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.     

Triterpene glycosides of alfalfa. IV. Medicoside J

A new triterpene glycoside has been isolated from the roots ofMedicago sativa L. (family Fabaceae) — medicoside J, and its structure has been established as a medicagenic acid 3-O-β-D-glucopyranoside 28-O-[O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside].     

Triterpene glycosides of alfalfa. IV. Medicoside J

A new triterpene glycoside has been isolated from the roots ofMedicago sativa L. (family Fabaceae) — medicoside J, and its structure has been established as a medicagenic acid 3-O--D-glucopyranoside 28-O-[O--D-xylopyranosyl-(1 4)-O--L-rhamnopyranosyl-(1 2)--L-arabinopyranoside].Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 610–613, September–December, 1986.     

Triterpene glycosides of alfalfa. V. Medicoside H

A new triterpene glycoside — medicoside H — has been isolated from the roots ofMedicago sativa L. (Fabaceae), and on the basis of chemical transformations and spectral characteristics its structure has been established as medicagenic acid 3-O-β-D-glucopyranoside 28-O-[O-α-L-rhamnopyronosyl-(1 → 2)-β-L-arabino-pyranoside]. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 673–677, September–October, 1989.     

Triterpene glycosides of alfalfa. V. Medicoside H

A new triterpene glycoside — medicoside H — has been isolated from the roots ofMedicago sativa L. (Fabaceae), and on the basis of chemical transformations and spectral characteristics its structure has been established as medicagenic acid 3-O--D-glucopyranoside 28-O-[O--L-rhamnopyronosyl-(1 2)--L-arabino-pyranoside].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 673–677, September–October, 1989.     

Triterpene glycosides ofSilphium perfoliatum. IV. Structure of siliphioside C

A passage from deca-1,4,9-triene (I) to (E,E)-dodeca-8,10-dienol (II) in five stages with an overall yield of 23% has been found by the selective transformations of deca-1,4,9-trien-1-yltrimethylsilane. Thus, under mild conditions, by the hydrogenation of (I) with the aid of 9-borabicyclo[3.3.1]nonane (9-BBN) followed by oxidation with H₂O₂ (E,E)-deca-6,8-dienol was obtained with a yield of 60%, and this was converted quantitatively into the corresponding tosylate. The ethynylation of the latter with lithium acetylide gave (E,E)-dodecadien-1-yne (III) on a Lindlar catalyst followed by the reaction of the resulting triene with 9-BBN, as described above for (I) led to the desired codlemone (II). The IR, PMR,¹³C NMR, UV, and mass spectra of the compound obtained are discussed.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 514–518, July–August, 1984.     

Triterpene glycosides of Hedera taurica VI. Structures of hederosides G,H1, H2, and I from the berries of Crimean ivy

We have isolated from Crimean ivy berries in addition previously known triterpene glycosides — 3-O-α-L-arabinopyranosyl-28-O-[O-α-L-rhamnopyranosyl-(1 → 4)-O-β-D-glycopyranosyl-(1 → 6)-β-D-glucopyranosyl]hederagenin, 3-O-[O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl]-28-O-[O-α-L-rhamnopyranosyl-(1 → 4)-O-β-D-glucopyranosyl-(1 → 6)-β-D-glycopyranosyl]hederagenin, the new triterpene glycosides hederoside H₂-3-O-[O-β-D-glycopyranosyl-(1 → 2)-β-D-glycopyranosyl-(1 → 2)-β-D-glucopyranosyl]-28-O-[O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]oleanolic acid- and hederoside I-3-O-[O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-28-O-[O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl]hederagenin. Details of their¹³C NMR spectra are given. M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 779–783, November–December, 1990.     

Triterpene glycosides of Gleditschia triacanthos IV. The structure of triacanthosides A1 and G

Summary The pericarps ofGleditschia triacanthos L. have yielded a new triterpene glycoside — triacanthoside A₁ — and it has been shown that it has the structure of echynocystic acid 3-O-[-D-xylopyranosyl-(14)--L-arabopyranosyl-(13)--D-glucopyranoside].It has been shown that the O-glycosidic moiety of triacanthoside G coincides in structure with triacanthoside A₁. The O-acyloside moiety of triacanthoside G contains the trisaccharide D-glucopyranosyl-(13)-O-L-arabopyranosyl-(14)-O-L-rhamnopyranose.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 314–316, May–June, 1973.     

Triterpene glycosides ofHedera canariensis IV. Structures of glycosides L-F3, L-G0, and L-Gla from the leaves of Algerian ivy

Three minor partially acetylated glycosides have been isolated from the leaves of Algerian ivy, Hedera canariensis Willd. (Araliaceae) — the previously known {3-O-[-L-rhamnopyranosyl-(12)-O--L-arabinopyranoside] 28-O-[-L-rhamnopyranosyl-(14)-O-(6-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranoside}s of oleanolic acid and of hederagenin (ciwujianoside C₄ and kizuta saponin K₁₁) and the new 3-O-[-L-rhamnopyranosyl-(12)--O-L-arabinopyranoside] 28-O-[-L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranoside of echinocystic acid (glycoside L-G₀). The structures of the glycosides isolated have been established on the basis of chemical transformations and¹H and¹³C NMR spectroscopy.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 81–86, January–February, 1999.     

Triterpene glycosides of Thalictrum squarrosum. III. Structures of squarrogenins 1 and 2

Two genins — squarrogenin 1 and squarrogenin 2 — have been isolated from nodding meadow rue by the hydrolysis of squarrosides A1 and A2. The compounds are epimeric at C-21 and have the following structures: 1 — (21R, 22S, 23R)-21-methoxy-21,23-epoxycycloart-24-ene-3,22-30-triol, C₃₁H₅₀O₅, mp 169–171°C (hexane-acetone), [] ₅₄₆ ²⁰ –11.06° (c 4.52; pyridine); and 2 — (21S, 22S, 23R)-21-methoxy-21,23-epoxycycloart-24-ene-3,22,30-triol, C₃₁H₅₀O₅, mp 190–193°C (hexane-acetone), [] ₅₄₆ ²⁰ +106.6° (c 0.3; pyridine). The results of¹H and¹³C NMR spectroscopy and of mass spectrometry for the new compounds are given.Irkutsk Institute of Organic Chemistry, Siberian Division of the USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 510–516, July–August, 1989.     

Triterpene glycosides of Thalictrum squarrosum. III. Structures of squarrogenins 1 and 2

Two genins — squarrogenin 1 and squarrogenin 2 — have been isolated from nodding meadow rue by the hydrolysis of squarrosides A1 and A2. The compounds are epimeric at C-21 and have the following structures: 1 — (21R, 22S, 23R)-21-methoxy-21,23-epoxycycloart-24-ene-3β,22β-30-triol, C₃₁H₅₀O₅, mp 169–171°C (hexane-acetone), [α] ₅₄₆ ²⁰ ?11.06° (c 4.52; pyridine); and 2 — (21S, 22S, 23R)-21-methoxy-21,23-epoxycycloart-24-ene-3β,22β,30-triol, C₃₁H₅₀O₅, mp 190–193°C (hexane-acetone), [α] ₅₄₆ ²⁰ +106.6° (c 0.3; pyridine). The results of¹H and¹³C NMR spectroscopy and of mass spectrometry for the new compounds are given.     

Triterpene glycosides of Hedera pastuchovii IV. The structure of pastuchoside B

Summary Pastuchoside B has been isolated and shown to be O--D-glycopyranosyl-(1 4)-O--D-glucopyranosyl-(1 3)-hederagenin.N. Narimanov Azerbaidzhan Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 425–429, July–August, 1971.     

Triterpene glycosides and their genins fromThalictrum foetidum. IV. Structure of cyclofoetigenin B

A glycoside isolated from the epigeal part ofThalictrum foetidum (Ranunculaceae) has yielded a new genin — cyclofoetigenin B — the structure of which has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,16,24,25,30-pentaol.Irkutsk Institute of Organic Chemistry of the Siberian Branch of the Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 312–320, May–June, 1986.