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Comparative Structure–Activity Analysis of the Antimicrobial Activity, Cytotoxicity, and Mechanism of Action of the Fungal Cyclohexadepsipeptides Enniatins and Beauvericin

1
Centrale Marseille, CNRS, iSm2 UMR 7313, Aix Marseille University, 13397 Marseille, France
2
Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon
3
Doctoral School of Science and Technology, PRASE, Lebanese University, Beirut 5, Lebanon
*
Authors to whom correspondence should be addressed.
Toxins 2019, 11(9), 514; https://doi.org/10.3390/toxins11090514
Received: 16 August 2019 / Revised: 27 August 2019 / Accepted: 2 September 2019 / Published: 3 September 2019
(This article belongs to the Section Mycotoxins)
Filamentous fungi, although producing noxious molecules such as mycotoxins, have been used to produce numerous drugs active against human diseases such as paclitaxel, statins, and penicillin, saving millions of human lives. Cyclodepsipeptides are fungal molecules with potentially adverse and positive effects. Although these peptides are not novel, comparative studies of their antimicrobial activity, toxicity, and mechanism of action are still to be identified. In this study, the fungal cyclohexadepsipeptides enniatin (ENN) and beauvericin (BEA) were assessed to determine their antimicrobial activity and cytotoxicity against human cells. Results showed that these peptides were active against Gram-positive bacteria, Mycobacterium, and fungi, but not against Gram-negative bacteria. ENN and BEA had a limited hemolytic effect, yet were found to be toxic at low doses to nucleated human cells. Both peptides also interacted with bacterial lipids, causing low to no membrane permeabilization, but induced membrane depolarization and inhibition of macromolecules synthesis. The structure–activity analysis showed that the chemical nature of the side chains present on ENN and BEA (either iso-propyl, sec-butyl, or phenylmethyl) impacts their interaction with lipids, antimicrobial action, and toxicity. View Full-Text
Keywords: cyclic fungal peptides; cyclohexadepsipeptide; enniatin; beauvericin; mycotoxin; antibiotic; antimicrobial peptide; AMP; Clostridium perfringens cyclic fungal peptides; cyclohexadepsipeptide; enniatin; beauvericin; mycotoxin; antibiotic; antimicrobial peptide; AMP; Clostridium perfringens
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MDPI and ACS Style

Olleik, H.; Nicoletti, C.; Lafond, M.; Courvoisier-Dezord, E.; Xue, P.; Hijazi, A.; Baydoun, E.; Perrier, J.; Maresca, M. Comparative Structure–Activity Analysis of the Antimicrobial Activity, Cytotoxicity, and Mechanism of Action of the Fungal Cyclohexadepsipeptides Enniatins and Beauvericin. Toxins 2019, 11, 514.

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