Skip to main content
SpringerLink
Log in
Book cover

Oxidative Stress and Antioxidant Defenses in Biology pp 181–209Cite as

Metabolic Detoxification of Plant Prooxidants

  • Chapter

Abstract

Whereas oxidants are chemicals capable of causing direct oxidative damage to living systems, prooxidants are compounds that must first undergo activation to cause oxidative damage (Ahmad, 1992). While oxidants tend to be small inorganic molecules, such as nitrogen oxides or ozone, a broad range of naturally occurring organic compounds have prooxidant properties. Prooxidant compounds are produced in great abundance by plants; because they upon activation initiate chain reactions that magnify their biological effects relative to their initial concentrations, they represent energy-efficient investments in defense against environmental stresses (Ahmad, 1992). Among those organisms susceptible to the toxic effects of plant prooxidants are insect and mammalian herbivores as well as microbial phytopathogens and plant competitors (Downum, 1992).

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Abdulrashid, N. and Clark, D.P. (1987) Isolation and genetic analysis of mutations allowing the degradation of furans and thiophenes by Escherichia coli. J. Bacteriol. 169, 1267–1271.

    PubMed  CAS  Google Scholar 

  • Ahmad, S. (1992) Biochemical defence of pro-oxidant plant allelochemicals by herbivorous insects. Biochem. Syst. Ecol. 20, 269–296.

    Article  CAS  Google Scholar 

  • Alam, K.Y. and Clark, D.P. (1991) Molecular cloning and sequence of the thdF gene, which is involved in thiophene and furan oxidation by Escherichia coli. J. Bacteriol. 173, 6018–6024.

    PubMed  CAS  Google Scholar 

  • Appel, H.M. (1993) Phenolics in ecological interactions: the importance of oxidation. J. Chem. Ecol. 19, 1521–1552.

    Article  CAS  Google Scholar 

  • Arnason, J.T., Guerin, B., Kraml, M.M., Mehta, B., Redmond, R.W. and Scaiano, J. (1992) Phototoxic and photochemical properties of sanguinarine. Photochem. Photobiol. 55, 35–38.

    Article  PubMed  CAS  Google Scholar 

  • Ashwood-Smith, M., Stanley, C., Towers, G.H.N, and Warrington, P.J. (1993) UV-A-mediated activity of pmethoxymethylcinnamate. Photochem. Photobiol. 57, 814–818.

    Article  PubMed  CAS  Google Scholar 

  • Asthana, A., Larson, R.R.A., Marley, K.A. and Tuveson, R.W. (1992) Mechanisms of citral phototoxicity. Photochem. Photobiol. 56, 211–222.

    Article  PubMed  CAS  Google Scholar 

  • Atallah, A., Landolph, J.R. and Hochstein, P. (1986) DT-diaphorase and quinone detoxification. Chemica Scripta 27A, 141–144.

    Google Scholar 

  • Beedham, C., Al-Tayib, Y. and Smith, J.A. (1992) Role of guinea pig and rabbit hepatic aldehyde oxidase in oxidative in vitro metabolism of cinchona antimalarials. Drug Metab. Disp. 20, 889–895.

    CAS  Google Scholar 

  • Berenbaum, M. (1981) Effects of linear furanocoumarins on an adapted specialist insect (Papilio polyxenes). Ecol. Entomol. 6, 345–351.

    Article  Google Scholar 

  • Berenbaum, M.R. (1987) Charge of the light brigade: insect adaptations to phototoxins. In Light-Activated Pesticides (J.R. Heitz and K.R. Downum, eds.), Washington, D.C.: ACS Symp. Ser. 339, 206–216.

    Chapter  Google Scholar 

  • Berenbaum, M.R. (1991a) Comparative processing of allelochemicals in Papilionidae. Arch. Insect Biochem. Physiol. 17, 213–222.

    Article  CAS  Google Scholar 

  • Berenbaum, M.R. (1991b) Coumarins. In Herbivores. Their Interactions with Secondary Plant Metabolites, (G.A. Rosenthal and M.R. Berenbaum, eds.), Academic Press, New York, vol. 1: 221–249.

    Google Scholar 

  • Berenbaum, M.R., Cohen, M.B. and Schuler, M.A. (1990) Cytochrome P450 in plant-insect interactions: inductions and deductions. In Molecular Insect Science, ( H. Hagedorn, J. Hildebrand, M.G. Kidwell, and J. Law, eds.), Plenum Pub. Co., New York, pp. 257–262.

    Google Scholar 

  • Berenbaum, M.R. and Feeny, P.P. (1981) Toxicity of angular furanocoumarins to swallowtails: escalation in the revolutionary arms race. Science 212, 927–929.

    Article  PubMed  CAS  Google Scholar 

  • Berenbaum, M.R., Nitao, J.K. and Zangerl, A.R. (1986) Constraints on chemical co-evolution: wild parsnips and the parsnip webworm. Evolution 40, 1215–1228.

    Article  CAS  Google Scholar 

  • Berenbaum, M.R. and Zangler, A.R. (1993) Fumarocoumarin metabolism in Papilio polyxenes: genetic variability, biochemistry, and ecological significance. Oecologia 95, 370–375.

    Article  Google Scholar 

  • Bickers, D.R. and Pathak, M.A. (1984) Psoralen pharmacology: studies on metabolism and enzyme induction. In Photobiologic, Toxicologic, and Pharmacologic Aspects of Psoralens (M.A. Pathak, ed.), Bethesda: National Cancer Institute Monograph NIH Publication No. 84-2692, pp. 77–83.

    Google Scholar 

  • Boyer, C.S. and Petersen, D.R. (1991) The metabolism of 3,7-dimethyl-2,6-octadienal (citral) in rat hepatic mitochondrial and cytosolic fractions. Interactions with aldehyde and alcohol dehydrogenases. Drug Met. and Disp. 19, 81–86.

    CAS  Google Scholar 

  • Bull, D.L., Ivie, G.W., Beier, R.C. and Pryor, N.W. (1986) In vitro metabolism of a linear furanocoumarin (8-methoxypsoralen, xanthotoxin) by mixed-function oxidases of larvae of black swallowtail butterfly and fall army worm. J. Chem. Ecol. 12, 885–892.

    Article  CAS  Google Scholar 

  • Chae, K.H. and Ham, H.S. (1986) Production of singlet oxygen and superoxide anion radicals by b-carbolines. Bull. Korean Chem. Soc. 7, 478–479.

    CAS  Google Scholar 

  • Cohen, M.B., Berenbaum, M.R. and Schuler, M.A. (1989) Induction of cytochrome P450-mediated detoxification in the black swallowtail. J. Chem. Ecol. 15, 2347–2355.

    Article  CAS  Google Scholar 

  • Cohen, M.B., Schuler, M.A. and Berenbaum, M.R. (1992) A host-inducible cytochrome P450 from a host-specific caterpillar: molecular cloning and evolution. Proc. Natl. Acad. Sci. USA 89, 10920–10924.

    Article  PubMed  CAS  Google Scholar 

  • Desjardins, A.E., Spencer, G.F. and Plattner, R.D. (1989) Tolerance and metabolism of furanocoumarins by the phytopathogenic fungus Gibberella pulicaris (Fusarium sambucinum). Phytochemistry 28, 2963–2969.

    Article  CAS  Google Scholar 

  • Desjardins, A.E., Spencer, G.R., Plattner, R.D. and Beremand, M.N. (1989) Furanocoumarin phytoalexins, trichothecene toxins, and infection of Pastinaca sativa by Fusarium sporotrichoides. Phytopathology 79, 170–175.

    Article  CAS  Google Scholar 

  • Diliberto, J.J., Srinivas, P., Overstreet, D., Usha, G., Burka, L.T. and Birnbaum, L.S. (1990) Metabolism of citral, an a,p-unsaturated aldehyde in male F344 rates. Drug Metab. Disp. 18, 866–875.

    CAS  Google Scholar 

  • Downum, K.R. (1992) Tansley Review No. 43. Light-activated plant defence. New Phytol. 122, 401–420.

    Article  CAS  Google Scholar 

  • Duffey, S.S. and Pasteels, J.M. (1993) Transient uptake of hypericin by chrysomelids is regulated by feeding behaviour. Physiol. Entomol. 18, 119–129.

    Article  CAS  Google Scholar 

  • Ernster, L. (1986) DT-Diaphorase: a historical review. Chemica Scripta 27A, 1–14.

    Google Scholar 

  • Feyereisen, R., Koerner, J.F., Farnsworth, D.E. and Nebert, D.W. (1989) Isolation and sequence of a cDNA encoding a cytochrome P450 from an insecticide-resistant strain of the house fly, Musca domestica. Proc. Natl. Acad. Sci. USA 88, 4558–4562.

    Google Scholar 

  • Fields, P.G., Arnason, J.T. and Philogene, B.J.R. (1990) Behavioural and physical adaptations of three insects that feed on the phototoxic plant Hypericum perforatum. Can. J. Zool. 68, 339–346.

    Article  Google Scholar 

  • Furuya, H., Shimizu, T., Hirano, K., Hatano, M., Fujii-Kuriyama, Y., Raag, R. and Poulos, T.L. (1989) Site-directed mutagenesis of rat liver cytochrome P-450d: catalytic activities toward benzphetamine and 7-ethoxycoumarin. Biochemistry 28, 6848–6857.

    Article  PubMed  CAS  Google Scholar 

  • Gonzalez, F.J. and Nebert, D.W. (1990) Evolution of the P450 gene superfamily: animal-plant “warfare”, molecular drive, and human genetic differences in drug oxidation. Trends in Genetics 6, 182–186.

    Article  PubMed  CAS  Google Scholar 

  • Goodwin, T.W. and Mercer, E.I. (1972) Introduction to Plant Biochemistry. Pergamon Press, New York.

    Google Scholar 

  • Guengerich, F.P., Muller-Enoch, D. and Blair, I.A. (1987) Oxidation of quinidine by human liver cytochrome P450. Mol. Pharmacol. 30, 287–295.

    Google Scholar 

  • Hasspieler, B.M., Arnason, J.T. and Downe, A.E.R. (1991) Metabolism of the phototoxin α-terthienyl in Culex tarsalis larvae: involvement of the polysubstrate monooxygenase system. Pestic. Biochem. Physiol. 40, 191–197.

    Article  CAS  Google Scholar 

  • Ikeda, G.J., Sapienza, P.P., Sager, A.O. and Kornhauser, A. (1990) Exretion and tissue distribution of 14C-labelled 8-methoxypsoralen in beagle dogs and miniature pigs. Food Chem. Toxicol. 28, 333–338.

    Article  PubMed  CAS  Google Scholar 

  • Isman, M.B. and Duffey, S.S. (1983) Pharmacokinetics of chlorogenic acid and rutin in larvae of Heliothis zea. J. Insect Physiol. 29, 295–300.

    Article  CAS  Google Scholar 

  • Ivie, G.W. (1987) Biological actions and metabolic transformations of furanocoumarins. In Light-Activated Pesticides (J.R. Heitz and K.R. Downum, eds.), Washington, D.C., ACS Symp. Ser. 339, 217–230.

    Chapter  Google Scholar 

  • Ivie, G.W., Beier, R.C., Bull, D.L. and Oertli, E.H. (1986) Fate of [14C]xanthotoxin (8-methoxypsoralen) in a goat and in bovine ruminal fluid. Am. J. Vet. Res. 47, 799–803.

    PubMed  CAS  Google Scholar 

  • Ivie, G.W., Bull, D.L., Beier, R.C., Pryor, N.W. and Oertli, E.H. (1983) Metabolic detoxification: mechanism of insect resistance to psoralens. Science 221, 374–376.

    Article  PubMed  CAS  Google Scholar 

  • Ivie, G.W., Bull, D.L., Beier, R.C. and Pryor N.W. (1986) Comparative metabolism of [3H] psoralen and [3H]-isopsoralen by black swallowtail (Papilio polyxenes Fabr.) caterpillars. J. Chem. Ecol. 12, 871–884.

    Article  CAS  Google Scholar 

  • Iyengar, S., Arnason, J.T., Philogene, B.J.R., Morand, P., Werstiuk, N.H. and Timmins, G. (1987) Toxicokinetics of the phototoxic allelochemical α-terthienyl in three herbivorous Lepidoptera. Pestic. Biochem. Physiol. 29, 1–9.

    Article  CAS  Google Scholar 

  • Iyengar, S., Arnason, J.T., Philogene, B.J.R., Werstiuk, N.H. and Morand, P. (1990) Comparative metabolism of the phototoxic allelochemical α-terthienyl in three species of lepidopterans. Pestic. Biochem. Physiol. 37, 154–164.

    Article  CAS  Google Scholar 

  • Jacob, J., Schmoldt, A., Augustin, C., Raab, G. and Grimmer, G. (1991) Rat liver microsomal ring- and S-oxidation of thiaarenes with central or peripheral rings. Toxicology 67, 181–194.

    Article  Google Scholar 

  • Joshi, P.C. and Pathak, M.A. (1983) Production of singlet oxygen and superoxide radicals by psoralens and their biological significance. Biochem. Biophys. Res. Commun. 112, 638–646.

    Article  PubMed  CAS  Google Scholar 

  • Knox, J.P., Samuels, R.I. and Dodge, A.D. (1987) Photodynamic action of hypericin. In Light-Activated Pesticides (J.R. Heitz and K.R. Downum, eds.), Washington, D.C., ACS Symp. Ser. 339, 265–270.

    Chapter  Google Scholar 

  • Kolis, S.J., Williams, T.H., Postma, E.J., Sasso, G.J., Confalone, P.N. and Schwartz, M.A. (1979) The metabolism of 14C-methoxsalen by the dog. Drug Metab. Disp. 7, 220–225.

    CAS  Google Scholar 

  • Kraul, H., Brix, R., Otto, A. and Hoffman, A. (1992) Dose-dependence of coumarin elimination and inhibitory effect of 8-methoxypsoralen. Pharmazie 47, 389–390.

    PubMed  CAS  Google Scholar 

  • Larson, R.A. and Marley, K.A. (1994) Oxidative mechanisms of phototoxicity. In Oxidants in the Environment. Advances in Environmental Science and Technology ( J.O. Nriagu and M.S. Simmons, eds.), New York, J. Wiley and Sons, 269–317.

    Google Scholar 

  • Larson, R.A., Marley, K.A., Tuveson, R.W. and Berenbaum, M.R. (1988) (3-carboline alkaloids: mechanisms of phototoxicity to bacteria and insects. Photochem. Photobiol. 48, 665–674.

    Google Scholar 

  • Lee, K. (1991) Glutathione-S-transferase activities in phytophagous insects: induction and inhibition by plant phototoxins and phenols. Insect Biochem. 21, 353–361.

    Article  CAS  Google Scholar 

  • Lee, K. and Berenbaum, M.R. (1989) Action of antioxidant enzymes and cytochrome P450 monooxygenases in the cabbage looper in response to plant photo toxins. Arch. Insect Biochem. Physiol. 10, 151–162.

    Article  Google Scholar 

  • Lee, K. and Berenbaum, M.R. (1993) Food utilization and antioxidant enzyme activities of black swallowtail in response to plant phototoxins. Arch. Insect Biochem. Physiol. 23, 79–89.

    Article  CAS  Google Scholar 

  • Lindroth, R. (1989a) Host plant alteration of detoxication activity in Papilio glaucus glaucus. Entomol. Exp. Appl. 50, 29–35.

    Article  CAS  Google Scholar 

  • Lindroth, R. (1989b) Biochemical detoxication: mechanism of differential tiger swallowtail tolerance to phenolic glycosides. Oecologia 81, 219–224.

    Google Scholar 

  • Lindroth, R. (1989c) Differential esterase activity in Papilio glaucus subspecies: absence of cross-resistance between allelochemicals and insecticides. Pestic. Biochem. Physiol. 35, 185–91.

    Article  CAS  Google Scholar 

  • Lindroth, R.L. (1991) Differential toxicity of plant allelochemicals to insects: role of enzymatic detoxification systems. In Insect-Plant Interactions (E.A. Bernays, ed.), CRC Press, Boca Raton, FL, III, 2–33.

    Google Scholar 

  • Ma, R., Cohen, M.B., Berenbaum, M.R. and Schuler, M.A. (1994) Black swallowtail (Papilio polyxenes) encode cytochrome P450s that selectively metabolize linear furanocoumarins. Arch. Biochem. Biophys. 310, 332–340.

    Article  PubMed  CAS  Google Scholar 

  • Maiti, M., Nandi, R. and Chaudhuri, K. (1982) Sanguinarine: a monofunctional intercalating alkaloid. FEBS Letts. 142, 280 - 284.

    Article  CAS  Google Scholar 

  • Mayuzumi, H., Sambongi, C., Kiroya, H., Shimizu, T., Tateishi, T. and Hatano, M. (1993) Effect of mutation of ionic amino acids of cytochrome P450 1A2 on catalytic activities toward 7-ethoxycoumarin and methanol. Biochemistry 32, 5622–5628.

    Article  PubMed  CAS  Google Scholar 

  • Mohammad, T., Baird, W.M. and Morrison, H. (1991) Photochemical covalent binding of p-methoxycinnamic acid to calf thymus DNA. Bioorg. Chem. 19, 88–100.

    Article  CAS  Google Scholar 

  • Moleyar, V. and Narasimham, P. (1987) Detoxification of essential oil component (citral and menthol) by Aspergillus niger and Rhizopus stolonifer. J. Sci. Food Agric. 39, 240–246.

    Article  Google Scholar 

  • Moore, D.E. (1980) Photosensitization by drugs: quinine as a photosensitizer. J. Pharm. Pharmacol. 32, 216–218.

    Article  PubMed  CAS  Google Scholar 

  • Murphy, S.E., Amin, S., Coletta, K. and Hoffman, D. 1992. Rat liver metabolism of benzo[b]naphtho[2,1-d]thiophene. Chem. Res. Toxicol. 5, 491–495.

    Article  PubMed  CAS  Google Scholar 

  • Murray, R.D.H., Mendez, J. and Brown, S.A. (1982) The Natural Coumarins: Occurrence, Chemistry and Biochemistry. J. Wiley and Sons, Chichester.

    Google Scholar 

  • Nitao, J.K. (1989) Enzymatic adaptation in a specialist herbivore for feeding on furanocoumarin-containing plants. Ecology 70, 629–635.

    Article  CAS  Google Scholar 

  • Pangilinan, N.C., Ivie, G.W., Clement, B.A., Beier, R.C. and Uwayjan, M. (1992) Fate of [14C]xanthotoxin (8-methoxypsoralen) in laying hens and a lactating goat. J. Chem. Ecol. 18, 253–270.

    Article  CAS  Google Scholar 

  • Parke, D. and Rahman, M. 1969. The effects of some terpenoids and other dietary nutrients on hepatic drug metabolizing enzymes. Biochem. J. 113, 12.

    Google Scholar 

  • Philogene, B.J.R., Arnason, J.T., Towers, G.H.N., Abramowski, Z., Campos, F., Champagne, D. and McLachlan, D. (1984) Berberine: a naturally occurring phototoxic alkaloid. J. Chem. Ecol. 10, 115–123.

    Article  CAS  Google Scholar 

  • Scheline, R.R. (1978) Mammalian Metabolism of Plant Xenobiotics. Academic Press, London.

    Google Scholar 

  • Schmid, J., Prox, A., Reuter, A., Zipp, H. and Koss, F.W. (1980) The metabolism of 8-methoxypsoralen in man. Eur. J. Drug Metab. Pharmacokinetics 5, 81–92.

    Article  CAS  Google Scholar 

  • Song, P.S. (1984) Photoreactive states of furanocoumarins. Natl. Cancer Inst. Monogr. 66, 15–19.

    PubMed  CAS  Google Scholar 

  • Specht, K.G., Kittler, L. and Midden, W.R. (1988) A new biological target of furanocoumarins: photochemical formation of covalent adducts with unsaturated fatty acids. Photochem. Photobiol. 47, 537–541.

    Article  PubMed  CAS  Google Scholar 

  • Spencer, G.F., Desjardins, A.E. and Plattner, R.F. (1990) 5-(2-carboxyethyl)-6-hydroxy-7-methoxybenzofuran, a fungal metabolite of xanthotoxin. Phytochemistry 29, 2495–2497.

    Google Scholar 

  • Tuveson, R.W., Larson, R.A., Marley, K.A., Wong, G.-R. and Berenbaum, M.R. (1989) Sanguinarine, a phototoxic H2O2-producing alkaloid. Photochem. Photobiol. 50, 733–738.

    Article  PubMed  CAS  Google Scholar 

  • Waterman, P.G. and Grundon, M.F. (1975) Chemistry and chemical taxonomy of the Rutales. Ann. Proc. Phytochem. Soc. Europe 22. Academic Press, New York.

    Google Scholar 

  • Witkamp, R.F., Nijmeijer, S.M., Mennes, W.C., Rozema, A.Z., Noordhoek, J. and Van Miert, A.S.J.P.A.M. (1993) Regioselective O-demethylation of scoparone (6,7-dimethoxycoumarin) to assess cytochrome P450 activities in vitro in rat. Effects of gonadal steroids and the involvement of constitutive P450 enzymes. Xenobiotica 23, 401–410.

    Article  PubMed  CAS  Google Scholar 

  • Yu, S.J. (1987) Quinone reductase of phytophagous insects and its induction by allelochemicals. Comp. Biochem. Physiol. 87B, 621–624.

    Article  Google Scholar 

Download references

Authors
  1. May R. Berenbaum
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Biochemistry, University of Nevada, Reno, Nevada, 89557-0014, USA

    Sami Ahmad

Rights and permissions

Reprints and permissions

Copyright information

© 1995 Chapman & Hall

About this chapter

Cite this chapter

Berenbaum, M.R. (1995). Metabolic Detoxification of Plant Prooxidants. In: Ahmad, S. (eds) Oxidative Stress and Antioxidant Defenses in Biology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9689-9_5

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-9689-9_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4615-9691-2

  • Online ISBN: 978-1-4615-9689-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation