Absolute configuration, stability, and interconversion of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine valine adducts and their phenylthiohydantoin derivatives

Roeder, 2000, Medicinal plants in China containing pyrrolizidine alkaloids, Pharmazie, 55, 711 Mattocks, 1986 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 and in vivo, Chem Res Toxicol, 23, 637, 10.1021/tx900402x Stegelmeier, 1999, Pyrrolizidine alkaloid plants, metabolism and toxicity, J Nat Toxins, 8, 95 Huxtable, 1980, Herbal teas and toxins: novel aspects of pyrrolizidine poisoning in the United States, Perspect Biol Med, 24, 1, 10.1353/pbm.1980.0078 Huxtable, 1989, Human health implications of pyrrolizidine alkaloids and herbs containing them, vol. 1, 41 Betz, 1994, Determination of pyrrolizidine alkaloids in commercial comfrey products (Symphytum sp.), J Pharm Sci, 83, 649, 10.1002/jps.2600830511 Edgar, 2002, Honey from plants containing pyrrolizidine alkaloids: a potential threat to health, J Agric Food Chem, 50, 2719, 10.1021/jf0114482 International Programme on Chemical Safety (IPCS), 1989 Zhao, 2012, Full structure assignments of pyrrolizidine alkaloid DNA adducts and mechanism of tumor initiation, Chem Res Toxicol, 25, 1985, 10.1021/tx300292h Xia, 2013, Pyrrolizidine alkaloids derived DHP-DNA adducts are a common biological biomarker of pyrrolizidine alkaloid-initiated tumorigenicity, Chem Res Toxicol, 6, 1384, 10.1021/tx400241c Robertson, 1977, Covalent interaction of dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione, Cancer Res, 37, 3141 Zhao, 2014, Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin, Chem Res Toxicol, 27, 1720, 10.1021/tx5002139 Törnqvist, 2002, Protein adducts: quantitative and qualitative aspects of their formation, analysis and applications, J Chromatogr B, 778, 279, 10.1016/S1570-0232(02)00172-1 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 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