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J Asian Nat Prod Res. 2012;14(11):1039-45. doi: 10.1080/10286020.2012.702761. Epub 2012 Oct 29.

Two new oxidation products obtained from the biotransformation of asiatic acid by the fungus Fusarium avenaceum AS 3.4594.

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1
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.

Abstract

Asiatic acid (AA) is a natural triterpenoid possessing anti-inflammatory, anticancer, neuroprotective, and hepatoprotective activities. Structural modification of AA may provide valuable information for further structure-activity relationship analysis. Biotransformation is an efficient, specific, and environment friendly technology for structural modification of complicated natural products. In this study, the capabilities of twenty-five strains of filamentous fungi to transform AA were screened. Two new and one known oxidation products metabolized by Fusarium avenaceum AS 3.4594 were isolated. Their chemical structures were characterized as 2-oxo-3β,15α,23-trihydroxyurs-12-en-28-oic acid (1), 3-oxo-2,15α,23-trihydroxyurs-1,12-dien-28-oic acid (2), and 2-oxo-3β,23-dihydroxyurs-12-en-28-oic-acid (3) by extensive analysis of spectroscopic data.

PMID:
23106376
DOI:
10.1080/10286020.2012.702761
[Indexed for MEDLINE]
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