Resorculins: hybrid polyketide macrolides from Streptomyces sp. MST-91080

Heather J. Lacey; Rachel Chen; Daniel Vuong; Ernest Lacey; Peter J. Rutledge; Yit-Heng Chooi; Andrew M. Piggott; Thomas J. Booth

doi:10.1039/d2ob02332f

Resorculins: hybrid polyketide macrolides from Streptomyces sp. MST-91080

Heather J. Lacey, Rachel Chen, Daniel Vuong, Ernest Lacey, Peter J. Rutledge, Yit-Heng Chooi, Andrew M. Piggott, Thomas J. Booth^*

^*Corresponding author for this work

School of Natural Sciences

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Abstract

Fourteen-membered macrolides are a class of compounds with significant clinical value as antibacterial agents. As part of our ongoing investigation into the metabolites of Streptomyces sp. MST-91080, we report the discovery of resorculins A and B, unprecedented 3,5-dihydroxybenzoic acid (α-resorcylic acid)-containing 14-membered macrolides. We sequenced the genome of MST-91080 and identified the putative resorculin biosynthetic gene cluster (rsn BGC). The rsn BGC is hybrid of type I and type III polyketide synthases. Bioinformatic analysis revealed that the resorculins are relatives of known hybrid polyketides: kendomycin and venemycin. Resorculin A exhibited antibacterial activity against Bacillus subtilis (MIC 19.8 μg mL⁻¹), while resorculin B showed cytotoxic activity against the NS-1 mouse myeloma cell line (IC₅₀ 3.6 μg mL⁻¹).

Original language	English
Pages (from-to)	2531-2538
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	21
Issue number	12
Early online date	28 Feb 2023
DOIs	https://doi.org/10.1039/d2ob02332f
Publication status	Published - 28 Mar 2023

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title = "Resorculins: hybrid polyketide macrolides from Streptomyces sp. MST-91080",

abstract = "Fourteen-membered macrolides are a class of compounds with significant clinical value as antibacterial agents. As part of our ongoing investigation into the metabolites of Streptomyces sp. MST-91080, we report the discovery of resorculins A and B, unprecedented 3,5-dihydroxybenzoic acid (α-resorcylic acid)-containing 14-membered macrolides. We sequenced the genome of MST-91080 and identified the putative resorculin biosynthetic gene cluster (rsn BGC). The rsn BGC is hybrid of type I and type III polyketide synthases. Bioinformatic analysis revealed that the resorculins are relatives of known hybrid polyketides: kendomycin and venemycin. Resorculin A exhibited antibacterial activity against Bacillus subtilis (MIC 19.8 μg mL−1), while resorculin B showed cytotoxic activity against the NS-1 mouse myeloma cell line (IC50 3.6 μg mL−1).",

author = "Lacey, {Heather J.} and Rachel Chen and Daniel Vuong and Ernest Lacey and Rutledge, {Peter J.} and Yit-Heng Chooi and Piggott, {Andrew M.} and Booth, {Thomas J.}",

year = "2023",

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doi = "10.1039/d2ob02332f",

language = "English",

volume = "21",

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T2 - hybrid polyketide macrolides from Streptomyces sp. MST-91080

AU - Lacey, Heather J.

AU - Chen, Rachel

AU - Vuong, Daniel

AU - Lacey, Ernest

AU - Rutledge, Peter J.

AU - Chooi, Yit-Heng

AU - Piggott, Andrew M.

AU - Booth, Thomas J.

PY - 2023/3/28

Y1 - 2023/3/28

N2 - Fourteen-membered macrolides are a class of compounds with significant clinical value as antibacterial agents. As part of our ongoing investigation into the metabolites of Streptomyces sp. MST-91080, we report the discovery of resorculins A and B, unprecedented 3,5-dihydroxybenzoic acid (α-resorcylic acid)-containing 14-membered macrolides. We sequenced the genome of MST-91080 and identified the putative resorculin biosynthetic gene cluster (rsn BGC). The rsn BGC is hybrid of type I and type III polyketide synthases. Bioinformatic analysis revealed that the resorculins are relatives of known hybrid polyketides: kendomycin and venemycin. Resorculin A exhibited antibacterial activity against Bacillus subtilis (MIC 19.8 μg mL−1), while resorculin B showed cytotoxic activity against the NS-1 mouse myeloma cell line (IC50 3.6 μg mL−1).

AB - Fourteen-membered macrolides are a class of compounds with significant clinical value as antibacterial agents. As part of our ongoing investigation into the metabolites of Streptomyces sp. MST-91080, we report the discovery of resorculins A and B, unprecedented 3,5-dihydroxybenzoic acid (α-resorcylic acid)-containing 14-membered macrolides. We sequenced the genome of MST-91080 and identified the putative resorculin biosynthetic gene cluster (rsn BGC). The rsn BGC is hybrid of type I and type III polyketide synthases. Bioinformatic analysis revealed that the resorculins are relatives of known hybrid polyketides: kendomycin and venemycin. Resorculin A exhibited antibacterial activity against Bacillus subtilis (MIC 19.8 μg mL−1), while resorculin B showed cytotoxic activity against the NS-1 mouse myeloma cell line (IC50 3.6 μg mL−1).

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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Resorculins: hybrid polyketide macrolides from Streptomyces sp. MST-91080

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Overcoming antibiotic resistance: rapid discovery of new antibacterial drug targets using chemicalproteomics

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Resorculins: hybrid polyketide macrolides from Streptomyces sp. MST-91080

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Overcoming antibiotic resistance: rapid discovery of new antibacterial drug targets using chemicalproteomics

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