Biotransformation of columbianadin by rat hepatic microsomes and inhibition of biotransformation products on NO production in RAW 264.7 cells in vitro |
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| Affiliation: | 1. School of Computer and Communication Engineering, University of Science and Technology Beijing, Beijing 100083, China;2. Beijing Key Laboratory of Knowledge Engineering for Materials Science, Beijing 100083, China;3. School of Metallurgical and Ecological Engineering, University of Science and Technology Beijing, Beijing 100083, China;1. Programas Multidisciplinarios de Posgrado en Ciencias Ambientales (PMPCA) de la Universidad Autónoma de San Luis Potosí, S. L. P., México;2. Instituto de Investigación de Zonas Desérticas (IIZD) de la Universidad Autónoma de San Luis Potosí, S. L. P., México;3. United States Department of Agriculture, Agricultural Research Service, 1815 North University Street, Peoria, IL 61604, USA;4. Department Food Science and Human Nutrition, University of Illinois at Urbana-Champaign, IL 61801, USA;1. Innovative Research and Education Center for Integrated Bioactive Materials and the Department of Bioactive Material Sciences, Jeonbuk National University, Jeonju, Republic of Korea;2. Department of Molecular Biology and the Institute for Molecular Biology and Genetics, Jeonbuk National University, Jeonju, Republic of Korea;3. R&D Center, General Bio Co., Ltd., Namwon, Republic of Korea;1. Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China;2. School of Chinese Materia Medica, Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 312 Anshanxi Road, Nankai District, Tianjin 300193, China;3. School of Pharmacy, Yantai University, No. 32 Road QingQuan, Laishan District, Yantai 264005, China;1. Department of Food Biotechnology and Environmental Science, Kangwon National University, Chuncheon 24341, Republic of Korea;2. CombiMed Co. Ltd., Yanggu 24510, Republic of Korea;3. Institute of Traditional Medicine & Bioscience, Daejeon University, Daejeon 34520, Republic of Korea |
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| Abstract: | Columbianadin (CBN, 1), 1-[(8S)-8,9-dihydro-2-oxo-2H-furo[2,3-h]-1-benzopyran-8-yl]-1-methylethyl-[(2Z)-2-methyl-2-butenoic acid]ester is a coumarin-type compound and one of the main bioactive constituents of the underground part of Angelica pubescens Maxim. f. biserrata Shan et Yuan. Although numerous investigations have been undertaken to study the biological activities of CBN, such as analgesic, anti-inflammatory, calcium-channel blocking, and platelet aggregation inhibiting functions, little attention has been paid to its metabolism and/or biotransformation. Biotransformation of CBN by rat liver microsomes in vitro was studied, and thirteen biotransformation products including eight hitherto unknown compounds [columbianadiratimetins A-H (3–10)] and five known compounds [columbianadin oxide (2), (+)-2,3-dihydro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-5-benzofurancarboxaldehyde (11), oroselol (12), columbianetin (13), and vaginol (14)] were produced by liver microsomes from rats pre-treated with sodium phenobarbital. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses which included IR, UV, EIMS, HRESIMS, 1D NMR and 2D NMR, respectively. The inhibition of CBN and its main biotransformation products on nitric oxide production induced by lipopolysaccharide was assayed in RAW 264.7 cells at concentrations ranging from 10 to 200 μM to evaluate the biological significance of biotransformation. |
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