Journal
PHYTOCHEMISTRY
Volume 69, Issue 18, Pages 3038-3042Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2008.06.007
Keywords
Dirigent protein; Moco cotton; Gossypium hirsutum; Malvaceae; (+)-Gossypol; Gossypol biosynthesis; Hemigossypol; Oxidative coupling; Peroxidase; Stereoselectivity
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The terpenoid gossypol, a secondary metabolite found in the cotton plant, is synthesized by a free radical dimerization of hemigossypol. Gossypol exists as an atropisomeric mixture because of restricted rotation around the central binaphthyl bond. The dimerization of hemigossypol is regiospecific in cotton. In the case of some moco cotton, the dimerization also exhibits a high level of stereoselectivity. The mechanism that controls this stereoselective dimerization is poorly understood. In this paper, we demonstrate that a dirigent protein controls this stereoselective dimerization process. A partially purified protein preparation from cotton flower petals, which by itself is unable to convert hemigossypol to gossypol, converts hemigossypol with a 30% atropisomeric excess into (+)-gossypol when combined with an exogenous laccase, which by itself produces racemic gossypol. Published by Elsevier Ltd.
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