Alkyl phenols and derivatives from Tapirira obtusa

Abstract

From the bark of Tapiria obtusa, six alkyl phenol derivatives were isolated: 1-hydroxy-3-[(Z)-7′-nonadecenyl]-benzene, 1-hydroxy-3-[(Z)-7′-heptadecenyl]-benzene, 1-hydroxy-3-[14′-phenyltetradecyl]-benzene, and 1-hydroxy-3-[16′-phenyltetradecyl]-benzene, and their possible biogenetic precursors, 1-(16′-phenyl-12′Z-hexadecenyl)-4-Z-cyclohexene-(1S*,3S*)-diol and (4S*,6S*)-dihydroxy-6-(14′Z-nonadecenyl)-2-cyclohexenone. The structures of these compounds were elucidated by chemical and spectroscopic analysis. (4S*,6S*)-Dihydroxy-6-(14′Z-nonadecenyl)-2-cyclohexenone showed cytotoxic activity.