The stilbenoids E-resveratrol (E-3,5,4'-trihydroxystilbene, 1), E-3,5,4'-trimethoxystilbene (2), E-3,4,4'-trimethoxystilbene (3) and E-3,4'-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5-8. Compounds 1-8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4'-trimethoxystilbene (6), which showed against DU-145 and LNCaP cells GI50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.
Antiproliferative activity of methylated analogues of E- and Z- resveratrol
CARDILE, Venera;CHILLEMI, ROSA GIOVANNA;LOMBARDO, LAURA;SCIUTO, Sebastiano;SPATAFORA, Carmela;TRINGALI, Corrado
2007-01-01
Abstract
The stilbenoids E-resveratrol (E-3,5,4'-trihydroxystilbene, 1), E-3,5,4'-trimethoxystilbene (2), E-3,4,4'-trimethoxystilbene (3) and E-3,4'-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5-8. Compounds 1-8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4'-trimethoxystilbene (6), which showed against DU-145 and LNCaP cells GI50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.File | Dimensione | Formato | |
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