Isolation and characterization of dinochrome A and B, anti-carcinogenic active carotenoids from the fresh Water red tide Peridinium bipes.
Two epimeric carotenoids, named dinochromes A (2) and B (3), were isolated from the fresh water red tide Peridinium bipes, as anti-carcinogenic compounds. The stereostructure of dinochrome A and B were characterized to be (3S,5R,6R,3'S,5'R,8'R)- and (3S,5R,6R,3'S,5'R,8'S)-5',8'-epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-beta,beta-carotene-3,5,3'-triol 3-O-acetate, respectively by (1)H- and (13)C-NMR, and circular dichroism (CD) data. Dinochromes A (2) and B (3) inhibit 12-O-tetradecanoyl phorbol 13-acetate (TPA)-stimulated (32)P-incorporation into the phosholipids of HeLa cells. Furthermore, dinochrome A was found to inhibit the proliferation of human malignant tumor cells, such as GOTO, OST and HeLa cells.
Maoka
Takashi
T
Kyoto Pharamceutical University, Kyoto, Japan. maoka@mbox.kyoto-inet.or.jp
Tsushima
Miyuki
M
Nishino
Hoyoku
H
D000818:Animals; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D002338:Carotenoids / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D004141:Dinoflagellida / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; C474097:dinochrome A; C474096:dinochrome B; D002338:Carotenoids