Isolation and partial synthesis of 3(R)- and 3(S)-deoxypumiloside; structural revision of the key metabolite from the camptothecin producing plant,Ophiorrhiza pumila |
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| Institution: | 1. Walter Reed National Medical Military Center, Bethesda, MD, USA;2. The Joint Pathology Center, Silver Spring, MD, USA;1. Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China;2. Department of Pharmaceutical Analysis, China Pharmaceutical University, Nanjing 210009, China;3. Department of Pharmacology, China Pharmaceutical University, Nanjing 210009, China;1. School of Food Science and Engineering, South China University of Technology, Guangzhou, 510641, China;2. Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University (BTBU), Beijing, 100048, China;3. Overseas Expertise Introduction Center for Discipline Innovation of Food Nutrition and Human Health (111 Center), Guangzhou, 510641, China;4. National Technology Innovation Center of Synthetic Biology, Tianjin, 300308, China |
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| Abstract: | Both the C-3 epimeric pair of 3(R)- and 3(S)-deoxypumiloside were found in Ophiorrhiza pumila (Rubiaceae), a source plant of camptothecinoid metabolites. These structures were confirmed by spectroscopic analysis and partial stereoselective syntheses. The configuration at C-3 of the previously reported “deoxypumiloside” is revised to 3(R) from 3(S). |
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