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Chlorosphaerolactylates A-D: The Natural Chlorinated Lactylates Isolated from the Portuguese Cyanobacterium Sphaerospermopsis Sp. LEGE 00249

submitted on 15.01.2020, 17:20 and posted on 20.01.2020, 05:31 by Ignacio Gutiérrez-del-Río, Nelly B. de Fraissinette, Raquel Castelo-Branco, Flavio Oliveira, João Morais, Saúl Redondo-Blanco, Claudio J. Villar, María José Iglesias, Raquel G. Soengas, Virginio Cepas, Yuly López Cubillos, Giacomo Sampietro, Liliana Rodolfi, Felipe Lombó, Sara M. Soto González, Fernando López Ortiz, Vitor M. Vasconcelos, Mariana Reis
The unprecedented natural chlorinated lactylates, chlorosphaerolactylates A-D (1-4), were isolated from the methanolic extract of the cyanobacterium Sphaerospermopsis sp. LEGE 00249 through a combination of bioassay-guided and MS-guided approaches. Compounds 1-4 are esters of (mono-, di- or tri-)chlorinated lauric acid and lactic acid, whose structures were assigned on the basis of spectrometric and spectroscopic methods inclusive of 1D and 2D NMR experiments. High-resolution mass-spectrometry datasets also demonstrated the existence of other minor components that were identified as chlorosphaero(bis)lactylate analogues. The chlorosphaerolactylates were tested for potential antibacterial, antifungal and antibiofilm properties using bacterial and fungal clinical isolates. Compounds 1-4 inhibited the growth of Staphylococcus aureus S54F9 and Candida parapsilosis SMI416, as well as, affected the biofilm formation of coagulase-negative Staphylococcus hominis FI31.


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