Literature DB >> 24684908

Molecular and chemical characterization of the biosynthesis of the 6-MSA-derived meroterpenoid yanuthone D in Aspergillus niger.

Dorte K Holm1, Lene M Petersen2, Andreas Klitgaard3, Peter B Knudsen4, Zofia D Jarczynska1, Kristian F Nielsen3, Charlotte H Gotfredsen5, Thomas O Larsen6, Uffe H Mortensen7.   

Abstract

Secondary metabolites in filamentous fungi constitute a rich source of bioactive molecules. We have deduced the genetic and biosynthetic pathway of the antibiotic yanuthone D from Aspergillus niger. Our analyses show that yanuthone D is a meroterpenoid derived from the polyketide 6-methylsalicylic acid (6-MSA). Yanuthone D formation depends on a cluster composed of ten genes including yanA and yanI, which encode a 6-MSA polyketide synthase and a previously undescribed O-mevalon transferase, respectively. In addition, several branching points in the pathway were discovered, revealing five yanuthones (F, G, H, I, and J). Furthermore, we have identified another compound (yanuthone X1) that defines a class of yanuthones that depend on several enzymatic activities encoded by genes in the yan cluster but that are not derived from 6-MSA.
Copyright © 2014 Elsevier Ltd. All rights reserved.

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Year:  2014        PMID: 24684908     DOI: 10.1016/j.chembiol.2014.01.013

Source DB:  PubMed          Journal:  Chem Biol        ISSN: 1074-5521


  31 in total

Review 1.  Advances in linking polyketides and non-ribosomal peptides to their biosynthetic gene clusters in Fusarium.

Authors:  Mikkel Rank Nielsen; Teis Esben Sondergaard; Henriette Giese; Jens Laurids Sørensen
Journal:  Curr Genet       Date:  2019-05-28       Impact factor: 3.886

Review 2.  Mass spectrometry tools and workflows for revealing microbial chemistry.

Authors:  Tal Luzzatto-Knaan; Alexey V Melnik; Pieter C Dorrestein
Journal:  Analyst       Date:  2015-08-07       Impact factor: 4.616

3.  Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products.

Authors:  Man-Cheng Tang; Xiaoqing Cui; Xueqian He; Zhuang Ding; Tianjiao Zhu; Yi Tang; Dehai Li
Journal:  Org Lett       Date:  2017-09-19       Impact factor: 6.005

4.  Induced sclerotium formation exposes new bioactive metabolites from Aspergillus sclerotiicarbonarius.

Authors:  Lene M Petersen; Jens C Frisvad; Peter B Knudsen; Marko Rohlfs; Charlotte H Gotfredsen; Thomas O Larsen
Journal:  J Antibiot (Tokyo)       Date:  2015-05-06       Impact factor: 2.649

5.  Characterization of four new antifungal yanuthones from Aspergillus niger.

Authors:  Lene M Petersen; Dorte K Holm; Peter B Knudsen; Kristian F Nielsen; Charlotte H Gotfredsen; Uffe H Mortensen; Thomas O Larsen
Journal:  J Antibiot (Tokyo)       Date:  2014-10-08       Impact factor: 2.649

Review 6.  Recent advances in the genome mining of Aspergillus secondary metabolites (covering 2012-2018).

Authors:  Jillian Romsdahl; Clay C C Wang
Journal:  Medchemcomm       Date:  2019-04-26       Impact factor: 3.597

7.  An in planta-expressed polyketide synthase produces (R)-mellein in the wheat pathogen Parastagonospora nodorum.

Authors:  Yit-Heng Chooi; Christian Krill; Russell A Barrow; Shasha Chen; Robert Trengove; Richard P Oliver; Peter S Solomon
Journal:  Appl Environ Microbiol       Date:  2014-10-17       Impact factor: 4.792

8.  Fungal Highly Reducing Polyketide Synthases Biosynthesize Salicylaldehydes That Are Precursors to Epoxycyclohexenol Natural Products.

Authors:  Ling Liu; Man-Cheng Tang; Yi Tang
Journal:  J Am Chem Soc       Date:  2019-12-05       Impact factor: 15.419

Review 9.  The importance of mass spectrometric dereplication in fungal secondary metabolite analysis.

Authors:  Kristian F Nielsen; Thomas O Larsen
Journal:  Front Microbiol       Date:  2015-02-17       Impact factor: 5.640

10.  Uncovering biosynthetic relationships between antifungal nonadrides and octadrides.

Authors:  Kate M J de Mattos-Shipley; Catherine E Spencer; Claudio Greco; David M Heard; Daniel E O'Flynn; Trong T Dao; Zhongshu Song; Nicholas P Mulholland; Jason L Vincent; Thomas J Simpson; Russell J Cox; Andrew M Bailey; Christine L Willis
Journal:  Chem Sci       Date:  2020-10-07       Impact factor: 9.825

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