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Inhibitors of Protoporphyrinogen Oxidase: A Brief Update

  • Chapter
Herbicide Classes in Development

Abstract

This contribution is a brief overview on recent findings. Further details have been published in Peroxidizing Herbicides (ed. by P. Böger and K. Wakabayashi) issued in 1999 by Springer Publ., Heidelberg, Germany.

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References

  • Adomat C, Böger P (2000) Cloning, sequence, expression, and characterization of protoporphyrinogen IX oxidase from chicory. Pestic Biochem Physiol 66: 49–62

    Article  CAS  Google Scholar 

  • Arnould S, Camadro J-M (1998) The domain structure of protoporphyrinogen oxidase, the molecular target of diphenyl ether-type herbicides. Proc Natl Acad Sci USA 95: 10553–10558

    Article  PubMed  CAS  Google Scholar 

  • Arnould S, Berthon JL, Hubert C, Dias M, Cibert C, Monet R, Camadro J-M (1997) Kinetics of protoporphyrinogen oxidase inhibition by diphenyleneiodonium derivatives. Biochemistry 36: 10178–10184

    Article  PubMed  CAS  Google Scholar 

  • Arnould S, Takahashi M, Camadro J-M (1998) Stability of recombinant yeast protoporphyrinogen oxidase: effect of diphenyl ether-type herbicides and diphenyleneiodonium. Biochemistry 37: 12818–12828

    Article  PubMed  CAS  Google Scholar 

  • Arnould S, Takahashi M, Camadro J-M (1999) Acylation stabilizes a protease-resistant conformation of protoporphyrinogen oxidase, the molecular target of diphenyl ether-type herbicides. Proc Natl Acad Sci USA 96: 14825–14830

    Article  PubMed  CAS  Google Scholar 

  • Birchfield NB, Lath B, Casida JE (1998) Human protoporphyrinogen oxidase: relation between the herbicide binding site and the flavin cofactor. Biochemistry 37: 6905–6910

    Article  PubMed  CAS  Google Scholar 

  • Böger P, Sandmann G (1998) Action of modern herbicides. In: Raghavendra AS (ed) Photosynthesis: a comprehensive treatise. Cambridge University Press, Cambridge, pp 337–351

    Google Scholar 

  • Böger P, Wakabayashi K (1999) General physiological characteristics and mode of action of peroxidizing herbicides. In: Böger P, Wakabayashi K (eds) Peroxidizing herbicides. Springer, Berlin Heidelberg New York, pp 163–190

    Google Scholar 

  • Camadoro J-M, Labbe P (1996) Cloning and characterization of the yeast HEM14 gene coding for protoporphyrinogen oxidase, the molecular target of diphenyl ether-type herbicides. J Biol Chem 271: 9120–9128

    Article  Google Scholar 

  • Camadro J-M, Matringe M, Scalla R, Labbe P (1991) Kinetic studies on protoporphyrinogen oxidase inhibition by diphenyl ether herbicides. Biochem J 277: 17–21

    PubMed  CAS  Google Scholar 

  • Camadro J-M, Thome F, Brouillet N, Labbe P (1994) Purification and properties protoporphyrinogen oxidase from the yeast Saccharomyces cerevisiae. Mitochondrial location and evidence for a precursor form of the protein. J Biol Chem 269: 32085–32091

    PubMed  CAS  Google Scholar 

  • Che F-S, Watanabe N, Iwano M, Inokuchi H, Takayama S, Yoshida S, Isogai A (2000) Molecular characterization and subcellular localization of protoporphyrinogen oxidase in spinach chloroplaste. Plant Physiol 124: 59–70

    Article  PubMed  CAS  Google Scholar 

  • Choi KW, Han OH, Lee HJ, Yun YH, Moon YH, Kim M, Kuk YI, Han SU, Guh JO (1998) Differential susceptibilities of wheat and barley to diphenyl ether herbicide oxyfluorfen. Biosci Biotechnol Biochem 62: 558–560

    Article  CAS  Google Scholar 

  • Corrigall AV, Siziba KB, Maneli MH, Shephard EG, Ziman M, Dailey TA, Dailey HA, Kirsch RE, Meissner PN (1998) Purification of and kinetic studies on a cloned protoporphyrinogen oxidase from the aerobic bacterium Bacillus subtilis. Arch Biochem Biophys 358: 251–256

    Article  PubMed  CAS  Google Scholar 

  • Cramer RD III, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA): effect of shape of binding of steroids to carrier proteins. J Am Chem Soc 110: 5959–5967

    Article  CAS  Google Scholar 

  • Dailey HA, Dailey TA (1996) Protoporphyrinogen oxidase of Myxococcus xanthus: expression, purification, and characterization of cloned enzyme. J Biol Chem 271: 8714–8718

    Article  PubMed  CAS  Google Scholar 

  • Dailey TA, Dailey HA (1998) Identification of an FAD superfamily containing protoporphyrinogen oxidases, monoamine oxidases, and phytoene desaturase. J Biol Chem 273: 13658–13662

    Article  PubMed  CAS  Google Scholar 

  • Dailey TA, Dailey HA, Meissner P, Prasad AR (1995) Cloning, sequence, and expression of mouse protoporphyrinogen oxidase. Arch Biochem Biophys 324: 379–384

    Article  PubMed  CAS  Google Scholar 

  • Dayan FE, Allen SN (2000) Predicting the activity of the natural phytotoxic diphenyl ether cyperine using comparative molecular field analysis. Pestic Manage Sci 56: 717–722

    Article  CAS  Google Scholar 

  • Dayan FE, Duke SO (1997) Phytotoxicity of protoporphyrinogen oxidase inhibitors: phenomenology, mode of action and mechanisms of resistance. In: Roe RM, Burton JD, Kuhr RJ (eds) Herbicides activity: toxicology, biochemistry and molecular biology. ISO Press Inc, Amsterdam, pp 11–35

    Google Scholar 

  • Dayan FE, Duke SO, Reddy KN, Hamper BC, Leschinski KL (1997) Effect of isoxazole herbicides on protoporphyrinogen oxidase and porphyrin physiology. J Agric Food Chem 45: 967–975

    Article  CAS  Google Scholar 

  • Deybach JC, Da Silva V, Grandchamp B, Nordmann Y (1985) The mitochondrial location of protoporphyrinogen oxidase. Eur J Biochem 149: 431–435

    Article  PubMed  CAS  Google Scholar 

  • Duke SO, Nandihalli UB, Lee HJ, Duke MV (1994) Protoporphyrinogen oxidase as the optimal herbicide site in the porphyrin pathway. In: Duke SO, Rebeiz CA (eds) Porphyric pesticides. ACS Symp Series 559, American Chemical Society, Washington, DC, pp 191–204

    Chapter  Google Scholar 

  • Durst GL (1998) Comparative molecular field analysis (CoMFA) of herbicidal protoporphyrinogen oxidase inhibitors using a standard steric and electrostatic fields and an alternative LUMO field. Quant Struct Act Relat 17: 419–426

    Article  CAS  Google Scholar 

  • Fujita T, Nakayama A (1999) Structure-activity relationship and molecular design of peroxidizing herbicides with cyclic imide structures and their relatives. In: Böger P, Wakabayashi K (eds) Peroxidizing herbicides. Springer, Berlin Heidelberg New York, pp 91–139

    Google Scholar 

  • Grossmann K, Schiffer H (1999) Protoporphyrinogen oxidase-inhibiting activity of the new, wheat-selective isoindolinone herbicide, cinidon ethyl. Pestic Sci 55: 687–695

    Article  CAS  Google Scholar 

  • Hansson M, Hederstedt L (1992) Cloning and characterization of the Bacillus subtilis hemEHY gene cluster, with encodes protoheme IX biosynthetic enzymes. J Bacteriol 174: 8081–8093

    PubMed  CAS  Google Scholar 

  • Hess FD (2000) Light-dependent herbicides: an overview. Weed Sci 48: 160–170

    Article  CAS  Google Scholar 

  • Horikoshi M, Hirooka T (1999) Selection of tobacco cell lines resistant to photobleaching herbicides. J Pestic Sci 24: 13–16

    CAS  Google Scholar 

  • Horikoshi M, Mametsuka K, Hirooka T (1999) Molecular basis of photobleaching herbicide resistance in tobacco. J Pestic Sci 24: 17–22

    CAS  Google Scholar 

  • Ichinose K, Che F-S, Kimura Y, Matsunobu A, Sato F, Yoshida S (1995) Selection and characterization of protoporphyrinogen oxidase inhibiting herbicide (S23142) resistant photomixotrophic cultured cells of Nicotiana tabaccum. J Plant Physiol 146: 693–698

    CAS  Google Scholar 

  • Ishida S, Miller-Sulger R, Kohno H, Böger P, Wakabayashi K (2000) Enzymatic activity of protoporphyrinogen-IX oxidase from various plant species: Its sensitivity to peroxidizing herbicides. J Pestic Sci 25: 18–23

    CAS  Google Scholar 

  • Jacobs JM, Jacobs NJ (1993) Porphyrin accumulation and export by isolated barley (Horduem vulgare) plastids. Plant Physiol 101: 1181–1187

    PubMed  CAS  Google Scholar 

  • Jacobs JM, Jacobs NJ, Sherman TD, Duke SO (1991) Effect of diphenyl ether herbicides on oxidation of protoporphyrinogen to protoporphyrin in organellar and plasma membrane enriched fractions of barley. Plant Physiol 97: 197–203

    Article  PubMed  CAS  Google Scholar 

  • Lederer B, Knörzer OC, Böger P (1999) Differential gene expression in plants stressed by the per-oxidizing herbicide oxyfluorfen. Z Naturforsch 54c: 764–770

    Google Scholar 

  • Lee HJ, Duke MV, Duke SO (1993) Cellular localization of protoporphyrinogen-oxidizing activities of etiolated barley Hordeum vulgare L. leaves: relationship to mechanism of action of protoporphyrinogen oxidase-inhibiting herbicides. Plant Physiol 102: 881–889

    PubMed  CAS  Google Scholar 

  • Lee HJ, Lee SB, Chung JS, Han SU, Han O, Guh JO, Jeon JS, An G, Back K (2000) Transgenic rice plants expressing a Bacillus subtilis protoporphyrinogen oxidase gene are resistant to diphenyl ether herbicide oxyfluorfen. Plant Cell Physiol 41: 743–749

    PubMed  CAS  Google Scholar 

  • Lermontova I, Grimm B (2000) Overexpression of plastidic protoporphyrinogen IX oxidase leads to resistance to the diphenyl-ether herbicide acifluorfen. Plant Physiol 122: 75–83

    Article  PubMed  CAS  Google Scholar 

  • Lermontova I, Kruse E, Mock N-P, Grimm B (1997) Cloning and characterization of a plastidal and mitochondrial isoform of tobacco protoporphyrinogen IX oxidase. Proc Natl Acad Sci USA 94: 8895–8900

    Article  PubMed  CAS  Google Scholar 

  • Lyga JW, Chang JH, Theodoridis G, Baum JS (1999) Structural replacements for the benzoxazinone protox inhibitor. Pestic Sci 55: 281–287

    CAS  Google Scholar 

  • Matringe M, Camadro J-M, Block MA, Joyard J, Scalla R, Labbe P, Douce R (1992a) Localization within the chloroplasts of protoporphyrinogen oxidase, the target enzyme for diphenyl ether-like herbicides. J Biol Chem 267: 4646–4651

    CAS  Google Scholar 

  • Matringe M, Mornet R, Scalla R (1992b) Characterization of [3H1 acifluorfen binding to purified pea etioplasts, and evidence that protoporphyrinogen oxidase specifically binds acifluorfen. Eur J Biochem 209: 861–868

    Article  CAS  Google Scholar 

  • Matsumoto H, Kashimoto Y, Warabi E (1999) Basis for common chickweed (Stellaria media) tolerance to oxyfluorfen. Pestic Biochem Physiol 64: 47–53

    Article  CAS  Google Scholar 

  • Mock H-P, Keetman U, Kruse E, Rank B, Grimm B (1998) Defense responses to tetrapyrroleinduced oxidative stress in transgenic plants with reduced uroporphyrinogen decarboxylase or coproporphyrinogen oxidase activity. Plant Physiol 116: 107–116

    Article  CAS  Google Scholar 

  • Molina A, Volrath S, Guyer D, Maleck K, Ryals J, Ward E (1999) Inhibition of protoporphyrinogen oxidase expression in Arabidopsis causes a lesion-mimic phenotype that induces systemic acquired resistance. Plant J 17: 667–678

    Article  PubMed  CAS  Google Scholar 

  • Nandihalli UB, Duke MV, Duke SO (1992) Quantitative structure-activity relationships of protoporphyrinogen oxidase-inhibiting diphenyl ether herbicides. Pestic Biochem Physiol 43: 193–211

    Article  CAS  Google Scholar 

  • Narita S, Tanaka R, Ito T, Osada K, Taketani S, Inokuchi H (1996) Molecular cloning and characterization of a cDNA that encodes protoporphyrinogen oxidase of Arabidopsis thaliana. Gene 182: 169–175

    Article  PubMed  CAS  Google Scholar 

  • Nishimura K, Taketani S, Inokuchi H (1995) Cloning of a human cDNA for protoporphyrinogen oxidase by complementation in vivo of a hemG mutant of Escherichia coll. J Biol Chem 270: 8076–8080

    Article  PubMed  CAS  Google Scholar 

  • Pornprom T, Matsumoto H, Usui K, Ishizuka K (1994) Characterization of oxyfluorfen tolerance in a selected soybean cell line. Pestic Biochem Physiol 50: 107–114

    Article  CAS  Google Scholar 

  • Randolph-Anderson BL, Sato R, Johnson AM, Harris EH, Hauser CR, Oeda K, Ishige F, Nishio S, Gillham NW, Boynton JE (1998) Isolation and characterization of a mutant protoporphyrinogen oxidase gene from Chlamydomonas reinhardtii conferring resistance to porphyric herbicides. Plant Mol Biol 38: 839–859

    Article  PubMed  CAS  Google Scholar 

  • Sasarman A, Letowski J, Czaika G, Ramirez V, Nead MA, Jacobs JM, Morais R (1993) Nucleotide sequence of the hemG gene involved in the protoporphyrinogen oxidase activity of Escherichia coli K12. Can J Microbiol 39: 1155–1161

    Article  PubMed  CAS  Google Scholar 

  • Smith AG, Marsh O, Elder GH (1993) Investigation of the subcellular location of the tetrapyrrole-biosynthesis enzyme coproporphyrinogen oxidase in higher plants. Biochem J 292: 503–508

    PubMed  CAS  Google Scholar 

  • Theodoridis G (1997) Structure-activity relationships of herbicidal aryltriazolinones. Pestic Sci 50: 283–290

    Article  CAS  Google Scholar 

  • Theodoridis G, Bahr JT, Hotzman FW, Sehgel S, Suarez DP (2000) New generation of protoxinhibiting herbicides. Crop Protection 19: 533–535

    Article  CAS  Google Scholar 

  • Vallon 0 (2000) New sequence motif in flavoproteins: evidence for common ancestry and tools to predict structure. Proteins Struct Funct Genet 38: 95–114

    Article  Google Scholar 

  • Warabi E, Usui K, Tanaka Y, Matsumoto H (2001) Resistance of a soybean cell line to oxyfluorfen by overproduction of mitochondrial protoporphyrinogen oxidase. Pestic Manage Sci 57: 743–748

    Article  CAS  Google Scholar 

  • Watanabe N, Che F-S, Iwano M, Takayama S, Nakano Y, Yoshida S, Isogai A (1998) Molecular characterization of photomixotrophic tobacco cells resistant to protoporphyrinogen oxidaseinhibiting herbicides. Plant Physiol 118: 751–758

    Article  PubMed  CAS  Google Scholar 

  • Yamato S, Katagiri M, Ohkawa H (1994) Purification and characterization of protoporphyrinogen-oxidizing enzyme with peroxidase activity and light-dependent herbicide resistance in tobacco cultured cells. Pestic Biochem Physiol 50: 72–82

    Article  CAS  Google Scholar 

  • Yanagida M, Matsumoto H, Usui K (1999) Responses of antioxidative systems to oxyfluorfen and their role in herbicidal tolerance of plants. J Weed Sci Tech 44: 67–76

    Article  CAS  Google Scholar 

  • Yanagida M, Matsumoto H, Usui K (2000) Determination of porphyrin-induced peroxidation of plant lipids by oxygen electrode. J Weed Sci Tech 45: 26–33

    Article  CAS  Google Scholar 

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Authors
  1. Hiroshi Matsumoto
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Editors and Affiliations

  1. Department of Plant Physiology and Biochemistry, University of Konstanz, D-78457, Konstanz, Germany

    Peter Böger

  2. Department of Physiology and Biochemistry, Tamagawa University, Machida-shi, Tokyo, 194-8610, Japan

    Ko Wakabayashi

  3. Sagami Chemical Research Center, Hayakawa 2743-1, Ayase Kanagawa, 252-1193, Japan

    Kenji Hirai

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© 2002 Springer-Verlag Berlin Heidelberg

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Matsumoto, H. (2002). Inhibitors of Protoporphyrinogen Oxidase: A Brief Update. In: Böger, P., Wakabayashi, K., Hirai, K. (eds) Herbicide Classes in Development. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-59416-8_8

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  • DOI: https://doi.org/10.1007/978-3-642-59416-8_8

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-63972-2

  • Online ISBN: 978-3-642-59416-8

  • eBook Packages: Springer Book Archive

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