Efficient radical trapping at the surface and inside the phospholipid membrane is responsible for highly potent antiperoxidative activity of the carotenoid astaxanthin.
The effects of the carotenoids beta-carotene and astaxanthin on the peroxidation of liposomes induced by ADP and Fe(2+) were examined. Both compounds inhibited production of lipid peroxides, astaxanthin being about 2-fold more effective than beta-carotene. The difference in the modes of destruction of the conjugated polyene chain between beta-carotene and astaxanthin suggested that the conjugated polyene moiety and terminal ring moieties of the more potent astaxanthin trapped radicals in the membrane and both at the membrane surface and in the membrane, respectively, whereas only the conjugated polyene chain of beta-carotene was responsible for radical trapping near the membrane surface and in the interior of the membrane. The efficient antioxidant activity of astaxanthin is suggested to be due to the unique structure of the terminal ring moiety.
Goto
S
S
Faculty of Pharmaceutical Sciences, University of Tokushima, Japan. Kogure@ph.tokushima-u.ac.jp
Kogure
K
K
Abe
K
K
Kimata
Y
Y
Kitahama
K
K
Yamashita
E
E
Terada
H
H
D000244:Adenosine Diphosphate / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D002308:Cardiolipins / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006860:Hydrogen Bonding; D007501:Iron / Q000737:chemistry*; D007700:Kinetics; D015227:Lipid Peroxidation; D008081:Liposomes / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010713:Phosphatidylcholines / Q000737:chemistry*; D013499:Surface Properties; D024341:Xanthophylls; D065146:Zeaxanthins; D019207:beta Carotene / Q000031:analogs & derivatives* / Q000737:chemistry*
D000975:Antioxidants; D002308:Cardiolipins; D005296:Ferrous Compounds; D005609:Free Radicals; D008081:Liposomes; D010713:Phosphatidylcholines; D024341:Xanthophylls; D065146:Zeaxanthins; D019207:beta Carotene; C020748:ferrous sulfate; D000244:Adenosine Diphosphate; C005948:astaxanthine; D007501:Iron