Carotenoids, tocopherols and thiols as biological singlet molecular oxygen quenchers.

Singlet molecular oxygen (1O2) has been shown to be generated in biological systems and is capable of damaging proteins, lipids and DNA. The ability of some biological antioxidants to quench 1O2 was studied by using singlet oxygen generated by the thermodissociation of the endoperoxide of 3,3'-(1,4-naphthylidene) dipropionate (NDPO2). The carotenoid lycopene was the most efficient 1O2 quencher (kq + kr = 31 x 10(9) M-1 s-1). Tocopherols and thiols were less effective. The singlet oxygen quenching ability decreased in the following order: lycopene, gamma-carotene, astaxanthin, canthaxanthin, alpha-carotene, beta-carotene, bixin, zeaxanthin, lutein, bilirubin, biliverdin, tocopherols and thiols. However, the compounds with low quenching rate constants occur at higher levels in biological tissues. Thus, carotenoids and tocopherols may contribute almost equally to the protection of tissues against the deleterious effects of 1O2. The quenching abilities of carotenoids and tocopherols were mainly due to physical quenching. In case of some thiols chemical quenching also plays a significant role. Carotenoids and tocopherols have been reported to exert a protective action against some types of cancer.