To establish a structure-activity relationship for procyanidins, we verified the cyto-protective effect of 13 grape seed procyanidins, ranging from monomers to trimers against H2 O2 -induced oxidative stress in PC-12 neuroblastoma cells. Our study demonstrated some procyanidins were able to significantly protect PC-12 cells from the H2 O2 -induced cytotoxicity suggesting they possess neuroprotective effects against oxidative stress. Procyanidins' protective effects against oxidative stress mainly depended on their polymerization degree in addition to their structural features. A positive correlation was found between procyanidins' polymerization degree and the protective effect against oxidative stress in PC-12 cells. The presence of 3- or 3'-galloylated groups in the C-ring of procyanidin molecules significantly increased their protective activity as well. These results demonstrated that galloylated high-molecular-mass procyanidins would be of more interesting as promising antioxidant natural compounds. This work for the first time demonstrated the structure-activity relationships of 13 procyanidins' antioxidative stress activity, which could have a significant impact on future development of procyanidins for healthy food products or drugs to treat disease such as neurodegenerative disorders. PRACTICAL APPLICATION This work evaluated the protective effect of procyanidins against oxidative stress in PC-12 neuroblastoma cells and established their activity-structure relationships, which provides useful cellular evidence for the further investigating the structure-optimizing and function-exploiting of procyanidins.

中文翻译：

---

葡萄籽原花青素对 H2O2 诱导的 PC-12 神经母细胞瘤细胞氧化应激的保护作用：构效关系

为了建立原花青素的构效关系，我们验证了 13 种葡萄籽原花青素对 PC-12 神经母细胞瘤细胞中 H2O2 诱导的氧化应激的细胞保护作用，范围从单体到三聚体。我们的研究表明，一些原花青素能够显着保护 PC-12 细胞免受 H2O2 诱导的细胞毒性，这表明它们具有抗氧化应激的神经保护作用。原花青素对氧化应激的保护作用主要取决于它们的聚合度以及它们的结构特征。原花青素的聚合度与PC-12细胞对氧化应激的保护作用呈正相关。存在 3- 或 3' 原花青素分子 C 环中的-没食子酰化基团也显着提高了它们的保护活性。这些结果表明，没食子酰化的高分子量原花青素作为有前途的抗氧化天然化合物将更有趣。这项工作首次展示了 13 种原花青素抗氧化应激活性的构效关系，这可能对未来开发用于健康食品或治疗神经退行性疾病等疾病的原花青素药物产生重大影响。实际应用这项工作评估了原花青素对 PC-12 神经母细胞瘤细胞氧化应激的保护作用，并建立了它们的活性-结构关系，