Characterization of Thitsiol Dimer Structures from Melanorrhoea usitata with Laccase Catalyst by NMR Spectroscopy

Author: Lu Rong   Kanamori Daisuke   Miyakoshi Tetsuo  

Publisher: Taylor & Francis Ltd

ISSN: 1023-666X

Source: International Journal of Polymer Analysis and Characterization, Vol.16, Iss.2, 2011-02, pp. : 86-94

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Abstract

The structures of thitsiol dimers from Melanorrhoea usitata were characterized by means of high-resolution NMR spectroscopy involving two-dimensional NMR measurements such as field gradient DQF-COSY, HMQC, and HMBC experiments. Almost all proton and carbon absorptions were assigned. The results showed that the main products of thitsiol dimers catalyzed by laccase are 1,1',2,2'-tetrahydroxy-3,3'-dialkenyl-5,5'-biphenyl (1), 1,1',2,2'-tetrahydroxy-3,3'-dialkenyl-6,5'-biphenyl (2), and 1,1',2,2'-tetrahydroxy-3,4'-dialkenyl-5,5'-biphenyl (3). The thitsiol dimers are almost all nuclear-nuclear (C-C) couplings, which differ from the nuclear-side chain (C-O-C) couplings of urushiol. Based on these results, the color of the lacquer film and the polymerization mechanism of thitsiol are discussed.

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