Curcuminoids form reactive glucuronides in vitro

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 2, 2007, Pages 538-544

  Pfeiffer, Erika ^a   Hoehle, Simone I ^a   Walch, Stephan G ^a   Riess, Alexander ^a   Sólyom, Anikó M ^b,c   Metzler, Manfred ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b UNIVERSITY OF ARIZONA   (United States)

^c Integrated Biomolecule Corporation   (United States)

Author keywords

Curcumin; Glucuronide; Microsomes; Microtubule proteins

Indexed keywords

RATTUS;

CURCUMIN; DRUG DERIVATIVE; GLUCURONIDE; MICROTUBULE PROTEIN; PHENOL DERIVATIVE;

ANIMAL; ARTICLE; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIVER MICROSOME; MALE; MASS SPECTROMETRY; METABOLISM; RAT; SPRAGUE DAWLEY RAT;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CURCUMIN; GLUCURONIDES; HUMANS; MALE; MASS SPECTROMETRY; MICROSOMES, LIVER; MICROTUBULE PROTEINS; PHENOLS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 34047229535     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0623283     Document Type: Article

References (28)

1. Scartezzini, P.; Speroni, E. Review on some plants of Indian traditional medicine with antioxidant activity. J. Ethnopharmacol. 2000, 71, 2.
2. Ammon, H. P.; Wahl, M. A. Pharmacology of Curcuma longa. Planta Med. 1991, 57, 1.
3. Sharma, R. A.; Gescher, A. J.; Steward, W. P. Curcumin: the story so far. Eur. J. Cancer 2005, 41, 1955.
4. Govindarajan, V. S. Turmeric - chemistry, technology, and quality. Crit. Rev. Food Sci. Nutr. 1980, 12, 199.
5. Aggarwal, B. B.; Kumar, A.; Bharti, A. C. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res. 2003, 23, 636.
6. Sharma, O. P. Antioxidant activity of curcumin and related compounds. Biochem. Pharmacol. 1976, 25, 1811.
7. Yang, F.; Lim, G. P.; Begum, A. N.; Ubeda, O. J.; Simmons, M. R.; Ambegaokar, S. S.; Chen, P. P.; Kayed, R.; Glabe, C. G.; Frautschy, S. A.; Cole, G. M. Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J. Biol. Chem. 2005, 280, 5892.
8. Lim, G. P.; Chu, T.; Yang, F.; Beech, W.; Frautschy, S. A.; Cole, G. M. The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse. J. Neurosci. 2001, 21, 8370.
9. Holder, G. M.; Plummer, J. L.; Ryan, A. J. The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat. Xenobiotica 1978, 8, 761.
10. Ravindranath, V.; Chandrasekhara, N. Metabolism of curcumin - studies with [3H]curcumin. Toxicology 1982, 22, 337.
11. Pan, M. H.; Huang, T. M.; Lin, J. K. Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab. Dispos. 1999, 27, 486.
12. Ireson, C.; Orr, S.; Jones, D. J.; Verschoyle, R.; Lim, C. K.; Luo, J. L.; Howells, L.; Plummer, S.; Jukes, R.; Williams, M.; Steward, W. P.; Gescher, A. Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res. 2001, 61, 1058.
13. Ireson, C. R.; Jones, D. J.; Orr, S.; Coughtrie, M. W.; Boocock, D. J.; Williams, M. L.; Farmer, P. B.; Steward, W. P.; Gescher, A. J. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol. Biomarkers Prev. 2002, 11, 105.
14. Asai, A.; Miyazawa, T. Occurrence of orally administered curcuminoid as glucuronide and glucuronide/sulfate conjugates in rat plasma. Life Sci. 2000, 67, 2785.
15. Hoehle, S. I.; Pfeiffer, E.; Solyom, A. M.; Metzler, M. Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver. J. Agric. Food Chem. 2006, 54, 756.
16. Pabon, H. J. J. A synthesis of curcumin and related compounds. Recl. Trav. Chim. Pays-Bas. 1964, 83, 379.
17. Lake, B. G. Preparation and characterization of microsomal fractions for studies on xenobiotic metabolism. In Biochemical Toxicology, A Practical Approach; Snell, K., Mulloch, B., Eds.; IRL Press: Oxford, U.K., 1987; pp 183.
18. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utulizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248.
19. Omura, T.; Sato, R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 1964, 239, 2370.
20. Shelanski, M. L.; Gaskin, F.; Cantor, C. R. Microtubule assembly in the absence of added nucleotides. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 765.
21. Pfeiffer, E.; Metzler, M. Interaction of p-benzoquinone and p-biphenoquinone with microtubule proteins in vitro. Chem. Biol. Interact. 1996, 102, 37.
22. Wang, J.; Davis, M.; Li, F.; Azam, F.; Scatina, J.; Talaat, R. A novel approach for predicting acyl glucuronide reactivity via Schiff base formation: development of rapidly formed peptide adducts for LC/MS/MS measurements. Chem. Res. Toxicol. 2004, 17, 1206.
23. Bailey, M. J.; Worrall, S.; de Jersey, J.; Dickinson, R. G. Zomepirac acyl glucuronide covalently modifies tubulin in vitro and in vivo and inhibits its assembly in an in vitro system. Chem. Biol. Interact. 1998, 115, 153.
24. Pfeiffer, E.; Hoehle, S. I.; Solyom, A. M.; Timmermann, B. N.; Metzler, M. Stable and unstable glucuronides in curcumin metabolism. Toxicol. Sci. 2003, 72, 313.
25. Pfeiffer, E.; Walch, S. G.; Riess, A.; Hoehle, S. I.; Solyom, A. M.; Metzler, M. Curcumin glucuronide inhibits cell-free microtubule assembly. Toxicologist 2006, 90, 139.
26. Balasubramanian, K. Molecular orbital basis for yellow curry spice curcumin's prevention of Alzheimer's disease. J. Agric. Food Chem. 2006, 54, 3512.
27. Tukey, R. H.; Strassburg, C. P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu. Rev. Pharmacol. Toxicol. 2000, 40, 581.
28. Cheng, A. L.; Hsu, C. H.; Lin, J. K.; Hsu, M. M.; Ho, Y. F.; Shen, T. S.; Ko, J. Y.; Lin, J. T.; Lin, B. R.; Ming-Shiang, W.; Yu, H. S.; Jee, S. H.; Chen, G. S.; Chen, T. M.; Chen, C. A.; Lai, M. K.; Pu, Y. S.; Pan, M. H.; Wang, Y. J.; Tsai, C. C.; Hsieh, C. Y. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 2001, 21, 2895.