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

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Standard

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

I: ACS chemical biology, 2024.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Maleckis, M, Wibowo, M, Williams, SE, Gotfredsen, CH, Sigrist, R, Souza, LDO, Cowled, MS, Charusanti, P, Gren, T, Saha, S, Moreira, JMA, Weber, T & Ding, L 2024, 'Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus', ACS chemical biology. https://doi.org/10.1021/acschembio.4c00121

APA

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. (Accepteret/In press). Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus. ACS chemical biology. https://doi.org/10.1021/acschembio.4c00121

Vancouver

Maleckis M, Wibowo M, Williams SE, Gotfredsen CH, Sigrist R, Souza LDO o.a. Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus. ACS chemical biology. 2024. https://doi.org/10.1021/acschembio.4c00121

Author

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. / Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus. I: ACS chemical biology. 2024.

Bibtex

@article{fa77e255de7847c7b4f89f8f32f5ec40,
title = "Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus",
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.",
author = "Matiss Maleckis and Mario Wibowo and Williams, {Sam E.} and Gotfredsen, {Charlotte H.} and Renata Sigrist and Souza, {Luciano D.O.} and Cowled, {Michael S.} and Pep Charusanti and Tetiana Gren and Subhasish Saha and Moreira, {Jos{\'e} M.A.} and Tilmann Weber and Ling Ding",
note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",
year = "2024",
doi = "10.1021/acschembio.4c00121",
language = "English",
journal = "A C S Chemical Biology",
issn = "1554-8929",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Maramycin, a Cytotoxic Isoquinolinequinone Terpenoid Produced through Heterologous Expression of a Bifunctional Indole Prenyltransferase/Tryptophan Indole-Lyase in S. albidoflavus

AU - Maleckis, Matiss

AU - Wibowo, Mario

AU - Williams, Sam E.

AU - Gotfredsen, Charlotte H.

AU - Sigrist, Renata

AU - Souza, Luciano D.O.

AU - Cowled, Michael S.

AU - Charusanti, Pep

AU - Gren, Tetiana

AU - Saha, Subhasish

AU - Moreira, José M.A.

AU - Weber, Tilmann

AU - Ding, Ling

N1 - Publisher Copyright: © 2024 American Chemical Society.

PY - 2024

Y1 - 2024

N2 - 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.

AB - 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.

U2 - 10.1021/acschembio.4c00121

DO - 10.1021/acschembio.4c00121

M3 - Journal article

C2 - 38743035

AN - SCOPUS:85193541869

JO - A C S Chemical Biology

JF - A C S Chemical Biology

SN - 1554-8929

ER -

ID: 393775108