Alkyl phenols and derivatives from Tapirira obtusa

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-hydroxy3-[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. (C) 2001 Elsevier Science Ltd. All rights reserved.