Biotransformation in vitro của các alcaloid pyrrolizidine ở các loài khác nhau. Phần I: Sự phân hủy microsome

Anjos BL, Nobre VMT, Dantas AFM et al (2010) Poisoning of sheep by seeds of Crotalaria retusa: Acquired resistance by continuous administration of low doses. Toxicon 55(1):28–32 Armstrong S, Zuckerman A (1970) Production of pyrroles from pyrrolizidine alkaloids by human embryo tissue. Nature 228(5271):569–573 BfR (2013) Pyrrolizidine alkaloids in herbal teas and teas. Scientific Opinion. http://www.bfr.bund.de/cm/349/pyrrolizidinealkaloids-in-herbal-teas-and-teas.pdf Bodi D, Ronczka S, Gottschalk C et al (2014) Determination of pyrrolizidine alkaloids in tea, herbal drugs and honey. Food Addit Contam Part A Chem Anal Control Expo Risk Assess 31(11):1886–1895. https://doi.org/10.1080/19440049.2014.964337 Bras G, Hill KR (1956) Veno-occlusive disease of the liver; essential pathology. Lancet 271(6935):161–163 Bras G, Berry DM, Gyorgy P (1957) Plants as aetiological factor in veno-occlusive disease of the liver. Lancet 272(6976):960–962 Bull LB, Dick AT, Mckenzie JS (1958) The acute toxic effects of heliotrine and lasiocarpine, and their N-oxides, on the rat. J Pathol Bacteriol 75(1):17–21 Cheeke PR (1984) Comparative toxicity and metabolism of pyrrolizidine alkaloids in ruminants and nonruminant herbivores. Can J Anim Sci 64:201–202 Cheeke PR (1988) Toxicity and metabolism of pyrrolizidine alkaloids. J Anim Sci 66(9):2343–2350 Chen MX, Li L, Zhong DF, Shen SJ, Zheng J, Chen XY (2016) 9-Glutathiony1-6,7-dihydro-1-hydroxymethy1-5H-pyrrolizine is the major pyrrolic glutathione conjugate of retronecine-type pyrrolizidine alkaloids in liver microsomes and in rats. Chem Res Toxicol 29(2):180–189 Chou MW, Jian Y, Williams LD et al (2003) Identification of DNA adducts derived from riddelliine, a carcinogenic pyrrolizidine alkaloid. Chem Res Toxicol 16(9):1130–1137 Chung WG, Buhler DR (2004) Differential metabolism of the pyrrolizidine alkaloid, senecionine, in Fischer 344 and Sprague–Dawley rats. Arch Pharm Res 27(5):547–553 Couet CE, Hopley J, Hanley AB (1996) Metabolic activation of pyrrolizidine alkaloids by human, rat and avocado microsomes. Toxicon 34(9):1058–1061 Culvenor CC, Downing DT, Edgar JA, Jago MV (1969) Pyrrolizidine alkaloids as alkylating and antimitotic agents. Ann N Y Acad Sci 163:837–847 Datta DV, Khuroo MS, Mattocks AR, Aikat BK, Chhuttani PN (1978) Veno-occlusive disease of liver due to heliotropium plant, used as medicinal herb (report of 6 cases with review of literature). J Assoc Physicians India 26(5):383–393 ECVAM (2014) Multi-study validation trial for cytochrome P450 induction providing a reliable human metabolically competent standard model or method using the human cryopreserved primary hepatocytes and the human cryopreserved HepaRG® cell line. https://www.oecd.org/chemicalsafety/testing/CYP-validation-project-report.pdf Fashe MM, Juvonen RO, Petsalo A, Rasanen J, Pasanen M (2015) Species-specific differences in the in vitro metabolism of lasiocarpine. Chem Res Toxicol 28(10):2034–2044 Fu PP, Xia QS, Lin G, Chou MW (2004) Pyrrolizidine alkaloids—genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metab Rev 36(1):1–55 Fu PP, Chou MW, Churchwell M et al (2010) High-performance liquid chromatography electrospray ionization tandem mass spectrometry for the detection and quantitation of pyrrolizidine alkaloid-derived DNA adducts in vitro and in vivo. Chem Res Toxicol 23(3):637–652 Fu PP, Xia Q, He X et al (2017) Detection of pyrrolizidine alkaloid DNA adducts in livers of cattle poisoned with Heliotropium europaeum. Chem Res Toxicol 30(3):851–858 He XB, Xia QS, Ma L, Fu PP (2016) 7-Cysteine-pyrrole conjugate: a new potential DNA reactive metabolite of pyrrolizidine alkaloids. J Environ Sci Health C 34(1):57–76 Hill KR (1960) The world-wide distribution of seneciosis in man and animals. Proc R Soc Med 53:281–283 Hill BD, Gaul KL, Noble JW (1997) Poisoning of feedlot cattle by seeds of Heliotropium europaeum. Aust Vet J 75(5):360–361 Hooper PT, Scanlan WA (1977) Crotalaria retusa poisoning of pigs and poultry. Aust Vet J 53(3):109–114 Huan J-Y, Miranda CL, Buhler DR, Cheeke PR (1998) Species differences in the hepatic microsomal enzyme metabolism of the pyrrolizidine alkaloids. Toxicol Lett 99(2):127–137 Jago MV, Edgar JA, Smith LW, Culvenor CC (1970) Metabolic Conversion of heliotridine-based pyrrolizidine alkaloids to dehydroheliotridine. Mol Pharmacol 6(4):402–411 Johnson AE, Molyneux RJ, Merrill GB (1985) Chemistry of toxic range plants—variation in pyrrolizidine alkaloid content of Senecio, Amsinckia, and Crotalaria species. J Agric Food Chem 33(1):50–55 Kedzierski B, Buhler DR (1986) Method for determination of pyrrolizidine alkaloids and their metabolites by high-performance liquid-chromatography. Anal Biochem 152(1):59–65 Lin G, Cui YY, Liu XQ, Wang ZT (2002) Species differences in the in vitro metabolic activation of the hepatotoxic pyrrolizidine alkaloid clivorine. Chem Res Toxicol 15(11):1421–1428 Lin G, Cui YY, Liu XQ (2003) Gender differences in microsomal metabolic activation of hepatotoxic clivorine in rat. Chem Res Toxicol 16(6):768–774 Lin G, Tang J, Liu XQ, Jiang Y, Zheng J (2007) Deacetylclivorine: a gender-selective metabolite of clivorine formed in female Sprague–Dawley rat liver microsomes. Drug Metab Dispos 35(4):607–613 Mattocks AR (1968) Toxicity of pyrrolizidine alkaloids. Nature 217(5130):723–727 Mattocks AR (1972) Acute hepatotoxicity and pyrrolic metabolites in rats dosed with pyrrolizidine alkaloids. Chem Biol Interact 5(4):227–242 Mattocks AR (1986) Chemistry and toxicology of pyrrolizidine alkaloids. Academic Press, London Mattocks AR, White INH (1971a) Conversion of pyrrolizidine alkaloids to N-oxides and to dihydropyrrolizine derivatives by rat-liver microsomes in-vitro. Chem Biol Interact 3(5):383–390 Mattocks AR, White INH (1971b) Pyrrolic metabolites from non-toxic pyrrolizidine alkaloids. Nat New Biol 231(21):114–118 McFarlane AL, Branday WJ (1945) Enlarged liver with ascites in children. Br Med J 1(4406):838–840 McLean EK (1970) The toxic actions of pyrrolizidine (Senecio) alkaloids. Pharmacol Rev 22(4):429–483 Mei N, Guo L, Fu PP, Fuscoe JC, Luan Y, Chen T (2010) Metabolism, genotoxicity, and carcinogenicity of comfrey. J Toxicol Environ Health B 13(7–8):509–526 Merz K-H, Schrenk D (2016) Interim relative potency factors for the toxicological risk assessment of pyrrolizidine alkaloids in food and herbal medicines. Toxicol Lett 263:44–57 Miranda CL, Reed RL, Guengerich FP, Buhler DR (1991) Role of cytochrome-P450IIIa4 in the metabolism of the pyrrolizidine alkaloid senecionine in human liver. Carcinogenesis 12(3):515–519 Mohabbat O, Srivastava RN, Younos MS, Merzad AA, Sediq GG, Aram GN (1976) Outbreak of hepatic veno-occlusive disease in northwestern Afghanistan. Lancet 2(7980):269–271 Pierson ML, Cheeke PR, Dickinson EO (1977) Resistance of rabbit to dietary pyrrolizidine (Senecio) alkaloid. Res Commun Chem Pathol Pharmacol 16(3):561–564 Roeder E (1995) Medicinal-Plants in Europe containing pyrrolizidine alkaloids. Pharmazie 50(2):83–98 Roeder E (2000) Medicinal plants in China containing pyrrolizidine alkaloids. Pharmazie 55(10):711–726 Schnell S, Mendoza C (1997) Closed form solution for time-dependent enzyme kinetics. J Theor Biol 187(2):207–212 Schoch TK, Gardner DR, Stegelmeier BL (2000) GC/MS/MS detection of pyrrolic metabolites in animals poisoned with the pyrrolizidine alkaloid riddelliine. J Nat Toxins 9(2):197–206 Schoental R (1968) Toxicology and carcinogenic action of pyrrolizidine alkaloids. Cancer Res 28(11):2237–2244 Schoental R (1970) Hepatotoxic activity of retrorsine, senkirkine and hydroxysenkirkine in newborn rats, and role of epoxides in carcinogenesis by pyrrolizidine alkaloids and aflatoxins. Nature 227(5256):401–409 Selzer G, Parker RG (1951) Senecio poisoning exhibiting as Chiari’s syndrome; a report on twelve cases. Am J Pathol 27(5):885–907 Shimshoni JA, Mulder PP, Bouznach A et al (2015) Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile. J Agric Food Chem 63(5):1664–1672 Shull LR, Buckmaster GW, Cheeke PR (1976) Factors influencing pyrrolizidine (Senecio) alkaloid metabolism—species, liver sulfhydryls and rumen fermentation. J Anim Sci 43(6):1247–1253 Stegelmeier BL, Gardner DR, James LF, Molyneux RJ (1996) Pyrrole detection and the pathologic progression of Cynoglossum officinale (houndstongue) poisoning in horses. J Vet Diagn Investig 8(1):81–90 Stuart KL, Bras G (1956) Veno-occlusive disease of the liver in Barbados; case reports. West Indian Med J 5(1):33–36 Theiler A (1919) Acute liver-atrophy and parenchymatous hepatitis in horses. Union of South Africa, 5th and 6th Reports of the Director of Veterinary Research, pp 7–165 Theiler A (1920) Dunsiekte in South African Horses (Enzootic Liver Cirrhosis). Union of South Africa, 7th and 8th Reports of the Director of Veterinary Research, pp 105–178 These A, Bodi D, Ronczka S, Lahrssen-Wiederholt M, Preiss-Weigert A (2013) Structural screening by multiple reaction monitoring as a new approach for tandem mass spectrometry—presented for the determination of pyrrolizidine alkaloids in plants. Anal Bioanal Chem 422(25):1245–1256 Ubiali DG, Boabaid FM, Borges NA et al (2011) Acute poisoning with Crotalaria spectabilis (Leg. Papilionoideae) seeds in pigs. Pesqui Vet Brasil 31(4):313–318 Wang YP, Yan J, Beger RD, Fu PP, Chou MW (2005) Metabolic activation of the tumorigenic pyrrolizidine alkaloid, monocrotaline, leading to DNA adduct formation in vivo. Cancer Lett 226(1):27–35. https://doi.org/10.1016/j.canlet.2004.11.039 WHO (1988) Environmental Health Criteria No. 80, http://www.inchem.org/documents/ehc/ehc/ehc080.htm Wiedenfeld H, Edgar J (2011) Toxicity of pyrrolizidine alkaloids to humans and ruminants. Phytochem Rev 10(1):137–151 Xia QS, Chou MW, Kadlubar FF, Chan PC, Fu PP (2003) Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine. Chem Res Toxicol 16(1):66–73 Yang YC, Yan J, Churchwell M et al (2001a) Development of a P-32-postlabeling/HPLC method for detection of dehydroretronecine-derived DNA adducts in vivo and in vitro. Chem Res Toxicol 14(1):91–100 Yang YC, Yan J, Doerge DR, Chan PC, Fu PP, Chou MW (2001b) Metabolic activation of the tumorigenic pyrrolizidine alkaloid, riddelliine, leading to DNA adduct formation in vivo. Chem Res Toxicol 14(1):101–109 Zhao YW, Xia QS, da Costa GG, Yu HT, Cai LN, Fu PP (2012) Full structure assignments of pyrrolizidine alkaloid DNA adducts and mechanism of tumor initiation. Chem Res Toxicol 25(9):1985–1996