Metabolism of the soy isoflavones daidzein, genistein and glycitein in human subjects. Identification of new metabolites having an intact isoflavonoid skeleton - PubMed (original) (raw)
Metabolism of the soy isoflavones daidzein, genistein and glycitein in human subjects. Identification of new metabolites having an intact isoflavonoid skeleton
Satu Maarit Heinonen et al. J Steroid Biochem Mol Biol. 2003 Dec.
Abstract
Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent diseases. Soy and soy foods are rich sources of isoflavones, which have been shown to possess several biological activities. In this study, the metabolism of soy isoflavones daidzein, genistein and glycitein was investigated in human subjects. The aim was to find and identify urinary phase I metabolites of isoflavones, which have an intact isoflavonoid skeleton, and which might possess some bioactivity. Six volunteers included three soy bars per day into their normal western diet for a 2-week period. Daily urine samples were collected before, and after the supplementation period. Urine samples were hydrolyzed with Helix pomatia, extracted with diethyl ether, purified with Sephadex LH-20 chromatography, and analyzed as trimethylsilyl derivatives using gas chromatography-mass spectrometry (GC-MS). The structures of the isoflavone metabolites were identified using authentic reference compounds. The metabolites, for which authentic reference compounds were not available, were identified by the interpretation of mass spectra. Several new isoflavone metabolites were identified, and the presence of previously reported metabolites confirmed. The metabolic pathways of daidzein, genistein and glycitein are presented on the basis of the identification of the metabolites in human urine after soy supplementation.
Similar articles
- Isoflavonoid levels in spot urine are associated with frequency of dietary soy intake in a population-based sample of middle-aged and older Chinese in Singapore.
Seow A, Shi CY, Franke AA, Hankin JH, Lee HP, Yu MC. Seow A, et al. Cancer Epidemiol Biomarkers Prev. 1998 Feb;7(2):135-40. Cancer Epidemiol Biomarkers Prev. 1998. PMID: 9488588 - Studies of the in vitro intestinal metabolism of isoflavones aid in the identification of their urinary metabolites.
Heinonen SM, Wähälä K, Liukkonen KH, Aura AM, Poutanen K, Adlercreutz H. Heinonen SM, et al. J Agric Food Chem. 2004 May 5;52(9):2640-6. doi: 10.1021/jf030681s. J Agric Food Chem. 2004. PMID: 15113171 - Dietary Soy Isoflavone: A Mechanistic Insight.
Chadha R, Bhalla Y, Jain A, Chadha K, Karan M. Chadha R, et al. Nat Prod Commun. 2017 Apr;12(4):627-634. Nat Prod Commun. 2017. PMID: 30520611 Review. - Soy for breast cancer survivors: a critical review of the literature.
Messina MJ, Loprinzi CL. Messina MJ, et al. J Nutr. 2001 Nov;131(11 Suppl):3095S-108S. doi: 10.1093/jn/131.11.3095S. J Nutr. 2001. PMID: 11694655 Review.
Cited by
- [A critical assessment of phytotherapy for prostate cancer].
Perabo FG, von Löw EC, Siener R, Ellinger J, Müller SC, Bastian PJ. Perabo FG, et al. Urologe A. 2009 Mar;48(3):270-1, 274-83. doi: 10.1007/s00120-008-1929-5. Urologe A. 2009. PMID: 19153707 Review. German. - Identification of the Metabolites of Both Formononetin in Rat Hepatic S9 and Ononin in Rat Urine Samples and Preliminary Network Pharmacology Evaluation of Their Main Metabolites.
Yang YZ, Wang T, Chen QL, Chen HB, He QS, Zhang YZ. Yang YZ, et al. Molecules. 2023 Nov 6;28(21):7451. doi: 10.3390/molecules28217451. Molecules. 2023. PMID: 37959870 Free PMC article. - Metabolomics Technologies for the Identification and Quantification of Dietary Phenolic Compound Metabolites: An Overview.
López-Yerena A, Domínguez-López I, Vallverdú-Queralt A, Pérez M, Jáuregui O, Escribano-Ferrer E, Lamuela-Raventós RM. López-Yerena A, et al. Antioxidants (Basel). 2021 May 25;10(6):846. doi: 10.3390/antiox10060846. Antioxidants (Basel). 2021. PMID: 34070614 Free PMC article. Review. - Soy-derived phytoalexins: mechanism of in vivo biological effectiveness in spite of their low bioavailability.
Oh J, Jang CH, Kim JS. Oh J, et al. Food Sci Biotechnol. 2018 Oct 25;28(1):1-6. doi: 10.1007/s10068-018-0498-7. eCollection 2019 Feb. Food Sci Biotechnol. 2018. PMID: 30815288 Free PMC article. Review. - Bioavailability and pharmacokinetics of genistein: mechanistic studies on its ADME.
Yang Z, Kulkarni K, Zhu W, Hu M. Yang Z, et al. Anticancer Agents Med Chem. 2012 Dec;12(10):1264-80. doi: 10.2174/187152012803833107. Anticancer Agents Med Chem. 2012. PMID: 22583407 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous