Design of Novel Hybrid Vitamin C Derivatives : Thermal Stability and Biological Activity
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概要
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Novel hybrid L-ascorbic acid (vitamin C) derivatives with other biologically active substances, 5-hydroxy-2-hydroxymethyl-β-pyrone (kojic acid) and α-tocopherol (vitamin E), linked at the C-2 or C-3 hydroxyl group were synthesized, and their thermal stability and inhibitory effects on tyrosinase activity, active oxygen species (AOS), and free radicals were estimated in vitro. It was found that a hydrophilic derivative, 2-O-(5-hydroxy-4H-pyran-4-one-2-methyl)-L-ascorbic acid (1), exyhibited good thermal stability and inhibitory activities against tyrosinase-catalyzed melanin formation, AOS, and free radicals compared to vitamin C and its conventional derivatives (such as the 2-phosphate, 6-stearate and 2,6-dipalmitate, and 2-O-octadecylascorbic acid), as well as vitamin E, kojic acid, and arbutin. It is apparent that 1 has the biological properties of vitamin C and kojic acid, and acts synergistically. The hydroxyl groups at the C-3 position of the vitamin C moiety and the C-5 position of the kojic acid moiety are critical for the biological activities. We consider that the kojic acid moiety of 1 counterbalances the diminution of the biological activity due to shielding of the biologically important C-2 hydroxyl group of the vitamin C moiety. In addition, the thermal stability was significantly improved relative to not only vitamin C but also kojic acid. Further, a lipophilic derivative, 3-O-[α-tocopheryloxy)-2-hydroxypropyl]-L-ascorbic acid, 2,was far more stable than vitamin C and its typical lipophilic derivatives. Compound 2 exhibited almost the same inhibitory activities against tyrosinase-catalyzed melanin formation, AOS, and free radicals as typical lipophilic derivatives, although these biological activities of 2 were lower than those of vitamin C.
- 公益社団法人日本薬学会の論文
- 1996-09-15
著者
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Ozaki Shoichiro
Department Of Applied Chemistry Faculty Of Engineering Ehime University
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MORISAKI Kazuo
Department of Applied Chemistry, Faculty of Engineering, Ehime University
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Morisaki K
Ehime Univ. Ehime
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Morisaki Kazuo
Department Of Applied Chemistry Faculty Of Engineering Ehime University
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