Transformation of naturally-occurring 1,9-trans-9,5-cis sweroside to all trans sweroside during acetylation of sweroside aglycone.

Abstract:

:From the rootstock of Scabiosa columbria L. loganin and sweroside were isolated. Sweroside showed moderate antibacterial activity. Pure sweroside was converted to the sweroside aglycone 1-acetoxy derivative (DABCO/Ac2O) after hydrolysis of the glucose unit. X-ray crystallography of the monoacetate showed unambiguously that it had been transformed to a new seco-iridoid having the novel trans diaxial configuration for the protons on C-1, C-9 and C-5. The mechanism for the rearrangement is discussed.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Horn MM,Drewes SE,Brown NJ,Munro OQ,Meyer JJ,Mathekga AD

doi

10.1016/s0031-9422(00)00460-x

subject

Has Abstract

pub_date

2001-05-01 00:00:00

pages

51-6

issue

1

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(00)00460-X

journal_volume

57

pub_type

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