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Cited by 9Microbial Natural Products and BiosynthesisIsoquinoline Alkaloid SynthesisPlant biochemistry and biosynthesis

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Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus

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Maleckis, Matiss, Wibowo, Mario, Williams, Sam E., Gotfredsen, Charlotte H., Sigrist, Renata, Souza, Luciano D. O., Cowled, Michael S., Charusanti, Pep, Gren, Tetiana, Saha, Subhasish, Moreira, José M. A., Weber, Tilmann, Ding, Ling·2024·ACS Chemical Biology
DOI 10.1021/acschembio.4c00121

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Abstract

Abstract Isoquinolinequinones represent an important family of natural alkaloids with profound biological activities. Heterologous expression of a rare bifunctional indole prenyltransferase /tryptophan indole-lyase enzyme from Streptomyces mirabilis P8-A2 in S. albidoflavus J1074 led to the activation of a putative isoquinolinequinone biosynthetic gene cluster and production of a novel isoquinolinequinone alkaloid, named maramycin ( 1 ). The structure of maramycin was determined by analysis of spectroscopic (1D/2D NMR) and MS spectrometric data. The prevalence of this bifunctional biosynthetic enzyme was explored and found to be a recent evolutionary event with only a few representatives in Nature. Maramycin exhibited moderate cytotoxicity against human prostate cancer cell lines, LNCaP and C4-2B. The discovery of maramycin ( 1 ) enriched the chemical diversity of natural isoquinolinequinones and also provided new insights into crosstalk between the host biosynthetic genes and the heterologous biosynthetic genes in generating new chemical scaffolds.

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Cites

Research works printed but not linked: 48

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Metadata

Authors
Maleckis, M., Wibowo, M., Williams, S. E., Gotfredsen, C. H., Sigrist, R., Souza, L. D. O., Cowled, M. S., Charusanti, P., Gren, T., Saha, S., Moreira, J. M. A., Weber, T., & Ding, L.
Affiliations
  • Novo Nordisk Foundation (DK)
  • Technical University of Denmark (DK)
  • University of Copenhagen (DK)
Corresponding author
  • Weber, Tilmann
  • Ding, Ling
ORCID
Venue
ACS Chemical Biology
Publisher
American Chemical Society (ACS)
Published
2024-05-14
Volume
19
Issue
6
Pages
1303-1310
ISSN
  • 1554-8929 (ISSN-L)
  • 1554-8937
DOI
10.1021/acschembio.4c00121
OpenAlex
W4396889550
Cited by
9
References
3
Citations by year
2026: 2 · 2025: 5 · 2024: 2
FWCI
2.57
Type
journal article
Language
en
Open access
Licence
Locations
  • ACS Chemical Biology (publishedVersion)
  • bioRxiv (Cold Spring Harbor Laboratory) (acceptedVersion, cc-by)
  • PubMed (publishedVersion)
  • Research at the University of Copenhagen (University of Copenhagen) (submittedVersion)
  • Technical University of Denmark, DTU Orbit (Technical University of Denmark, DTU) (submittedVersion)
Funders
  • Danmarks Grundforskningsfond (DNRF137)
  • Novo Nordisk Fonden (NNF16OC0021746, NNF20CC0035580, NNF22OC0079021, NNF22OC0079928)
Topics
  • Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
  • Physical Sciences › Chemistry › Organic Chemistry › Isoquinoline Alkaloid Synthesis
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
Keywords
Streptomyces albidoflavus, bifunctional enzyme, heterologous expression, alkaloid biosynthesis, gene cluster activation, structure elucidation, cytotoxicity, prostate cancer, LNCaP cells
MeSH terms
Antineoplastic Agents, Dimethylallyltranstransferase, Multigene Family, Humans, Isoquinolines, Streptomyces, Terpenes, Cell Line, Tumor

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