Formicolides A and B, Antioxidative and Antiangiogenic 20-Membered Macrolides from a Wood Ant Gut Bacterium.
Joon Soo AnJi Yun LeeEunji KimHyungju AhnYong-Joon JangBora ShinSunghoon HwangJongheon ShinYeo Joon YoonSang-Kook LeeDong-Chan OhPublished in: Journal of natural products (2020)
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.
Keyphrases
- high resolution
- magnetic resonance
- solid state
- endothelial cells
- high glucose
- electronic health record
- molecular dynamics
- induced apoptosis
- copy number
- big data
- cell cycle arrest
- density functional theory
- molecular docking
- diabetic rats
- mass spectrometry
- signaling pathway
- genome wide
- cell death
- endoplasmic reticulum stress
- oxidative stress
- anti inflammatory
- machine learning
- monte carlo
- gene expression
- deep learning
- transcription factor