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Patterns of phenolic compounds in leafy galls of tobacco

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Abstract

The chemical composition of ethanolic and aqueous extracts from leafy galls produced after infection of Nicotiana tabacum L. plants with Rhodococcus fascians was drastically changed compared to uninfected controls. Chlorogenic acid was abundant both in uninfected and infected plants, but caffeic acid and another cinnamoyl analogue were new in leafy galls. The most pronounced product induced in leafy galls was identified as 7-O-methyl-6-O-β-D-glucopyranosyl coumarin (7-methyl esculin). This is the first report of the presence of this coumarin derivative in tobacco. Interestingly, 7-methyl esculin did not accumulate in the presence of avirulent R. fascians strains nor was it found in leafy galls on other plant species. However, it did appear in crown galls induced by Agrobacterium tumefaciens on tobacco plants. Intriguingly, none of the phenolics known to accumulate in Solanaceae under pathogen attack were found in leafy galls. 7-Methyl esculin barely affected growth of R. fascians nor was it catabolized. Microscopical analysis showed that autofluorescent compounds were located mainly in the abundant meristematic regions of the leafy galls. We postulate that 7-methyl esculin might locally influence plant cell division.

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Abbreviations

ES-MS:

electrospray ionization mass spectrometry

1H-NMR:

proton nuclear magnetic resonance

References

  • Aliotta G, Cafiero G, Fiorentino A, Strumia S (1993) Inhibition of radish germination and root growth by coumarin and phenylpropanoids. J Chem Ecol 19: 175–183

    Article  CAS  Google Scholar 

  • Binns AN, Chen RH, Wood HN, Lynn DG (1987) Cell division promoting activity of naturally occurring dehydrodiconiferyl glucosides: do cell wall components control cell division? Proc Natl Acad Sci USA 84: 980–984

    Article  PubMed  CAS  Google Scholar 

  • Crespi M, Messens E, Caplan AB, Van Montagu M, Desomer J (1992) Fasciation induction by the phytopathogen Rhodococcus fascians depends upon a linear plasmid encoding a cytokinin synthase gene. EMBO J 11: 795–804

    PubMed  CAS  Google Scholar 

  • Cussans NJ, Huckerby TN (1975) Carbon-13 NMR spectroscopy of heterocyclic compounds. IV. A 20 MHz study of chemical shifts and carbon-proton coupling constants in a series of hydroxy, methoxy and glucosyl coumarins. Tetrahedron 31: 2719–2726

    Article  CAS  Google Scholar 

  • Cuypers B, Schmelzer E, Hahlbrock K (1988) In situ localization of rapidly accumulated phenylalanine ammonia-lyase mRNA around penetration sites of Phytophthora infestans in potato leaves. Mol Plant-Microbe Interact 1: 157–160

    Google Scholar 

  • De Bruyn A, Anteunis M, Van Beeumen J (1977) Chemical shifts of aldohexopyranose revisited and application to glycosylglucose. Bull Soc Chim Belges 86: 259–265

    Google Scholar 

  • Elia S, Gosselé F, Vantomme R, Swings J, De Ley J (1984) Corynebacterium fascians: phytopathogenicity and numerical analysis of phenotypic features. Phytopathol Z 110: 89–105

    Article  CAS  Google Scholar 

  • Fischer FC, van Doorne H, Lim MI, Baerheim Svendsen A (1976) Bacteriostatic activity of some coumarin derivatives. Phytochemistry 15: 1078–1079

    Article  CAS  Google Scholar 

  • Graham TL (1991) A rapid, high resolution high performance liquid chromatography profiling procedure for plant and microbial aromatic secondary metabolites. Plant Physiol 95: 584–593

    Article  PubMed  CAS  Google Scholar 

  • Guedes MEM, Kuć J, Hammerschmidt R, Bostock R (1982) Accumulation of six sesquiterpenoid phytoalexins in tobacco leaves infiltrated with Pseudomonas lachrymans. Phytochemistry 21: 2987–2988

    Article  CAS  Google Scholar 

  • Halverson LJ, Stacey G (1986) Signal exchange in plant-microbe interactions. Microbiol Rev 50: 193–225

    PubMed  CAS  Google Scholar 

  • Jacobs M, Rubery PH (1988) Naturally occurring auxin transport regulators. Science 241: 346–349

    Article  PubMed  CAS  Google Scholar 

  • Jurd L, Corse J, King AD Jr, Bayne H, Mihara K (1971) Antimicrobial properties of 6,7-dihydroxy-, 7,8-dihydroxy-, 6-hydroxy- and 8-hydroxycoumarins. Phytochemistry 10: 2971–2974

    Article  CAS  Google Scholar 

  • Kauss H, Jeblick W, Ziegler J, Krabler W (1994) Pretreatment of parsley (Petroselinum crispum L.) suspension cultures with methyl jasmonate enhances elicitation of activated oxygen species. Plant Physiol 105: 89–94

    PubMed  CAS  Google Scholar 

  • Khalil MK (1992) Nature of growth regulators effects on Nicotiana tabacum seed germination. Angew Bot 66: 106–108

    CAS  Google Scholar 

  • Kostova IN, Nikolov NM, Chipilska LN (1993) Antimicrobial properties of some hydroxycoumarins and Fraxinus ornus bark extracts. J Ethnopharmacol 39: 205–208

    Article  PubMed  CAS  Google Scholar 

  • Kupidlowska E, Kowalec M, Sulkowski G, Zobel AM (1994) The effect of coumarins on root elongation and ultrastructure of meristematic cell protoplast. Ann Bot 73: 525–530

    Article  CAS  Google Scholar 

  • Lassak EV, Pinhey JT (1967) The proton magnetic resonance of some coumarins and 2,2-dimethylchromens: further examples of interring spin-spin coupling. J Chem Soc C 20: 2000–2001

    Article  Google Scholar 

  • Lummerzheim M, de Oliveira D, Castresana C, Miguens FC, Louzada E, Roby D, Van Montagu M, Timmerman B (1993) Identification of compatible and incompatible interactions between Arabidopsis thaliana and Xanthomonas campestris pv. campestris and characterization of the hypersensitive response. Mol Plant-Microbe Interact 6: 532–544

    CAS  Google Scholar 

  • Matern Y, Kneusel RE (1988) Phenolic compounds in plant disease resistance. Phytoparasitica 16: 153–170

    Article  CAS  Google Scholar 

  • Miller JH (1972) Experiments in molecular genetics. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY

    Google Scholar 

  • Mo Y-Y, Gross DC (1991) Plant signal molecules activate the syrB gene, which is required for syringomycin production by Pseudomonas syringae pv. syringae. J Bacteriol 173: 5784–5792

    PubMed  CAS  Google Scholar 

  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bio assays with tobacco tissue cultures. Physiol Plant 15: 473–497

    Article  CAS  Google Scholar 

  • Nemestothy GS, Guest DI (1990) Phytoalexin accumulation, phenylalanine ammonia lyase activity and ethylene biosynthesis in fosetyl-Al treated resistant and susceptible tobacco cultivars infected with Phytophthora nicotianae var. nicotianae. Physiol Mol Plant Pathol 37: 207–219

    Article  CAS  Google Scholar 

  • Nicholson RL, Hammerschmidt R (1992) Phenolic compounds and their role in disease resistance. Annu Rev Phytopathol 30: 369–389

    Article  CAS  Google Scholar 

  • Nolte P, Secor GA, Gudmestad NC, Henningson PJ (1993) Detection and identification of fluorescent compounds in potato tuber tissue with corky patch syndrome. Am Potato J 70: 649–666

    Article  CAS  Google Scholar 

  • Nykolov N, Iossifova T, Vassileva E, Kostova I, Stoev G (1993) Reverse-phase high pressure liquid Chromatographic analysis of hydroxycoumarins in plant extracts. Quantitative determination of hydroxycoumarins in Fraxinus ornus. Phytochem Anal 4: 86–88

    Article  CAS  Google Scholar 

  • Rowbotham JB, Schaefer T (1973) Experimental and theoretical estimates of sigma and π electron contributions to long-range spin-spin coupling constants in coumarin and its methyl derivatives. Can J Chem 51: 953–960

    Article  CAS  Google Scholar 

  • Siqueira JO, Nair MG, Hammerschmidt R, Safir GR (1991) Significance of phenolic compounds in plant-soil-microbial systems. Crit Rev Plant Sci 10: 63–121

    Article  CAS  Google Scholar 

  • Staskawicz BJ, Ausubel FM, Baker BJ, Ellis JG, Jones JDG (1995) Molecular genetics of plant disease resistance. Science 268: 661–667

    Article  PubMed  CAS  Google Scholar 

  • Stoessl A, Stothers JB, Ward EWB (1976) Sesquiterpenoid stress compounds of the Solanaceae. Phytochemistry 15: 855–872

    Article  CAS  Google Scholar 

  • Tanguy J, Martin C (1972) Phenolic compounds and the hypersensitivity reaction in Nicotiana tabacum infected with tobacco mosaic virus. Phytochemistry 11: 19–28

    Article  CAS  Google Scholar 

  • Taylor LP, Jorgensen R (1992) Conditional male fertility in chalcone synthase-deficient petunia. J Hered 83: 11–17

    CAS  Google Scholar 

  • Tilford PE (1936) Fasciation of sweet peas caused by Phytomonas fascians n. sp. J Agric Res 53: 383–394

    Google Scholar 

  • VanEtten HD, Matthews DE, Matthews PS (1989) Phytoalexin detoxification: importance for pathogenicity and practical implications. Annu Rev Phytopathol 27: 143–164

    Article  Google Scholar 

  • Vasse J, de Billy F, Truchet G (1993) Abortion of infection during the Rhizobium meliloti-alfalfa symbiotic interaction is accompanied by a hypersensitive reaction. Plant J 4: 555–566

    Article  Google Scholar 

  • Vervliet G, Holsters M, Teuchy H, Van Montagu M, Schell J (1975) Characterization of different plaque-forming and defective temperate phages in Agrobacterium strains. J Gen Virol 26: 33–48

    Article  PubMed  CAS  Google Scholar 

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Correspondence to Marc Van Montagu.

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Vereecke, D., Messens, E., Klarskov, K. et al. Patterns of phenolic compounds in leafy galls of tobacco. Planta 201, 342–348 (1997). https://doi.org/10.1007/s004250050076

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  • DOI: https://doi.org/10.1007/s004250050076

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