2. Academic Validation
  3. Formicolides A and B, Antioxidative and Antiangiogenic 20-Membered Macrolides from a Wood Ant Gut Bacterium

Formicolides A and B, Antioxidative and Antiangiogenic 20-Membered Macrolides from a Wood Ant Gut Bacterium

  • J Nat Prod. 2020 Sep 25;83(9):2776-2784. doi: 10.1021/acs.jnatprod.0c00772.
Joon Soo An 1,  Ji Yun Lee 1,  Eunji Kim 1,  Hyungju Ahn 1,  Yong-Joon Jang 2,  Bora Shin 1,  Sunghoon Hwang 1,  Jongheon Shin 1,  Yeo Joon Yoon 1,  Sang Kook Lee 1,  Dong-Chan Oh 1
Affiliations

Affiliations

  • 1 Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
  • 2 Natura Center of Life and Environment, Seoul 08826, Republic of Korea.
PMID: 32892623 DOI: 10.1021/acs.jnatprod.0c00772
Abstract

Two new macrolides, formicolides A (1) and B (2), were isolated from Streptomyces sp. BA01, a gut Bacterial strain of the wood ant (Formica yessensis). Their 20-membered macrocyclic lactone structures were established using NMR and mass spectrometric data. The relative configurations of the formicolides were determined by J-based configuration analysis utilizing ROESY, HETLOC, and HECADE NMR spectroscopic data. Genomic and bioinformatics analysis of the Bacterial strain enabled us to identify the type-I polyketide synthase pathway employing a trans-acyltransferase system. The absolute configurations of 1 and 2 are proposed based on detailed analysis of the sequences of the ketoreductases in the modular gene cluster and statistical comparative analysis of the experimental NMR chemical shifts and quantum mechanical calculations. Formicolides A and B (1 and 2) induced quinone reductase activity in murine Hepa-1c1c7 cells and antiangiogenic activity by suppression of tube formation in human umbilical vein endothelial cells.

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