Biotransformation of capsaicin by Penicillium janthinellum AS 3.510 |
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| Affiliation: | 1. College of Bioengineering, Beijing Polytechnic, Beijing 100029, China;2. The Second Affiliated Hospital of Dalian Medical University, Dalian 116044, China;3. College of Pharmacy, Dalian Medical University, Dalian 116044, China;1. Chulabhorn Research Institute, Kamphaeng Phet 6, Talat Bang Khen, Lak Si, Bangkok 10210, Thailand;2. Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, Thailand;1. CAS Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration and Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China;2. Southwest University for Nationalities, Chengdu 610041, PR China;3. Syngenta Jealott’s Hill International Research Centre, Berkshire RG42 6EY, UK;1. Key Laboratory of Tibetan Medicine Research of CAS and Key Laboratory for Tibetan Medicine of Qinghai Province, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, PR China;2. Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China;1. National Research Institute of Brewing, 3-7-1 Kagamiyama, Higashi-hiroshima, Hiroshima 739-0046, Japan;2. LECO Japan Corporation, 2-13-4 Shiba, Minato-ku, Tokyo 105-0014, Japan;1. Unidad de Biotecnología, Centro de Investigación Científica de Yucatán, A.C. (CICY), Calle 43 #130 (32 y 34), Col. Chuburná de Hidalgo, Mérida, Yucatán, 97205, Mexico;2. Unidad de Investigación Médica, Centro Médico Ignacio García Téllez, Instituto Mexicano del Seguro Social (IMSS), Calle 41 No. 439, Col. Industrial, Mérida, Yucatán, 97150, Mexico;1. Ecole Nationale Supérieure de Chimie de Rennes/Université de Rennes 1, CNRS, UMR 6226, 11 allée de Beaulieu, CS 50837, 35708 Rennes cedex 7, France;2. Université de Rennes 1, CNRS, UMR 6226, Equipe Matière Condensée et Systèmes Electroactifs, Campus de Beaulieu, 35042 Rennes cedex, France;3. Université Européenne de Bretagne, 5 boulevard Laënnec, 35000 Rennes, France |
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| 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. |
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| Keywords: | Capsaicin Biotransformation |
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