Evidence map›Paper›PMID 27065235›Full record

ArticleNature chemical biology2016

Plant-like biosynthesis of isoquinoline alkaloids in Aspergillus fumigatus.

Joshua A Baccile, Joseph E Spraker, Henry H Le, Eileen Brandenburger, Christian Gomez, Jin Woo Bok, Juliane Macheleidt, Axel A Brakhage, Dirk Hoffmeister, Nancy P Keller and 1 more

Open access · greenAbstract read
In one paragraph

Article in Nature chemical biology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.

0numbers the graph read from it
0cells of the map it votes in
48citing papers in PubMed
9.2field-weighted citation impact, top 2% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

48 citing papers in PubMed, 96 citations in OpenAlex.

  1. Article
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  6. Genome Mining of Isoindolinone-Containing Peptide Natural Products.Journal of the American Chemical Society · 2025
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  10. A Timeline of Biosynthetic Gene Cluster Discovery inJournal of fungi (Basel, Switzerland) · 2024
    Article
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  14. The Transcriptome Response to Azole Compounds inJournal of fungi (Basel, Switzerland) · 2023
    Article
  15. Review
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  18. Review
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  20. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

11 authors at 4 institutions in 2 countries.

Joshua A BaccileBoyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York, USA.ORCID 0000-0003-4334-755X
Joseph E SprakerDepartment of Plant Pathology, University of Wisconsin-Madison, Madison, Wisconsin, USA.ORCID 0000-0002-5429-0328
Henry H LeBoyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York, USA.ORCID 0000-0003-2942-2357
Eileen BrandenburgerDepartment of Pharmaceutical Microbiology at the Hans-Knöll-Institute, Friedrich Schiller University, Jena, Germany.
Christian GomezBoyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York, USA.
Jin Woo BokInstitute for Microbiology, Friedrich Schiller University, Jena, Germany.
Juliane MacheleidtInstitute for Microbiology, Friedrich Schiller University, Jena, Germany.
Axel A BrakhageInstitute for Microbiology, Friedrich Schiller University, Jena, Germany.
Dirk HoffmeisterDepartment of Pharmaceutical Microbiology at the Hans-Knöll-Institute, Friedrich Schiller University, Jena, Germany.
Nancy P KellerDepartment of Bacteriology, University of Wisconsin-Madison, Madison, Wisconsin, USA.
Frank C SchroederBoyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York, USA.
Cornell University · USLeibniz-Institut für Naturstoff-Forschung und Infektionsbiologie e. V. - Hans-Knöll-Institut (HKI) · DEUniversity of Wisconsin–Madison · USFriedrich Schiller University Jena · DE

Funding

CHEMISTRY OF BIOLOGICAL SYSTEMST32GM008500 · NIGMS · CORNELL UNIVERSITY ITHACA · PI LIN, HENING · 1996 to 2020
$5.4M
Comprehensive analysis of NRPS-derived metabolomes of three Aspergillus speciesR01GM112739 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI KELLER, NANCY P · 2015 to 2023
$2.8M
NIGMS NIH HHS R01 GM112739NIGMS NIH HHS T32 GM008500
6 · The paper itself

Abstract

Natural product discovery efforts have focused primarily on microbial biosynthetic gene clusters (BGCs) containing large multimodular polyketide synthases and nonribosomal peptide synthetases; however, sequencing of fungal genomes has revealed a vast number of BGCs containing smaller NRPS-like genes of unknown biosynthetic function. Using comparative metabolomics, we show that a BGC in the human pathogen Aspergillus fumigatus named fsq, which contains an NRPS-like gene lacking a condensation domain, produces several new isoquinoline alkaloids known as the fumisoquins. These compounds derive from carbon-carbon bond formation between two amino acid-derived moieties followed by a sequence that is directly analogous to isoquinoline alkaloid biosynthesis in plants. Fumisoquin biosynthesis requires the N-methyltransferase FsqC and the FAD-dependent oxidase FsqB, which represent functional analogs of coclaurine N-methyltransferase and berberine bridge enzyme in plants. Our results show that BGCs containing incomplete NRPS modules may reveal new biosynthetic paradigms and suggest that plant-like isoquinoline biosynthesis occurs in diverse fungi.

Indexed as

Biosynthetic PathwaysAlkaloidsAspergillus fumigatusIsoquinolinesMetabolomicsMolecular StructureMultigene FamilyPlantsAlkaloidsisoquinolineIsoquinolines

Identifiers

PMID27065235
PMCPMC5049701
OpenAlexW2316565238

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.