Synthesis of daidzein 7-O-β-d-glucuronide-4′-O-sulfate

Steroids

Volumn 72, Issue 13, 2007, Pages 851-854

  Soidinsalo, Otto ^a   Wähälä, Kristiina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Daidzein; Glucuronide; Isoflavone; Mixed conjugate; Phytoestrogen; Sulfate

Indexed keywords

DAIDZEIN; DAIDZEIN 7 O BETA DEXTRO GLUCURONIDE 4' O SULFATE; PHYTOESTROGEN; UNCLASSIFIED DRUG;

ARTICLE; DIET; DRUG SYNTHESIS; GLUCURONIDATION;

ISOFLAVONES; PHYTOESTROGENS;

EID: 34548610309     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.07.001     Document Type: Article

References (13)

1. Adlercreutz H., van der Wildt J., Kinzel J., Attalla H., Wähälä K., Mäkelä T., et al. Lignan and isoflavonoid conjugates in human urine. J Steroid Mol Biol 52 (1995) 97-103
2. Yasuda T., Kano Y., Saito K., and Ohsawa K. Urinary and biliary metabolites of daidzin and daidzein in rats. Biol Pharm Bull 17 (1994) 1369-1374
3. Tsuchihashi R., Okawa M., Nohara T., Okabe H., and Kinjo J. Soy isoflavone metabolites isolated from human urine. Nat Med 58 (2004) 71-75
4. Kinjo J., Tsuchihashi R., Morito K., Hirose T., Aomori T., Nagao T., et al. Interactions of phytoestrogens with estrogen receptors α and β (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol Pharm Bull 27 (2004) 185-188
5. 3]isoflavone internal standards. Anal Biochem 309 (2002) 158-172
6. Wähälä K., and Hase T. Expedient synthesis of polyhydroxyisoflavones. J Chem Soc, Perkin Trans 1 (1991) 3005-3008
7. Al-Maharik N.I., Kaltia S.A., and Wähälä K. Regioselective mono-O-carboxymethylation of polyhydroxyisoflavones. Molecular 3 (1999) 20-24 Online
8. Hongu M., Saito K., and Tsujihara K. Solid-liquid phase transfer catalyzed novel glycosylation reaction of phenols. Synth Commun 29 (1999) 2775-2781
9. Li M., Han X., and Yu B. Synthesis of quercetin 3-O-(2″-galloyl)-α-l-arabinopyranoside. Tetrahedron Lett 43 (2002) 9467-9470
10. Needs P.W., and Williamson G. Syntheses of daidzein-7-yl β-d-glucopyranosiduronic acid and daidzein-4′-7-yl di-β-d-glucopyranosiduronic acid. Carbohyd Res 330 (2001) 511-515
11. Needs P., and Kroon P. Convenient synthesis of metabolically important quercetin glucuronides and sulfates. Tetrahedron 62 (2006) 6862-6868
12. Kiso Y., Ukawa K., Nakamura S., Ito K., and Akita T. Efficient removal of protecting groups by a "push-pull" mechanism II. Deprotection of O-benzyltyrosine with thioanisole-trifluoroacetic acid system without O-to-C rearrangements. Chem Pharm Bull 28 (1980) 673-676
13. Soidinsalo O., and Wähälä K. Synthesis of phytoestrogenic isoflavonoid disulfates. Steroids 69 (2004) 613-616