Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159

Feng-Lin Hsu, Li Ming Yang, Shwu Fen Chang, Li Hsuan Wang, Chung-Yi Hsu, Pan Chun Liu, Shwu Jiuan Lin

Research output: Contribution to journalArticle

11 Citations (Scopus)

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-β-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.

Original languageEnglish
Pages (from-to)659-666
Number of pages8
JournalApplied Microbiology and Biotechnology
Volume74
Issue number3
DOIs
Publication statusPublished - Mar 2007

Fingerprint

Beauveria
Gallic Acid
Biotransformation
Metabolites
Pyrans
Acids
Fermentation
Vanillic Acid
Benzoic Acid
Mammals
Benzoic acid
Genistein
Methylprednisolone
Response Elements
Bioactivity
Luciferases
Reporter Genes
Soybeans
Metabolism
Toxicology

Keywords

  • Beauveria sulfurescens
  • Biotransformation
  • Gallic-acid

ASJC Scopus subject areas

  • Biotechnology
  • Microbiology
  • Bioengineering
  • Microbiology (medical)

Cite this

Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. / Hsu, Feng-Lin; Yang, Li Ming; Chang, Shwu Fen; Wang, Li Hsuan; Hsu, Chung-Yi; Liu, Pan Chun; Lin, Shwu Jiuan.

In: Applied Microbiology and Biotechnology, Vol. 74, No. 3, 03.2007, p. 659-666.

Research output: Contribution to journalArticle

Hsu, Feng-Lin ; Yang, Li Ming ; Chang, Shwu Fen ; Wang, Li Hsuan ; Hsu, Chung-Yi ; Liu, Pan Chun ; Lin, Shwu Jiuan. / Biotransformation of gallic acid by Beauveria sulfurescens ATCC 7159. In: Applied Microbiology and Biotechnology. 2007 ; Vol. 74, No. 3. pp. 659-666.
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