Biosynthesis of artemisinin in Artemisia annua |
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| Affiliation: | 1. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan;2. Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan;3. Kunming Institute of Botany, Chinese Academy of Science, Kunming 650204, China;4. Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan;1. College of Pharmaceutical Science, Soochow University, 199 Ren Ai Road, Suzhou 215123, China;2. Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, #190 Kaiyuan Avenue, Guangzhou 510530, China;3. Molecular Imaging Laboratory, MGH/MIT/HMS Athinoula A. Martinos Center for Biomedical Imaging, Department of Radiology, Massachusetts General Hospital/Harvard Medical School, Building 75, Charlestown, MA 02129, United States;1. Department of Traditional Chinese Orthopedics, Shanghai East Hospital, Tongji University School of Medicine, Shanghai, China;2. Department of Emergency Surgery, Shanghai East Hospital, Tongji University School of Medicine, Shanghai, China;3. Department of Rheumatology and Immunology, Shanghai East Hospital, Tongji University School of Medicine, Shanghai, China |
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| Abstract: | The isotope ratios (3H:14C) in arteannuin B and artemisinin biosynthesized in Artemisia annua from [4R-3H1,2-14C]-, [5-3H2,2-14C]- and [2-3H2,2-14C](3RS)- mevalonate have revealed that two specific 1,2-hydride shifts take place during the oxidation and lactonization of the germacrane skeleton to yield dihydrocostunolide. The gem-methyls of DMAPP retain their identity until the final steps of artemisinin biosynthesis. Arteannuin B is considered to be a late precursor of artemisinin and the following biosynthetic sequence is suggested: farnesylpyrophosphate → germacrane skeleton → dihydrocostunolide → cadinanolide → arteannuin B → artemisinin. |
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