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

Research output: Contribution to journalReview articlepeer-review

8 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 languageEnglish
Pages (from-to)936-942
Number of pages7
JournalJournal of Natural Products
Volume85
Issue number4
DOIs
StatePublished - 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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