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Cardenolide und Pregnanderivate aus den Wurzeln von Trachycalymma fimbriatum (W EIMARCK ) B ULLOCK Glykoside und Aglykone, 322. Mitteilung
Author(s) -
Elber R.,
Weiss Ek.,
Reichstein T.
Publication year - 1969
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.19690520841
Subject(s) - chemistry , cardenolide , pregnane , stereochemistry , hydrolysis , glycoside , biochemistry
The roots of Trachycalymma fimbriatum (W EIMARCK ) B ULLOCK contain both cardenolide and pregnaneglycosides. Elimination of 2‐deoxysugars by mild acid hydrolysis gave a mixture from which some anhydroderivatives and the following compounds could be isolated: uzarigenin ( l ), ascleposide = 3‐O‐(6‐deoxy‐β‐ D ‐allopyranosyl)‐uzarigenin ( 4 ), coroglaucigenin ( 6 ) and two pregnane derivatives (H and J). Compound H could be identified as 3β,14β‐dihydroxy5α, 17α‐pregnan‐20‐one ( 10 ). Compound J is probably a new substance, for which we tentatively assign structure 18 , i.e. 3β8β,14β‐trihydroxy‐5α,17α‐pregnan‐20‐one. We suspect H and J to be artefacts produced from the corresponding 17b‐derivatives during acid hydrolysis. 17‐iso‐H is probably a precursor in the biosynthesis of uzarigenin. The cardenolides of Trachycalymma fimbriatum are the same as found in Asclepias glaucophylla, a closely related species, while the pregnane derivatives of the latter are distinctly higher hydroxylated.