Triterpene glycosides of Acanthophyllum gypsophiloides III. Structure of the O-glycosidic carbohydrate chain of acanthophyllosides B and C

Summary From an extract of the roots ofAcanthophyllum gypsophiloides we have isolated new triterpene glycosides — acanthophylloside B (a gypsogenin decaoside) and acanthophylloside C (a gypsogenin undecaoside). Acanthophylloside C differs from acanthophylloside B by the presence of glucose, bound to the carboxy group of D-glucuronic acid.On saponification with alkali, acanthophyllosides B (I) and C (II) split off the acyloside carbohydrate chain and form a progenin — a gypsogenin tetraoside (III). The carbohydrate chain of (III) is attached at position 3 and has the structure [O-D-galactopyranosyl-(1 4)-O-L-arabopyranosyl-(1 4)]-[O-D-galactopyranosyl-(1 2)]-D-glucuronopyranose.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 177–183, March–April, 1975.     

Triterpene glycosides ofAcanthophyllum gypsophiloides

Chemistry of Natural Compounds -     

Triterpene glycosides ofAcanthophyllum gypsophiloides V. D-quinovose in acanthophyllosides B and C

Summary It has been established that the carbohydrate moiety of acanthophyllosides B and C contain D-quinovose. Corrected structural formulas of acanthophyllosides B and C have been put forward. The hypothesis has been expressed that D-quinovose is present in a number of glycosides isolated from plants of the family Caryophyllaceae.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–809, November–December, 1977.     

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 ofAcanthophllum gypsophiloides VI. Structure of acanthophylloside D

Summary A new triterpene glycoside — acanthophylloside D — has been isolated from the roots ofAcanthophyllum gypsophiloides Rgl. It is a decaoside of quillaic acid containing O-glycosidic and O-acylosidic carbohydrate chains identical in structure with the analogous fragments of acanthophylloside B.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 176–180, March–April, 1979.     

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 ofCauliphyllum robustum. The structures of caulosides B and C

Summary Two triterpene glycosides — caulosides b and c — have been isolated from a methanolic extract of the leaves ofCaulophyllum robustum maxim. Cauloside b has been identified as hederagenin 3--L-rhamnopyranosyl-(12)--L-arabinopyranoside, while cauloside c has the structure of hederagenin 3-0--L-arabinopyranosyl(13)--L-pyranosyl-(12)--L-arabinopyranoside.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 174–176, March–April, 1979.     

Triterpene glycosides of Gypsophila patrinii III. The structure of philoside B

Summary The structure of philoside B — a gypsogenin nonaoside isolated from the roots ofGypsophila patrinii — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan'Branch, Academy of Sciences of the USSR. Correspondence Institute of Soviet Commerce. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 603–607, September–October, 1974.     

Triterpene glycosides ofSilphium perfoliatum. IV. Structure of siliphioside C

The epigeal part ofSilphium perfoliatum has a yielded a new triterpene glycoside, silphioside C — C₅₀H₈₀O₁₉, mp 207–210°C (from aqueous methanol), []_D ²⁵ +19.3 ± 2°C (c 0.88; methanol). On the basis of acid hydrolysis, mild alkaline saponification, and the results of GLC and of IR, mass, and¹H and¹³C spectroscopy the structure of silphioside C had been established as 28--D-glucopyranosyl 3-O-[O--D-glucopyranosyl-(12)-(6-O-acetyl--D-glucopyranosyl)oleanolate.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pyatigorsk Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii. No. 4, pp. 519–522, July–August, 1985.