Synthetic carotenoids, novel polyene polyketones and new capsorubin isomers as efficient quenchers of singlet molecular oxygen.
Novel synthetic polyene polyketones and new synthetic capsorubin isomers were examined for their ability to quench singlet molecular oxygen (1O2) generated by the thermodissociation of the endoperoxide of 3,3'-(1,4-naphthylene) dipropionate (NDPO2). C28-polyene-tetrone (1) exhibits the highest physical quenching rate constant with 1O2 (kq = 16 x 10(9) M-1 s-1). For comparison, the rate constant for the most efficient biological carotenoid, lycopene (3) is kq = 9 x 10(9) M-1 s-1 and that of beta-carotene (5) kq = 5 x 10(9) M-1 s-1. The presence of two oxalyl chromophores at the ends of the polyene chain seems to enhance the 1O2 quenching ability in the C28-polyene-tetrone (1). C28-polyene-tetrone-diacetal (2) (kq = 9 x 10(9) M-1 s-1) and C40-epiisocapsorubin (4) (kq = 8 x 10(9) M-1 s-1) also have high 1O2 quenching abilities. Two carotenoids from plants, phytoene and phytofluene, were much less efficient, kq values being below 10(7) M-1 s-1. Due to the very high singlet oxygen quenching abilities, C28-polyene-tetrone (1), C28-polyene-tetrone-diacetal (2) and C40-epiisocapsorubin (4) may have potential use in preventing 1O2-induced damage in biological and non-biological systems.
Devasagayam
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TP
Institut für Physiologische Chemie I, Universität Düsseldorf, Fed. Rep. Germany.
Werner
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T
Ippendorf
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Martin
H D
HD
Sies
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H
D002338:Carotenoids / Q000031:analogs & derivatives* / Q000737:chemistry*; D007536:Isomerism; D007659:Ketones; D010100:Oxygen; D010777:Photochemistry; D026082:Singlet Oxygen; D013329:Structure-Activity Relationship; D024341:Xanthophylls
D007659:Ketones; D024341:Xanthophylls; D026082:Singlet Oxygen; D002338:Carotenoids; C035624:capsorubin; D010100:Oxygen