Samet Alexander V, Shevchenko Oksana G, Rusak Vyacheslav V, Chartov Eduard M, Myshlyavtsev Andrey B, Rusanov Daniil A, Semenova Marina N, Semenov Victor V
N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991 Moscow, Russian Federation.
Institute of Biology of the Komi Scientific Center of the Ural Branch of RAS, 28 Kommunisticheskaya Street, 167982 Syktyvkar, Russian Federation.
J Nat Prod. 2019 Jun 28;82(6):1451-1458. doi: 10.1021/acs.jnatprod.8b00878. Epub 2019 Jun 18.
Free-radical-scavenging capacity antioxidant and membrane-protective properties of natural and related synthetic allylpolyalkoxybenzenes with different numbers of alkoxy/methoxy groups in the aromatic ring were evaluated using several in vitro models. These included the DPPH assay, inhibition of lipid peroxidation products accumulation, inhibition of HO-induced hemolysis, and oxidation of oxyhemoglobin. A synthetic protocol for the synthesis of natural nothoapiol () from a parsley seed metabolite, apiol (), was developed. A structure-activity relationship study revealed that both the methylenedioxy fragment and methoxy groups in the aromatic ring are favorable for antioxidant activity. Hydroxyapiol (), containing a hydroxy group in the aromatic core, was identified as the most potent compound. The pentaalkoxy-substituted nothoapiol () showed antioxidant activity in mouse brain homogenates, whereas in mouse erythrocytes it exhibited a marked pro-oxidant effect. Despite their low free-radical-scavenging capacity, allylpolyalkoxybenzenes can contribute to the total antioxidant potencies of plant essential oils.
使用多种体外模型评估了天然及相关合成的芳环中具有不同数量烷氧基/甲氧基的烯丙基聚烷氧基苯的自由基清除能力、抗氧化和膜保护特性。这些模型包括DPPH测定、脂质过氧化产物积累抑制、HO诱导的溶血抑制以及氧合血红蛋白氧化。开发了一种从欧芹籽代谢物芹菜脑苷脂（）合成天然新芹菜脑苷脂（）的合成方案。结构-活性关系研究表明，芳环中的亚甲二氧基片段和甲氧基均有利于抗氧化活性。在芳环核心含有羟基的羟基芹菜脑苷脂（）被确定为最有效的化合物。五烷氧基取代的新芹菜脑苷脂（）在小鼠脑匀浆中表现出抗氧化活性，而在小鼠红细胞中则表现出明显的促氧化作用。尽管烯丙基聚烷氧基苯的自由基清除能力较低，但它们可对植物精油的总抗氧化能力有所贡献。
