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Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159.
Appl Microbiol Biotechnol. 2007 Mar; 74(3):659-66.AM

Abstract

Preparative-scale fermentation of gallic acid (3,4,5-trihydroxybenzoic acid) (1) with Beauveria sulfurescens ATCC 7159 gave two new glucosidated compounds, 4-(3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-methoxy-benzoic acid (4), 3-hydroxy-4,5-dimethoxy-benzoic acid 3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yl ester (7), along with four known compounds, 3-O-methylgallic acid (2), 4-O-methylgallic acid (3), 3,4-O-dimethylgallic acid (5), and 3,5-O-dimethylgallic acid (6). The new metabolite genistein 7-O-beta-D-4''-O-methyl-glucopyranoside (8) was also obtained as a byproduct due to the use of soybean meal in the fermentation medium. The structural elucidation of the metabolites was based primarily on 1D-, 2D-NMR, and HRFABMS analyses. Among these compounds, 2, 3, and 5 are metabolites of gallic acid in mammals. This result demonstrated that microbial culture parallels mammalian metabolism; therefore, B. sulfurescens might be a useful tool for generating mammalian metabolites of related analogs of gallic acid (1) for complete structural identification and for further use in investigating pharmacological and toxicological properties in this series of compounds. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter gene assay was used to initially screen for the biological activity of the 6 compounds, 2-6 and 8, along with 1 and its chemical O-methylated derivatives 9-13. Among the 12 compounds tested, 11-13 were found to be significant, but less active than the reference compounds of methylprednisolone and dexamethasone.

Authors+Show Affiliations

Graduate Institute of Pharmacognosy Science, College of Pharmacy, Taipei Medical University, 250 Wu-Hsing St., Taipei, 110, Taiwan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17111140

Citation

Hsu, Feng-Lin, et al. "Biotransformation of Gallic Acid By Beauveria Sulfurescens ATCC 7159." Applied Microbiology and Biotechnology, vol. 74, no. 3, 2007, pp. 659-66.
Hsu FL, Yang LM, Chang SF, et al. Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. Appl Microbiol Biotechnol. 2007;74(3):659-66.
Hsu, F. L., Yang, L. M., Chang, S. F., Wang, L. H., Hsu, C. Y., Liu, P. C., & Lin, S. J. (2007). Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. Applied Microbiology and Biotechnology, 74(3), 659-66.
Hsu FL, et al. Biotransformation of Gallic Acid By Beauveria Sulfurescens ATCC 7159. Appl Microbiol Biotechnol. 2007;74(3):659-66. PubMed PMID: 17111140.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. AU - Hsu,Feng-Lin, AU - Yang,Li-Ming, AU - Chang,Shwu-Fen, AU - Wang,Li-Hsuan, AU - Hsu,Chung-Yi, AU - Liu,Pan-Chun, AU - Lin,Shwu-Jiuan, Y1 - 2006/11/17/ PY - 2006/06/06/received PY - 2006/09/26/accepted PY - 2006/09/25/revised PY - 2006/11/18/pubmed PY - 2007/6/20/medline PY - 2006/11/18/entrez SP - 659 EP - 66 JF - Applied microbiology and biotechnology JO - Appl. Microbiol. Biotechnol. VL - 74 IS - 3 N2 - Preparative-scale fermentation of gallic acid (3,4,5-trihydroxybenzoic acid) (1) with Beauveria sulfurescens ATCC 7159 gave two new glucosidated compounds, 4-(3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-methoxy-benzoic acid (4), 3-hydroxy-4,5-dimethoxy-benzoic acid 3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yl ester (7), along with four known compounds, 3-O-methylgallic acid (2), 4-O-methylgallic acid (3), 3,4-O-dimethylgallic acid (5), and 3,5-O-dimethylgallic acid (6). The new metabolite genistein 7-O-beta-D-4''-O-methyl-glucopyranoside (8) was also obtained as a byproduct due to the use of soybean meal in the fermentation medium. The structural elucidation of the metabolites was based primarily on 1D-, 2D-NMR, and HRFABMS analyses. Among these compounds, 2, 3, and 5 are metabolites of gallic acid in mammals. This result demonstrated that microbial culture parallels mammalian metabolism; therefore, B. sulfurescens might be a useful tool for generating mammalian metabolites of related analogs of gallic acid (1) for complete structural identification and for further use in investigating pharmacological and toxicological properties in this series of compounds. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter gene assay was used to initially screen for the biological activity of the 6 compounds, 2-6 and 8, along with 1 and its chemical O-methylated derivatives 9-13. Among the 12 compounds tested, 11-13 were found to be significant, but less active than the reference compounds of methylprednisolone and dexamethasone. SN - 0175-7598 UR - https://www.unboundmedicine.com/medline/citation/17111140/Biotransformation_of_gallic_acid_by_Beauveria_sulfurescens_ATCC_7159_ L2 - https://dx.doi.org/10.1007/s00253-006-0692-z DB - PRIME DP - Unbound Medicine ER -