Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ 142 20 Prague, Czech Republic.
Department of Biochemistry and Microbiology, University of Chemistry and Technology Prague, CZ 166 28 Prague, Czech Republic.
J Agric Food Chem. 2020 Oct 7;68(40):11197-11206. doi: 10.1021/acs.jafc.0c03997. Epub 2020 Sep 23.
Authentic standards of food flavonoids are important for human metabolic studies. Their isolation from biological materials is impracticable; however, they can be prepared . Twelve sulfated metabolites of luteolin, myricetin, and ampelopsin were obtained with arylsulfotransferase from and fully characterized by high-performance liquid chromatography, MS, and NMR. The compounds were tested for their ability to scavenge 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid), and ,-dimethyl--phenylenediamine radicals, to reduce ferric ions and Folin-Ciocalteu reagent, and to inhibit -butyl hydroperoxide-induced lipid peroxidation of rat liver microsomes. The activity differed considerably even between monosulfate isomers. The parent compounds and myricetin-3'--sulfate were the most active while other compounds displayed significantly lower activity, particularly luteolin sulfates. No mutagenic activity of the parent compounds and their main metabolites was observed; only myricetin showed minor pro-mutagenicity. The prepared sulfated metabolites are now available as authentic standards for future and metabolic studies.
天然的食物类黄酮标准品对于人类代谢研究非常重要。虽然从生物材料中分离它们是不切实际的，但可以制备。从 中用芳基磺基转移酶获得了 12 种木樨草素、杨梅素和蛇葡萄素的硫酸化代谢物，并通过高效液相色谱、MS 和 NMR 进行了全面表征。测试了这些化合物清除 1,1-二苯基-2-苦基肼、2,2'-联氮双（3-乙基苯并噻唑啉-6-磺酸）自由基、还原铁离子和 Folin-Ciocalteu 试剂以及抑制 -丁基过氧化物诱导的大鼠肝微粒体脂质过氧化的能力。即使是单硫酸盐异构体之间的活性也有很大差异。母体化合物和杨梅素-3'-O-硫酸盐活性最高，而其他化合物活性明显较低，特别是木樨草素硫酸盐。母体化合物及其主要代谢物没有观察到致突变活性，只有杨梅素显示出轻微的促突变活性。现在可以使用这些制备的硫酸化代谢物作为未来代谢研究的天然标准品。
