Kinobeon A, purified from cultured safflower cells, is a novel and potent singlet oxygen quencher
Languages of publication
We recently reported that kinobeon A, produced from safflower cells, suppressed the free radical-induced damage of cell and microsomal membranes. In the present study, we investigated whether kinobeon A quenches singlet oxygen, another important active oxygen species. Kinobeon A inhibited the singlet oxygen-induced oxidation of squalene. The second-order rate constant between singlet oxygen and kinobeon A was 1.15 × 1010 M-1s-1 in methanol containing 10% dimethyl sulfoxide at 37°C. Those of α-tocopherol and β-carotene, which are known potent singlet oxygen quenchers, were 4.45 × 108 M-1s-1 and 1.26 × 1010 M-1s-1, respectively. When kinobeon A was incubated with a thermolytic singlet oxygen generator, its concentration decreased. However, this change was extremely small compared to the amount of singlet oxygen formed and the inhibitory effect of kinobeon A on squalene oxidation by singlet oxygen. In conclusion, kinobeon A was a strong singlet oxygen quencher. It reacted chemically with singlet oxygen, but it was physical quenching that was mainly responsible for the elimination of singlet oxygen by kinobeon A. Kinobeon A is expected to have a preventive effect on singlet oxygen-related diseases of the skin or eyes.
- Arisawa F, Tatsuzawa H, Kambayashi Y, Kuwano H, Fujimori K, Nakano M (2003) MCLA-dependent chemiluminescence suggests that singlet oxygen plays a pivotal role in myeloperoxidase-catalyzed bactericidal action in neutrophil phagosomes. Luminescence 18: 229-238.
- Bellus D (1978) Quenchers of singlet oxygen. In Singlet Oxygen, Reactions with Organic Compounds and Polymers. Randy B, Rabek JF, eds, pp 61-110. Wiley-Intersciencs, Chichester.
- Di Mascio P, Kaiser S, Sies H (1989) Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch Biochem Biophys 274: 532-538.
- Halliwell B, Gutteridge JMC (1999) Free Radicals in Biology and Medicine, 3rd edn. Oxford University Press, New York, Oxford.
- Kaiser S, Di Mascio P, Murphy ME, Sies H (1990) Physical and chemical scavenging of singlet molecular oxygen by tocopherols. Arch Biochem Biophys 277: 101-108.
- Kanehira T, Takekoshi S, Nagata H, Matsuzaki K, Kambayashi Y, Osamura RY, Homma T (2003) A novel and potent biological antioxidant, Kinobeon A, from cell culture of safflower. Life Sci 74: 87-97.
- Klotz L-R, Briviba K, Sies H (2000) Signaling by singlet oxygen in biological systems. In Antioxidant and Redox Regulation of Genes. Sen CK, Sies H, Baeuerle PA, eds, pp 1-20, Academic Press, CA.
- Kohno Y, Egawa Y, Itoh S, Nagaoka S, Takahashi M, Mukai K (1995) Kinetic study of quenching reaction of singlet oxygen and scavenging reaction of free radical by squalene in n-butanol. Biochem Biophys Acta 1256: 52-56.
- Nakano M, Kambayashi Y, Tatsuzawa H, Komiyama T, Fujimori K (1998) Useful 1O2 (1Δg) generator, 3-(4'-methyl-1'-naphthyl)-propionic acid, 1',4'-endoperoxide (NEPO), for dioxygenation of squalene (a skin surface lipid) in an organic solvent and bacterial killing in aqueous medium. FEBS Lett 432: 9-12.
- Niki E (1990) Free radical initiators as source of water- or lipid-soluble peroxyl radacals. Methods Enzymol 186: 100-108.
- Niki E, Tsuchiya J, Yoshikawa Y, Yamamoto Y, Kamiya Y (1986) Oxidation of lipids. XIII. Antioxidant activities of α-, β-, γ-, and δ-tocopherol. Bull Chem Soc Jpn 59: 497-501.
- Tatsuzawa H, Maruyama N, Misawa N, Fujimori K, Hori K, Sano Y, Kambayashi Y, Nakano M (1998) Inactivation of bacterial respiratory chain enzymes by singlet oxygen. FEBS Lett 439: 329-333.
- Tatsuzawa H, Maruyama T, Hori K, Sano Y, Nakano M (1999) Singlet oxygen (1ΔgO2) as the principal oxidant in myeloperoxidase-mediated bacterial killing in neutrophil phagosome. Biochem Biophys Res Commun 262: 647-650.
- Tatsuzawa H, Maruyama T, Misawa N, Fujimori K, Nakano M (2000) Quenching of singlet oxygen by carotenoids produced in Escherichia coli - attenuation of singlet oxygen-mediated bacterial killing by carotenoids. FEBS Lett 484: 280-284.
- Wakayama S, Kusaka K, Kanehira T, Yamada Y, Kawazu K, Kobayashi A (1994) Kinobeon A, a novel red pigment produced in safflower tissue cultures systems. Z Naturforsch 49c: 1-5.
- Yamamoto Y, Brodsky MH, Baker JC, Ames AN (1987) Detection and characterization of lipid hydroperoxides at picomole levels by high-performance liquid chromatography. Anal Biochem 160: 7-13.
- Young RH, Wehrly K, Martin RL (1971) Solvent effects in dye-sensitized photooxidation reactions. J Am Chem Soc 93: 5774-5779.
Publication order reference