhederagenin) and hederoside D₁ 3-O-[O--D-glucopyranosyl]-(12)--D-glucopyranosyl]hederagenin and also the known glycosides 3-O--D-glucopyranosyloleanolic acid and 3-O-[O--D-glucopyranosyl-(12)--L-arabinopyranosyl]hederagenin. The structures of these compounds were established on the basis of the results of chemical methods and¹H and¹³C NMR spectroscopy.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 228–230, March–April, 1990.     

Structure of psolusoside B — A nonholostane triterpene glycoside of the holothurian genus Psolus

The structure of psolusoside B — a minor triterpene oligoglycoside from the holothurianPsolus fabricii and the main glycoside fromPsolus sp. has been determined by the methods of partial acid hydrolysis, methylation,¹³C NMR, and FAB mass spectrometry as 20S-acetoxy-3-{2-O-[O--D-glucopyranosyl-(1 4)-O--D-glucopyranosyl]-4-O-(6-O-sulfato--D-glucopyranosyl)--D-xylo-pyranosyloxy}holosta-7,25-diene-18,16-carbolactone. 3-[O-(3-O-Methyl-6-O-sulfato--D-glucopyranosyl)-(1 3)-O-(6-O-sulfato--D-glucopyranosyl)-(1 4)-O--D-quinovopyranosyl-(12)--D-xylopyranosyloxy]holosta-9(11),25-dien-16-one (psolusoside A), known previously forPsolus fabricii, has been identified in a holothurian —Psolus sp. — from Kraternaya Bay (island of Ushishir).Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 361–368, May–June, 1989.