title: Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina.
abstract: In search of more potent derivatives of sinomenine (1), a clinically available natural alkaloid for the treatment of rheumatoid arthritis (RA), biocatalyzed cross-coupling of sinomenine and guaiacol (2) by Antrodiella semisupina, provided two unique C-C coupled (3 and 4) and one C-O linked (5) novel metabolites. The structures of the metabolites were elucidated by means of MS, 2D NMR techniques and X-ray analysis. 4 exhibited more potent inhibitory activity on IL-6 production than 1 in human synovial sarcoma cell (SW982), and 5 stimulated IL-6 production.
authors.affiliation: Key Lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. China.
authors.forename: Zhang-Shuang
authors.initials: ZS
authors.lastname: Deng
authors.forename: Jian-Xin
authors.initials: JX
authors.lastname: Li
authors.forename: Peng
authors.initials: P
authors.lastname: Teng
authors.forename: Peng
authors.initials: P
authors.lastname: Li
authors.forename: Xiao-Ru
authors.initials: XR
authors.lastname: Sun
mesh_terms: D001487:Basidiomycota / Q000378:metabolism*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006139:Guaiacol / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009019:Morphinans / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D009019:Morphinans; C009271:sinomenine; D006139:Guaiacol