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Elucidation of a Diurnal Pattern of Catechin Exudation by Centaurea stoebe

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Abstract

The exudation of secondary metabolites at phytotoxic concentrations has been proposed as a mechanism of invasion for some exotic plant species. Catechin is a natural flavanoid implicated in the potential allelopathic interactions of Centaurea stoebe. However, recent studies have shown that catechin is highly unstable and not likely to accumulate in growing medium at phytotoxic concentrations. All previous studies that investigated the allelopathic potential of catechin assumed a continuous exudation of this compound by C. stoebe. Contrary to this, but similar to many other plant secondary metabolites, we hypothesized that catechin exudation may exhibit a pulsed pattern that could facilitate its transient accumulation. Further, we aimed at optimizing a more sensitive detection technique. We tested the hypothesis by quantifying the diurnal pattern of catechin release by C. stoebe in a hydroponic system. Using sample processing, based on a solid phase extraction technique, and more sensitive fluorescent detection parameters, we were able to quantify catechin in the picomolar range from the growing medium. Catechin exudation exhibited a possible diurnal rhythm with respect to light intensity, with the highest concentration at 6 h after exposure to sunlight. Catechin also was found to undergo a degradation reaction resulting in a transient abundance of pyrocatechol in our system.

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References

  • Blair, A. C., Hanson, B. D., Brunk, G. R., Marrs, R. A., Westra, P., Nissen, S. J., and Hufbauer, R. A. 2005. New techniques and findings in the study of a candidate allelochemical implicated in invasion success. Ecology Lett. 8: 1039–1047.

    Article  Google Scholar 

  • Blair, A. C., Nissen, S. J., Brunk, G. R., and Hufbauer, R. A. 2006. Lack of evidence for an ecological role of the putative allelochemical (±)-catechin in spotted knapweed invasion success. J. Chem. Ecol. 32: 2327–2331.

    Article  CAS  PubMed  Google Scholar 

  • Ditomaso, J. M. 2000. Invasive weeds in rangelands: species, impacts, and management. Weed Sci. 48: 255–265.

    Article  CAS  Google Scholar 

  • Donovan, J. L., Luthria, D. L., Stremple, P., and Waterhouse, A. L. 1999. Analysis of (+)-catechin, (−)-epicatechin and their 3′- and 4′-O-methylated analogs: A comparison of sensitive methods. J. Chromatogr. B. 726: 277–283.

    Article  CAS  Google Scholar 

  • Ervin, G. N. and Wetzel, R. G. 2000. Allelochemical autotoxicity in the emergent wetland macrophyte Juncus effusus (Juncaceae). Am. J. Bot. 87: 853–860.

    Article  CAS  PubMed  Google Scholar 

  • Falik, O., Reides, P., Gersani, M., and Novoplansky, A. 2005. Root navigation by self inhibition. Pl. Cell Environ. 28: 562–569.

    Article  Google Scholar 

  • Geiger, D. R., and Servaites, J. C. 1994. Diurnal regulation of photosynthetic carbon metabolism in C3 plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 45: 235–256

    Article  Google Scholar 

  • Perry, L. G., Thelen, G. C., Ridenour, W. M., Callaway, R. M., Paschke, M. W., and Vivanco, J. M. 2007. Concentrations of the allelochemical (±)-catechin in Centaura maculosa soils. J. Chem. Ecol. 33: 2337–2344.

    Article  CAS  PubMed  Google Scholar 

  • Rice, E. L.1984. Allelopathy. 2nd edn. Academic Press, New York. pp. 1–20.

    Google Scholar 

  • Seigler, D. S. 1995. Plant Secondary Metabolism. Kluwer. Boston. p201

    Google Scholar 

  • Snyder, L. R., Kirkland, J. L., and Glajch, J. L.1997. Practical HPLC Method Development. 2nd. edn. Wiley, New York. p. 81.

    Google Scholar 

  • Stermitz, F. R., Hufbauer, R. A., and Vivanco, J. M. 2009. Retraction. Enantiomeric-dependent phytotoxic and antimicrobial activity of (±)-catechin. A rhizosecreted racemic mixture from spotted knapweed. Plant Physiol. 151, 967.

    Article  CAS  Google Scholar 

  • Stöggl, W. M., Huck, C. W., and Bonn, G. K. 2004. Structural elucidation of catechin and epicatechin in sorrel leaf extracts using liquid-chromatography coupled to diode array-, fluorescence-, and mass spectrometric detection. J. Sep. Sci. 27: 524–528.

    Article  PubMed  Google Scholar 

  • Tharayil, N., Bhowmik, P. C., and Xing, B. 2008. Bioavailability of allelochemicals as affected companion compounds in soil matrices. J. Agric. Food Chem. 56: 3706–3713.

    Article  CAS  PubMed  Google Scholar 

  • Tharayil, N., Bhowmik, P. C., Alpert, P., Walker, E., Xing, B., and Amarasiriwardena, D. 2009. Dual purpose secondary compounds: Phytotoxins of Centaurea diffusa also facilitates nutrient uptake. New Phytol. 181: 424–434.

    Article  CAS  PubMed  Google Scholar 

  • Urbanczyk-Wochniak, E., Baxter, C., Kolbe, A., Kopka, J., Sweetlove, L. J., and Fernie, A. R. 2005. Profiling of diurnal patterns of metabolite and transcript abundance in potato (Solanum tuberosum) leaves. Planta 221: 891–903.

    Article  CAS  PubMed  Google Scholar 

  • WU, J. C., Xie, W., Pawliszyn, J. 2000. Automated in-tube solid phase microextraction coupled with HPLC-ES-MS for the determination of catechins and caffeine in tea. Analyst 125: 2216–2000.

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

The authors thank Ragan Callaway and Giles Thelen for supplying the Centaurea maculosa seeds for this study, Frank Stermitz, Harsh Bais, Jorge Vivanco, Ragan Callaway, Ruth Hufbauer, and two anonymous reviewers for providing constructive comments on an earlier version of this manuscript. This study was partially funded by the SC LIFE project. Technical Contribution No. 5751 of the Clemson University Experiment Station.

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Correspondence to Nishanth Tharayil.

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Tharayil, N., Triebwasser, D.J. Elucidation of a Diurnal Pattern of Catechin Exudation by Centaurea stoebe . J Chem Ecol 36, 200–204 (2010). https://doi.org/10.1007/s10886-010-9749-7

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  • DOI: https://doi.org/10.1007/s10886-010-9749-7

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