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Kahalalide F analogues from the mucous secretion of Indian sacoglossan mollusc Elysia ornata

2015; Elsevier BV; Volume: 72; Issue: 5 Linguagem: Inglês

10.1016/j.tet.2015.12.003

1464-5416

Maria Letizia Ciavatta, Prabha Devi, Marianna Carbone, Véronique Mathieu, Róbert Kiss, Agostino Casapullo, Margherita Gavagnin,

Chemical synthesis and alkaloids

Bioassay-guided fractionation of the CHCl3/MeOH extract of Elysia ornata mucus showing antifungal activity led us to isolate kahalalide F (KF) along with two unprecedented related peptides. The structures of kahalalide Z1 (1) and kahalalide Z2 (2), were established by combination of NMR spectroscopic and mass spectrometry data, also including Marfey amino acid analysis. Compounds 1 and 2 displayed significant antimicrobial properties against several fungal pathogens infesting economically important plants, food, and fish, and were also found to inhibit the in vitro growth of a series of cancer cell lines in a comparable fashion with KF.