Abstract
Allyl alcohol has long been known to produce periportal necrosis of the liver in rats and mice (Miessner 1891; Piazza 1915). Also it is known that allyl alcohol is metabolized by the cytosolic enzyme alcohol dehydrogenase to acrolein (Rees and Tarlow 1967; Serafini-Cessi 1972). The latter is considered as one of the most important toxic metabolites responsible for the damage induced by allyl alcohol in liver and other tissues. Acrolein is in fact the most toxic member of the class of 2-alkenals (Beauchamp et al. 1985; Schauenstein et al. 1977), α-β unsaturated aldehydes which also include crotonaldehyde, pentenal, hexenal and so on. Acrolein is a powerful electrophile which reacts even spontaneously with nucleophiles such as sulphydryl groups (Esterbauer et al. 1975). The reaction is markedly accelerated by the activity of GSH-transferases. Cellular GSH is primarily involved in the reaction and the result is a dramatic loss of GSH stores (Hanson and Anders 1978; Zitting and Heinonen 1980; Dawson et al. 1984; Ohno et al. 1985; Jaeschke et al. 1987). The covalent binding of allyl alcohol metabolites to liver cells has been demonstrated with various techniques (Reid 1972).
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References
Beauchamp RO Jr, Andjelkovich DA, Kligerman AD, Morgan KT, d’A. Heck H (1985) A critical review of the literature on acrolein toxicity. CRC Crit Rev Toxicol 14:309–380
Benedetti A, Comporti M, Esterbauer H (1980) Indentification of 4-hydroxynonenal as a cytotoxic product originating from the peroxidation of liver microsomal lipids. Biochim Biophys Acta 620:281–296
Benedetti A, Casini AF, Ferrali M, Fulceri R, Comporti M (1981) Cytotoxic effects of carbonyl compounds (4-hydroxyalkenals) originating from the peroxidation of microsomal lipids. In: Slater TF, Garner A (eds) Recent advances in lipid peroxidation and tissue injury. Brunei, Uxbridge, pp 56-85
Benedetti A, Comporti M, Fulceri R, Esterbauer H (1984a) Cytotoxic aldehydes originating from the peroxidation of liver microsomal lipids. Identification of 4,5-dihydroxydecenal. Biochim Biophys Acta 792:172–181
Benedetti A, Fulceri R, Comporti M (1984b) Inhibition of calcium sequestration activity of liver microsomes by 4-hydroxynonenal originating from the peroxidation of liver microsomal lipids. Biochim Biophys Acta 793:489–493
Benedetti A, Pompella A, Fulceri R, Romani A, Comporti M (1986) Detection of 4-hydroxynonenal and other lipid peroxidation products in the liver of bromobenzene-poisoned mice. Biochim Biophys Acta 876:658–666
Bielawski J, Lehninger AL (1966) Stoichiometric relationships in mitochondrial accumulation of calcium and phosphate supported by hydrolysis of adenosine triphosphate. J Biol Chem 241:4316–4322
Casini AF, Pompella A, Comporti M (1985) Liver glutathione depletion induced by bromobenzene, iodobenzene, and diethylmaleate poisoning and its relation to lipid peroxidation and necrosis. Am J Pathol 118:225–237
Casini AF, Maellaro E, Pompella A, Ferrali M, Comporti M (1988) Lipid peroxidation, protein thiols and calcium homeostasis in bromobenzene-induced liver damage. Biochem Pharmacol, (in press)
Dawson JR, Norbeck K, Anundi I, Moldéus P (1984) The effectiveness of N-acetylcysteine in isolated hepatocytes, against the toxicity of paracetamol, acrolein, and paraquat. Arch Toxicol 55:11–15
Dianzani MU (1982) Biochemical effects of saturated and unsaturated aldehydes. In: McBrien DCH, Slater TF (eds) Free radicals, lipid peroxidation and cancer. Academic, London, pp 129–158
Esterbauer H (1982) Aldehydic products of lipid peroxidation. In: McBrien DCH, Slater TF (eds) Free radicals, lipid peroxidation and cancer. Academic, London, pp 101–128
Esterbauer H (1985) Lipid peroxidation products: formation, chemical properties and biological activities. In: Poli G, Cheeseman KH, Dianzani MU, Slater TF (eds) Free radicals in liver injury. IRL, Oxford, pp 29–47
Esterbauer H, Zollner H, Scholz N (1975) Reaction of glutathione with conjugated carbonyls. Z Naturforsch [c] 30:466–473
Esterbauer H, Cheeseman KH, Dianzani MU, Poli G, Slater TF (1982) Separation and characterization of the aldehydic products of lipid peroxidation stimulated by ADP-Fe2+ in rat liver microsomes. Biochem J 208:129–140
Hanson SK, Anders MW (1978) Effect of diethyl maleate treatment, fasting, and time of administration on allyl alcohol hepatotoxicity. Toxicol Lett 1:301–305
Jaeschke H, Kleinwaechter C, Wendel A (1987) The role of acrolein in allyl alcohol-induced lipid peroxidation and liver cell damage in mice. Biochem Pharmacol 36:51–58
Jocelyn PC, Kamminga A (1974) The non-protein thiol of rat liver mitochondria. Biochim Biophys Acta 343:356–362
Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265–275
Meredith MJ, Reed DJ (1982) Status of the mitochondrial pool of glutathione in the isolated hepatocyte. J Biol Chem 257:3747–3753
Meredith NJ, Reed DJ (1983) Depletion in vitro of mitochondrial glutathione in rat hepatocytes and enhancement of lipid peroxidation by adriamycin and 1.3-bis(2-chloroethyl)-1-nitrosourea (BCNU). Biochem Pharmacol 32:1383–1388
Miessner H (1891) Berlin Klin Wochenschr 28:819–822
Ohno Y, Ormstad K, Ross D, Orrenius S (1985) Mechanism of allyl alcohol toxicity and protective effects of low-molecular-weight thiols studied with isolated rat hepatocytes. Toxicol Appl Pharmacol 78:169–179
Piazza JG (1915) Zur Kenntnis der Wirkung der Allylverbindungen. Z Exp Pathol Ther 17:318–341
Pompella A, Maellaro E, Casini AF, Ferrali M, Ciccoli L, Comporti M (1987) Measurement of lipid peroxidation in vivo: a comparison of different procedures. Lipids 22:206–211
Rees KR, Tarlow MJ (1967) The hepatotoxic action of allyl formate. Biochem J 104:757–761
Reid WD (1972) Mechanism of allyl alcohol-induced hepatic necrosis. Experientia 28:1058–1061
Schauenstein E, Esterbauer H, Zollner H (eds) (1977) Aldehydes in biological systems. Pion, London, pp 25–102
Sedlak J, Lindsay RH (1968) Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman’s reagent. Anal Biochem 25:192–205
Serafini-Cessi F (1972) Conversion of allyl alcohol into acrolein by rat liver. Biochem J 128:1103–1107
Vignais PM, Vignais PV (1973) Fuscin, an inhibitor of mitochondrial SH-dependent transportlinked functions. Biochim Biophys Acta 325:357–374
Wahlländer A, Soboll S, Sies H (1979) Hepatic mitochondrial and cytosolic glutathione content and the subcellular distribution of GSH-S-transferases. FEBS Lett 97:138–140
Witz G, Lawrie NJ, Zaccaria A, Ferran HE Jr, Goldstein BD (1986) The reaction of 2-thiobarbituric acid with biologically active alpha, beta-unsaturated aldehydes. J Free Radic Biol Med 2:33–39
Zitting A, Heinonen T (1980) Decrease of reduced glutathione in isolated rat hepatocytes caused by acrolein, acrylonitrile, and the thermal degradation products of styrene copolymers. Toxicology 17:333–341
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Pompella, A., Romani, A., Fulceri, R., Maellaro, E., Benedetti, A., Comporti, M. (1988). Detection of 4-Hydroxynonenal and Other Lipid Peroxidation Products in the Liver of Allyl Alcohol-Intoxicated Mice. In: Nigam, S.K., McBrien, D.C.H., Slater, T.F. (eds) Eicosanoids, Lipid Peroxidation and Cancer. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-73424-3_28
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DOI: https://doi.org/10.1007/978-3-642-73424-3_28
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