Antitumorigenic activities of chalcones (II). Photo-isomerization of chalcones and the correlation with their biological activities

Biological & Pharmaceutical Bulletin
S IwataS Shibata

Abstract

Some chalcones are known to be phototransformed in a solution from trans into cis isomers. 3-Hydroxy-3'-methylchalcone (3'Me-3-C) has been found to be isomerized from trans into cis by irradiation of daylight in the methanolic solution. The presence of a hydroxyl in the 2'- or 4-position in the trans-chalcone structure prevents phototransformation into cis isomers. The feasibility of phototransformation of chalcones was discussed using UV-spectral analysis. The phototransformed cis-3'Me-3-C showed more potent antitumorigenic activity than the original trans form. The generally recognized parallelism between antitumorigenic and antiinflammatory activities was not observed in trans and cis 3'-Me- and 4'-Me-3C, which are antitumorigenic but inactive in 12-O-tetradecanoylphorbol 13-acetate (TPA)- and arachidonic acid (AA)-induced mouse ear edema. However, inhibitory activity against ornithine decarboxylase (ODC) was commonly observed in both naturally occurring and synthetic antitumorigenic chalcones.

Citations

Sep 4, 2009·Journal of Hematology & Oncology·Subhash PadhyeFazlul H Sarkar
Mar 5, 2013·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Eva KupetzHeike Bunjes
Nov 28, 2006·Chemistry and Physics of Lipids·V Yu SvetlichnyT I Syrejshchikova
Oct 13, 2015·The Journal of Organic Chemistry·Mark SigalovIrina Sterkhova
Feb 13, 2015·Natural Product Research·Yuanyuan ZhengXiaohong Chen
Jun 10, 2003·Journal of Mass Spectrometry : JMS·Junmei Zhang, Jennifer S Brodbelt
Jun 27, 2019·The Journal of Organic Chemistry·Mark V SigalovBagrat A Shainyan

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