Oligomeric flavanoids. part 14. Proguibourtinidins based on (-)-fisetinidol and (+)-epifisetinidol units☆
Review articleOpen access

AbstractThe rare series of proguibourtinidins ( 3,4', 7-trihy- droxy functionality) based on the fisetinidol (3,3',4',7-tetrahydroxy functionality) 5-deoxy flavan-3-ol unit is extended by identification of (+)-guibourtinidol-(4β,6)-(-)-fisetinidol and the (+)-guibourtini- dol-(4α,6) and (4β,6)-(+)-epifisetinidols. These metabolites are formed in low yields via acid-catalyzed coupling of (+)-guibourtaca- cidin and (-)-fisetinidol, the high activation energy of generating a 4-C benzylic carbocation being attributable to the poor electron donating properties of the phenol B-ring of the flavan-3,4-diol. Stereo-electronic principles operating in the in vitro process pre- sumably also control their formation in Nature.

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