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Formicins, <i>N</i>-Acetylcysteamine-Bearing Indenone Thioesters from a Wood Ant-Associated Bacterium

Young Eun Du, Woong Sub Byun, Seok Beom Lee, Sunghoon Hwang, Yern‐Hyerk Shin, Bora Shin, Yong-Joon Jang, Suckchang Hong, Jongheon Shin, Sang Kook Lee, Dong‐Chan Oh

2020Organic Letters33 citationsDOI

Abstract

Formicins A–C (1–3) were discovered from Streptomyces sp. associated with wood ants. The structures of 1 and 2 were elucidated as indenone thioesters bearing N-acetylcysteamine based on spectroscopic analysis. The configurations of 1–3 were determined by the analysis of ROESY correlations, the phenylglycine methyl ester method, and chemical derivatization from 3 to 2. Formicin A inhibited the growth of human triple-negative breast cancer cells by regulating the liver kinase B1-mediated AMPK signaling pathway.

Topics & Concepts

ChemistryBacteriaANTDerivatizationStereochemistryBiochemistryOrganic chemistryBiologyEcologyGeneticsHigh-performance liquid chromatographyMicrobial Natural Products and BiosynthesisFungal Biology and ApplicationsAntimicrobial Peptides and Activities
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