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Biotransformation of capsaicin by Penicillium janthinellum AS 3.510

Author:
Xin, Xiu-Lan, Wang, Yan, Fan, Guang-Jun, Chen, Liang, Sun, Cheng-Peng
Source:
Phytochemistry letters 2017 v.19 pp. 210-214
ISSN:
1874-3900
Subject:
Penicillium janthinellum, biocatalysis, biotransformation, capsaicin, hydroxylation, metabolites, methylation, nuclear magnetic resonance spectroscopy
Abstract:
Biocatalysis of capsaicin (1) was performed by Penicillium janthinellum AS 3.510. Nine metabolites including four new compounds were afforded, and their structures were elucidated as (8S)-trans-8-hydroxy-8-hydroxymethyl-N-vanillyl-6-nonenamide (2), 6-hydroxy-8-methyl-N-vanillyl-7-nonenamide (3), trans-8-methoxy-8-methyl-N-vanillyl-6-nonenamide (4), 6-methoxy-8-methyl-N-vanillyl-7-nonenamide (5), dihydrocapsaicin (6), ω-1-hydroxydihydrocapsaicin (7), ω-1-hydroxycapsaicin (8), ω-hydroxycapsaicin (9), N-(4-hydroxy-3-methoxybenzyl)-5-[3-(propan-2-yl)oxiran-2-yl]pentanamide (10) by 1D and 2D NMR and HRESIMS spectra. The biotransformation processes include hydroxylation, methylation, reduction, and epoxylation.
Agid:
5629396