Abstract
A simple HPLC technique for the quantitative determination of phytotoxins (stagonolide A and herbarumin I) in liquid culture of the fungus Stagonospora cirsii S-47 has been developed. Some examples of its application are given. The technique was tested in a study of effects of the concentration of refined sunflower oil and the cultivation duration on the production level of these toxins. At an oil concentration of 0.5% or higher in modified Czapek medium with vitamins, the accumulation of S. cirsii biomass and the concentration of stagonolide A increased, while the concentration of herbarumin I decreased. Maximal amounts of both phytotoxins were obtained on the tenth day of submerged S. cirsii cultivation in flasks. When S. cirsii was grown in the same medium supplied with 1% of oil in a laboratory bioreactor, the maximal concentration of stagonolide A (116 mg/L) in the liquid culture was achieved after 5 days of fermentation followed by its considerable reduction after 6 days, while after 7 days of the submerged growth the maximal content of herbarumin I (116 mg/L) increased sharply. The technique of the phytotoxins analysis was used to monitor them during their isolation, as well as for preparative HPLC.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Spiridonov, Yu.Ya. and Zhemchuzhin, S.G., Agrokhimiya, 2010, no. 7, pp. 73–91.
Spiridonov, Yu.Ya. and Zhemchuzhin, S.G., Agrokhimiya, 2016, no. 5, pp. 76–85.
Kazakova, A.N., Kuznetsov, V.M., Musavirova, L.R., Mikhailova, N.N., Bogomazova, A.A., Mudrik, T.P., and Zlotskii, S.S., Bashk. Khim. Zh., 2013, vol. 20, no. 1.
Kuznetsov, V.M., Khusnitdinov, K.R., Mryasova, L.M., Kolbin, A.M., Khusnitdinov, R.N., Abdrakhmanov, I.B., and Mustafin, A.G., Bashk.Khim. Zh., 2013, vol. 20, no. 2, pp. 110–114.
Spiridonov, Yu.Ya. and Shestakov, V.G., Zashch. Karantin Rast., 2009, no. 8, pp. 18–22.
Vurro, M., in Novel Biotechnologies for Biocontrol Agent Enhancement and Management, NATO Security Through Science Series, Vurro, M. and Gressel, J., Eds., Dordrecht: Springer, 2007, pp. 53–74.
Berestetskii, A.O., App. Biochem. Microbiol., 2008, vol. 44, no. 5, pp. 501–514.
Duke, S.O., Owens, D.K., and Dayan, F.E., in Biopesticides: State of the Art and Future Opportunities, ACS Symp. Ser., 2014, vol. 1172, pp. 31–43.
Berestetskii, A.O., Vestn. Zashch. Rast., 2017, vol. 91, no. 1, pp. 5–12.
Rivero-Cruz, J.F., García-Aguirre, G., Cerda-García-Rojas, C., and Mata, R., Tetrahedron, 2000, vol. 56, no. 30, pp. 5337–5344.
Yuzikhin, O., Mitina, G., and Berestetskiy, A., J. Agric. Food Chem., 2007, vol. 55, no. 19, pp. 7707–7711.
Berestetskiy, A., Dmitriev, A., Mitina, G., Lisker, I., Andolfi, A., and Evidente, A., Phytochemistry, 2008, vol. 69, no. 4, pp. 953–960.
RF Patent no. 2543665, 2015.
Evidente, A., Berestetskiy, A., Andolfi, A., Zonno, M.C., Cimmino, A., and Vurro, M., Phytochem. Anal., 2006, vol. 17, no. 5, pp. 357–364.
Masi, M., Moeini, S.A., Boari, A., Cimmino, A., Vurro, M., and Evidente, A., Nat. Prod. Res., 2018, vol. 32, no. 13, p. 1611.
Gao, L., Cheng, X., Zhang, J., and Burns, D.J., Rapid Commun. Mass Spectrom., 2007, vol. 21, no. 21, pp. 3497–3504.
Angeli, I., Minoli, M., Ravelli, A., Gigli, F., and Lodi, F., Forensic Sci. Int., 2012, vol. 218, no. 1.
Moret, S., Hidalgo, M., and Sanchez, J.M., ISRN Chromatogr., 2012, vol. 2012.
Solaiman, D.K.Y., Ashby, R.D., and Foglia, T.A., in Handbook of Industrial Biocatalysis, Hou, C.T., Ed., Boca Raton, FL: Taylor and Francis Group, LLC, 2005, pp. 14–1-14-9.
Shih, I.-L., Tsai, K.-L., and Hsieh, C., Biochem. Eng. J., 2007, vol. 33, no. 3, pp. 193–201.
Junker, B., Mann, Z., Gailliot, P., Byrne, K., and Wilson, J., Biotechnol. Bioeng., 1998, vol. 60, no. 5, pp. 580–588.
Saygun, A., Sahin-Yesilcubuk, N., and Aran, N., J. Am. Oil Chem. Soc., 2014, vol. 91, no. 9, pp. 1521–1530.
Vurro, M., Andolfi, A., Boari, A., Zonno, M.C., Caretto, S., Avolio, F., and Evidente, A., Biol. Control, 2012, vol. 60, no. 2, pp. 192–198.
Fang, M., Wang, J., Huang, Y., and Zhao, Y., Front. Chem. China, 2006, vol. 1, no. 1, pp. 15–19.
ACKNOWLEDGMENTS
The authors would like to thank D.M. Kochura and I.S. Chisty, the staff of the Laboratory of Molecular Modeling, Research Institute of Hygiene, Occupational Pathology, and Human Ecology, Federal Medical Biological Agency, Russia, for the spectral analysis of the substances, as well as M.Yu. Belozerov (All-Russia Institute of Plant Protection) for help in the initial stages of the study.
Funding
The work was financially supported by the Russian Science Foundation (project no. 16-16-00085).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.
Additional information
Translated by T. Borisova
Rights and permissions
About this article
Cite this article
Berestetskiy, A.O., Poluektova, E.V., Sabashuk, Y.A. et al. Development of Chromatography Techniques for Analysis and Preparative Isolation of Phytotoxic Metabolites Produced by Stagonospora cirsii. Appl Biochem Microbiol 55, 684–690 (2019). https://doi.org/10.1134/S000368381906005X
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S000368381906005X