Antitumorigenic activities of chalcones (II). Photo-isomerization of chalcones and the correlation with their biological activities.
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.
Iwata
S
S
Research Laboratory, Minophagen Pharmaceutical Co., Ltd., Kanagawa, Japan.
Nishino
T
T
Inoue
H
H
Nagata
N
N
Satomi
Y
Y
Nishino
H
H
Shibata
S
S
D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000494:pharmacology*; D002455:Cell Division / Q000187:drug effects; D002599:Chalcone / Q000737:chemistry / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D005260:Female; D006367:HeLa Cells; D006801:Humans; D007536:Isomerism; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D008815:Mice, Inbred Strains; D009955:Ornithine Decarboxylase / Q000378:metabolism; D010743:Phospholipids / Q000378:metabolism; D010777:Photochemistry; D011960:Receptors, Estrogen / Q000037:antagonists & inhibitors; D012867:Skin / Q000201:enzymology
D016588:Anticarcinogenic Agents; D010743:Phospholipids; D011960:Receptors, Estrogen; D002599:Chalcone; D009955:Ornithine Decarboxylase