Skip to main content
SpringerLink
Log in

Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity

  • Published:
Current Microbiology Aims and scope Submit manuscript

Abstract

Microbial transformations of two natural compounds dihydrojasmone (1) and cis-jasmone (3) in the growing cultures of selected twenty strains have been investigated. The studies have demonstrated a biocatalytic potential of tested microorganisms for the enantioselective hydroxylation of jasmonates. The substrates underwent an effective regio- and stero-selective hydroxylation at the allylic position in the cyclopentenone ring, and the corresponding optically pure keto-alcohols (2, 4) were obtained. The process of biohydroxylation depended on the composition of reaction medium. In the studied cultures, (+)-(R)-4-hydroxydihydrojasmone (2) and (+) and (−)-4-hydroxyjasmone (4a, 4b) were produced in good yields and high enantiomeric excesses. Moreover, the introduction of the hydroxy group into the molecule of jasmonate ketones 1 and 3 leads to biologically active derivatives 2 and 4 that regulate the behaviour of aphids Myzus persicae by termination of their feeding.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Aldridge DC, Galt S, Giles D, Turner WD (1971) Metabolites of Lasiodiplodia theobromae. J Chem Soc C:1623–1627

  2. Anderson JP, Badruzsaufari E, Schenk PM, Manners JM, Desmond OJ, Ehlert C, Maclean DJ, Ebert PR, Kazan K (2004) Antagonistic interaction between abscisic acid and jasmonate-ethylene signalling pathways modulates defense gene expression and disease resistance in Arabidopsis. Plant Cell 16:3460–3479

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  3. Beale MH, Ward JL (1998) Jasmonates: key players in the plant defence. Nat Prod Rep 15:533–548

    Article  CAS  PubMed  Google Scholar 

  4. Birkett MA, Campbell CAM, Chamberlain K, Guerrieri E, Hick AJ, Martin JL, Matthes M, Napier JA, Pettersson J, Pickett JA, Poppy GM, Pow EM, Pey BJ, Smart LE, Wadhams GH, Wadhams LJ, Woodcock CM (2000) New roles for cis-jasmone as an insect semiochemical and in plant defence. Proc Natl Acad Sci USA 97:9329–9334

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  5. Cheong JJ, Choi YD (2003) Methyl jasmonate as a vital substance in plants. Trends in Genet 19:409–413

    Article  CAS  Google Scholar 

  6. Crabalona L (1967) Presence of leavorotatory methyl jasmonate, methyl cis-2(2-penten-1-yl)-3-oxocyclopentenyl acetate, in the essential oil Tunisian rosemary C. R Acad Sci 264:2074–2076

    CAS  Google Scholar 

  7. Creelman RA, Mullet JE (1997) Biosynthesis and action of jasmonates in plants. Annu Rev Plant Physiol Plant Mol Biol 48:355–381

    Article  CAS  PubMed  Google Scholar 

  8. Dathe W, Rönsch H, Preiss A, Schade W, Sembdner G, Schreiber K (1981) Endogenous plant hormones of the broad bean, Vicia faba L. (-)-Jasmonic acid, a plant growth inhibitor in pericarp. Planta 155:530–535

    Article  Google Scholar 

  9. Dathe W, Schindler C, Schneider G, Schmidt J, Porzel A, Jensen E, Yamaguchi I (1991) Cucurbic acid and its 6,7-stereoisomers. Phytochemistry 30:1909–1914

    Article  CAS  Google Scholar 

  10. Demole E, Lederer E, Mercier D (1962) Isolement et determination de la structure du jasmonate de methyle, constituent odorant caracteristique de l’essence de jasmine. Helv Chim Acta 45:675–685

    Article  CAS  Google Scholar 

  11. Farmer EE (1994) Fatty acid signalling in plants and their associated microorganisms. Plant Mol Biol 26:1423–1437

    Article  CAS  PubMed  Google Scholar 

  12. Farmer EE, Ryan CA (1990) Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc Natl Acad Sci USA 87:7713–7716

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  13. Fukui H, Koshimizu K, Yamazaki Y, Usuda S (1977) Structures of plant growth regulators from seeds of Cucurbita pepo L. Agric Boil Chem 41:189–194

    Article  CAS  Google Scholar 

  14. Gliszczyńska A, Łysek A, Janeczko T, Świtalska M, Wietrzyk J, Wawrzeńczyk C (2011) Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites. Bioorg Med Chem 19:2464–2469

    Article  PubMed  Google Scholar 

  15. Gliszczyńska A, Wawrzeńczyk C (2008) Oxidative biotransformation of farnesol and 10,11-epoxyfarnesol by fungal strains. J Mol Catal B-Enzym 52–53:40–48

    Article  Google Scholar 

  16. Grimes HD, Koetje DS, Franceschi VR (1992) Expression, activity, and cellular accumulation of methyl jasmonate-responsive lipoxygenase in soybean seedlings. Plant Physiol 100:433–443

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  17. Gundlach H, Muller MJ, Kutchan T, Zenk MH (1992) Jasmonic acid is a signal transducer in elicitor-induced plant cel cultures. Proc Natl Acad Sci USA 89:2389–2393

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  18. Hardie J, Holyoak M, Taylor NJ, Griffiths DC (1992) The combination of electronic monitoring and video-assisted observations of plant penetration by aphids and behavioural effect of polygodial. Entomol Exp Appl 62:233–239

    Article  Google Scholar 

  19. Hill RK, Edwards AG (1965) The absolute configuration of methyl jasmonate. Tetrahedron 21:1501–1507

    Article  CAS  Google Scholar 

  20. Liechti R, Farmer EE (2002) The jasmonate pathway. Science 296:1649–1650

    Article  CAS  PubMed  Google Scholar 

  21. Masayoshi M, Tadashi K (1984) Eur Pat Appl EP 115860(A2):19840815

    Google Scholar 

  22. Miersch O, Brückner B, Schmidt J, Sembdner G (1992) Cyclopentane fatty acids from Gibberella fujikuroi. Phytochemistry 31:3835–3837

    Article  CAS  Google Scholar 

  23. Miersch O, Meyer A, Vorkfield S, Sembdner G (1986) Occurrence of (+)-7-iso-jasmonic acid in Vicia faba L. and its biological activity. J Plant Growth Reg 5:91–100

    Article  CAS  Google Scholar 

  24. Miersch O, Sembdner G, Schreiber K (1998) Occurrence of jasmonic acid analogues in Vicia faba. Phytochemistry 28:339–340

    Article  Google Scholar 

  25. Morkunas I, Mai VC, Gabryś B (2011) Expression profiling of selected glutathione transferase genes in Zea mays (L) seedlings infested with cereal aphids. Acta Physiol Plant 33:2057–2073

    Article  CAS  Google Scholar 

  26. Parthier B (1990) Jasmonates: hormonal regulators or stress factors in leaf senescence? J Plant Growth Regul 9:57–63

    Article  CAS  Google Scholar 

  27. Pinheiro L, Marsaioli AJ (2007) Microbial monooxygenases applied to fragrance compounds. J Mol Catal B-Enzym 44:78–86

    Article  CAS  Google Scholar 

  28. Pinheiro L, Oliveira LGD, Marsaioli AJ (2009) Assessing the absolute configuration of (7S, 8R)-epoxyjasmone. J Mol Catal B-Enzym 60:133–137

    Article  CAS  Google Scholar 

  29. Popova LP, Tsonew TD, Vaklinova SG (1988) Changes in some photosynthetic and photorespiratory properties in barley leaves after treatment with methyl jasmonate. J Plant Physiol 132:257–261

    Article  CAS  Google Scholar 

  30. Ranjan R, Lewak S (1992) Jasmonic acid promotes germination and lipase activity in non-stratified apple embryos. Physiol Plant 86:335–339

    Article  CAS  Google Scholar 

  31. Rohwer CL, Erwin JE (2008) Horticultural applications of jasmonates: a review. J Hortic Sci Biotechnol 83:283–304

    CAS  Google Scholar 

  32. Sembdner G, Parthier B (1993) The biochemistry and the physiological and molecular actions of jasmonates. Annu Rev Plant Physiol Plant Mol Biol 44:569–589

    Article  CAS  Google Scholar 

  33. Ueda J, Kato J (1980) Isolation and identification of a senescence-promoting substrate from wormwood (Artemisia absinthium L.). Plant Physiol 66:246–249

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  34. Yamane H, Takagi H, Abe H, Yokota T, Takahashi N (1981) Identification of jasmonic acid in three species of higher plants and its biological activities. Plant Cell Physiol 22:689–697

    CAS  Google Scholar 

  35. Yoshihara T, Omer EA, Koshino H, Sakamura S, Kikuta Y, Koda Y (1989) Structure of a tuber-inducing stimulus from potato leaves (Solanum tuberosum L.). Agric Boil Chem 53:2835–2837

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This Project was financed by the European Union from the European Regional Development Found Grant No. POIG.01.03.01-00-158/09-03.

Author information

Authors and Affiliations

  1. Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland

    Anna Gliszczyńska & Witold Gładkowski

  2. Department of Biology and Ecology, University of Zielona Góra, Szafrana 1, 65-516, Zielona Góra, Poland

    Katarzyna Dancewicz & Beata Gabryś

Authors
  1. Anna Gliszczyńska
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Witold Gładkowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Katarzyna Dancewicz
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Beata Gabryś
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anna Gliszczyńska.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gliszczyńska, A., Gładkowski, W., Dancewicz, K. et al. Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity. Curr Microbiol 71, 83–94 (2015). https://doi.org/10.1007/s00284-015-0831-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00284-015-0831-9

Keywords

Search

Navigation