Structural elucidation of hydroxylated metabolites of the isoflavan equol by gas chromatography-mass spectrometry and high-performance liquid chromatography-mass spectrometry

Drug Metabolism and Disposition

Volumn 34, Issue 1, 2006, Pages 51-60

  Rüfer, Corinna E ^a   Glatt, Hansruedi ^b   Kulling, Sabine E ^c  

^a FEDERAL RESEARCH INSTITUTE OF NUTRITION AND FOOD   (Germany)

^b GERMAN INSTITUTE OF HUMAN NUTRITION   (Germany)

^c UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYEQUOL; 3 HYDROXYEQUOL; 3' HYDROXYEQUOL; 4 HYDROXYEQUOL; 6 HYDROXYEQUOL; 6,3' HYDROXYEQUOL; 8 HYDROXYEQUOL; 8,3' HYDROXYEQUOL; AROCLOR; DRUG METABOLITE; EQUOL; ISOFLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DIODE; DRUG METABOLISM; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROXYLATION; LIVER MICROSOME; MALE; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; RAT; SOYBEAN; STRUCTURE ANALYSIS; URINALYSIS;

ANIMALS; AROCLORS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; HYDROXYLATION; ISOFLAVONES; MALE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; STEREOISOMERISM;

ANIMALIA; GLYCINE MAX; RATTUS NORVEGICUS;

EID: 29944435941     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.105.004929     Document Type: Article

References (30)

1. Arora A, Nair MG, and Strasburg GM (1998) Antioxidant activities of isoflavones and their biological metabolites in a liposomal system. Arch Biochem Biophys 356:133-141.
2. Axelson M, Kirk DN, Farrant RD Cooley G, Lawson AM, and Setchell KD (1982) The identification of the weak oestrogen equol [7-hydroxy-3-(4′- hydroxyphenyl)-chroman] in human urine. Biochem J 201:353-357.
3. Burke MD, Thompson S, Elcombe CR, Halpert J, Haaparanta T, and Mayer RT (1985) Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochrome P-450. Biochem Pharmacol 34:3337-3345.
4. Burke MD, Thompson S, Weaver R, Wolf C, and Mayer R (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem Pharmacol 48:923-936.
5. Chang YC and Nair MG (1995) Metabolism of daidzein and genistein by intestinal bacteria. J Nat Prod 58:1892-1896.
6. Correia MA (1995) Rat and human liver cytochromes P450, in Cytochrome P450: Structure, Mechanism and Biochemistry (Ortiz de Montellano PR, ed) pp 607-630. Plenum Press, New York.
7. Frankenfeld CL, McTiernan A, Aiello EJ, Thomas WK, LaCroix K, Schramm J, Schwartz SM, Holt VL, and Lampe JW (2004) Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women. Cancer Epidemiol Biomarkers Prev 13:1156-1162.
8. Heinonen S, Wahala K, and Adlercreutz H (1999) 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. Anal Biochem 2742:211-219.
9. Heinonen SM, Hoikkala A, Wahala K, and Adlercreutz H (2003) Metabolism of the soy isoflavones daidzein, genistein and glycitein in human subjects. Identification of new metabolites having an intact isoflavonoid skeleton. J Steroid Biochem Mol Biol 87:285-299.
10. Joannou GE, Kelly GE, Reeder AY, Waring M, and Nelson C (1995) A urinary profile study of dietary phytoestrogens. The identification and mode of metabolism of new isoflavonoids. J Steroid Biochem Mol Biol 54:167-184.
11. Kelly GE, Nelson C, Waring MA, Joannou GE, and Reeder AY (1993) Metabolites of dietary (soya) isoflavones in human urine. Clin Chim Acta 223:9-22.
12. Kostelac D, Rechkemmer G, and Briviba K (2003) Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element. J Agric Food Chem 51:7632-7635.
13. Kulling SE, Honig DM, and Metzler M (2001) Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. J Agric Food Chem 49:3024-3033.
14. Kulling SE, Honig DM, Simat TJ, and Metzler M (2000) Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein. J Agric Food Chem 48:4963-4972.
15. Lake BG (1987) Preparation and characterization of microsomal fractions for studies on xenobiotic metabolism, in Biochemical Toxicology (Snell K and Mullock B eds), pp 138-215. IRL Press, Oxford.
16. Lamberton J, Suares H, and Watson K (1978) Catalytic hydrogenation of isoflavones. The preparation of (+/-)-equol and related isoflavans. Aust J Chem 31:455-457.
17. Lund TD, Munson DJ, Haldy ME, Setchell KD, Lephart ED, and Handa RJ (2004) Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback. Biol Reprod 70:1188-1195.
18. Marrian GF and Haselwood GAD (1932) Equol, a new active phenol isolated from ketohydroxyestrin fraction of mare's urine. Biochem J 26:1226-1232.
19. Morito K, Hirose T, Kinjo J, Hirakawa T, Okawa M, Nohara T, Ogawa S, Inoue S, Muramatsu M, and Masamune Y (2001) Interaction of phytoestrogens with estrogen receptors alpha and beta. Biol Pharm Bull 24:351-356.
20. Muthyala RS, Ju YH, Sheng S, Williams LD, Doerge DR, Katzenellenbogen BS, Helferich WG, and Katzenellenbogen JA (2004) Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta. Bioorg Med Chem 12:1559-1567.
21. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. 1. Evidence for its hemoprotein nature. J Biol Chem 61:461-467.
22. Rimbach G, De Pascual-Teresa S, Ewins BA, Matsugo S, Uchida Y, Minihane AM, Turner R, VafeiAdou K, and Weinberg PD (2003) Antioxidant and free radical scavenging activity of isoflavone metabolites. Xenobiotica 33:913-925.
23. Rowland I, Faughnan M, Hoey L, Wahala K, Williamson G, and Cassidy A (2003) Bioavailability of phyto-oestrogens. Br J Nutr 89:S45-S58.
24. Rowland IR, Wiseman H, Sanders TA, Adlercreutz H, and Bowey EA (2000) Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora. Nutr Cancer 36:27-32.
25. Setchell KD, Brown NM, and Lydeking-Olsen E (2002) The clinical importance of the metabolite equol - a clue to the effectiveness of soy and its isoflavones. J Nutr 132:3577-3584.
26. Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, et al. (2005) S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr 81:1072-1079.
27. Shutt DA and Braden AWH (1968) The significance of equol in relation to the oestrogenic responses in sheep ingesting clover with a high formononetin content. Aust J Agric Res 19:545-555.
28. Turner R, Baron T, Wolffram S, Minihane AM, Cassidy A, Rimbach G, and Weinberg PD (2004) Effect of circulating forms of soy isoflavones on the oxidation of low density lipoprotein. Free Radic Res 382:209-216.
29. Wahala K, Koskimies JK, Mesilaakso M, Salakka AK, Leino TK, and Adlercreutz H (1997) The synthesis, structure and anticancer activity of cis- and trans-4′,7-dihydroxyisoflavan-4-ols. J Org Chem 62:7690-7693.
30. Wessely F and Prillinger F (1939) Die Konstitution des Equols. Chem Universitätslaborat Wien 72:629-633.