Chemical structure of flavonols in relation to modulation of angiogenesis and immune-endothelial cell adhesion
Chemical structure of flavonols in relation to modulation of angiogenesis and immune-endothelial cell adhesion
复制标题
DOI：
10.1016/j.jnutbio.2005.06.006
复制
发表时间：
2006-03-01
影响因子：
5.6
通讯作者：
Meydani, M
中科院分区：
文献类型：
--
作者：
Kim, JD;Liu, LP;Meydani, M
黄酮类化合物的抗氧化活性被认为有助于与食用水果和蔬菜有关的几种健康益处。研究了四种羟基（oh）含量不同的黄酮醇杨梅素(M)、槲皮素(Q)、山奈酚(K)和高良姜素(G)对人脐静脉内皮细胞（HUVECs）的抗氧化活性和细胞毒性，以及潜在的抗血管生成和细胞粘附作用。这些黄酮醇在细胞培养基（无细胞体系）中的相对抗氧化能力和细胞内抗氧化活性分别为M=Q > K=G，它们的b环上分别存在3、2、1和0个-OH基团。b环上-OH基团数目越多，黄酮醇对HUVEC的毒性越小，LD50为：M(100亩M)> Q(50亩M)> K(20亩M)> G（10亩M）。这些黄酮醇在大约0.5 LD50剂量下抑制血管内皮生长因子（VEGF）刺激的HUVEC管状结构的形成：M (47%)> Q (37%)> K (15%)> G(14%)，这与它们的-OH基团的数量没有线性关系。然而，黄酮醇对活化的U937单核细胞粘附HUVEC的抑制程度与b环上-OH基团的数量有关。当用这些黄酮醇预处理U937细胞时，这一点尤为突出。而活化的HUVECs经黄酮醇预处理后，-OH片段的数量对其粘附及粘附分子的表达均无明显影响。黄酮醇b环上不同数量的-OH基团的存在可能有助于其抗氧化活性和毒性，并可能在其生物作用的效力中发挥重要作用，例如血管生成和免疫内皮细胞粘附，这分别是癌症和动脉粥样硬化发生的重要过程。(c) 2006爱思唯尔公司版权所有。
The antioxidant activity of flavonoids has been suggested to contribute to several health benefits associated with the consumption of fruits and vegetables. Four flavonols - myricetin (M), quercetin (Q), kaempferol (K) and galangin (G), all with different numbers of hydroxyl moieties (-OH) - were examined for their antioxidant activity and cylotoxicity oil human umbilical vein endothelial cells (HUVECs) and for their potential antiangiogenic and cell adhesion effects. The relative antioxidant capacity of these flavonols in cell Culture medium (cell-free system) and their intracellular antioxidant activity were M=Q > K=G, which correlated respectively with the presence of 3, 2, 1 and 0 moieties of -OH on their B-ring. The higher the numbers of -OH moieties on the B-ring the less toxic the flavonol was to HUVEC, and the LD50 was determined as: M (100 mu M)> Q (50 mu M)> K (20 mu M)> G (10 mu M). These flavonols at approximate to 0.5 LD50 doses suppressed the vascular endothelial growth factor (VEGF)-stimulated HUVEC tubular structure formation by: M (47%)> Q (37%)> K (15%)> G (14%), which was not linearly associated with their numbers of -OH moieties. However, the magnitude of flavonols' suppression of activated U937 monocytic cells adhesion to HUVEC was associated with the number of -OH moieties oil the B-ring. This was prominent when U937 cells were pretreated with these flavonols. In contrast, the numbers of -OH moiety had no apparent influence on the adhesion or expression of adhesion molecules when activated HUVECs were pretreated with these flavonols. The presence of different numbers of -OH moieties on the B-ring of the flavonols may contribute to their antioxidant activity as well as their toxicity and may play an important role in their potency for biological action such as angiogenesis and immune-endothelial cell adhesion, which, respectively, are important processes in the development of cancer and atherosclerosis. (c) 2006 Elsevier Inc. All rights reserved.