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香豆素衍生物对人低密度脂蛋白自由基引发和光敏化过氧化的抗氧化及促氧化作用。

Antioxidative and prooxidative effects of coumarin derivatives on free radical initiated and photosensitized peroxidation of human low-density lipoprotein.

作者信息

Liu Z Q, Yu W, Liu Z L

机构信息

National Laboratory of Applied Organic Chemistry, Lanzhou University, Gansu, People's Republic of China.

出版信息

Chem Phys Lipids. 1999 Dec;103(1-2):125-35. doi: 10.1016/s0009-3084(99)00101-2.

DOI:10.1016/s0009-3084(99)00101-2
PMID:10701080
Abstract

The antioxidative and/or prooxidative activity of 4-methylcoumanrin (MC), 7-hydroxy-4-methylcoumarin (HMC) and 7,8-dihydroxy-4-methylcoumarin (DHMC), respectively, in the peroxidation of human low-density lipoprotein (LDL) has been studied. The peroxidation was initiated either thermally by water-soluble initiator 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH), or photochemically by a triplet sensitizer benzophenone (BP) or its water-soluble analogue disodium 3,3'-disulfobenzophenonate (DSBP). The reaction kinetics were monitored by the uptake of oxygen and the depletion of alpha-tocopherol (TOH) present in the native LDL. Kinetic analysis of the peroxidation process demonstrated that DHMC is a good antioxidant for both the AAPH-initiated and BP- and DSBP-photosensitized peroxidation; HMC is a prooxidant for the AAPH-initiated and DSBP-photosensitized peroxidation, but an antioxidant for the BP-sensitized peroxidation; MC is a prooxidant in all of these initiation conditions. The antioxidative action of the coumarin derivatives may include trapping the initiating radicals, trapping the propagating lipid peroxyl radicals, recycling alpha-tocopherol and/or deactivating the excited photosensitizer.

摘要

分别研究了4-甲基香豆素(MC)、7-羟基-4-甲基香豆素(HMC)和7,8-二羟基-4-甲基香豆素(DHMC)在人低密度脂蛋白(LDL)过氧化反应中的抗氧化和/或促氧化活性。过氧化反应通过水溶性引发剂2,2'-偶氮二(2-脒基丙烷盐酸盐)(AAPH)热引发,或通过三重态敏化剂二苯甲酮(BP)或其水溶性类似物3,3'-二磺基二苯甲酮二钠(DSBP)光化学引发。通过监测氧气的吸收和天然LDL中存在的α-生育酚(TOH)的消耗来监测反应动力学。过氧化过程的动力学分析表明,DHMC对AAPH引发的以及BP和DSBP光敏化的过氧化反应都是良好的抗氧化剂;HMC对AAPH引发的和DSBP光敏化的过氧化反应是促氧化剂,但对BP敏化的过氧化反应是抗氧化剂;MC在所有这些引发条件下都是促氧化剂。香豆素衍生物的抗氧化作用可能包括捕获引发自由基、捕获传播的脂质过氧自由基、回收α-生育酚和/或使激发的光敏剂失活。

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