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Xenobiotica
the fate of foreign compounds in biological systems
Volume 22, 1992 - Issue 11
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Original Article

Microsomal formation of a pyrrolic alcohol glutathione conjugate of the pyrrolizidine alkaloid senecionine

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Pages 1321-1327 | Received 04 Dec 1991, Accepted 20 Apr 1992, Published online: 23 Apr 2010

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Xiaobo He, Qingsu Xia, Qiang Shi & Peter P. Fu. (2020) Effects of glutathione and cysteine on pyrrolizidine alkaloid-induced hepatotoxicity and DNA adduct formation in rat primary hepatocytes. Journal of Environmental Science and Health, Part C 38:2, pages 109-123.
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Xiaobo He, Qingsu Xia & Peter P. Fu. (2017) 7-Glutathione-pyrrole and 7-cysteine-pyrrole are potential carcinogenic metabolites of pyrrolizidine alkaloids. Journal of Environmental Science and Health, Part C 35:2, pages 69-83.
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Xiaobo He, Qingsu Xia, Liang Ma & Peter P. Fu. (2016) 7-cysteine-pyrrole conjugate: A new potential DNA reactive metabolite of pyrrolizidine alkaloids. Journal of Environmental Science and Health, Part C 34:1, pages 57-76.
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Peter P. Fu, Qingsu Xia, Ge Lin & Ming W. Chou. (2004) Pyrrolizidine Alkaloids—Genotoxicity, Metabolism Enzymes, Metabolic Activation, and Mechanisms. Drug Metabolism Reviews 36:1, pages 1-55.
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Articles from other publishers (29)

Yisheng He, Lin Zhu, Jiang Ma & Ge Lin. (2021) Metabolism-mediated cytotoxicity and genotoxicity of pyrrolizidine alkaloids. Archives of Toxicology 95:6, pages 1917-1942.
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Ina Geburek, Dieter Schrenk & Anja These. (2020) In vitro biotransformation of pyrrolizidine alkaloids in different species: part II—identification and quantitative assessment of the metabolite profile of six structurally different pyrrolizidine alkaloids. Archives of Toxicology 94:11, pages 3759-3774.
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Lan Gao, Lukas Rutz & Dieter Schrenk. (2020) Structure-dependent hepato-cytotoxic potencies of selected pyrrolizidine alkaloids in primary rat hepatocyte culture. Food and Chemical Toxicology 135, pages 110923.
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Ina Geburek, Angelika Preiss-Weigert, Monika Lahrssen-Wiederholt, Dieter Schrenk & Anja These. (2020) In vitro metabolism of pyrrolizidine alkaloids – Metabolic degradation and GSH conjugate formation of different structure types. Food and Chemical Toxicology 135, pages 110868.
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Xin He, Zi-jun Wu, Li-li Wang, Xue Gao, Yue Hai, Wen-li Liu, Le-mei Du, Lei Zhang, Ai-hong Yang & Nan-nan Huang. (2019) An important mechanism of herb-induced hepatotoxicity: To produce RMs based on active functional groups-containing ingredients from phytomedicine by binding CYP450s. Chinese Herbal Medicines 11:3, pages 239-257.
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Jia Ning, Lu Chen, Marije Strikwold, Jochem Louisse, Sebastiaan Wesseling & Ivonne M. C. M. Rietjens. (2019) Use of an in vitro–in silico testing strategy to predict inter-species and inter-ethnic human differences in liver toxicity of the pyrrolizidine alkaloids lasiocarpine and riddelliine. Archives of Toxicology 93:3, pages 801-818.
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Peter P. Fu. (2016) Pyrrolizidine Alkaloids: Metabolic Activation Pathways Leading to Liver Tumor Initiation. Chemical Research in Toxicology 30:1, pages 81-93.
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Karl-Heinz Merz & Dieter Schrenk. (2016) Interim relative potency factors for the toxicological risk assessment of pyrrolizidine alkaloids in food and herbal medicines. Toxicology Letters 263, pages 44-57.
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Xiaobo He, Liang Ma, Qingsu Xia & Peter P. Fu. (2016) 7- N -Acetylcysteine-pyrrole conjugate—A potent DNA reactive metabolite of pyrrolizidine alkaloids. Journal of Food and Drug Analysis 24:4, pages 682-694.
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Meixia Chen, Liang Li, Dafang Zhong, Shuijie Shen, Jiang Zheng & Xiaoyan Chen. (2016) 9-Glutathionyl-6,7-dihydro-1-hydroxymethyl-5 H -pyrrolizine Is the Major Pyrrolic Glutathione Conjugate of Retronecine-Type Pyrrolizidine Alkaloids in Liver Microsomes and in Rats . Chemical Research in Toxicology 29:2, pages 180-189.
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Liang Ma, Hengqiang Zhao, Qingsu Xia, Lining Cai & Peter P. Fu. (2015) Synthesis and phototoxicity of isomeric 7,9-diglutathione pyrrole adducts: Formation of reactive oxygen species and induction of lipid peroxidation. Journal of Food and Drug Analysis 23:3, pages 577-586.
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Qingsu Xia, Liang Ma, Xiaobo He, Lining Cai & Peter P. Fu. (2015) 7-Glutathione Pyrrole Adduct: A Potential DNA Reactive Metabolite of Pyrrolizidine Alkaloids. Chemical Research in Toxicology 28:4, pages 615-620.
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Ying Chen, Lili Ji, Aizheng Xiong, Li Yang & Zhengtao Wang. (2012) Involvement of intracellular glutathione in regulating isoline-induced cytotoxicity in human normal liver L-02 cells. Toxicology and Industrial Health 29:6, pages 567-575.
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Helmut Wiedenfeld. 2013. Natural Products. Natural Products 359 379 .
George E. Burrows & Ronald J. Tyrl. 2012. Toxic Plants of North America. Toxic Plants of North America 150 256 .
Changhong Wang, Yan Li, Jiangguo Gao, Yuqi He, Aizhen Xiong, Li Yang, Xuemei Cheng, Yueming Ma & Zhengtao Wang. (2011) The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Analytical and Bioanalytical Chemistry 401:1, pages 275-287.
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Helmut Wiedenfeld & John Edgar. (2010) Toxicity of pyrrolizidine alkaloids to humans and ruminants. Phytochemistry Reviews 10:1, pages 137-151.
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Sen PANG, Xue-Feng LI, Zhiqian LIU & Cheng-Ju WANG. (2010) <I>ZmGT1</I> Transports Glutathione Conjugates and Its Expression Is Induced by Herbicide Atrazine. PROGRESS IN BIOCHEMISTRY AND BIOPHYSICS 37:10, pages 1120-1127.
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Aizhen Xiong, Li Yang, Yuqi He, Fang Zhang, Jun Wang, Han Han, Changhong Wang, S. W. Annie Bligh & Zhengtao Wang. (2009) Identification of metabolites of adonifoline, a hepatotoxic pyrrolizidine alkaloid, by liquid chromatography/tandem and high-resolution mass spectrometry. Rapid Communications in Mass Spectrometry 23:24, pages 3907-3916.
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Rowan E Moore, Derek Knottenbelt, Jacqueline B Matthews, Robert J Beynon & Phillip D Whitfield. (2008) Biomarkers for ragwort poisoning in horses: identification of protein targets. BMC Veterinary Research 4:1.
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. (2007) Opinion of the Panel on contaminants in the food chain [CONTAM] related to pyrrolizidine alkaloids as undesirable substances in animal feed. EFSA Journal 5:5.
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Jennifer M. Duringer, Donald R. Buhler & A. Morrie Craig. (2004) Comparison of hepatic in vitro metabolism of the pyrrolizidine alkaloid senecionine in sheep and cattle. American Journal of Veterinary Research 65:11, pages 1563-1572.
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T. Mroczek & K. Glowniak. 2002. Natural Products in the New Millennium: Prospects and Industrial Application. Natural Products in the New Millennium: Prospects and Industrial Application 1 46 .
Yanyan Cui & Ge Lin. (2000) Simultaneous analysis of clivorine and its four microsomal metabolites by high-performance liquid chromatography. Journal of Chromatography A 903:1-2, pages 85-92.
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Michael W. Lamé, A. Daniel Jones, Dennis W. Wilson, Sheryl K. Dunston & H.J. Segall. (2000) Protein Targets of Monocrotaline Pyrrole in Pulmonary Artery Endothelial Cells. Journal of Biological Chemistry 275:37, pages 29091-29099.
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Jian-Ya Huan, Cristobal L Miranda, Donald R Buhler & Peter R Cheeke. (1998) Species differences in the hepatic microsomal enzyme metabolism of the pyrrolizidine alkaloids. Toxicology Letters 99:2, pages 127-137.
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Jennifer A. Field & E. M. Thurman. (1996) Glutathione Conjugation and Contaminant Transformation. Environmental Science & Technology 30:5, pages 1413-1418.
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Chong Chao Yan & Ryan J. Huxtable. (1995) Effect of the pyrrolizidine alkaloid, monocrotaline, on bile composition of the isolated, perfused rat liver. Life Sciences 57:6, pages 617-626.
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Michael J. Higgins, Gyula Ficsor, C. S. Aaron, Thomas W. Petry, Roger L. Yu & Stephen B. Friedman. (2006) Micronuclei in mice treated with monocrotaline with and without phenobarbital pretreatment. Environmental and Molecular Mutagenesis 26:1, pages 37-43.
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