Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Kanda-surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
Molecules. 2011 Dec 15;16(12):10457-70. doi: 10.3390/molecules161210457.
The radical-scavenging activity of dietary phytophenols has been investigated by many researches due to their antioxidant, anti-inflammatory and anticancer property but the radical-scavenging effect of 2-phytophenol and the phytophenol:co-antioxidants, vitamin C and thiol combination under nearly anaerobic conditions still remains unknown. The radical-scavenging activity for seventeen phytophenols and for six synthetic phenols (positive controls) was investigated using the induction period method in the polymerization of methyl methacrylates (MMA) initiated by thermal decomposition of benzoyl peroxide (BPO) by monitoring differential scanning calorimetery (DSC). The k(inh) for the phytophenols was likely with the range 0.5 × 10³ M⁻¹s⁻¹-2.2 × 10³ M⁻¹s⁻¹, whereas that for synthetic phenols, hydroquinone and galvinoxyl, was with the range 7 × 10³ M⁻¹s⁻¹-8 × 10³ M⁻¹s⁻¹. Also, the additive scavenging effect of the (-)-epigallocatechin (EGC):(-)-epicatechin (EC) and the (+)-catechin:epicatechin (EC) combination was observed at 1:1 molar ratio, whereas that of the EC:quercetin combination showed the cancel (prooxidative) effect. Furthermore, the EGC:ASDB (L-ascorbyl 2,6-dibutylate) or 2-ME (2-mercaptoethanol) combination showed the prooxidative effect. Such enhancement of prooxidation in the combination may increase their toxic effects due to their cooxidation. Also, the synergic, additive or cancel effects of the flavonoid:vitamins E combination on the induction period in the BPO (a PhCOO* radical) and 2,2'-azobisisobutyronitrile (AIBN, an R* radical) systems are discussed.
由于膳食植物酚具有抗氧化、抗炎和抗癌特性,许多研究都研究了其清除自由基的活性,但在近厌氧条件下,2-植物酚和植物酚:共抗氧化剂、维生素 C 和硫醇的组合的清除自由基的效果仍不清楚。使用热分解过氧化二苯甲酰 (BPO)引发的甲基丙烯酸甲酯 (MMA)聚合中的诱导期方法,通过监测差示扫描量热法 (DSC),研究了十七种植物酚和六种合成酚(阳性对照)的清除自由基活性。植物酚的 k(inh)可能在 0.5×10³ M⁻¹s⁻¹-2.2×10³ M⁻¹s⁻¹范围内,而合成酚、对苯二酚和邻苯醌的 k(inh)在 7×10³ M⁻¹s⁻¹-8×10³ M⁻¹s⁻¹范围内。此外,(-)-表没食子儿茶素 (EGC):(-)-表儿茶素 (EC)和(+)-儿茶素:表儿茶素 (EC)组合的加性清除效果在 1:1 摩尔比下观察到,而 EC:槲皮素组合表现出取消(促氧化)效果。此外,EGC:ASDB(L-抗坏血酸 2,6-二丁酯)或 2-ME(2-巯基乙醇)组合表现出促氧化作用。这种组合中促氧化作用的增强可能会由于它们的共氧化而增加它们的毒性作用。此外,还讨论了类黄酮:维生素 E 组合对 BPO(PhCOO自由基)和 2,2'-偶氮二异丁腈 (AIBN,R自由基)体系中诱导期的协同、加性或取消作用。