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. 2021 Mar 5;23(5):1648-1652.
doi: 10.1021/acs.orglett.1c00068. Epub 2021 Feb 16.

Chemical Exchanges between Multilateral Symbionts

Munhyung Bae  1 , Emily Mevers  1 , Gleb Pishchany  1 , Sarah G Whaley  2 , Charles O Rock  2 , David R Andes  3 , Cameron R Currie  4 , Monica T Pupo  5 , Jon Clardy  1
Affiliations

Chemical Exchanges between Multilateral Symbionts

Munhyung Bae et al. Org Lett. .

Abstract

Herein is a report on the molecular exchange occurring between multilateral symbiosis partners-a tit-for-tat exchange that led to the characterization of two new metabolites, conocandin B (fungal-derived) and dentigerumycin F (bacterial-derived). The structures were determined by NMR, mass spectrometry, genomic analysis, and chemical derivatizations. Conocandin B exhibits antimicrobial activity against both the bacterial symbionts of fungus-growing ant and human pathogenic strains by selectively inhibiting FabH, thus disrupting fatty acid biosynthesis.

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Figures

Figure 1.
Figure 1.
Chemical structures of the isolated dentigerumycins and conocandins.
Figure 2.
Figure 2.. Structural characterization of conocandin B and C.
a. Key 2D NMR correlations for conocandin B and C (2 and 3). b. ΔS-R values of MTPA ester (4 and 5) of conocandin B. c. ΔS-R values of MTPA ester (6 and 7) of conocandin C.
Figure 3.
Figure 3.. Antibacterial activity and mechanism of action of conocandin B.
a. MIC values for conocandin B against Pseudonocardia strains and select human pathogens. Abbreviations are as follow: GP, gram positive; and GN, gram negative. b. MIC values for conocandin B against strains of S. aureus that overexpress individual fatty acid biosynthetic genes.
See this image and copyright information in PMC

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