Ectyoplasin, a novel cytotoxic cyclic peptide from Ectyoplasia ferox sponge

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 spectrome...

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Bibliographic Details
Published in:Natural product research 2022-08, Vol.36 (15), p.3957-3964
Main Authors: Ortiz-Celiseo, Araceli, Valerio-Alfaro, Gerardo, Sosa-Rueda, Javier, López-Fentanes, Fernando C., Domínguez-Melendez, Vanihamin, Cen-Pacheco, Francisco
Format: Article
Language:English
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
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Summary: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.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2021.1902326