Biotransformation of 4-Hydroxybenzen Derivatives by Hairy Root Cultures of Polygonum multiflorum Thunb. |
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Authors: | Chun-Yan Yan Rong-Min Yu Zhang Zhang Ling-Yi Kong |
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Institution: | Department of Natural Medicinal Chemistry, College of Traditional Chinese Medicines, China Pharmaceutical University, Nanjing 210038, China;Department of Natural Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Jinan University, Guangzhou 510632, China |
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Abstract: | The biotransformation of four 4-hydroxybenzen derivatives (1,4-benzenediol (compound 1), 4-hydroxybenzaldehyde (compound 2), 4-hydroxybenzyl alcohol (compound 3) and 4-hydroxybenzoic acid (compound 4)) by the hairy root cultures of Polygonum multiflorum Thunb. as a new biocatalyst was investigated. It was found that the substrates were transformed to their corresponding glucosides, 4-hydroxyphenyl β-D-glucopyranoside (arbutin, compound 1a), 4-hydroxymethylphenyl β-D-glucopyranoside (gastrodin, compounds 2a, 3a) and 4-carboxyphenyl α-Dglucopyranoside (compound 4a), respectively. In the meantime, the hairy roots of P. multlflorum were able to stereoselectively and regioselectively glucosylate phenolic hydroxyl groups of compounds 1-4, but the cultures could not glucosylate the aldehyde group of compound 2 or the benzylic hydroxyl group of compound 3, and no glucosyl esterification of carboxyl groups of compound 4 was detected. On the other hand, the result also showed that the hairy roots of P. multiflorum were able to reduce the 4-hydroxybenzaldehyde to its corresponding alcohol.This is the first report that substrate 4 has been converted into its α-D-glucopyranoside by a plant biotransformation system. |
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Keywords: | 4-hydroxybenzen derivatives arbutin biotransformation gastrodin hairy root cultures Polygonum multiflorum |
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