Chemical Characterization of the Mold Product Decumbin

Abstract

The molecular formula of decumbin is C₁₆H₂₄O₄. The four oxygen atoms correspond to two free secondary hydroxyl groups and a lactone moiety. The five rings or double bonds required by the molecular formula are assigned to a strain-free α-β unsaturated lactone ring, the lactone carbonyl, a second unit which absorbs a mole of hydrogen perhaps a cyclopropane ring, and another more stable ring presumably a five or six-membered carbocycle. There is only one C-methyl group by the Kuhn-Roth procedure. Decumbin and a more recently reported compound called brefeldin A are evidently identical.