Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina.
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.
Deng
Zhang-Shuang
ZS
Key Lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. China.
Li
Jian-Xin
JX
Teng
Peng
P
Li
Peng
P
Sun
Xiao-Ru
XR
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
D009019:Morphinans; C009271:sinomenine; D006139:Guaiacol