Triterpene glycosides of Acanthophyllum gypsophiloides IV. The structure of acanthophyllosides B and C

Summary Alternative structures for the acyloside chain of acanthophylloside B and C have been established.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 728–734, November–December, 1975.     

Triterpene glycosides ofAcanthophyllum gypsophiloides

Chemistry of Natural Compounds -     

Triterpene glycosides of plants of the family Caryophyllaceae

In this review, tables of 25 glycosides are given and the previously unknown structures of 11 of them are established. Characteristic features of the glycosides of the family Caryophyllaceae are considered. Methods are shown for isolating the glycosides and, using acanthophylloside B — a compound having carbohydrate chains of complex structure — as example, methods of determining their structures are demonstrated.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 417–433, July–August, 1981. Original article submitted May 6, 1981.     

Triterpene glycosides ofSilphium perfoliatum. III. Structure of silphioside E

A new triterpene glycoside — silphioside E — has been isolated from the epigeal part ofSilphium perfoliatum L. and its structure has been established on the basis of chemical transformations and spectral characteristics as oleanolic acid 28-0-β-D-glycopyranoside 3-0-[0-β-D-glycopyranosyl-(1 → 2)-β-D-glucopyranoside].     

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.