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Glykoside von Marsdenia erecta R. Br. 2. Mitteilung: Versuche zur Strukturbestimmung der Genine. Glykoside und Aglykone, 330. Mitteilung
Author(s) -
Saner A.,
Stöckel K.,
Reichstein T.
Publication year - 1972
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.19720550419
Subject(s) - chemistry , pregnane , glycoside , hydrolysis , stereochemistry , organic chemistry
Structures for the genins of the ester glycosides of Marsdenia erecta are suggested. They are based on the behaviour in alkaline hydrolysis of these ester glycosides, their NMR. and mass spectra and ORD. data. All genins are derived from three acyl‐free pregnane derivatives, i.e. drevogenin‐P ( 1 ), 17 β‐marsdenin ( 3 ) and marsectohexol ( 7 ). The structure of 1 is known, 3 and 7 are new compounds, i.e. 3 = 3β,8β,11α,12β,14β‐pentahydroxy‐Δ 5 ‐pregnen‐20‐one and 7 = 3β,8β,11α,12β,14β,20ξ‐hexahydroxy‐Δ 5 ‐pregnene. Formulae 13–17 were attributed to the acyl‐genins A‐1, A‐2, A‐3, A‐4 and A‐5, but only two of them were pure compounds, i.e . acyl‐genin A‐3 = 11,12‐di‐O‐tiglyl‐17β‐marsdenin ( 15 ) and acyl‐genin A‐5 = 11,12‐di‐O‐acetyl‐marsectohexoi ( 17 ). Acyl‐genin A‐1 is a mixture of the two esters 13a + 13b derived from drevogenin‐P, and similarly acyl‐genin A‐2 is a mixture of the esters 14a + 14b derived from 17β‐marsdenin. The poorly characterised acyl‐genin A‐4 is most probably a mixture of the esters 16a + 16b , also derived from 17β‐marsdenin.