pH-dependent, stereoselective dimerization of sinomenine |
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| Authors: | Deng Zhang-Shuang Zhao Yu He Cui-Cui Jin Jie He Yun-Mian Li Jian-Xin |
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| Affiliation: | Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China. |
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| Abstract: | In a continuing study on discovery of more potent derivatives of sinomenine (1), a clinically available alkaloid for rheumatoid arthritis (RA) treatment, oxidation of sinomenine provided two unique stereoisomers, disinomenines 2 and 3. The structure of 3 was determined by MS, NMR, and X-ray analysis. The formation of 2 and 3 via oxidation of sinomenine by potassium permanganate (KMnO4) exhibited a pH-dependent stereoselectivity. The bioassay results using human synovial sarcoma cells (SW982) showed that 2 inhibited, while 3 stimulated, IL-6 production. |
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