Issue 11, 2015

Genome mining and molecular characterization of the biosynthetic gene cluster of a diterpenic meroterpenoid, 15-deoxyoxalicine B, in Penicillium canescens

Abstract

Meroterpenoids are a class of secondary metabolites that are produced from polyketide and terpenoid precursors. 15-Deoxyoxalicine B (1) belongs to one structural group consisting of a unique pyridinyl-α-pyrone polyketide subunit and a diterpenoid subunit connected through a characteristic asymmetric spiro carbon atom. An understanding of the genes involved in the biosynthesis of this class of compounds should provide a means to facilitate engineering of second-generation molecules and increasing production of first-generation compounds. We found that the filamentous fungus Penicillium canescens produces 15-deoxyoxalicine B (1). Using targeted gene deletions, we have identified a cluster of 12 responsible contiguous genes. This gene cluster includes one polyketide synthase gene which we have designated olcA. Chemical analysis of wild-type and gene deletion mutant extracts enabled us to isolate and characterize 7 additional metabolites that are either intermediates or shunt products of the biosynthetic pathway. Two of the compounds identified have not been reported previously. Our data have allowed us to propose a biosynthetic pathway for 15-deoxyoxalicine B (1).

Graphical abstract: Genome mining and molecular characterization of the biosynthetic gene cluster of a diterpenic meroterpenoid, 15-deoxyoxalicine B, in Penicillium canescens

Associated articles

Supplementary files

Article information

Article type
Edge Article
Submitted
01 Jun 2015
Accepted
06 Aug 2015
First published
06 Aug 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 6537-6544

Genome mining and molecular characterization of the biosynthetic gene cluster of a diterpenic meroterpenoid, 15-deoxyoxalicine B, in Penicillium canescens

J. Yaegashi, J. Romsdahl, Y. Chiang and C. C. C. Wang, Chem. Sci., 2015, 6, 6537 DOI: 10.1039/C5SC01965F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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