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). 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 CC 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 to those of (S) -disinomenine and sinomenine (17% and 12% inhibition, respectively).
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