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Planta

, Volume 233, Issue 1, pp 37–48 | Cite as

Polyketide derivatives active against Botrytis cinerea in Gerbera hybrida

  • Satu Koskela
  • Päivi P. Söderholm
  • Miia Ainasoja
  • Tero Wennberg
  • Karel D. Klika
  • Vladimir V. Ovcharenko
  • Irene Kylänlahti
  • Tiina Auerma
  • Jari Yli-Kauhaluoma
  • Kalevi Pihlaja
  • Pia M. VuorelaEmail author
  • Teemu H. TeeriEmail author
Original Article

Abstract

A previously isolated cDNA molecule from Gerbera hybrida (Asteraceae) codes for a new chalcone synthase-like polyketide synthase, 2-pyrone synthase (2PS). 2PS is able to synthesise 4-hydroxy-6-methyl-2-pyrone (triacetolactone), a putative precursor for gerberin and parasorboside, two abundant glucosides in gerbera. In this study, we show that gerbera plants transformed with the gene for 2PS in an antisense orientation and unable to synthesise gerberin and parasorboside are susceptible to Botrytis cinerea infection. In addition to the preformed glucosides, the transgenic plants also lack several compounds that are induced in control plants when infected with the mould. Some of these induced substances are effective in inhibiting fungal growth both in vitro and in vivo. Two of the phytoalexins were identified as the aglycones of gerberin and trans-parasorboside. The third phytoalexin is a rare coumarin, 4-hydroxy-5-methylcoumarin; however, it is typical of many plants of the sunflower family Asteraceae. The coumarin cannot be structurally derived from either gerberin or parasorboside, but may be derived from a related polyketide intermediate.

Keywords

Botrytis Gerbera Gerberin Parasorboside Polyketides Transgenic plants 

Abbreviations

2PS

2-pyrone synthase

CHS

Chalcone synthase

DMSO

Dimethyl sulfoxide

Glc

Glucose

HPLC

High performance liquid chromatography

MIC

Minimal inhibitory concentration

MS

Mass spectroscopy

NMR

Nuclear magnetic resonance

THF

Tetrahydrofuran

TLC

Thin layer chromatography

Notes

Acknowledgments

We wish to acknowledge Marja-Leena Lahdenperä from Kemira Agro Oy, for providing the Botrytis cinerea strain, and Professor Kielo Haahtela from the Department of Biosciences, University of Helsinki, for providing Heterobasidium annosum and Rhizoctonia solani mould strains. We also thank Jussi-Pekka Rauha from the Division of Pharmacognosy, University of Helsinki for preliminary mass spectroscopic analyses and advisory discussions. This study was supported by grants from the National Technology Agency, the Academy of Finland (grant no. 4284 to K.P., grant no. 51935 to S.K. and the Programme for Centres of Excellence in Research) and the Finnish Pharmaceutical Society (to P.S.).

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Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Satu Koskela
    • 1
  • Päivi P. Söderholm
    • 2
  • Miia Ainasoja
    • 3
  • Tero Wennberg
    • 2
  • Karel D. Klika
    • 4
  • Vladimir V. Ovcharenko
    • 4
  • Irene Kylänlahti
    • 5
  • Tiina Auerma
    • 1
  • Jari Yli-Kauhaluoma
    • 5
  • Kalevi Pihlaja
    • 4
  • Pia M. Vuorela
    • 6
    Email author
  • Teemu H. Teeri
    • 3
    • 1
    Email author
  1. 1.Institute of BiotechnologyUniversity of HelsinkiHelsinkiFinland
  2. 2.Division of Pharmaceutical Biology, Faculty of PharmacyUniversity of HelsinkiHelsinkiFinland
  3. 3.Department of Agricultural SciencesUniversity of HelsinkiHelsinkiFinland
  4. 4.Structural Chemistry Group, Department of ChemistryUniversity of TurkuTurkuFinland
  5. 5.Division of Pharmaceutical Chemistry, Faculty of PharmacyUniversity of HelsinkiHelsinkiFinland
  6. 6.Pharmaceutical Sciences, Department of BiosciencesÅbo Akademi UniversityTurkuFinland

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