Adenostemmoic acid B suppresses NO production by downregulating the expression and inhibiting the enzymatic activity of iNOS |
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| Affiliation: | 1. Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan;2. Department of Chemistry, Faculty of Mathematics and Natural Sciences, IPB University, IPB Dramaga Campus, Bogor, West Java 16680, Indonesia;3. Tropical Biopharmaca Research Center, IPB University, Taman Kencana Campus, Bogor, West Java 16128, Indonesia;4. The United Graduate School of Drug Discovery and Medical Information Sciences of Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan;1. College of Biology and Environmental Science, Jishou University, Jishou 416000, China;2. School of Pharmaceutical Sciences, Jishou University, Jishou 416000, China;3. School of Medicine, Jishou University, Jishou 416000, China;4. Key Laboratory of Tujia Medicine Inheritance and Innovation, National Ethnic Affairs Commission of the People''s Republic of China, Jishou University, Jishou 416000, China;5. National Engineering Technology Research Center for Modernization of Traditional Chinese Medicine, Jishou University, Zhuhai 519085, China;1. School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, PR China;2. National Demonstration Center for Experimental Ethnopharmacology Education, South-Central Minzu University, Wuhan 430074, PR China;1. Department of Natural Product Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan 250012, China;2. Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), No 28789 Jingshi Dong Road, Jinan 250103, China;3. Shaanxi Key Laboratory of Phytochemistry, Baoji 721013, Shaanxi, China;1. State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Bioactive Natural Product Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China;2. Department of Medicinal Chemistry, School of Pharmacy, Nanjing Medical University, 101 longmian Avenue, Nanjing 211166, PR China;1. CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS), Lanzhou 730000, People’s Republic of China;2. University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China;3. College of Life Science, Northwest Normal University, Lanzhou 730070, People’s Republic of China;4. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran |
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| Abstract: | Adenostemmoic acid B (AB) is a major compound found in Adenostemma lavenia; it shows anti-melanogenic, anti-inflammatory, and cytotoxic activities. By modifying the 19th position (carboxy: involved in the avoidance of cytotoxicity) of AB, we succeed to separate these activities. Short-chain alkylation of the carboxy group enhanced anti-melanogenic activity, while long-chain alkylation (hydrophobic) resulted in the suppression of nitric oxide (NO) production and inducible NO synthase (iNOS) expression without anti-melanogenic activity. Re-modification of hydrophilic properties in these long-chain derivatives restored anti-melanogenic activity but did not suppress NO production. Unexpectedly, AB and derivatives with long chains linked by an anhydride bond were new iNOS inhibitors. These results suggest that AB modulates multiple physiological activities by regulating different targets, including iNOS. |
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| Keywords: | Chemical biology Nitric oxide Kaurenoic acid Natural product Anti-inflammation Melanogenesis |
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