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Polyketide derivatives active against Botrytis cinerea in Gerbera hybrida

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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.

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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

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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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Authors and Affiliations

  1. Institute of Biotechnology, University of Helsinki, P.O. Box 56, FI-00014, Helsinki, Finland

    Satu Koskela, Tiina Auerma & Teemu H. Teeri

  2. Division of Pharmaceutical Biology, Faculty of Pharmacy, University of Helsinki, P.O. Box 56, FI-00014, Helsinki, Finland

    Päivi P. Söderholm & Tero Wennberg

  3. Department of Agricultural Sciences, University of Helsinki, P.O. Box 27, FI-00014, Helsinki, Finland

    Miia Ainasoja & Teemu H. Teeri

  4. Structural Chemistry Group, Department of Chemistry, University of Turku, FI-20014, Turku, Finland

    Karel D. Klika, Vladimir V. Ovcharenko & Kalevi Pihlaja

  5. Division of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Helsinki, P.O. Box 56, FI-00014, Helsinki, Finland

    Irene Kylänlahti & Jari Yli-Kauhaluoma

  6. Pharmaceutical Sciences, Department of Biosciences, Åbo Akademi University, BioCity, Artillerigatan 6A, FI-20520, Turku, Finland

    Pia M. Vuorela

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  1. Satu Koskela
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Correspondence to Pia M. Vuorela or Teemu H. Teeri.

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Koskela, S., Söderholm, P.P., Ainasoja, M. et al. Polyketide derivatives active against Botrytis cinerea in Gerbera hybrida . Planta 233, 37–48 (2011). https://doi.org/10.1007/s00425-010-1277-8

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