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 language | English |
|---|---|
| Pages (from-to) | 359-363 |
| Number of pages | 5 |
| Journal | Planta Medica |
| Volume | 70 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Apr 2004 |
Keywords
- Antihypertensive testing
- Diterpenoids
- Glucosidation
- Microbial hydroxylation
- ent-16β-hydroxybeyeran-19-oic acid
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry