Identification of isoflavone metabolites dihydrodaidzein, dihydrogenistein, 6′-OH-O-dma, and cis-4-OH-equol in human urine by gas chromatography-mass spectroscopy using authentic reference compounds
Identification of isoflavone metabolites dihydrodaidzein, dihydrogenistein, 6′-OH-O-dma, and cis-4-OH-equol in human urine by gas chromatography-mass spectroscopy using authentic reference compounds
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DOI：
10.1006/abio.1999.4279
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发表时间：
1999-10-15
影响因子：
2.9
通讯作者：
Adlercreutz, H
中科院分区：
文献类型：
--
作者：
Heinonen, S;Wähälä, K;Adlercreutz, H
对大豆主要异黄酮——大豆黄酮和金雀异黄酮的代谢产物进行了检查。六名志愿者将大豆纳入正常饮食一周，并在食用大豆之前和之后分析尿液样本。采用 Sephadex LH-20 吸收色谱和气相色谱-电子电离质谱 (GC-EIMS) 进行尿液代谢物的分离和表征。分离出的异黄酮的结构通过使用真实的参考化合物进行了确认。通过将尿液化合物的保留时间和光谱与合成的参考标准品进行比较，除了已知的异黄酮类大豆黄酮、染料木黄酮、黄豆黄素和已知的代谢物雌马酚、O-去甲基安哥拉素和二氢黄豆苷元之外，还鉴定了二氢染料木黄酮、6'-OH-O-去甲基安哥拉素和顺式-4-OH-牛尿酚。还鉴定出哺乳动物木脂素肠内酯和肠二醇。通过比较两种甲硅烷基化试剂 N,O-双-(三甲基甲硅烷基)-三氟乙酰胺 (BSTFA) 和吡啶:六甲基二硅氮烷:三甲基氯 (QSM) 来检查异黄酮的 GC-MS 衍生化，这两种试剂均用于这些化合物的衍生化。硅烷化实验揭示了衍生产物的组成存在显着差异。对早期公布的二氢金雀异黄酮和 6'-OH-O-dma 的数据进行了一些更正。 (C) 1999 年学术出版社。
The metabolic products of daidzein and genistein, the principal isoflavones of soy, were examined. Six volunteers included soy into their normal diet for a a-week period and urine samples were analyzed before and after soy consumption. Isolation and characterization of the urinary metabolites were carried out with absorption chromatography on Sephadex LH-20 and gas chromatography-electron ionization mass spectrometry (GC-EIMS). The structures of the isoflavones isolated were confirmed by using authentic reference com pounds. Dihydrogenistein, 6'-OH-O-desmethylangolensin, and cis-4-OH-equol were identified, in addition to known isoflavonoids daidzein, genistein, glycitein, and the known metabolites equol, O-desmethylangolensin, and dihydrodaidzein, by comparing the retention times and the spectra of the urinary compounds with those of the synthesized reference standards. The mammalian lignans enterolactone and enterodiol were also identified. Derivatization of the isoflavones for GC-MS was examined by comparing two silylating reagents, N,O-bis-(trimethylsilyl)-trifluoroacetamide (BSTFA) and pyridine:hexamethyldisilazan:trimethylchloro (QSM), both used for the derivatization of these compounds. The silylation experiments revealed significant differences in the compositions of the derivatization products. Some corrections were made concerning the earlier published data of dihydrogenistein and 6'-OH-O-dma. (C) 1999 Academic Press.