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Tacamine-type alkaloids from Tabernaemontana bovina together with their configuration determination
Affiliation:1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;3. Bristol-Myers Squibb Co., Lawrenceville, NJ 08648, USA;4. Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, China;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;2. School of Public Health, Kunming Medical University, Kunming 650500, China;3. Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, China;4. Department of Botany and Biodiversity Research, University of Vienna, Rennweg 14, A-1030 Vienna, Austria;1. Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan;2. Research Center for Infectious Disease Control, Research Institute for Microbial Diseases, Osaka University, 3-1 Yama-daoka, Suita, Osaka 565-0871, Japan;3. National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki, Kanagawa 210-9501, Japan;4. Department of Malaria Vaccine Development, Research Institute for Microbial Diseases, Osaka University, 3-1 Yamadaoka, Suita, Osaka 565-0871, Japan;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China;2. University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China;3. School of Traditional Chinese Medicine, Guangdong Pharmaceutical University, Guangzhou 510006, People’s Republic of China;1. Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907, United States;2. Department of Biological Sciences, Purdue University, West Lafayette, IN 47907, United States;3. Interdepartmental NMR Facility, Purdue University, West Lafayette, IN 47907, United States;4. Department of Chemistry, Purdue University, West Lafayette, IN 47907, United States
Abstract:Eleven undescribed tacamine type alkaloids, named tabercamines A–K were isolated from leaves of Tabernaemontana bovina, together with six known alkaloids. The planar structure of the undescribed alkaloids were determined by comprehensive spectroscopic data analysis. Their absolute configuration were established based on the combination of the electronic circular dichroism and single X-ray crystal diffraction analysis. The NMR rules (in acetone-d6) of identifying of the stereo-configuration at C-20/16 was established.
Keywords:Tacamine alkaloids  Tabercamines A–K  Configuration determination
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