Curcumin uptake and metabolism

BioFactors

Volumn 39, Issue 1, 2013, Pages 14-20

  Metzler, Manfred ^a   Pfeiffer, Erika ^a   Schulz, Simone I ^a,b   Dempe, Julia S ^a,c  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b BAYER PHARMA AG   (Germany)

^c Dr Knoell Consult GmbH   (Germany)

Author keywords

Bioavailability; Curcumin; Degradation; Intestinal absorption; Metabolism

Indexed keywords

CURCUMIN;

ALKALINITY; ARTICLE; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG DEGRADATION; DRUG METABOLISM; DRUG STABILITY; DRUG TISSUE LEVEL; DRUG TRANSPORT; DRUG UPTAKE; DRUG URINE LEVEL; HUMAN; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; BIOLOGICAL AVAILABILITY; BIOTRANSFORMATION; CURCUMIN; DRUG STABILITY; HUMANS; TISSUE DISTRIBUTION;

ANIMALIA; CURCUMA LONGA;

EID: 84874117896     PISSN: 09516433     EISSN: 18728081     Source Type: Journal    
DOI: 10.1002/biof.1042     Document Type: Article

References (43)

1. Wang, Y. J., Pan, M. H., Cheng, A. L., Lin, L. I., and Ho, Y. S., et al. ( 1997) Stability of curcumin in buffer solutions and characterization of its degradation products. J. Pharmaceut. Biomed. Anal. 15, 1867-1876.
2. Roughley, P. J. and Whiting, D. A. ( 1973) Experiments in the biosynthesis of curcumin. J. Chem. Soc. Perkin I 20, 2379-2388.
3. Tønnesen, H. H. and Karlsen, J. ( 1985) Studies on curcumin and curcuminoids. V. Alkaline degradation of curcumin. Z. Lebensm. Unters. Forsch. 180, 132-134.
4. Gordon, O. N. and Schneider, C. ( 2012) Vanillin and ferulic acid: not the major degradation products of curcumin. Trends Mol. Med. 18, 361-363.
5. Schneider, C., Amberg, A., Feurle, J., Roβ, A., and Roth, M., et al. ( 1998) 2-[(4′-Hydroxy-3′-methoxy)-phenoxy]-4-(4″-hydroxy-3″-methoxyphenyl)-8-hydroxy-6-oxo-3-oxabicyclo[3.3.0]-7-octene: unusual product of the soybean lipoxygenase-catalyzed oxygenation of curcumin. J. Mol. Catal. B 4, 219-227.
6. Griesser, M., Pistis, V., Suzuki, T., Tejera, N., and Pratt, D. A. et al. ( 2011) Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin. J. Biol. Chem. 286, 1114-1124.
7. Tóth, G., Roth, M., Weckerle, B., and Schreier, P. ( 2000) Structural elucidation of two novel products from the soybean lipoxygenase-catalyzed dioxygenation of curcumin. Magn. Reson. Chem. 38, 51-54.
8. Tønnesen, H. H., Karlsen, J., and van Henegouwen, G. B. ( 1986) Studies on curcumin and curcuminoids. VIII. Photochemical stability of curcumin. Z. Lebensm. Unters. Forsch. 183, 116-122.
9. Pfeiffer, E., Hoehle, S. I., Walch, S. G., Riess, A., and Sólyom, A. M., et al. ( 2007) Curcuminoids form reactive glucuronides in vitro. J. Agric. Food Chem. 55, 538-544.
10. Pfeiffer, E., Höhle, S., Solyom, A. M., and Metzler, M. ( 2003) Studies on the stability of turmeric constituents. J. Food Engin. 56, 257-259.
11. Holder, G. M., Plummer, J. L., and Ryan, A. J. ( 1978) The metabolism and excretion of curcumin (1, 7-bis-(4-hydroxy-3-methoxyphenyl)-1, 6-heptadiene-3, 5-dione) in the rat. Xenobiotica 8, 761-768.
12. Hoehle, S. I., Pfeiffer, E., Sólyom, A. M., and Metzler, M. ( 2006) Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver. J. Agric. Food Chem. 54, 756-764.
13. Pan, M. H., Huang, T. M., and Lin, J. K. ( 1999) Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab. Dispos. 27, 486-494.
14. 3H]curcumin. Toxicology 22, 337-344.
15. Asai, A. and Miyazawa, T. ( 2000) Occurrence of orally administered curcuminoid as glucuronide and glucuronide/sulfate conjugates in rat plasma. Life Sci. 67, 2785-2793.
16. 2 production. Cancer Res. 61, 1058-1064.
17. Ireson, C. R., Jones, D. J. L., Orr, S., Coughtrie, M. W. H., and Boocock, D. J., et al. ( 2002) Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol. Biomarkers Prev. 11, 105-111.
18. Hoehle, S. I., Pfeiffer, E., and Metzler, M. ( 2007) Glucuronidation of curcuminoids by human microsomal and recombinant UDP-glucuronosyltransferases. Mol. Nutr. Food Res. 51, 932-938.
19. Usta, M., Wortelboer, H. M., Vervoort, J., Boersma, M. G., and Rietjens, I. M. C. M., et al. ( 2007) Human glutathione S-transferase-mediated glutathione conjugation of curcumin and efflux of these conjugates in Caco-2 cells. Chem. Res. Toxicol. 20, 1895-1902.
20. Wahlström, B. and Blennow, G. ( 1978) A study on the fate of curcumin in the rat. Acta Pharmacol. Toxicol. 43, 86-92.
21. Anand, P., Kunnumakkara, A. B., Newman, R. A., and Aggarwal, B. B. ( 2007) Bioavailability of curcumin: problems and promises. Mol. Pharmaceut. 4, 807-818.
22. Esatbeyoglu, T., Huebbe, P., Ernst, I. M. A., Chin, D., and Wagner, A. E. et al. ( 2012) Curcumin-from molecule to biological function. Angew. Chem. Int. Ed. 51, 5308-5332.
23. Yang, K. Y., Lin, L. C., Tseng, T. Y., Wang, S. C., and Tsai, T. H. ( 2007) Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS. J. Chromatogr. B 853, 183-189.
24. Cheng, A. L., Hsu, C. H., Lin, J. K., Hsu, M. M., and Ho, Y. F., et al. ( 2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 21, 2895-2900.
25. Sharma, R. A., McLelland, H. R., Hill, K. A., Ireson, C. R., and Euden, S. A., et al. ( 2001) Pharmacodynamic and pharmacokinetic study of oral curcuma extract in patients with colorectal cancer. Clin. Cancer Res. 7, 1894-1900.
26. Sharma, R. A., Euden, S. A., Platton, S. L., Cooke, D. N., and Shafayat, A., et al. ( 2004) Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance. Clin. Cancer Res. 10, 6847-6854.
27. Vareed, S. K., Kakarala, M., Ruffin, M. T., Crowell, J. A., and Normolle, D. P., et al. ( 2008) Pharmacokinetics of curcumin conjugate metabolites in healthy human subjects. Cancer Epidemiol. Biomarkers Prev. 17, 1411-1417.
28. Lao, C. D., Ruffin, M. T., Normolle, D., Heath, D. D., and Murray, S. I., et al. ( 2006) Dose escalation of a curcuminoid formulation. BMC Compl. Altern. Med. 6, 10.
29. Carroll, R. E., Benya, R. V., Turgeon, D. K., Vareed, S., and Neuman, M., et al. ( 2011) Phase IIa clinical trial of curcumin for the prevention of colorectal neoplasia. Cancer Prev. Res. 4, 354-364.
30. Ravindranath, V. and Chandrasekhara, N. ( 1980) Absorption and tissue distribution of curcumin in rats. Toxicology 16, 259-265.
31. Garcea, G., Jones, D. J. L., Singh, R., Dennison, A. R., and Farmer, P. B., et al. ( 2004) Detection of curcumin and its metabolites in hepatic tissue and portal blood of patients following oral administration. Br. J. Cancer 90, 1011-1015.
32. Ravindranath, V. and Chandrasekhara, N. ( 1981) In vitro studies on the intestinal absorption of curcumin in rats. Toxicology 20, 251-257.
33. Wahlang, B., Pawar, Y. B., and Bansal, A. K. ( 2011) Identification of permeability-related hurdles in oral delivery of curcumin using the Caco-2 cell model. Eur. J. Pharmaceut. Biopharmaceut. 77, 275-282.
34. Dempe, J. S., Scheerle, R. K., Pfeiffer, E., and Metzler, M. ( 2012) Metabolism and permeability of curcumin in cultured Caco-2 cells. Mol. Nutr. Food Res., DOI: 10.1002/mnfr.201200113.
35. Yee, S. ( 1997) In vitro permeability across Caco-2 cells (colonic) can predict in vivo (small intestinal) absorption in man-fact or myth. Pharm. Res. 14, 763-766.
36. Press, B. and Di Grandi, D. ( 2008) Permeability for intestinal absorption: Caco-2 assay and related issues. Curr. Drug Metab. 9, 893-900.
37. Garcea, G., Berry, D. P., Jones, D. J. L., Singh, R., and Dennison, A. R., et al. ( 2005) Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences. Cancer Epidemiol. Biomarkers Prev. 14, 120-125.
38. López-Lázaro, M. ( 2008) Anticancer and carcinogenic properties of curcumin: considerations for its clinical development as a cancer chemopreventive and chemotherapeutic agent. Mol. Nutr. Food Res. 52, S103-S127.
39. Sharma, R. A., Gescher, A. J., and Steward, W. P. ( 2005) Curcumin: the story so far. Eur. J. Cancer 41, 1955-1968.
40. Zhou, H., Beevers, C. S., and Huang, S. ( 2011) Targets of curcumin. Curr. Drug Targets 12, 332-347.
41. Anand, P., Thomas, S. G., Kunnumakkara, A. B., Sundaram, C., and Harikumar, K. B., et al. ( 2008) Biological activities of curcumin and its analogues (congeners) made by man and mother nature. Biochem. Pharmacol. 76, 1590-1611.
42. Shen, L. and Ji, H. F. ( 2009) Contribution of degradation products to the anticancer activity of curcumin. Clin. Cancer Res. 15, 7108.
43. Shen, L. and Ji, H. F. ( 2012) The pharmacology of curcumin: is it the degradation products? Trends Mol. Med. 18, 138-144.