Pharmacokinetics and pharmacodynamics of curcumin

Advances in Experimental Medicine and Biology

Volumn 595, Issue , 2007, Pages 453-470

  Sharma, Ricky A ^a,b   Steward, William P ^c   Gescher, Andreas J ^d  

^a UNIFORMED SERVICES UNIVERSITY OF THE HEALTH SCIENCES   (United States)

^b BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^c UNIVERSITY OF LEICESTER   (United Kingdom)

^d UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; AZOXYMETHANE; CURCUMIN; DRUG METABOLITE; HEXAHYDROCURCUMIN; PLACEBO; TETRAHYDROCURCUMIN; UNCLASSIFIED DRUG;

ALKALINE PHOSPHATASE BLOOD LEVEL; ANGIOGENESIS; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; CANCER CHEMOTHERAPY; CARCINOGENESIS; CLINICAL TRIAL; COLORECTAL CANCER; DIARRHEA; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG DOSE ESCALATION; DRUG GLUCURONIDATION; DRUG INHIBITION; DRUG METABOLISM; DRUG POTENCY; DRUG SAFETY; DRUG STRUCTURE; DRUG SULFATION; HUMAN; LACTATE DEHYDROGENASE BLOOD LEVEL; NAUSEA; NONHUMAN; PRIORITY JOURNAL; REVIEW; SIDE EFFECT; STRUCTURE ACTIVITY RELATION; UNSPECIFIED SIDE EFFECT;

ANIMALIA; CURCUMA; CURCUMA LONGA;

EID: 84934443492     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-0-387-46401-5_20     Document Type: Review

References (80)

1. B. Brouk, Plants Consumed by Man. New York: Academic Press, 1975, p. 331.
2. D. Eigner and D. Sholz, Ferula asa-foetida and curcuma longa in traditional medical treatment and diet in Nepal. J Ethnopharmacol 67, 1-6 (1999).
3. J. Milobedzka, V. Kostanecki, and V. Lampe, Structure. Chem Ber 43, 2163 (1910).
4. D. D. Heath, F. Khwaja, and C. L. Rock, Curcumin content of turmeric and curry powders. FASEB J 18, A125 (2004).
5. H. P. Ammon and M. A. Wahl, Pharmacology of curcuma longa. Planta Med 57, 1-7 (1991).
6. B. B. Aggarwal, A. Kumar, and A. C. Bharti, Anticancer potential of curcumin: Preclinical and clinical studies. Anticancer Res 23, 363-398 (2003).
7. B. Joe, M. Vijaykumar, and B. R. Lokesh, Biological properties of curcumin: Cellular and molecular mechanisms of action. Crit Rev Food Sci Nutr 44, 97-111 (2004).
8. B. Wahlstrom and G. Blennow, A study on the fate of curcumin in the rat. Acta Pharmacol Toxicol 43, 86-92 (1978).
9. V. Ravindranath and N. Chandrasekhara, Absorption and tissue distribution of curcumin in rats. Toxicology 16, 259-265 (1980).
10. V. Ravindranath and N. Chandrasekhara, In vitro studies on the intestinal absorption of curcumin in rats. Toxicology 20, 251-257 (1981).
11. V. Ravindranath and N. Chandrasekhara, Metabolism of curcumin: Studies with [3H] curcumin. Toxicology 22, 337-344 (1981).
12. G. M. Holder, J. L. Plummer, and A. J. Ryan, 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 (1978).
13. M. H. Pan, T. M. Huang, and J. K. Lin, Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab Dispos 27, 486-494 (1999).
14. 2 production. Cancer Res 61, 1058-1064 (2001).
15. C R. Ireson, D. J. L. Jones, S. Orr, M. W. H. Coughtrie, D. Boocock, M. L. Williams, P. B. Farmer, W. P. Steward, and A. J. Gescher, Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol Biomarkers Prev 11, 97-104 (2002).
16. R. A. Sharma, C. R. Ireson, R. D. Verschoyle, et al., Effects of dietary curcumin on glutathione S-transferase and malondialdehyde-DNA adducts in rat liver and colon mucosa: Relationship with drug levels. Clin Cancer Res 7, 1452-1458 (2001).
17. G. Shoba, D. Joy, T. Joseph, M. Majeed, R. Rajendran, and P. S. S. R. Srinivas, Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Med 64, 353-356 (1998).
18. A. L. Cheng, C, H. Hsu, J. K. Lin, et al., Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res 21, 2895-2900 (2001).
19. M. T. Ruffin, D. P. Normolle, D. D. Heath, J. M. Bailey, S. I. Murray, M. E. Boggs, J. A. Crowell, C. L. Rock, and D. E. Brenner, Dose escalation of curcumin in healthy adults. Cancer Epidemiol Biomarkers Prev 12(Pt 2 Suppl S), 1324S-1324S (2003).
20. R. A. Sharma, H. R. McLelland, K. A. Hill, et al., Pharmacodynamic and pharmacokinetic study of oral Curcuma extract in patients with colorectal cancer. Clin Cancer Res 7, 1894-1900 (2001).
21. R. A. Sharma, S. A. Euden, S. L. Platton, et al., Phase I clinical trial of oral curcumin: Biomarkers of systemic activity and compliance. Clin Cancer Res 10, 6847-6854 (2004).
22. G. Garcea, D. P. Berry, D. J. L. Jones, et al., 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 (2005).
23. G. Garcea, D. J. L. Jones, R. Singh, et al., Detection of curcumin and its metabolites in hepatic tissue and portal blood of patients following oral administration. Br J Cancer 90, 1011-1015 (2004).
24. NCI, DCPC, Clinical development plan: Curcumin. J Cell Biochem 26S, 72-85 (1996).
25. C. V. Rao, A. Rivenson, B. Simi, and B. S. Reddy, Chemoprevention of colon carcinogenesis by dietary curcumin, a naturally occurring plant phenolic compound. Cancer Res 55, 259-266 (1995).
26. K. B. Soni, A. Rajan, and R. Kuttan, Reversal of aflatoxin induced liver damage by turmeric and curcumin. Cancer Lett 66, 115-121 (1992).
27. T. Kawamori, R. Lubet, V. E. Steele, et al., Chemopreventative effect of curcumin, a naturally occurring anti-inflammatory agent, during the promotion/progression stages of colon cancer. Cancer Res 59, 597-601 (1999).
28. H. S. Samaha, G. J. Kelloff, V. Steele, C. V. Rao, and B. S. Reddy, Modulation of apoptosis by sulindac, curcumin, phenylethyl-3-methylcaffeate, and 6-phenylhexyl isothiocyanate, Apoptotic index as a biomarker in colon cancer chemoprevention and promotion. Cancer Res 57, 1301-1305 (1997).
29. S. R. Volate, D. M. Davenport, S. J. Muga, and M. Wargovich, Modulation of aberrant crypt foci and apoptosis by dietary herbal supplements (quercetin, curcumin, silymarin, ginseng and rutin). Carcinogenesis 26, 1450-1456 (2005).
30. C. Luongo, A. R. Moser, S. Gledhill, and W. F Dove, Loss of Apc(+) in intestinal adenomas from Min mice. Cancer Res 54, 5947-5952 (1994).
31. S. Perkins, R. D. Verschoyle, K. A. Hill, I. Parveen, M. D. Threadgill, R. A. Sharma, M. L. Williams, W. P. Steward, and A. J. Gescher, Chemopreventive efficacy and pharmacokinetics of curcumin in the Min/+ mouse, a model of familial adenomatous polyposis. Cancer Epidemiol Biomarkers Prev 11, 535-540 (2002).
32. R. G. Tunstall, R. A. Sharma, S. Perkins, S. Sale, R. Singh, P. B. Farmer, W. P. Steward, and A. J. Gescher, Cyclooxygenase-2 expression and oxidative DNA adducts in murine intestinal adenomas: Modification by dietary curcumin and implications for clinical trials. Eur J Cancer 42, 415-421 (2006).
33. A. H. Conney, Enzyme induction and dietary chemicals as approaches to cancer chemoprevention: The seventh DeWitt S. Goodman Lecture. Cancer Res 63, 7005-7031 (2003).
34. N. Li, X. Chen, J. Liao, et al. Inhibtion of 7,12-dimethylbenz[a] anthracene (DMBA)-induced oral carcinogenesis in hamsters by tea and curcumin. Carcinogenesis 23, 1307-1313 (2002).
35. K. Imaida, S. Tamano, K. Kato, Y. Ikeda, M. Asamoto, S. Takahashi, Z. Nir, M. Murakoshi, H. Nishino, and T. Shirai, Lack of chemopreventive effects of lycopene and curcumin on experimental rat prostate carcinogenesis. Carcinogenesis 22, 467-472 (2001).
36. B. B. Aggarwal, S. Shishodia, Y. Takada, S. Banerjee, R. A. Newman, C. E. Bueso-Ramos, and J. E. Price, Curcumin suppresses the paclitaxel-induced nuclear factor-kappa B pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice.Clin Cancer Res 11, 7490-7498 (2005).
37. S. V. Bava, V. T. Puliappadamba, A. Deepti, A. Nair, D. Karunagaran, and R. J. Anto, Sensitization of taxol-induced apoptosis by curcumin involves down-regulation of nuclear factor-kappa B and the serine/threonine kinase Akt and is independent of tubulin polymerization. J Biol Chem 280, 6301-6308 (2005)
38. Y. Shukla, A. Arora, and P. Taneja, Antimutagenic potential of curcumin on chromosomal aberrations in Wistar rats. Mutat Res: Genet Toxicol Environ Mutag 515, 197-202 (2002).
39. M. E. Egan, M. Pearson, S. A. Weiner, et al., Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects. Science 304, 600-602 (2004).
40. S. V. Singh, X. Hu, S. K. Srivastava, et al., Mechanism of inhibition of benzo[a]pyrene-induced forestomach cancer in mice by dietary curcumin. Carcinogenesis 19, 1357-1360 (1998).
41. M. Susan and M.A. Rao, Induction of glutathione S-transferase activity by curcumin in mice. Drug Res 42, 962-964 (1992).
42. J. T. Piper, S. S. Singhal, M. Salameh, R. T. Torman, Y. C. Awasthi, and S. Awasthi, Mechanisms of anticarcinogenic properties of curcumin: The effect of curcumin on glutathione linked detoxification enzymes in rat liver. Int J Biochem Cell Biol 30, 445-456 (1998).
43. W. A. Nijhoff, G. M. Groen, and W. H. M. Peters, Induction of rat hepatic and intestinal glutathione S-transferases and glutathione by dietary naturally occurring anticarcinogens. Int J Oncol 3, 1131-1139 (1993).
44. A. T. Dinkova-Kostova and P. Talalay, Relation of structure of curcumin analogs to their potencies as inducers of Phase 2 detoxification enzymes. Carcinogenesis 20, 911-914 (1999).
45. J. D. Hayes and D. J. Pulford, The glutathione S-transferases supergene family. Crit Rev Biochem Mol Biol 30, 445-600 (1995).
46. A. Duvoix, S. Delhalle, R. Blasius, et al., Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor kappaB inhibition. Biochem Pharmacol 68, 1101-1111 (2004).
47. P. K. Lala and C. Chakraborty, Role of nitric oxide in carcinogenesis and tumour progression. Lancet Oncol 2, 149-156 (2001).
48. T. deRojas-Walker, S. Tamir, H. Ji, J. S. Wishnok, and S. R. Tannenbaum, Nitric oxide induces oxidative damage in addition to deaminiation in macrophage DNA. Chem Res Toxicol 8, 473-477 (1995).
49. M. Graziewicz, D. A. Wink, and F. Laval, Nitric oxide inhibits DNA ligase activity: Potential mechanisms for NO-mediated DNA damage. Carcinogenesis 17, 2501-2505 (1996).
50. S. Ambs, W. P. Bennett, W. G. Merrium, et al., Relationship between p53 mutations and inducible nitric oxide synthase expression in human colorectal cancer. J Natl Cancer Inst 91, 86-88; reply 1510-1511 (1999).
51. A. Von Knethen and B. Brune B, Cyclooxygenase-2: An essential regulator of NO-mediated apoptosis. FASEB J 11, 887-895 (1997).
52. A. Von Knethen, D. Callsen, and B. Brune, NF-κB and AP-1 activation by nitric oxide attenuated apoptotic death in RAW 264.7 macrophages. Mol Biol Cell 10, 361-370 (1999).
53. I. Brouet and H. Ohshima, Curcumin, an anti-tumour promoter and anti-inflammatory agent, inhibits induction of nitric oxide synthase in activated macrophages. Biochem Biophys Res Commun 206, 533-540 (1995).
54. M. M. Chan, H. I. Huang, M. R. Fenton,and D. Fong, In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties. Biochem Pharmacol 55, 1955-1962 (1998).
55. A. Raysid and A. Lelo, The effect of curcumin and placebo on human gall-bladder function: An ultrasound study. Aliment Pharmacol Ther 13, 245-249 (1999).
56. S. M. Plummer, K. A. Hill, M. F. W. Festing, W. P. Steward, A. J. Gescher, and R. A. Sharma, Clinical development of leukocyte cyclooxygenase 2 activity as a systemic biomarker for cancer chemopreventive agents. Cancer Epidemiol Biomarkers Prev 10, 1295-1299 (2001).
57. S. M. Plummer, K. A. Holloway, M. M. Manson, et al., Inhibition of cyclo-oxygenase 2 expression in colon cells by the chemopreventive agent curcumin involves inhibition of NF-κB activation via the NIK/IKK signalling complex. Oncogene 18, 6013-6020 (1999).
58. F. Zhang, N. K. Altorki, J. R. Mestre, et al., Curcumin inhibits cyclooxygenase-2 transcription in bile acid- and phorbol ester-treated human gastrointestinal epithelial cells. Carcinogenesis 20, 445-451 (1999).
59. A. C. Bharti, N. Donato, and B. B. Aggarwal, Curcumin (diferuloylmethane) inhibits constitutive and IL-6-inducible STAT3 phosphorylation in human multiple myeloma cells. J Immunol 171, 3863-3871 (2003).
60. K. Sugimoto, H. Hanai, K. Tozawa, et al., Curcumin prevents and ameliorates trinitrobenzene sulfonic acid-induced colitis in mice. Gastroenterology 123, 1912-1922 (2002).
61. R. R. Satoskar, S. J. Shah, and S. G. Shenoy, Evaluation of anti-inflammatory property of curcumin (diferuloyl methane) in patients with post-operative inflammation. Int J Clin Pharmacol Ther Toxicol 24, 651-654 (1986).
62. S. D. Deodhar, R. Sethi, and R. C. Srimal, Preliminary study on antirheumatic activity of curcumin (diferuloyl methane). Indian J Med Res 71, 632-634 (1980).
63. P. R. Holt, S. Katz, and R. Kirshoff, Curcumin therapy in inflammatory bowel disease: A pilot study. Dig Dis Sci 11, 2191-2193 (2005).
64. B. Lal, A. K. Kapoor,O. P. Asthana, et al., Efficacy of curcumin in the managememtn of chronic anterior uveitis. Phytother Res 13, 318-322 (1999).
65. B. Lal, A. K. Kapoor, P. K. Agrawal, et al., Role of curcumin in idiopathic inflammatory orbital pseudotumours. Phytother Res 14, 443-447 (2000).
66. R. Kuttan, P. C. Sudheeran, and C. D. Josph, Turmeric and curcumin as topical agents in cancer therapy. Tumori 73, 29-31 (1987).
67. W. H.Chan and H. Wu, Anti-apoptotic effects of curcurnin on photosensitized human epidermal carcinoma A431 cells. J Cell Biochem 92, 200-212 (2004).
68. M. C. Jiang, H. F. Yang Yen, J. J. Y. Yen, et al., Curcumin induces apoptosis in immortalized NIH 3T3 and malignant cancer cell lines. Nutr Cancer 26, 111-120 (1996).
69. C. H. Yan, M. S. Jamaluddin, B. Aggarwal, J. Myers, and D.D. Boyd, Gene expression profiling identifies activating transcription factor 3 as a novel contributor to the proapoptotic effect of curcumin. Mol Cancer Therapeut. 4, 233-241 (2005).
70. M. L. Kuo, T. S. Huang, and J. K. Lin, Curcumin, an antioxidant and anti-tumor promoter, induces apoptosis in human leukemia cells. Biochim Biophys Acta 1317, 95-100 (1996).
71. G. P. Collett and F. C. Campbell, Curcumin induces c-jun N-terminal kinase-dependent apoptosis in HCT116 human colon cancer cells. Carcinogenesis 25, 2183-2189 (2004).
72. M. M. Y. Chan, Inhibition of tumor necrosis factor by curcumin, a phytochemical. Biochem Pharmacol 49, 1551-1556 (1995).
73. Y. Abe, S. Hashimoto, and T. Horie, Curcumin inhibition of inflammatory cytokine production by human peripheral blood monocytes and alveolar macrophages. Pharmacol Res 39, 41-47 (1999).
74. B. Gupta and B. Ghosh, Curcuma longa inhibits TNF-alpha induced expression of adhesion molecules on human umbilical vein endothelial cells. Int J Immnopharmacol 21, 745-757 (1999).
75. Y. Moon, W. C. Glasgow, and T. E. Eling, , Curcumin suppresses interleukin 1 beta-mediated microsomal prostaglandin E synthase 1 by altering early growth response gene 1 and other signaling pathways. J Pharmacol Exp Ther 315, 788-795 (2005).
76. E. Balogun, M. Hoque, P. F. Gong, E. Killeen, C. J. Green, R. Foresti, J. Alam, and R. Motterlini, , Curcurmin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element. Biochem J 371, 887-895 (2003).
77. C. K. Andreadi, L. M. Howells, P. A. Atherfold, and M. M. Manson, Involvement of Nrf2, p38, B-Raf, and nuclear factor-kappa B, but not phosphatidylinositol 3-kinase, in induction of hemeoxygenase-1 by dietary polyphenols. Mol Pharmacol 69, 1033-1040 (2006).
78. P. F. Firozi, V. S. Aboobaker, and R. K. Bhattacharya, Action of curcumin on the cytochrome P450-system catalyzing the activation of aflatoxin B1. Chem-Biol Interact 100, 41-51 (1996).
79. H. P. Ciolino, P. J. Daschner, T. T. Wang, and G. C. Yeh, Effect of curcumin on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Biochem Pharmacol 56, 197-206 (1998).
80. M. S. Woo, S. H. Jung, S. Y. Kim, J. W. Hyun, K. H. Ko, W. K. Kim, and H. S. Kim, Curcumin suppresses phorbol ester-induced matrix metalloproteinase-9 expression by inhibiting the PKC to MAPK signaling pathways in human astroglioma cells. Biochem Biophys Res Commun 335, 1017-1025 (2005).