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Toxins 2015, 7(8), 2701-2722; doi:10.3390/toxins7082701

Molecular Cloning and Functional Analysis of Gene Clusters for the Biosynthesis of Indole-Diterpenes in Penicillium crustosum and P. janthinellum

1
Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North 4442, New Zealand
2
AgResearch, Grasslands Research Centre, Private Bag 11 008, Palmerston North 4442, New Zealand
*
Author to whom correspondence should be addressed.
Academic Editor: Jiujiang Yu
Received: 19 May 2015 / Revised: 22 June 2015 / Accepted: 2 July 2015 / Published: 23 July 2015
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Abstract

The penitremane and janthitremane families of indole-diterpenes are abundant natural products synthesized by Penicillium crustosum and P. janthinellum. Using a combination of PCR, cosmid library screening, and Illumina sequencing we have identified gene clusters encoding enzymes for the synthesis of these compounds. Targeted deletion of penP in P. crustosum abolished the synthesis of penitrems A, B, D, E, and F, and led to accumulation of paspaline, a key intermediate for paxilline biosynthesis in P. paxilli. Similarly, deletion of janP and janD in P. janthinellum abolished the synthesis of prenyl-elaborated indole-diterpenes, and led to accumulation in the latter of 13-desoxypaxilline, a key intermediate for the synthesis of the structurally related aflatremanes synthesized by Aspergillus flavus. This study helps resolve the genetic basis for the complexity of indole-diterpene natural products found within the Penicillium and Aspergillus species. All indole-diterpene gene clusters identified to date have a core set of genes for the synthesis of paspaline and a suite of genes encoding multi-functional cytochrome P450 monooxygenases, FAD dependent monooxygenases, and prenyl transferases that catalyse various regio- and stereo- specific oxidations that give rise to the diversity of indole-diterpene products synthesized by this group of fungi. View Full-Text
Keywords: indole-diterpene; penitrems; shearinines; janthitremanes; gene clusters indole-diterpene; penitrems; shearinines; janthitremanes; gene clusters
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Nicholson, M.J.; Eaton, C.J.; Stärkel, C.; Tapper, B.A.; Cox, M.P.; Scott, B. Molecular Cloning and Functional Analysis of Gene Clusters for the Biosynthesis of Indole-Diterpenes in Penicillium crustosum and P. janthinellum. Toxins 2015, 7, 2701-2722.

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