Selective oxidation-reduction and esterification of asiatic acid by Pestalotiopsis microspora and anti-HCV activity |
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| Institution: | 1. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, China;2. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China;1. Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan;2. Chemistry Department, Faculty of Science, Helwan University, Cairo 11795, Egypt;1. Department of Radiation Oncology, Hubei Cancer Hospital, Wuhan, China;2. Department of Pathology, Hubei Cancer Hospital, Wuhan 430071, China;1. School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China;2. School of Pharmacy, Guangdong Medical University, Dongguan 523808, China;3. Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China;4. South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou 510006, China;1. School of Pharmacy, Nantong University, Nantong 226001, China;2. School of Medical, Nantong University, Nantong 226001, China |
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| Abstract: | Microbial transformation of asiatic acid (AA) by an endophytic fungus, Pestalotiopsis microspora, yielded six metabolites: 2-oxo-3β,15α,23-trihydroxyurs-12-ene-28-oic acid (1); 2-oxo-3β,15α,22α,23-tetrahydroxyurs-12-ene-28-oic acid (2); 2-oxo-3β,15α,23,30-tetrahydroxyurs-12-ene-28-oic acid (3); 2α,3β,15α,23,30-pentahydroxyurs-12-ene-28-oic acid methyl ester (4); 2α,3α,15α,23-tetrahydroxyurs-12-ene-28-oic acid (5); 2α,3α,15α,23,30-pentahydroxyurs-12-ene-28-oic acid (6). The structure elucidation of these products was confirmed based on the spectroscopic data. Compounds 2–6 were new. A possible biotransformation pathway is proposed. The anti-HCV activity of compounds 1–6 was also evaluated. |
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| Keywords: | Asiatic acid Selective oxidation-reduction Esterification Anti-HCV activity |
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