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Opposid, vermutliche Struktur . Glykoside und Aglykone, 302. Mitt.
Author(s) -
Hausschildrogat P.,
Weiss E. K.,
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.19670500816
Subject(s) - chemistry , aglycone , stereochemistry , glycoside
The hypothetical structure 1 is proposed for opposide (C 29 H 44 O 11 ), a new glycoside from the seeds of Acokanthera oppositifolia (LAM.) CODD. Opposide is derived from the new aglycone gratogenin, which is most probably the 1β, 3β, 5β, 11α, 14β‐pentahydroxy‐card‐20:22‐enolide ( 8 ) (C 23 H 34 O 7 ) and which is bound glycosidically through position 3 to the α‐pyranosidic form of 6‐desoxy‐L‐talose. The hydrolysis of opposide by HCl in acetone gave an anhydrogenin (C 23 H 32 O 6 ) instead of the intact aglycone. In analogy to the reaction sequence observed by VOLPP and TAMM for ouabagenin, the structure of the anhydrogenin is deduced to be that of a 3β, 5β, 14β‐trihydroxy‐1α, 11α‐epoxy‐card‐20:22‐enolide ( 6 ). The above mentioned structures are based on the course of acetylation and especially on NMR.‐spectra.