Novel biotransformation processes of dihydroartemisinic acid and artemisinic acid to their hydroxylated derivatives by two plant cell culture systems |
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| Institution: | 1. College of Pharmacy, Jinan University, Guangzhou 510632, China;2. School of Chinese Materia Medica, Guangzhou University of Chinese Medicines, Guangzhou 510006, China;1. Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of Biomedical Materials, College of Chemistry and Materials Science, Analysis and Testing Center, Key Laboratory of applied photochemistry, Nanjing Normal University, Nanjing 210023, China;2. Department of Physical Science and Technology, Nanjing Normal University, Nanjing 210023, China;1. Department of Chemistry, School of Arts and Sciences, The Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, United States;2. W. Harry Feinstone, Department of Molecular Microbiology and Immunology, Bloomberg School of Public Health, The Johns Hopkins University, Baltimore, MD 21205, United States;3. The Johns Hopkins Malaria Research Institute, Bloomberg School of Public Health, The Johns Hopkins University, Baltimore, MD 21205, United States;1. Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil;2. Departamento de Biofísica, Universidade Federal de São Paulo, São Paulo, SP, Brazil;1. Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan, PR 00931-3346, United States;2. Department of Pharmacology, Chicago College of Osteopathic Medicine, Midwestern University, 555, 31st Street, Downers Grove, IL 60515, United States |
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| Abstract: | Novel biotransformation processes of dihydroartemisinic acid (1) and artemisinic acid (2) to their hydroxylated derivatives were investigated using the cell suspension cultures of Catharanthus roseus and Panax quinquefolium crown galls as two biocatalyst systems. Five biotransformation products, 3-α-hydroxydihydroartemisinic acid (3), 3-β-hydroxydihydroartemisinic acid (4), 15-hydroxy-cadin-4-en-12-oic acid (5), 3-α-hydroxyartemisinic acid (6) and 3-β-hydroxyartemisinic acid (7), were isolated by chromatograph methods and identified by the analysis of 1H NMR, 13C NMR, and ESI-MS spectra. Compounds 3–5 were obtained for the first time by biotransformation process. It was also the first time to transform artemisinic acid to yield epimeric 3-hydroxy artemisinic acids in plant cell culture system. The biocatalyst system of C. roseus cell cultures showed a great capacity of regio- and stereo-selective hydroxylation in allyl group of the exogenous substrates. The results also showed that the biocatalyst system of P. quinquefolium crown galls possessed the ability to hydroxylate propenyl group of exogenous substrates in a regio- and substrate-selective manner. Furthermore, the in vitro antitumor activity of the hydroxyl products was evaluated by MTT assay. The result indicated that α-hydroxyl products possessed stronger antitumor activity than β-hydroxyl products against the HepG2 and GLC-82 cell lines. |
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