Chemical synthesis of citrus Flavanone glucuronides

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 14, 2010, Pages 8437-8443

  Khan, Muhammad Kamran ^a   Rakotomanomana, Njara ^a   Loonis, Michele ^a   Dangles, Olivier ^a  

^a UNIVERSITY OF AVIGNON   (France)

Author keywords

bioavailability; chemical synthesis; conjugation; Flavanone; glucuronide

Indexed keywords

FLAVANONE DERIVATIVE; GLUCURONIDE; PLANT EXTRACT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CITRUS FRUIT; SYNTHESIS; CITRUS;

CITRUS; FLAVANONES; GLUCURONIDES; MOLECULAR STRUCTURE; PLANT EXTRACTS;

CITRUS; CITRUS X PARADISI;

EID: 77954870400     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1010403     Document Type: Article

References (28)

1. Tomas-Barberan, F. A; Clifford, M. N. Flavanones, chalcones and dihydrochalcones - nature, occurrence and dietary burden J. Sci. Food Agric. 2000, 80, 1073-1080
2. Erlund, I. Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology Nutr. Res. (N.Y.) 2004, 24, 851-874
3. Tripoli, E.; Guardia, M. L.; Giammanco, S.; Majo, D. D.; Giammanco, M. Citrus flavonoids: molecular structure, biological activity and nutritional properties: a review Food Chem. 2007, 104, 466-479
4. Benavente-Garcia, O.; Castillo, J. Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity J. Agric. Food Chem. 2008, 56, 6185-6205
5. Manach, C.; Morand, C.; Gil-Izquierdo, A.; Bouteloup-Demange, C.; Remesy, C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice Eur. J. Clin. Nutr. 2003, 57, 235-242
6. Felgines, C.; Texier, O.; Morand, C.; Manach, C.; Scalbert, A.; Regerat, F.; Remesy, C. Bioavailability of the flavanone naringenin and its glycosides in rats Am. J. Physiol. Gastrointest. Liver Physiol. 2000, 279, G1148-G1154
7. Choudhury, R.; Chowrimootoo, G.; Srai, K.; Debnam, E.; Rice-Evans, C. A. Interaction of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation Biochem. Biophys. Res. Commun. 1999, 265, 410-415
8. Serra, H.; Mendes, T.; Bronze, M. R.; Simplicio, A. L. Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones Bioorg. Med. Chem. 2008, 16, 4009-4018
9. Matsumoto, H.; Ikoma, Y.; Sugiura, M.; Yano, M.; Hasegawa, Y. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma J. Agric. Food Chem. 2004, 52, 6653-6659
10. Mullen, W.; Archeveque, M. A.; Edwards, C. A.; Matsumoto, H.; Crozier, A. Bioavailability and metabolism of orange juice flavanones in humans: impact of a full-fat yogurt J. Agric. Food Chem. 2008, 56, 11157-11164
11. Brett, G. M.; Hollands, W.; Needs, P. W.; Teucher, B.; Dainty, J. R.; Davis, B. D.; Brodbelt, J. S.; Kroon, P. A. Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion Br. J. Nutr. 2009, 101, 664-675
12. Fischer, B.; Nudelman, A.; Ruse, M.; Herzig, J.; Gottlieb, H. E.; Keinan, E. A novel method for stereoselective glucuronidation J. Org. Chem. 1984, 49, 4988-4993
13. Pearson, A. G.; Kiefel, M. J.; Ferro, V.; Itzstein, M. V. Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid Carbohydr. Res. 2005, 340, 2077-2085
14. Al-Maharik, N.; Botting, N. P. A facile synthesis of isoflavone 7- O -glucuronides Tetrahedron Lett. 2006, 47, 8703-8706
15. Needs, P. W.; Kroon, P. A. Convenient syntheses of metabolically important quercetin glucuronides and sulfates Tetrahedron 2006, 62, 6862-6868
16. Galland, S.; Rakotomanomana, N.; Dufour, C.; Mora, N.; Dangles, O. Synthesis of hydroxycinnamic acid glucuronides and investigation of their affinity for human serum albumin Org. Biomol. Chem. 2008, 6, 4253-4260
17. González-Manzano, S.; González-Paramás, A.; Santos-Buelga, C.; Duenãs, M. Preparation and characterization of catechin sulfates, glucuronides, and methylethers with metabolic interest J. Agric. Food Chem. 2009, 57, 1231-1238
18. Boumendjel, A.; Blanc, M.; Williamson, G.; Barron, D. Efficient synthesis of flavanone glucuronides J. Agric. Food Chem. 2009, 57, 7264-7267
19. Bouktaib, M.; Atmanib, A.; Rolando, C. Regio- and stereo-selective synthesis of the major metabolite of quercetin, quercetin-3- O -β- d -glucuronide Tetrahedron Lett. 2002, 43, 6263-6266
20. Learmonth, D. A. A concise synthesis of the 3- O -β- d-and 4′- O -β- d -glucuronide conjugates of trans -resveratrol Bioconjugate Chem. 2003, 14, 262-267
21. Chakraborti, A. K.; Nayak, M. K.; Sharma, L. Selective deprotection of aryl acetates, benzoates, pivalates, and tosylates under non-hydrolytic and virtually neutral conditions J. Org. Chem. 1999, 64, 8027-8030
22. Brown, R. T.; Scheinmann, F.; Stachulski, A. V. Intermediates for glucuronide synthesis: 7-hydroxycoumarin glucuronide J. Chem. Res. (S) 1997, 370-371
23. Yoshimura, M.; Sano, A.; Kamei, J. I.; Obata, A. Identification and quantification of metabolites of orally administered naringenin chalcone in rats J. Agric. Food Chem. 2009, 57, 6432-6437
24. Jez, J. M.; Bowman, M. E.; Noel, J. P. Role of hydrogen bonds in the reaction mechanism of chalcone isomerase Biochemistry 2002, 41, 5168-5176
25. Si-Ahmed, K.; Tazerouti, F.; Badjah-Hadj-Ahmed, A. Y.; Aturki, Z.; Orazio, G. D.; Rocco, A.; Fanali, S. Analysis of hesperetin enantiomers in human urine after ingestion of blood orange juice by using nano-liquid chromatography J. Pharm. Biomed. Anal. 2010, 51, 225-229
26. Weintraub, R. A.; Ameer, B.; Johnson, J. V.; Yost, R. A. Trace determination of naringenin and hesperitin by tandem mass spectrometry J. Agric. Food Chem. 1995, 43, 1966-1968
27. Zhou, D.; Xu, Q.; Xue, X.; Zhang, F.; Liang, X. Identification of O -diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and collision-induced dissociation mass spectrometry J. Pharm. Biomed. Anal. 2006, 42, 441-448
28. Duenas, M.; Mingo-Chornet, H.; Pérez-Alonso, J. J.; Paola-Naranjo, R. D.; González-Paramás, A. M.; Santos-Buelga, C. Preparation of quercetin glucuronides and characterization by HPLC-DAD-ESI/MS Eur. Food Res. Technol. 2008, 227, 1069-1076