Isolation and Identification of New Apocarotenoids from Annatto (<i>Bixa orellana</i>) Seeds

Abstract

Five apocarotenoids were isolated in trace amounts from the seed coat of the Bixa orellana L. fruits. Their structures were established by means of UV−visible, 400 and 500 MHz 1H and 100 and 120 MHz 13C NMR spectroscopy, and mass spectrometry. Methyl (7Z,9Z,9‘Z)-apo-6‘-lycopenoate, methyl (9Z)-apo-8‘-lycopenoate, methyl (all-E)-apo-8‘-lycopenoate are new carotenoids, and the other two, methyl (all-E)-8‘-apo-β-caroten-8‘-oate and methyl (all-E)-apo-6‘-lycopenoate, have not been previously found in annatto. Keywords: Bixa orellana; annatto; apocarotenoids; structure elucidation