Effect of endocannabinoids on soybean lipoxygenase-1 activity

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• 作者：Minh Duc Nguyen ; Dang Hung Nguyen ; Jae-Myung Yoo ; Pyung-Keun Myung ; Mee Ree Kim ; Dai-Eun Sok
• 关键词：13-HpODE ; 13(S)-hydroperoxyoctadecadienoic acid ; 15(S)-HpETE ; 15(S)-hydroperoxyeicosatatraenoic acid ; Eox ; active ferric enzyme form ; Ered ; inactive ferrous enzyme form ; LOX ; lipoxygenase ; NA-DA ; N-arachidonoyl dopamine ; NA-Gly ; N-arachidonoyl glycine ; NA
• 刊名：Bioorganic Chemistry
• 出版年：2013
• 出版时间：August, 2013
• 年：2013
• 卷：49
• 期：Complete
• 页码：24-32
• 全文大小：1302 K

文摘

Endocannabinoids appear to be involved in a variety of physiological processes. Lipoxygenase activity has been known to be affected by unsaturated fatty acids or phenolic compounds. In this study, we examined whether endocannabinoids containing both N-acyl group and phenolic group can affect the activity of soybean lipoxygenase (LOX)-1, similar to mammalian 15-lipoxygenase in physicochemical properties. First, N-arachidonoyl dopamine and N-oleoyl dopamine were found to inhibit soybean LOX-1-catalyzed oxygenation of linoleic acid in a non-competitive manner with a K_i value of 3.7 ¦ÌM and 6.2 ¦ÌM, respectively. Meanwhile, other endocannabinoids failed to show a remarkable inhibition of soybean LOX-1. Separately, N-arachidonoyl dopamine and N-arachidonoyl serotonin were observed to inactivate soybean LOX-1 with K_in value of 27 ¦ÌM and 24 ¦ÌM, respectively, and k₃ value of 0.12 min^?1 and 0.35 min^?1, respectively. Furthermore, such an inactivation was enhanced by ascorbic acid, but suppressed by 13(S)-hydroperoxy-9,11-octadecadienoic acid. Taken together, it is proposed that endocannabinoids containing polyunsaturated acyl moiety and phenolic group may be efficient for the inhibition as well as inactivation of 15-lipoxygenase.