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Bioactivity-Guided Metabolite Profiling of Feijoa (Acca sellowiana) Cultivars Identifies 4-Cyclopentene-1,3-dione as a Potent Antifungal Inhibitor of Chitin Synthesis

  • Mona Mokhtari
    Mona Mokhtari
    School of Biological Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
  • Michael D. Jackson
    Michael D. Jackson
    School of Biological Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
  • Alistair S. Brown
    Alistair S. Brown
    School of Biological Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
  • David F. Ackerley
    David F. Ackerley
    School of Biological Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
    Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New Zealand
  • Nigel J. Ritson
    Nigel J. Ritson
    Foretaste Feijoa Fruit Ltd., Takaka 7082, New Zealand
  • Robert A. Keyzers
    Robert A. Keyzers
    Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New Zealand
    School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
  • , and 
  • Andrew B. Munkacsi*
    Andrew B. Munkacsi
    School of Biological Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
    Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New Zealand
    *Tel.: +64 4 463 5171. E-mail: [email protected]
Cite this: J. Agric. Food Chem. 2018, 66, 22, 5531–5539
Publication Date (Web):March 16, 2018
https://doi.org/10.1021/acs.jafc.7b06154
Copyright © 2018 American Chemical Society

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    Abstract

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    Pathogenic fungi continue to develop resistance against current antifungal drugs. To explore the potential of agricultural waste products as a source of novel antifungal compounds, we obtained an unbiased GC-MS profile of 151 compounds from 16 commercial and experimental cultivars of feijoa peels. Multivariate analysis correlated 93% of the compound profiles with antifungal bioactivities. Of the 18 compounds that significantly correlated with antifungal activity, 5 had not previously been described from feijoa. Two novel cultivars were the most bioactive, and the compound 4-cyclopentene-1,3-dione, detected in these cultivars, was potently antifungal (IC50 = 1–2 μM) against human-pathogenic Candida species. Haploinsufficiency and fluorescence microscopy analyses determined that the synthesis of chitin, a fungal-cell-wall polysaccharide, was the target of 4-cyclopentene-1,3-dione. This fungal-specific mechanism was consistent with a 22–70-fold reduction in antibacterial activity. Overall, we identified the agricultural waste product of specific cultivars of feijoa peels as a source of potential high-value antifungal compounds.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.7b06154.

    • GC-MS chromatogram of the FFF6 feijoa cultivar and list of compounds detected in the 16 feijoa cultivars with their experimental and literature LRI values and similarity indices to the NIST database (PDF)

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