Hydroxylation and glucosidation of ent-16β-Hydroxybeyeran-19-oic acid by Bacillus megaterium and Aspergillus niger

Li Ming Yang, Feng-Lin Hsu, Juei Tang Cheng, Cheng Hao Chang, Pan Chun Liu, Shwu Jiuan Lin

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

ent-16β-Hydroxybeyeran-19-oic acid (1) has potential antihypertensive activity. To obtain novel and more-effective compounds, 1 was incubated with Bacillus megaterium ATCC 14581 and Aspergillus niger CCRC 32720. The structures of the metabolites were determined by HR-FAB-MS, 1D- and 2D-NMR spectral data, and enzymatic hydrolysis. Bacillus megaterium hydroxylated and glucosidated 1 to yield ent-7α,16β-dihydroxybeyeran-19-oic acid (2), ent-16β-hydroxybeyeran-19-oic acid α-D-glucopyranosyl ester (3), and ent-7α,16β-dihydroxybeyeran-19-oic acid α-D-glucopyranosyl ester (4). Aspergillus niger hydroxylated 1 to yield ent-1β,7α, 16β-trihydroxybeyeran-19-oic acid (5) and ent-1β,7α-dihydroxy- 16-oxobeyeran-19-oic acid (6). Metabolites 3-5 were characterized as new compounds. In addition, 2, 3, 5, and 6 were tested for antihypertensive effects, and we found that 5 and 6 were more potent than the parent compound 1.

Original languageEnglish
Pages (from-to)359-363
Number of pages5
JournalPlanta Medica
Volume70
Issue number4
DOIs
Publication statusPublished - Apr 2004

Keywords

  • Antihypertensive testing
  • Diterpenoids
  • ent-16β-hydroxybeyeran-19-oic acid
  • Glucosidation
  • Microbial hydroxylation

ASJC Scopus subject areas

  • Plant Science
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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