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Oxidative biotransformation of stemofoline alkaloids

Journal Article


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.

Publication Date


  • 2021

Citation


  • Phaya, M., Chalom, S., Ingkaninan, K., Ounnunkad, K., Chandet, N., Pyne, S. G., & Mungkornasawakul, P. (2021). Oxidative biotransformation of stemofoline alkaloids. Artificial Cells, Nanomedicine and Biotechnology, 49(1), 166-172. doi:10.1080/21691401.2021.1883044

Scopus Eid


  • 2-s2.0-85100831015

Start Page


  • 166

End Page


  • 172

Volume


  • 49

Issue


  • 1

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.

Publication Date


  • 2021

Citation


  • Phaya, M., Chalom, S., Ingkaninan, K., Ounnunkad, K., Chandet, N., Pyne, S. G., & Mungkornasawakul, P. (2021). Oxidative biotransformation of stemofoline alkaloids. Artificial Cells, Nanomedicine and Biotechnology, 49(1), 166-172. doi:10.1080/21691401.2021.1883044

Scopus Eid


  • 2-s2.0-85100831015

Start Page


  • 166

End Page


  • 172

Volume


  • 49

Issue


  • 1