Ectyoplasin, a novel cytotoxic cyclic peptide from Ectyoplasia ferox sponge

• Published in: Natural product research Vol. 36; no. 15; pp. 3957 - 3964
• Main Authors: Ortiz-Celiseo, Araceli, Valerio-Alfaro, Gerardo, Sosa-Rueda, Javier, López-Fentanes, Fernando C., Domínguez-Melendez, Vanihamin, Cen-Pacheco, Francisco
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.08.2022; Taylor & Francis Ltd
• Subjects: Apoptosis; Cell death; Cervical carcinoma; Cervix; Cyclic heptapeptide; cytotoxic activity; Cytotoxicity; Ectyoplasia ferox; five cell lines; In vitro methods and tests; Leukemia; Lymphocytes T; Magnetic resonance spectroscopy; Mass spectrometry; Mass spectroscopy; Multiple myeloma; NMR; NMR spectroscopy; Nuclear magnetic resonance; Planar structures; Prostate cancer; Sarcoma; Stereochemistry; Tumor cell lines; Cyclic heptapeptide; Ectyoplasia ferox; cytotoxic activity; five cell lines
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2021.1902326

A new cyclic heptapeptide, ectyoplasin (1), was isolated from a methanol extract of the sponge Ectyoplasia ferox. The planar structure of 1, cyclo(-Leu 1 -Asn 2 -Ala 3 -Val 4 -Thr 5 -Pro 6 -Gly 7 -), was determined by one and two-dimensional NMR spectroscopy and high-resolution tandem mass spectrometry. Its absolute stereochemistry was solved by Marfey's method. The in vitro assays show that ectyoplasin (1) possess significant cytotoxic activity (2.9 − 23.5 µM) against the cell lines, DU-145 (human prostate cancer), Jurkat (human T-cell acute leukaemia), MM144 (human multiple myeloma), HeLa (human cervical carcinoma) and CADO-ES1 (human Ewing's sarcoma). The DU-145 cell line showed apoptotic cell death in response to ectyoplasin (1) treatment.