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Die Cardenolide und Pregnan‐Glykoside der Wurzeln von Asclepias lilacina W EIMARCK . I. Isolierungen Glykoside und Aglykone, 290. Mitteilung
Author(s) -
Sawlewicz Ludwika,
Weiss Ek.,
Reichstein T.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500218
Subject(s) - chemistry , cardenolide , glycoside , stereochemistry , pregnane , hydrolysis , organic chemistry
The dried roots of Asclepias lilacina contain ca. 14% glykosides, in which both cardenolides and ester glycosides of pregnane derivatives are present, the latter predominating. Uzarigenin, coroglaucigenin, and their corresponding glycosides ascleposide and frugoside, resp., were shown to be present; of these four, uzarigenin was isolated in crystalline form. The ester glycosides, some of which could be isolated in a crystalline state, are predominantly composed of the aglycones 20‐O‐acetyl‐12‐O‐benzoyl‐sarcostin and 12,20‐di‐O‐benzoyl‐sarcostin, besides which esters of desacetyl‐metaplexigenin, lineolon, and dihydrosarcostin are also present. These aglycones are mostly attached to various trisaccharides which are composed of at least two 2‐deoxy‐sugar residues. Mild acid hydrolysis gave, besides the genins, 7 sugars, namely cymarose, oleandrose, digitoxose, 3‐O‐methyl‐6‐deoxy‐D‐allose (U3), as well as 3 unknown sugars U1, U2 and U5 which are probably disaccharides. U1 and U2 were isolated in crystalline form; they are isomeric and have been named asclepobiose and lilacinobiose; they are probably composed of units similar to those in the isomeric pachybiose.