Title

Oxidative biotransformation of stemofoline alkaloids

Publication Name

Artificial Cells, Nanomedicine and Biotechnology

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 (IC = 11.01 ± 1.49 µM) than its precursor 1a (IC = 45.1 ± 5.46 µM) as an inhibitor against acetylcholinesterase. 50 50

Open Access Status

This publication may be available as open access

Volume

49

Issue

1

First Page

166

Last Page

172

Funding Sponsor

Chiang Mai University

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Link to publisher version (DOI)

http://dx.doi.org/10.1080/21691401.2021.1883044