Jang Moon Hee, Kim Hyun Young, Kang Ki Sung, Yokozawa Takako, Park Jeong Hill
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 151-742, Korea.
Arch Pharm Res. 2009 Mar;32(3):341-5. doi: 10.1007/s12272-009-1305-z. Epub 2009 Apr 23.
The hydroxyl radical (*OH) scavenging and ferrous ion chelating activities of four isoquinoline alkaloids isolated from Coptis chinensis Franch were studied for the identification of their structural characteristics to scavenge *OH. The *OH was generated via Fe(II)-catalazed Fenton reaction in this study and the reliable measurement of *OH scavenging activities of isoquinoline alkaloids were achieved using electron spin resonance (ESR) spectrometry method. At the 1 mM concentration, berberrubine (85%) showed the strongest *OH scavenging activity and the next were in the decreasing order of coptisine (79%), berberine (23%), and palmatine (22%). The ferrous ion chelating effects of the alkaloids showed similar pattern with their *OH scavenging effects. These results suggest that *OH scavenging effects of the alkaloids were closely related to their ferrous ion chelating activities. In addition, metal chelating functional groups such as hydroxy group at C-9 and methylenedioxy group at C-9 and C-10 were thought to contribute to the *OH scavenging activities of the isoquinoline alkaloids.
研究了从黄连中分离得到的四种异喹啉生物碱的羟自由基(OH)清除能力和亚铁离子螯合活性,以确定它们清除OH的结构特征。本研究通过Fe(II)催化的芬顿反应产生OH,并采用电子自旋共振(ESR)光谱法可靠地测定了异喹啉生物碱的OH清除活性。在1 mM浓度下,小檗红碱(85%)表现出最强的OH清除活性,其次是黄连碱(79%)、黄连素(23%)和巴马汀(22%),呈递减顺序。生物碱的亚铁离子螯合作用与其OH清除作用呈现相似的模式。这些结果表明,生物碱的OH清除作用与其亚铁离子螯合活性密切相关。此外,C-9位的羟基以及C-9和C-10位的亚甲二氧基等金属螯合官能团被认为有助于异喹啉生物碱的OH清除活性。