Synthesis and phototoxicity of isomeric 7,9-diglutathione pyrrole adducts: Formation of reactive oxygen species and induction of lipid peroxidation

Mattocks, 1986 Huxtable, 1989, Human health implications of pyrrolizidine alkaloids and herbs containing them, vol. 1, 41 Fu, 2001, Genotoxic pyrrolizidine alkaloids and pyrrolizidine alkaloid N-oxides – mechanisms leading to DNA adduct formation and tumorigenicity, J Environ Sci Health, Part C, 19, 353, 10.1081/GNC-100107580 Fu, 2002, Pyrrolizidine alkaloids-tumorigenic components in Chinese herbal medicines and dietary supplements, J Food Drug Anal, 10, 198 Fu, 2004, Pyrrolizidine alkaloids-genotoxicity, metabolism enzymes, metabolic activation, and mechanisms, Drug Metab Rev, 36, 1, 10.1081/DMR-120028426 Fu, 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, 637, 10.1021/tx900402x Roeder, 2000, Medicinal plants in China containing pyrrolizidine alkaloids, Pharmazie, 55, 711 Edgar, 2002, Honey from plants containing pyrrolizidine alkaloids: a potential threat to health, J Agric Food Chem, 50, 2719, 10.1021/jf0114482 Edgar, 2015, Pyrrolizidine alkaloids: potential role in the etiology of cancers, pulmonary hypertension, congenital anomalies, and liver disease, Chem Res Toxicol, 28, 4, 10.1021/tx500403t International Programme on Chemical Safety (IPCS), 1989 Yang, 2001, Metabolic activation of the tumorigenic pyrrolizidine alkaloid, riddelliine, leading to DNA adduct formation in vivo, Chem Res Toxicol, 14, 101, 10.1021/tx000150n Fu, 2007, Detection, hepatotoxicity, and tumorigenicity of pyrrolizidine alkaloids in Chinese herbal plants and herbal dietary supplements, J Food Drug Anal, 15, 400 Chen, 2010, Genotoxicity of pyrrolizidine alkaloids, J Appl Toxicol, 30, 183 Zhao, 2012, Full structure assignments of pyrrolizidine alkaloid DNA adducts and mechanism of tumor initiation, Chem Res Toxicol, 25, 1985, 10.1021/tx300292h Xia, 2003, Human liver microsomal metabolism and DNA adduct formation of the tumorigenic pyrrolizidine alkaloid, riddelliine, Chem Res Toxicol, 16, 66, 10.1021/tx025605i Xia, 2013, Pyrrolizidine alkaloids-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity, Chem Res Toxicol, 26, 1384, 10.1021/tx400241c Zhao, 2011, Photoirradiation of dehydropyrrolizidine alkaloids–formation of reactive oxygen species and induction of lipid peroxidation, Toxicol Lett, 205, 302, 10.1016/j.toxlet.2011.06.020 Wang, 2014, Metabolic activation of pyrrolizidine alkaloids leading to phototoxicity and photogenotoxicity in human HaCaT keratonicytes, J Environ Sci Health, Part C, 32, 362, 10.1080/10590501.2014.969980 Lame, 1990, Isolation and identification of a pyrrolic glutathione conjugate metabolite of the pyrrolizidine alkaloid monocrotaline, Toxicol Lett, 51, 321, 10.1016/0378-4274(90)90075-W Buhler, 1991, Mechanisms for pyrrolizidine alkaloid activation and detoxification, Adv Exp Med Biol, 283, 597, 10.1007/978-1-4684-5877-0_75 Mattocks, 1991, Identity of a biliary metabolite formed from monocrotaline in isolated, perfused rat liver, Toxicon, 29, 409, 10.1016/0041-0101(91)90015-J Reed, 1992, Microsomal formation of a pyrrolic alcohol glutathione conjugate of the pyrrolizidine alkaloid senecionine, Xenobiotica, 22, 1321, 10.3109/00498259209053160 Lin, 1998, Microsomal formation of a pyrrolic alcohol glutathione conjugate of clivorine. Firm evidence for the formation of a pyrrolic metabolite of an otonecine-type pyrrolizidine alkaloid, Drug Metab Dispos, 26, 181 Tamta, 2012, Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates, Xenobiotica, 42, 1038, 10.3109/00498254.2012.679978 Fashe, 2014, Identification of a new reactive metabolite of pyrrolizidine alkaloid retrorsine: (3H-pyrrolizin-7-yl)methanol, Chem Res Toxicol, 27, 1950, 10.1021/tx5002964 Yan, 1995, Relationship between glutathione concentration and metabolism of the pyrrolizidine alkaloid, monocrotaline, in the isolated, perfused liver, Toxicol Appl Pharmacol, 130, 132, 10.1006/taap.1995.1017 Xia, 2015, 7-Glutathione pyrrole adduct: a potential DNA reactive metabolite of pyrrolizidine alkaloids, Chem Res Toxicol, 28, 615, 10.1021/tx500417q Yang, 2001, Development of a 32P-postlabeling/HPLC method for detection of dehydroretronesine-derived DNA adducts in vitro and in vivo, Chem Res Toxicol, 14, 91, 10.1021/tx000149o Cherng, 2005, Photodecomposition of retinyl palmitate in ethanol by UVA light – formation of photodecomposition products, reactive oxygen species, and lipid peroxides, Chem Res Toxicol, 18, 129, 10.1021/tx049807l Xia, 2006, UVA photodecomposition of retinyl palmitate – formation of singlet oxygen and superoxide, and their role in induction of lipid peroxidation, Toxicol Lett, 163, 30, 10.1016/j.toxlet.2005.09.010 Chiang, 2010, Photoirradiation of azulene and guaiazulene–formation of reactive oxygen species and induction of lipid peroxidation, J Photochem Photobiol A Chem, 211, 123, 10.1016/j.jphotochem.2010.02.007 Jeanmougin, 1987, Dosimetry of solar ultraviolet radiation. Daily and monthly changes in Paris, Ann Dermatol Venereol, 114, 671 Jiang, 2015, Absolute configuration, stability, and interconversion of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine valine adducts and their phenylthiohydantoin derivatives, J Food Drug Anal, 23, 318, 10.1016/j.jfda.2015.01.004 Robertson, 1977, Covalent interaction of dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione, Cancer Res, 37, 3141 Lin, 2000, Characterization of rat liver microsomal metabolites of clivorine, an hepatotoxic otonecine-type pyrrolizidine alkaloid, Drug Metab Dispos, 28, 1475 Herreño-Sáenz, 2007, UVA photoirradiation of methylated benzo[a]pyrene and benzo[e]pyrene leading to induction of lipid peroxidation, Int J Environ Res Public Health, 4, 145, 10.3390/ijerph2007040009 Basu-Modak, 1993, Singlet oxygen: a primary effector in the ultraviolet A/near-visible light induction of the human heme oxygenase gene, Cancer Res, 53, 4505 Sortino, 1998, Molecular mechanism of photosensitization XI. Membrane damage and DNA cleavage photoinduced by enoxacin, Photochem Photobiol, 68, 652, 10.1111/j.1751-1097.1998.tb02525.x Floyd, 2001, Oxidative biochemical markers: clues to understanding aging in long-lived species, Exp Gerontol, 36, 619, 10.1016/S0531-5565(00)00231-X Stadtman, 1997, Reactive oxygen-mediated protein oxidation in aging and disease, Chem Res Toxicol, 10, 485, 10.1021/tx960133r