Nitric oxide formation and corresponding relaxation of porcine coronary arteries induced by plant phenols: Essential structural features

被引:86
作者
Taubert, D [1 ]
Berkels, R [1 ]
Klaus, W [1 ]
Roesen, R [1 ]
机构
[1] Univ Cologne, Inst Pharmacol, Dept Pharmacol, Gleueler Str 24, D-50931 Cologne, Germany
关键词
cardiovascular disease; flavonoids; Mediterranean diet; nitric oxide; plant phenols; vasorelaxation;
D O I
10.1097/00005344-200211000-00008
中图分类号
R5 [内科学];
学科分类号
1002 ; 100201 ;
摘要
The high intake of polyphenols is thought to, contribute to the beneficial cardiovascular effects of plant-centered diets. A putative mechanism underlying the cardioprotective activity is thought to be a plant phenol-induced increase of nitric oxide formation by the constitutive endothelial nitric oxide synthase. Twenty-eight phenols of different classes commonly occurring in plant foods were examined for their capability of enhancing the endothelial nitric oxide release of isolated porcine coronary arteries by direct real-time measurement of the luminal surface nitric oxide concentration with an amperometric microsensor. Additionally, the relaxing activity of the phenols was measured on porcine coronary rings. Quercetin, myricetin, leucocyanidol, and oligomeric proanthocyanidins induced the highest increases in nitric oxide release (Delta[NO] > 8.5 nM); caffeic acid, fisetin, hyperosid, and isoquercitrin were moderately active (5 nM > Delta[NO] < 8.5 nM); the other.. phenolic compounds caused only marginal increases of the nitric oxide levels (Delta[NO] < 5 nM). The nitric oxide-stimulating activity of the phenols was uniformly positively correlated with their vasorelaxing activity. However, endothelium-dependent vasorelaxations were limited to phenols inducing nitric oxide elevations > 5 nM (= K-m value of the: soluble guanylate cyclase). Analysis of structure-activity relations revealed that a high nitric oxide activity was confined to a flavan-moiety with free hydroxyl-residues at C-3, C-3, C-4', C-5, and C-7 and a hydroxyl-, oxo-, or phenolic substituent at C-4, whereas the caffeic acid scaffolding emerged as the minimally essential motif for the nitric oxide-dependent vasorelaxation.
引用
收藏
页码:701 / 713
页数:13
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