Biocatalyzed cross-coupling of sinomenine and 1,2-dihydroxybenzene by Coriolus unicolor

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Sinomenine is a clinically available drug for the treatment of rheumatoid arthritis (RA).In a continuous research aiming at discovery of sinomenine derivates with better bioactivity,a cross-coupling reaction of sinomenine and 1,2-dihydroxybenzene catalyzed by a fungus Coriolus unicolor afforded an unique C-C cross-coupled compound 2,together with (S)-disinomenine and (R)-disinomenine.The structure of 2 was elucidated by MS and NMR spectroscopy.Compound 2 was further assayed for the inhibitory activity on IL-6 overproduction in SW982 cells and exhibited a much more potent activity on IL-6 (96% inhibition)compared with those of (S)-disinomenine and sinomenine (17% and 12% inhibition,respectively).
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