Literature DB >> 27310134

New Aspercryptins, Lipopeptide Natural Products, Revealed by HDAC Inhibition in Aspergillus nidulans.

Matthew T Henke1,2, Alexandra A Soukup1,2, Anthony W Goering1,2, Ryan A McClure1,2, Regan J Thomson1,2, Nancy P Keller1,2, Neil L Kelleher1,2.   

Abstract

Unlocking the biochemical stores of fungi is key for developing future pharmaceuticals. Through reduced expression of a critical histone deacetylase in Aspergillus nidulans, increases of up to 100-fold were observed in the levels of 15 new aspercryptins, recently described lipopeptides with two noncanonical amino acids derived from octanoic and dodecanoic acids. In addition to two NMR-verified structures, MS/MS networking helped uncover an additional 13 aspercryptins. The aspercryptins break the conventional structural orientation of lipopeptides and appear "backward" when compared to known compounds of this class. We have also confirmed the 14-gene aspercryptin biosynthetic gene cluster, which encodes two fatty acid synthases and several enzymes to convert saturated octanoic and dodecanoic acid to α-amino acids.

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Year:  2016        PMID: 27310134      PMCID: PMC5119465          DOI: 10.1021/acschembio.6b00398

Source DB:  PubMed          Journal:  ACS Chem Biol        ISSN: 1554-8929            Impact factor:   5.100


  30 in total

1.  Piperazimycins: cytotoxic hexadepsipeptides from a marine-derived bacterium of the genus Streptomyces.

Authors:  Eric D Miller; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

2.  MS/MS networking guided analysis of molecule and gene cluster families.

Authors:  Don Duy Nguyen; Cheng-Hsuan Wu; Wilna J Moree; Anne Lamsa; Marnix H Medema; Xiling Zhao; Ronnie G Gavilan; Marystella Aparicio; Librada Atencio; Chanaye Jackson; Javier Ballesteros; Joel Sanchez; Jeramie D Watrous; Vanessa V Phelan; Corine van de Wiel; Roland D Kersten; Samina Mehnaz; René De Mot; Elizabeth A Shank; Pep Charusanti; Harish Nagarajan; Brendan M Duggan; Bradley S Moore; Nuno Bandeira; Bernhard Ø Palsson; Kit Pogliano; Marcelino Gutiérrez; Pieter C Dorrestein
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-24       Impact factor: 11.205

3.  Large-scale metabolomics reveals a complex response of Aspergillus nidulans to epigenetic perturbation.

Authors:  Jessica C Albright; Matthew T Henke; Alexandra A Soukup; Ryan A McClure; Regan J Thomson; Nancy P Keller; Neil L Kelleher
Journal:  ACS Chem Biol       Date:  2015-04-03       Impact factor: 5.100

4.  Mapping Microbial Response Metabolomes for Induced Natural Product Discovery.

Authors:  Dagmara K Derewacz; Brett C Covington; John A McLean; Brian O Bachmann
Journal:  ACS Chem Biol       Date:  2015-06-17       Impact factor: 5.100

5.  Aspergillus has distinct fatty acid synthases for primary and secondary metabolism.

Authors:  D W Brown; T H Adams; N P Keller
Journal:  Proc Natl Acad Sci U S A       Date:  1996-12-10       Impact factor: 11.205

6.  Illuminating the diversity of aromatic polyketide synthases in Aspergillus nidulans.

Authors:  Manmeet Ahuja; Yi-Ming Chiang; Shu-Lin Chang; Mike B Praseuth; Ruth Entwistle; James F Sanchez; Hsien-Chun Lo; Hsu-Hua Yeh; Berl R Oakley; Clay C C Wang
Journal:  J Am Chem Soc       Date:  2012-05-01       Impact factor: 15.419

7.  Proteomics-based discovery of koranimine, a cyclic imine natural product.

Authors:  Bradley S Evans; Ioanna Ntai; Yunqiu Chen; Sarah J Robinson; Neil L Kelleher
Journal:  J Am Chem Soc       Date:  2011-04-26       Impact factor: 15.419

Review 8.  Recent advances in genome mining of secondary metabolite biosynthetic gene clusters and the development of heterologous expression systems in Aspergillus nidulans.

Authors:  Junko Yaegashi; Berl R Oakley; Clay C C Wang
Journal:  J Ind Microbiol Biotechnol       Date:  2013-12-17       Impact factor: 3.346

9.  Chemical induction of silent biosynthetic pathway transcription in Aspergillus niger.

Authors:  K M Fisch; A F Gillaspy; M Gipson; J C Henrikson; A R Hoover; L Jackson; F Z Najar; H Wägele; R H Cichewicz
Journal:  J Ind Microbiol Biotechnol       Date:  2009-06-12       Impact factor: 3.346

10.  Apicidin F: characterization and genetic manipulation of a new secondary metabolite gene cluster in the rice pathogen Fusarium fujikuroi.

Authors:  Eva-Maria Niehaus; Slavica Janevska; Katharina W von Bargen; Christian M K Sieber; Henning Harrer; Hans-Ulrich Humpf; Bettina Tudzynski
Journal:  PLoS One       Date:  2014-07-24       Impact factor: 3.240

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  21 in total

1.  Discovery of the Tyrobetaine Natural Products and Their Biosynthetic Gene Cluster via Metabologenomics.

Authors:  Elizabeth I Parkinson; James H Tryon; Anthony W Goering; Kou-San Ju; Ryan A McClure; Jeremy D Kemball; Sara Zhukovsky; David P Labeda; Regan J Thomson; Neil L Kelleher; William W Metcalf
Journal:  ACS Chem Biol       Date:  2018-03-13       Impact factor: 5.100

2.  Prioritizing Natural Product Diversity in a Collection of 146 Bacterial Strains Based on Growth and Extraction Protocols.

Authors:  Max Crüsemann; Ellis C O'Neill; Charles B Larson; Alexey V Melnik; Dimitrios J Floros; Ricardo R da Silva; Paul R Jensen; Pieter C Dorrestein; Bradley S Moore
Journal:  J Nat Prod       Date:  2016-11-11       Impact factor: 4.050

3.  In the fungus where it happens: History and future propelling Aspergillus nidulans as the archetype of natural products research.

Authors:  Lindsay K Caesar; Neil L Kelleher; Nancy P Keller
Journal:  Fungal Genet Biol       Date:  2020-10-06       Impact factor: 3.495

4.  Interrogation of Benzomalvin Biosynthesis Using Fungal Artificial Chromosomes with Metabolomic Scoring (FAC-MS): Discovery of a Benzodiazepine Synthase Activity.

Authors:  Kenneth D Clevenger; Rosa Ye; Jin Woo Bok; Paul M Thomas; Md Nurul Islam; Galen P Miley; Matthew T Robey; Cynthia Chen; KaHoua Yang; Michael Swyers; Edward Wu; Peng Gao; Chengcang C Wu; Nancy P Keller; Neil L Kelleher
Journal:  Biochemistry       Date:  2018-03-20       Impact factor: 3.162

5.  Overexpression of a three-gene conidial pigment biosynthetic pathway in Aspergillus nidulans reveals the first NRPS known to acetylate tryptophan.

Authors:  Calvin T Sung; Shu-Lin Chang; Ruth Entwistle; Green Ahn; Tzu-Shyang Lin; Vessela Petrova; Hsu-Hua Yeh; Mike B Praseuth; Yi-Ming Chiang; Berl R Oakley; Clay C C Wang
Journal:  Fungal Genet Biol       Date:  2017-01-17       Impact factor: 3.495

6.  Response of Secondary Metabolism of Hypogean Actinobacterial Genera to Chemical and Biological Stimuli.

Authors:  Brett C Covington; Jeffrey M Spraggins; Audrey E Ynigez-Gutierrez; Zachary B Hylton; Brian O Bachmann
Journal:  Appl Environ Microbiol       Date:  2018-09-17       Impact factor: 4.792

7.  Identification of the First Diketomorpholine Biosynthetic Pathway Using FAC-MS Technology.

Authors:  Matthew T Robey; Rosa Ye; Jin Woo Bok; Kenneth D Clevenger; Md Nurul Islam; Cynthia Chen; Raveena Gupta; Michael Swyers; Edward Wu; Peng Gao; Paul M Thomas; Chengcang C Wu; Nancy P Keller; Neil L Kelleher
Journal:  ACS Chem Biol       Date:  2018-04-17       Impact factor: 5.100

Review 8.  On top of biosynthetic gene clusters: How epigenetic machinery influences secondary metabolism in fungi.

Authors:  Brandon T Pfannenstiel; Nancy P Keller
Journal:  Biotechnol Adv       Date:  2019-02-07       Impact factor: 14.227

9.  NAD+-dependent HDAC inhibitor stimulates Monascus pigment production but inhibit citrinin.

Authors:  Yan Hu; Youxiang Zhou; Zejing Mao; Huihui Li; Fusheng Chen; Yanchun Shao
Journal:  AMB Express       Date:  2017-08-23       Impact factor: 3.298

10.  Duplication and Functional Divergence of Branched-Chain Amino Acid Biosynthesis Genes in Aspergillus nidulans.

Authors:  Joel T Steyer; Damien J Downes; Cameron C Hunter; Pierre A Migeon; Richard B Todd
Journal:  mBio       Date:  2021-06-22       Impact factor: 7.867

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