Planta Med 2019; 85(18): 1446
DOI: 10.1055/s-0039-3399787
Main Congress Poster
Poster Session 1
© Georg Thieme Verlag KG Stuttgart · New York

Assembly of a fungal macrocyclic polylactone is catalyzed by two iterative polyketide synthases

Authors

  • W Bunnak

    1   Department of Chemistry, Special Research Unit for Advanced Magnetic Resonance and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University,, Bangkok 10900, Thailand

  • P Wonnapinij

    2   Department of Genetics, Faculty of Science, Kasetsart University,, Bangkok 10900, Thailand

  • A Sriboonlert

    2   Department of Genetics, Faculty of Science, Kasetsart University,, Bangkok 10900, Thailand

  • CM Lazarus

    3   School of Biological Sciences, University of Bristol,, Bristol BS8 1TQ, UK

  • P Wattana-Amorn

    1   Department of Chemistry, Special Research Unit for Advanced Magnetic Resonance and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University,, Bangkok 10900, Thailand
Further Information

Publication History

Publication Date:
20 December 2019 (online)

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Menisporopsin A is a bioactive macrocyclic polylactone produced by the fungus Menisporopsis theobromae BCC 4162. With the transcriptomic results during the production phase of menisporopsin A, non-reducing polyketide synthase (NR-PKS) gene namely men 1 and reducing polyketide synthase (R-PKS) gene namely men 2 are believed to participate in the menisporopsin A biosynthesis. Both genes were cloned into vectors for heterologous expression in Aspergillus oryzae NSAR1 and the transformants were analyzed using HPLC and metabolites produced were identified by NMR, HR-MS and their optical activities. Three major metabolites produced by transformants are (-)-orthosporin, (-)-6-hydroxymellein and structural derivative of menisporopsin A, ascotrichalactone A, which differs from menisporopsin A only in the presence of a keto group as highlighted in [Fig. 1]. Based on these results, we can conclude that the formation of macrocyclic polylactone requires only R and NR-PKSs and trans-acting ketoreductase is needed for the final step of menisporopsin A biosynthesis [1].

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Fig. 1 Structures of (a) menisporopsin A and (b) ascotrichalactone A.
 

  • References

  • 1 Bunnak W, Wonnapinij P, Sriboonlert A, Lazarus CM, Wattana-Amorn P. Heterologous biosynthesis of a fungal macrocyclic polylactone requires only two iterative polyketide synthases. Org Biomol Chem 2019; 17: 374-379
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