Hamuramicin C, a Cytotoxic Bicyclic Macrolide Isolated from a Wasp Gut Bacterium

Joon Soo An; Hyung Ju Lim; Ji Yun Lee; Yong Joon Jang; Sang Jip Nam; Sang Kook Lee; Dong Chan Oh

doi:10.1021/acs.jnatprod.1c01075

Hamuramicin C, a Cytotoxic Bicyclic Macrolide Isolated from a Wasp Gut Bacterium

Joon Soo An, Hyung Ju Lim, Ji Yun Lee, Yong Joon Jang, Sang Jip Nam, Sang Kook Lee, Dong Chan Oh

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Review article › peer-review

12 Scopus citations

Abstract

A new bicyclic macrolide, hamuramicin C (1), was isolated from Streptomyces sp. MBP16, a gut bacterial strain of the wasp Vespa crabro flavofasciata. Its 22-membered macrocyclic lactone structure was determined by NMR and mass spectrometry. The relative configurations of hamuramicin C (1) were assigned by J-based configuration analysis utilizing ¹H rotating frame Overhauser effect spectroscopy and heteronuclear long-range coupling NMR spectroscopy. Genomic and bioinformatic analyses of the bacterial strain enabled identification of the type-I polyketide synthase pathway, which employs a trans-acyltransferase system. The absolute configurations of 1 were proposed based on the analysis of the sequences of ketoreductases in the modular gene cluster. Moreover, hamuramicin C (1) demonstrated significant inhibitory activity against diverse human cancer cell lines (HCT116, A549, SNU-638, SK-HEP-1, and MDA-MB-231).

Original language	English
Pages (from-to)	936-942
Number of pages	7
Journal	Journal of Natural Products
Volume	85
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.1c01075
State	Published - 22 Apr 2022

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea grants funded by the Korean Government (Ministry of Science and ICT) (2021R1A4A2001251 and 2020R1A2C2003518).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

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title = "Hamuramicin C, a Cytotoxic Bicyclic Macrolide Isolated from a Wasp Gut Bacterium",

abstract = "A new bicyclic macrolide, hamuramicin C (1), was isolated from Streptomyces sp. MBP16, a gut bacterial strain of the wasp Vespa crabro flavofasciata. Its 22-membered macrocyclic lactone structure was determined by NMR and mass spectrometry. The relative configurations of hamuramicin C (1) were assigned by J-based configuration analysis utilizing 1H rotating frame Overhauser effect spectroscopy and heteronuclear long-range coupling NMR spectroscopy. Genomic and bioinformatic analyses of the bacterial strain enabled identification of the type-I polyketide synthase pathway, which employs a trans-acyltransferase system. The absolute configurations of 1 were proposed based on the analysis of the sequences of ketoreductases in the modular gene cluster. Moreover, hamuramicin C (1) demonstrated significant inhibitory activity against diverse human cancer cell lines (HCT116, A549, SNU-638, SK-HEP-1, and MDA-MB-231).",

author = "An, {Joon Soo} and Lim, {Hyung Ju} and Lee, {Ji Yun} and Jang, {Yong Joon} and Nam, {Sang Jip} and Lee, {Sang Kook} and Oh, {Dong Chan}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea grants funded by the Korean Government (Ministry of Science and ICT) (2021R1A4A2001251 and 2020R1A2C2003518). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

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AU - An, Joon Soo

AU - Lim, Hyung Ju

AU - Lee, Ji Yun

AU - Jang, Yong Joon

AU - Nam, Sang Jip

AU - Lee, Sang Kook

AU - Oh, Dong Chan

N1 - Funding Information: This work was supported by the National Research Foundation of Korea grants funded by the Korean Government (Ministry of Science and ICT) (2021R1A4A2001251 and 2020R1A2C2003518). Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/4/22

Y1 - 2022/4/22

N2 - A new bicyclic macrolide, hamuramicin C (1), was isolated from Streptomyces sp. MBP16, a gut bacterial strain of the wasp Vespa crabro flavofasciata. Its 22-membered macrocyclic lactone structure was determined by NMR and mass spectrometry. The relative configurations of hamuramicin C (1) were assigned by J-based configuration analysis utilizing 1H rotating frame Overhauser effect spectroscopy and heteronuclear long-range coupling NMR spectroscopy. Genomic and bioinformatic analyses of the bacterial strain enabled identification of the type-I polyketide synthase pathway, which employs a trans-acyltransferase system. The absolute configurations of 1 were proposed based on the analysis of the sequences of ketoreductases in the modular gene cluster. Moreover, hamuramicin C (1) demonstrated significant inhibitory activity against diverse human cancer cell lines (HCT116, A549, SNU-638, SK-HEP-1, and MDA-MB-231).

AB - A new bicyclic macrolide, hamuramicin C (1), was isolated from Streptomyces sp. MBP16, a gut bacterial strain of the wasp Vespa crabro flavofasciata. Its 22-membered macrocyclic lactone structure was determined by NMR and mass spectrometry. The relative configurations of hamuramicin C (1) were assigned by J-based configuration analysis utilizing 1H rotating frame Overhauser effect spectroscopy and heteronuclear long-range coupling NMR spectroscopy. Genomic and bioinformatic analyses of the bacterial strain enabled identification of the type-I polyketide synthase pathway, which employs a trans-acyltransferase system. The absolute configurations of 1 were proposed based on the analysis of the sequences of ketoreductases in the modular gene cluster. Moreover, hamuramicin C (1) demonstrated significant inhibitory activity against diverse human cancer cell lines (HCT116, A549, SNU-638, SK-HEP-1, and MDA-MB-231).

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JF - Journal of Natural Products

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Hamuramicin C, a Cytotoxic Bicyclic Macrolide Isolated from a Wasp Gut Bacterium

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