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 journalArticle

14 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

Fingerprint

Bacillus megaterium
Hydroxylation
Aspergillus niger
Aspergillus
hydroxylation
Bacilli
Acids
acids
antihypertensive effect
Metabolites
Antihypertensive Agents
Esters
esters
metabolites
Enzymatic hydrolysis
enzymatic hydrolysis
spectral analysis
Hydrolysis
Nuclear magnetic resonance

Keywords

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

ASJC Scopus subject areas

  • Plant Science
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Hydroxylation and glucosidation of ent-16β-Hydroxybeyeran-19-oic acid by Bacillus megaterium and Aspergillus niger. / Yang, Li Ming; Hsu, Feng-Lin; Cheng, Juei Tang; Chang, Cheng Hao; Liu, Pan Chun; Lin, Shwu Jiuan.

In: Planta Medica, Vol. 70, No. 4, 04.2004, p. 359-363.

Research output: Contribution to journalArticle

Yang, Li Ming ; Hsu, Feng-Lin ; Cheng, Juei Tang ; Chang, Cheng Hao ; Liu, Pan Chun ; Lin, Shwu Jiuan. / Hydroxylation and glucosidation of ent-16β-Hydroxybeyeran-19-oic acid by Bacillus megaterium and Aspergillus niger. In: Planta Medica. 2004 ; Vol. 70, No. 4. pp. 359-363.
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