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

W Bunnak; P Wonnapinij; A Sriboonlert; CM Lazarus; P Wattana-Amorn

doi:10.1055/s-0039-3399787

Planta Medica, Table of Contents

Planta Med 2019; 85(18): 1446
DOI: 10.1055/s-0039-3399787

Main Congress Poster

Poster Session 1

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

W Bunnak

¹Department 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

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

,

A Sriboonlert

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

,

CM Lazarus

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

,

P Wattana-Amorn

¹Department 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

› Author Affiliations

Abstract

Full Text

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].

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

References

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

Figures

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