Ectyoplasin, a novel cytotoxic cyclic peptide from <i>Ectyoplasia ferox</i> sponge

Ortiz-Celiseo, Araceli; Valerio‐Alfaro, Gerardo; Sosa-Rueda, Javier; López-Fentanes, Fernando C.; Domínguez-Meléndez, Vanihamin; Cen-Pacheco, Francisco

doi:10.1080/14786419.2021.1902326

Cited by 4 publications

(3 citation statements)

References 12 publications

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“…371 As always, many peptidic MNPs were reported from sponges in 2022. Such isolates include subarmigeride A 939 from an Indonesian Suberea, 372 various friomaramides 940, 941 and shagamides 942-947 from an Antarctic Inatella, 373 ectyoplasin 948 from a Mexican Ectyoplasia, 374 cyclopsammocinamide A 949 and B 950 which are of the opposite enantiomeric series to known cyclocinamide A, 375 and a new aciculitin 951 from a Poecillastra dredged from a Japanese sea-mount. 376 Two separate samples of the prolic genus Theonella yielded three theonellapeptolides 952-954 and theonellamide/ theopalauamides 955-957, respectively.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

Carroll,

Copp,

Grkovic

et al. 2024

Nat. Prod. Rep.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

Carroll,

Copp,

Grkovic

et al. 2024

Nat. Prod. Rep.

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“…Compound 39 possesses significant cytotoxic activity against DU-145, Jurkat, MM144, HeLa, and CADO-ES1 cell lines, with IC 50 values ranging from 2.9 to 23.5 µM, being more remarkable against DU-145 cell line with an IC 50 value of 2.91 µM (the positive control, doxorubicin, showed IC 50 values of 10 −7 –10 −8 M). Moreover, it was shown that 39 induced apoptosis in DU-145 cells [ 164 ].…”

Section: New Marine-derived Cyclopeptides Reported From January 2018 ...mentioning

confidence: 99%

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

et al. 2023

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Cyclopeptides are considered as one of the most important classes of compounds derived from marine sources, due to their structural diversity and a myriad of their biological and pharmacological activities. Since marine-derived cyclopeptides consist of different amino acids, many of which are non-proteinogenic, they possess various stereogenic centers. In this respect, the structure elucidation of new molecular scaffolds obtained from natural sources, including marine-derived cyclopeptides, can become a very challenging task. The determination of the absolute configurations of the amino acid residues is accomplished, in most cases, by performing acidic hydrolysis, followed by analyses by liquid chromatography (LC). In a continuation with the authors’ previous publication, and to analyze the current trends, the present review covers recently published works (from January 2018 to November 2022) regarding new cyclopeptides from marine organisms, with a special focus on their biological/pharmacological activities and the absolute stereochemical assignment of the amino acid residues. Ninety-one unreported marine-derived cyclopeptides were identified during this period, most of which displayed anticancer or antimicrobial activities. Marfey’s method, which involves LC, was found to be the most frequently used for this purpose.

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“…The methanolic extract of A. indica (117 g, 2.8 % dry weight) was fractionated by liquidliquid extraction following the Kupchan method. Briefly, the extract was suspended in a methanol/water mixture (MeOH/H2O; 1 L, 1:1) and was successively separated with hexane (Hex; 3 × 1 L), dichloromethane (DCM; 3 × 1 L), and ethyl acetate (EtOAc; 3 × 1 L) (Sigma-Aldrich, St. Louis Mo., USA) to obtain four fractions of increasing polarity (25)(26)(27) . The dichloromethane fraction (21.0 g) was subjected to silica gel 60 column chromatography (5 cm of internal diameter and 35 cm of length) (Merck, Darmstadt, Germany) with Hex:EtOAc (6:4), and, subsequently, in a medium-pressure Lobar LiChroprep-Si60 column (Merck, Darmstadt, Germany) with Hex:Acetone (7:3) as the eluent.…”

Section: Isolation Procedures Of the Compoundsmentioning

confidence: 99%

Acción ixodicida de productos naturales de plantas nativas mexicanas

Sosa-Rueda

Villarauz

Domínguez-Meléndez

et al. 2023

Rev. Mex. Cienc. Pecu.

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This work determined the acaricidal effect of 18 Mexican plants against Rhipicephalus microplus. The results of the larvicidal assay revealed that 5 methanolic extracts produced high activity (86-100 % mortality), 3 extracts exhibited relatively high activity (71-85 % mortality), 2 extracts displayed moderate activity (56-70 % mortality), 2 extracts presented low activity (31-55 % mortality) and 6 extracts showed non-significant acaricidal activity (0-30 % mortality). Extracts inducing >56 % mortality were subsequently assayed against engorged ticks of R. microplus by adult immersion test at a concentration of 5.0% w/v. In general terms, the results on larvae and adult ticks indicated that the methanolic extracts of Annona globiflora, Annona scleroderma, Litchi chinensis and Azadirachta indica showed the greatest activities. The crude extract of A. indica was subjected to chromatographic purification, which has led to the isolation of 3-O-butyl-(-)-epigallocatechin (1), 3-O-butyl-(-)-epicatechin (2), (-)-epigallocatechin (3), (+)-gallocatechin (4), (-)-epicatechin (5), β-sitosterol (6), stigmasterol (7), stigmasterol glucoside (8), triolein (9), azadirachtin A (10), and the octadecanoic acid-tetrahydrofuran-3,4-vinyl ester (11). The isolated compounds' chemical structures were identified by the interpretation of NMR and HRESI-MS spectroscopic data. The isolated compounds were assayed against engorged ticks of R. microplus at a concentration of 6 mM. Based on the results obtained, it was concluded that 3-O-butyl-(-)-epigallocatechin (1), 3-O-butyl-(-)-epicatechin (2), azadirachtin A (10), and octadecanoic acid-tetrahydrofuran-3,4-vinyl ester (11) show the highest effectiveness.

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Ectyoplasin, a novel cytotoxic cyclic peptide from Ectyoplasia ferox sponge

Cited by 4 publications

References 12 publications

Marine natural products

Marine natural products

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

Acción ixodicida de productos naturales de plantas nativas mexicanas

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