Importance of metabolic activation study to the safe use of chinese herbal medicines

Current Drug Metabolism

Volumn 13, Issue 5, 2012, Pages 652-658

  Ma, Bin ^a   Li, Na ^a   Lin, Ge ^a  

^a Prince of Wales Hospital   (Hong Kong)

Author keywords

Metabolic activation; Protein DNA adducts; Safety of Chinese herbal medicines

Indexed keywords

ARISTOLOCHIC ACID; BENZO[A]PYRENE; HERBACEOUS AGENT; PLANT TOXIN; PYRROLIZIDINE ALKALOID;

ARTICLE; BIOTRANSFORMATION; DRUG CONTAMINATION; DRUG METABOLISM; DRUG SAFETY; DRUG SYNTHESIS; LD 50; LIVER TOXICITY; MEDICAL ERROR; NEPHROTOXICITY; PHYTOTOXICITY; PLANNING; PRACTICE GUIDELINE; SEED PRODUCTION; TILLAGE;

EID: 84861872055     PISSN: 13892002     EISSN: 18755453     Source Type: Journal    
DOI: 10.2174/1389200211209050652     Document Type: Article

References (59)

1. Huang, K.C. In The Pharmacology of Chinese Herbs, 2nd ed.; CRC Press: Boca Raton, FL, 1998.
2. Roeder, E. Medicinal plants in China containing pyrrolizidine alkaloids. Pharmazie, 2000, 55, 711-726.
3. Willett, K.L.; Roth, R.A.; Walker, L. Workshop overview: Hepatotoxicity assessment for botanical dietary supplements. Toxicol. Sci., 2004, 79, 4-9.
4. Baillie, T.A. Future of toxicology-metabolic activation and drug design: challenges and opportunities in chemical toxicology. Chem. Res. Toxicol., 2006, 19, 889-893.
5. Atrakchi, A.H. Interpretation and considerations on the safety evaluation of human drug metabolites. Chem. Res. Toxicol., 2009, 22, 1217-1220.
6. Chan, K. Some aspects of toxic contaminants in herbal medicines. Chemosphere, 2003, 52, 1361-1371.
7. Mustafa, O.; Brendan, M.; Pei, C. Comparison of the terpene lactones and flavonols contents in G-biloba commercial samples and the NIST standard reference materials using LC/UV/MS. J. Food Drug Anal., 2007, 15, 55-62.
8. Lin, G.; Wang, J.Y.; Li, N.; Li, M.; Gao, H.; Ji, Y.; Zhang, F.; Wang, H.L.; Zhou, Y.; Ye, Y.; Xu, H.X.; Zheng, J. Hepatic sinusoidal obstruction syndrome associated with consumption of Gynura segtum. J. Hepatol., 2011, 54, 666-673.
9. Ko, R.J. A U.S. perspective on the adverse reactions from traditional Chinese medicines. J. Chin. Med. Assoc. 2004, 67, 109-116.
10. Ono, T.; Hayashida, M.; Uekusa, K.; Lai, C.F.; Hayakawa, H.; Nihira, M.; Ohno, Y. An accidental case of aconite poisoning due to Kampo herbal medicine ingestion. Leg. Med.(Tokyo), 2009, 11, 132-135.
11. Yang, A.K.; He, S.M.; Liu, L.; Liu, J.P.; Wei, M.Q.; Zhou, S.F. Herbal interactions with anticancer drugs: mechanistic and clinical considerations. Curr. Med. Chem., 2010, 17, 1635-1678.
12. Abad, M.J.; Bedoya, L.M.; Bermejo, P. An update on drug interactions with the herbal medicine Ginkgo biloba. Curr. Drug Metab., 2010, 11, 171-181.
13. Colalto, C. Herbal interactions on absorption of drugs: Mechanisms of action and clinical risk assessment. Pharmacol. Res., 2010, 62, 207-227.
14. Badawi, A.F.; Stern, S.J.; Lang, N.P.; Kadlubar, F.F. Cytochrome P-450 and acetyltransferase expression as biomarkers of carcinogen- DNA adduct levels and human cancer susceptibility. Prog. Clin. Biol. Res., 1996, 395, 109-140.
15. Shulgin, A.T. Narcotic pepper-chemistry and pharmacology of piper-methysticum and related species. Bull. Narcotics, 1973, 25, 59-74.
16. Jamieson, D.D.; Duffield, P.H. The antinociceptive actions of Kava components in mice. Clin. Exp. Pharmacol. Physiol., 1990, 17, 495-508.
17. Singh, Y.N. Kava - an overview. J. Ethnopharmacol., 1992, 37, 13-45.
18. Fu, P.P.; Xia, Q.S.; Chou, M.W.; Lin, G. Detection, hepatotoxicity, and tumorigenicity of pyrrolizidine alkaloids in Chinese herbal plants and herbal dietary supplements. J. Food Drug Anal., 2007, 15, 400-415.
19. Fu, P.P.; Xia, Q.; Lin, G.; Chou, M.W. Pyrrolizidine alkaloids - genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metab. Rev., 2004, 36, 1-55.
20. Dai, N.; Yu, Y.C; Ren, T.H.; Wu, J.G.; Jiang, Y.; Shen, L.G.; Zhang, J. Gynura root induces hepatic veno-occlusive disease: a case report and review of the literature. World J. Gastroenterol., 2007, 13, 1628-1631.
21. Mattocks, A.R. Toxicity of pyrrolizidine alkaloids. Nature, 1968, 217, 723-728.
22. Mattocks, A.R. Chemistry and toxicology of pyrrolizidine alkaloids. 1st ed.; Academic Press: London, 1986.
23. Wang, Y.P.; Yan, J.; Fu, P.P.; Chou, M.W. Human liver microsomal reduction of pyrrolizidine alkaloid N-oxides to form the corresponding carcinogenic parent alkaloid. Toxicol. Lett., 2005, 155, 411-420.
24. Xia, Q.; Chou, M.W.; Lin, G.; Fu, P.P. Metabolic formation of DHP-derived DNA adducts from a representative otonecine type pyrrolizidine alkaloid clivorine and the extract of Ligularia hodgsonnii hook. Chem. Res. Toxicol., 2004, 17, 702-708.
25. Xia, Q.; Chou, M.W.; Edgar, J.A.; Doerge, D.R.; Fu, P.P. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine. Cancer Lett., 2006, 231, 138-145.
26. Xia, Q.; Yan, J.; Chou, M.W.; Fu, P.P. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine- type pyrrolizidine alkaloid, heliotrine. Toxicol. Lett., 2008, 178, 77-82.
27. Wang, Y.P.; Fu, P.P.; Chou, M.W. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, retrorsine, leading to DNA adduct formation in vivo. Int. J. Environ. Res. Public Health, 2005, 2, 74-79.
28. Wang, Y.P.; Yan, J.; Beger, R.D.; Fu, P.P.; Chou, M.W. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, monocrotaline, leading to DNA adduct formation in vivo. Cancer Lett., 2005, 226, 27-35.
29. Kumar, V.; Poonam; Prasad, A.K.; Parmar, V.S. Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities. Nat. Prod. Rep., 2003, 20, 565-583.
30. Stiborova, M.; Frei, E.; Arlt, V.M.; Schmeiser, H.H. Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy. Mutat. Res., 2008, 658, 55-67.
31. Shibutani, S.; Dong, H.; Suzuki, N.; Ueda, S.; Miller, F.; Grollman, A.P. Selective toxicity of aristolochic acids I and II. Drug Metab. Dispos., 2007, 35, 1217-1222.
32. de Jonge, H.; Vanrenterghem, Y. Aristolochic acid: the common culprit of Chinese herbs nephropathy and Balkan endemic nephropathy. Nephrol. Dial. Transplant. 2008, 23, 39-41.
33. Arlt, V.M.; Wiessler, M.; Schmeiser, H.H. Using polymerase arrest to detect DNA binding specificity of aristolochic acid in the mouse H-ras gene. Carcinogenesis, 2000, 21, 235-242.
34. Amacher, D.E. The discovery and development of proteomic safety biomarkers for the detection of drug-induced liver toxicity. Toxicol. Appl. Pharmacol., 2010, 245, 134-142.
35. Clarke, C.J.; Haselden, J.N. Metabolic profiling as a tool for understanding mechanisms of toxicity. Toxicol Pathol, 2008, 36, 140-147.
36. Swenberg, J.A. Toxicological considerations in the application and interpretation of DNA adducts in epidemiological studies. IARC Sci. Publ., 2004, 157, 237-246.
37. Zhou, S.F.; Xue, C.C.; Yu, X.Q.; Wang, G. Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. Curr. Drug Metab., 2007, 8, 526-553.
38. Pfau, W.; Schmeiser, H.H.; Wiessler, M. 32P-postlabelling analysis of the DNA adducts formed by aristolochic acid I and II. Carcinogenesis, 1990, 11, 1627-1633.
39. Stiborova, M.; Fernando, R.C.; Schmeiser, H.H.; Frei, E.; Pfau, W.; Wiessler, M. Characterization of DNA adducts formed by aristolochic acids in the target organ (forestomach) of rats by 32Ppostlabelling analysis using different chromatographic procedures. Carcinogenesis, 1994, 15, 1187-1192.
40. Arlt, V.M.; Pfohl-Leszkowicz, A.; Cosyns, J.; Schmeiser, H.H. Analyses of DNA adducts formed by ochratoxin A and aristolochic acid in patients with Chinese herbs nephropathy. Mutat. Res., 2001, 494, 143-150.
41. Dharmananda, S. Safety issue affecting herbs: pyrrolizidine alkaloids. http://www.itmonline.org/arts/pas.htm. (Accessed November 26, 2010)
42. ANZFA, Australia New Zealand Food Authority, Pyrrolizidine Alkaloids in Food a Toxicological Review and Risk Assessment. Technical report series, No. 2. http://www.foodstandards.gov.au/-srcfiles/TR2.pdf. (Accessed March 14, 2011).
43. Kempf, M.; Reinhard, A.; Beuerle, T. Pyrrolizidine alkaloids (PAs) in honey and pollen-legal regulation of PA levels in food and animal feed required. Mol. Nutr. Food Res., 2010, 54, 158-168.
44. Medicines and Healthcare Products Regulatory Agency. MLX 296: proposals to prohibit the sale, supply or importation of unlicensed herbal medicinal products for internal use which contain Senecio species. http://www.mhra.gov.uk/ Publications/Consultations/Medicinescons ultations/MLXs/CON1004416 (Accessed November 26, 2010).
45. Medicines and Healthcare Products Regulatory Agency. Public consultation: Proposals to prohibit the sale, supply or importation of unlicensed medicinal products for internal use which contain Senecio species and proposals to amend three existing orders. http://www.mhra.gov.uk/home/idcplg?IdcService=GET- FILE&dD ocName=CON2030749&RevisionSelectionMethod=LatestRelease d. (Accessed November 26, 2010).
46. Lin, G.; Li, S.L.; Li, M.; Li, N.; Chan, S.S.K.; Chan, W.Y.; Zhao, Z.Z. Qianliguang (Senecio scandens) safety dilemma: dose is the key? Planta Med., 2009, 75, 1107-1111.
47. International Program on Chemical Safety. Environmental health criteria 80: pyrrolizidine alkaloids. http://www.inchem.org/documents/ehc/ehc/ehc080.htm. (Accessed November 15, 2010)
48. International Program on Chemical Safety. Health and safety guide no. 26: pyrrolizidine alkaloids health and safety guide. http://www.inchem.org/ documents/hsg/hsg/hsg026.htm. (Accessed November 15, 2010)
49. Lin, G.; Li, N.; Li, M; Chan, W.Y.; Fu, P.P.; Xu, H.X. Potential biomarker for the assessment of hepatotoxicity induced by metabolic activation of pyrrolizidine alkaloids. Drug Metab. Rev., 2010, 42(S1), 196.
50. Wang, X.; Kanel, G.C.; DeLeve, L.D. Support of sinusoidal endothelial cell glutathione prevents hepatic veno-occlusive disease in the rat. Hepatology, 2000, 31, 428-434.
51. Teicher, B.A.; Crawford, J.M.; Holden, S.A.; Lin, Y.; Cathcart, K.N.; Luchette, C.A.; Flatow, J. Glutathione monoethyl ester can selectively protect liver from high dose BCNU or cyclophosphamide. Cancer, 1988, 62, 1275-1281.
52. Lin G, Nnane, I.P.; Cheng, T.Y. The effects of pretreatment with glycyrrhizin and glycyrrhetinic acid on the retrorsine-induced hepatotoxicity in rats. Toxicon, 1999, 37, 1259-1270.
53. Lin, G.; Cui, Y.Y.; Liu, X.Q. Gender differences in microsomal metabolic activation of hepatotoxic clivorine in rat. Chem. Res. Toxicol., 2003, 16, 768-774.
54. Lin, G.; Tang, J.; Liu, X.Q.; Jiang, Y.; Zheng, J. Deacetylclivorine: a gender-selective metabolite of clivorine formed in female Sprague- Dawley rat liver microsomes. Drug Metab. Dispos., 2007, 35, 607-613.
55. Lin, G.; Cui, Y.Y.; Liu, X.Q.; Wang, Z.T. Species differences in the in vitro metabolic activation of the hepatotoxic pyrrolizidine alkaloid clivorine. Chem. Res. Toxicol., 2002, 15, 1421-1428.
56. Krumbiegel, G.; Hallensleben, J.; Mennicke, W.H.; Rittmann, N.; Roth, H.J. Studies on the metabolism of aristolochic acids I and II. Xenobiotica, 1987, 17, 981-991.
57. Rosenquist, T.A.; Einolf, H.J.; Dickman, K.G.; Wang, L.; Smith, A.; Grollman, A.P. Cytochrome P450 1A2 detoxicates aristolochic acid in the mouse. Drug Metab. Dispos., 2010, 38, 761-768.
58. Xiao, Y.; Xue, X.; Wu, Y.F.; Xin, G.Z.; Qian, Y.; Xie, T.P.; Gong, L.K.; Ren, J. beta-Naphthoflavone protects mice from aristolochic acid-I-induced acute kidney injury in a CYP1A dependent mechanism. Acta Pharmacol. Sin., 2009, 30, 1559-1565.
59. Xiao, Y.; Ge, M.; Xue, X.; Wang, C.; Wang, H.; Wu, X.; Li, L.; Liu, L.; Qi, X.; Zhang, Y.; Li, Y.; Luo, H.; Xie, T.; Gu, J.; Ren, J. Hepatic cytochrome P450s metabolize aristolochic acid and reduce its kidney toxicity. Kidney Int., 2008, 73, 1231-1239.