Isolation and identification of phase 1 metabolites of curcuminoids in rats

Planta Medica

Volumn 78, Issue 12, 2012, Pages 1351-1356

  Li, Jun ^a   Liu, Yue ^a   Wei, Jun Qi ^a   Wang, Kun ^a   Chen, Li Xia ^a   Yao, Xin Sheng ^a   Qiu, Feng ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Curcuma longa; curcuminoids; enantiomers; metabolites from faeces and urine; rat; Zingiberaceae

Indexed keywords

1,5 EPOXY 3 CARBONYL 1,7 BIS(4 HYDROXYPHEYL) 4,6 HEPTADIENE; 3 HYDROXY 1,7 BIS(3 HYDROXYPHENYL)HEPTANE A; 3 HYDROXY 1,7 BIS(3 HYDROXYPHENYL)HEPTANE B; 3 HYDROXY 1,7 BIS(4 HYDROXYPHENYL)HEPTANE A; 3 HYDROXY 1,7 BIS(4 HYDROXYPHENYL)HEPTANE B; 3 HYDROXY[1 (4 HYDROXYPHENYL) 7 (3 HYDROXYPHEY)]HEPTANE A; 3 HYDROXY[1 (4 HYDROXYPHENYL) 7 (3 HYDROXYPHEY)]HEPTANE B; 3,5 DIHYDROXY 1,7 BIS(4 HYDROXYPHENYL)HEPTANE A; 3,5 DIHYDROXY 1,7 BIS(4 HYDROXYPHENYL)HEPTANE B; 5 HYDROXY 3 PLATYPHYLLONE; CURCUMIN; DEMETHOXYCURCUMIN; DIDEMETHOXYCURCUMIN; DRUG METABOLITE; HEXAHYDROCURCUMIN; HEXAHYDROCURCUMINOL; HEXAHYDRODEMETHOXYCURCUMIN A; HEXAHYDRODEMETHOXYCURCUMIN B; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRAL CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG FECES LEVEL; DRUG ISOLATION; DRUG METABOLISM; DRUG STRUCTURE; DRUG URINE LEVEL; ELECTROSPRAY MASS SPECTROMETRY; HETERONUCLEAR MULTIPLE BOND CORRELATION; MALE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALS; BIOTRANSFORMATION; CURCUMIN; FECES; MALE; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR STRUCTURE; RATS; RATS, WISTAR;

CURCUMA LONGA; RATTUS; ZINGIBERACEAE;

EID: 84865373533     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1314990     Document Type: Article

References (34)

1. Cuomo J, Appendino G, Dern AS, Schneider E, McKinnon TP, Brown MJ, Togni S, Dixon BM. Comparative absorption of a standardized curcuminoid mixture and its lecithin formulation. J Nat Prod: 2011; 74 664 669
2. Aftab N, Vieira A. Antioxidant activities of curcumin and combinations of this curcuminoid with other phytochemicals. Phytother Res: 2010; 24 500 502
3. Masuda T, Hidaka K, Shinohara A, Maekawa T, Takeda Y, Yamaguchi H. Chemical studies on antioxidant mechanism of curcuminoid: analysis of radical reaction products from curcumin. J Agric Food Chem: 1999; 47 71 77 (Pubitemid 29179626)
4. Kuo CF, Chyau CC, Wang TS, Li CR, Hu TJ. Enhanced antioxidant and anti-inflammatory activities of Monascus pilosus fermented products by addition of turmeric to the medium. J Agric Food Chem: 2009; 57 11397 11405
5. Jordan WC, Drew CR. Curcumin - a natural herb with anti-HIV activity. J Natl Med Assoc: 1996; 88 333
6. Kim MK, Choi GJ, Lee HS. Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. J Agric Food Chem: 2003; 51 1578 1581
7. Deters M, Siegers C, Muhl P, Hänsel W. Choleretic effects of curcuminoids on an acute cyclosporin-induced cholestasis in the rat. Planta Med: 1999; 65 610 613 (Pubitemid 29503226)
8. Liu H, Li Z, Qiu D, Gu Q, Lei Q, Mao L. The inhibitory effects of different curcuminoids on β -amyloid protein, β -amyloid precursor protein and β -site amyloid precursor protein cleaving enzyme 1 in swAPP HEK293 cells. Neurosci Lett: 2010; 485 83 88
9. Zhao J, Zhao Y, Zheng W, Lu Y, Feng G, Yu S. Neuroprotective effect of curcumin on transient focal cerebral ischemia in rats. Brain Res: 2008; 1229 224 232
10. Haddad M, Sauvain M, Deharo E. Curcuma as a parasiticidal agent: a review. Planta Med: 2011; 77 672 678
11. Huang TY, Tsai TH, Hsu CW, Hsu YC. Curcuminoids suppress the growth and induce apoptosis through caspase-3-dependent pathways in glioblastoma multiforme (GBM) 8401 cells. J Agric Food Chem: 2010; 58 10639 10645
12. Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R. Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett: 1995; 94 79 83
13. Volak LP, Ghirmai S, Cashman JR, Court MH. Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos: 2008; 36 1594 1605
14. Graber-Maier A, Berger Büter K, Aeschlimann J, Bittel C, Kreuter M, Drewe J, Gutmann H. Effects of Curcuma extracts and curcuminoids on expression of P-glycoprotein and cytochrome P450 3A4 in the intestinal cell culture model LS180. Planta Med: 2010; 76 1866 1870
15. Lao CD, Ruffin MT 4th, Normolle D, Heath DD, Murray SI, Bailey JM, Boggs ME, Crowell J, Rock CL, Brenner DE. Dose escalation of a curcuminoid formulation. BMC Complement Altern Med: 2006; 6 10
16. Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS, Ko JY, Lin JT, Lin BR, Ming-Shiang W, Yu HS, Jee SH, Chen GS, Chen TM, Chen CA, Lai MK, Pu YS, Pan MH, Wang YJ, Tsai CC, Hsieh CY. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res: 2001; 21 2895 2900
17. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of curcumin: problems and promises. Mol Pharm: 2007; 4 807 818
18. Hoehle SI, Pfeiffer E, Sólyom AM, Metzler M. Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver. J Agric Food Chem: 2006; 54 756 764 (Pubitemid 43274111)
19. Hoehle SI, Pfeiffer E, Metzler M. Glucuronidation of curcuminoids by human microsomal and recombinant UDP-glucuronosyltransferases. Mol Nutr Food Res: 2007; 51 932 938 (Pubitemid 47292266)
20. Pfeiffer E, Hoehle SI, Walch SG, Riess A, Solyom AM, Metzler M. Curcuminoids form reactive glucuronides in vitro. J Agric Food Chem: 2007; 55 538 544 (Pubitemid 46586343)
21. Asai A, Miyazawa T. Occurrence of orally administered curcuminoid as glucuronide and glucuronide/sulfate conjugates in rat plasma. Life Sci: 2000; 67 2785 2793
22. Garcea G, Jones DJ, Singh R, Dennison AR, Farmer PB, Sharma RA, Steward WP, Gescher AJ, Berry DP. Detection of curcumin and its metabolites in hepatic tissue and portal blood of patients following oral administration. Br J Cancer: 2004; 90 1011 1015 (Pubitemid 38499692)
23. Zeng Y, Qiu F, Liu Y, Qu G, Yao X. Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats. Drug Metab Dispos: 2007; 35 1564 1573 (Pubitemid 47296049)
24. Alegrio LV, Braz-filho R, Gottlieb OR. Diarylheptanoids and isoflavonoids from Centrolobium species. Phytochemistry: 1989; 28 2359 2362
25. Zhang L, Bai B, Liu X, Wang Y, Li M, Zhao D. α -Glucosidase inhibitors from Chinese Yam (Dioscorea opposita Thunb.). Food Chem: 2011; 126 203 206
26. Kiuchi F, Goto Y, Sugimoto N, Akao N, Kondo K, Tsuda Y. Nematocidal activity of turmeric: synergistic action of curcuminoids. Chem Pharm Bull: 1993; 41 1640 1643 (Pubitemid 23326798)
27. Lee SL, Huang WJ, Lin WW, Lee SS, Chen CH. Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs. Bioorg Med Chem: 2005; 13 6175 6181 (Pubitemid 41400139)
28. Uehara SI, Yasuda I, Akiyama K, Morita H, Takeya K, Itokawa H. Diarylheptanoids from the rhizomes of Curcuma xanthorrhiza and Alpinia officinarum. Chem Pharm Bull: 1987; 35 3298 3304
29. Terazawa M, Koga T, Okuyama H, Miyake M. Phenolic compounds in living tissue of woods III. Platyphylloside, a new diarylheptanoid glucoside from the green back of shirakamba (Betula platyphylla Sukatchev var. japonica Hara) [Betulaceae]. Mokuzai Gakkaishi: 1984; 30 391 403
30. Chen J, Gonzalez-Laredo RF, Karchesy JJ. Minor diarylheptanoid glycosides of Alnus rubra bark. Phytochemistry: 2000; 53 971 973 (Pubitemid 30233134)
31. Murugan P, Pari L. Antioxidant effect of tetrahydrocurcumin in streptozotocin-nicotinamide induced diabetic rats. Life Sci: 2006; 79 1720 1728 (Pubitemid 44374550)
32. Murugan P, Pari L. Influence of tetrahydrocurcumin on erythrocyte membrane bound enzymes and antioxidant status in experimental type 2 diabetic rats. J Ethnopharmacol: 2007; 113 479 486 (Pubitemid 47361566)
33. Nakamura Y, Ohto Y, Murakami A, Osawa T, Ohigashi H. Inhibitory effects of curcumin and tetrahydrocurcuminoids on the tumor promoter-induced reactive oxygen species generation in leukocytes in vitro and in vivo. Jpn J Cancer Res: 1998; 89 361 370 (Pubitemid 28226915)
34. Pan MH, Lin-Shiau SY, Lin JK. Comparative studies on the suppression of nitric oxide synthase by curcumin and its hydrogenated metabolites through down-regulation of IκB kinase and NFκB activation in macrophages. Biochem Pharmacol: 2000; 60 1665 1676