Oxidative biotransformation of stemofoline alkaloids.

Abstract:

:Biotransformations of stemofoline (1a), (2'S)-hydroxystemofoline (2a), (11Z)-1',2'-didehydrostemofoline (3a) and stemocurtisine (4) were studied through fermentation with Cunninghamella elegans TISTR 3370. Three new stemofoline derivatives; 6 R-hydroxystemofoline (1b), (2'S, 6 R)-dihydroxystemofoline (2b) and (11Z,6R)-1',2'-didehydro-6-hydroxystemofoline (3b), together with the known compound 1',2'-didehydrostemofoline-N-oxide (3c), were produced by C-hydroxylation and N-oxidation reactions. Stemocurtisine was not biotransformed under these conditions. The transformed product 1b was four times more potent (IC50 = 11.01 ± 1.49 µM) than its precursor 1a (IC50 = 45.1 ± 5.46 µM) as an inhibitor against acetylcholinesterase.

authors

Phaya M,Chalom S,Ingkaninan K,Ounnunkad K,Chandet N,Pyne SG,Mungkornasawakul P

doi

10.1080/21691401.2021.1883044

keywords:

["Biotransformation","Cunninghamella elegans","Stemona alkaloids","stemofoline"]

subject

Has Abstract

pub_date

2021-12-01 00:00:00

pages

166-172

issue

1

eissn

2169-1401

issn

2169-141X

journal_volume

49

pub_type

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