RESUMO
The first taxonomic descriptions of the sponge diversity at El Pelado Marine Protected Area in the province of Santa Elena, Ecuador is reported. Tedania (Tedania) ecuadoriensis Jaramillo & Hajdu, sp. nov. is described from its shallow waters. In addition, Callyspongia (Callyspongia) aff. californica (sensuCruz-Barraza and Carballo 2008; non sensuDickinson 1945) and Cliona aff. euryphylle are reported for the first time. The former species is likely distributed over 4,000 km along the Tropical Eastern Pacific, whereas the latter might be an example of a trans-isthmian lineage. An amended diagnosis for Callyspongia (Callyspongia) and an updated identification key for the subgenera of Callyspongia are provided.
RESUMO
In the search for bioactive marine natural products from zoantharians of the Tropical Eastern Pacific, four new tyrosine dipeptides, named valdiviamides A-D (1-4), were isolated from Antipathozoanthus hickmani, and two new tyramine derivatives, 5 and 6, from Parazoanthus darwini. The phenols of all six tyrosine derivatives are substituted by bromine and/or iodine atoms at the ortho positions of the hydroxyl. The planar structures of these aromatic alkaloids were elucidated from 1D and 2D NMR experiments in combination with HRESIMS data, and the absolute configurations of 1-4 were deduced from comparison between experimental and calculated electronic circular dichroism spectra. As halogenated tyrosine derivatives could represent chemotaxonomic markers of these genera, we decided to undertake the first chemical investigation of another species, Terrazoanthus cf. patagonichus. As expected, no halogenated metabolite was evidenced in the species, but we report herein the identification of two new zoanthoxanthin derivatives, named zoamides E (7) and F (8), from this species. Antimicrobial and cytotoxicity bioassays revealed that valdiviamide B (2) displayed moderate cytotoxicity against the HepG2 cell line with an IC50 value of 7.8 µM.
Assuntos
Antozoários/química , Tirosina/análogos & derivados , Tirosina/farmacologia , Animais , Anti-Infecciosos/farmacologia , Antineoplásicos/farmacologia , Bactérias/efeitos dos fármacos , Linhagem Celular Tumoral , Dicroísmo Circular , Ensaios de Seleção de Medicamentos Antitumorais , Halogenação , Humanos , Testes de Sensibilidade Microbiana , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oceano Pacífico , Tirosina/químicaRESUMO
Two new zoanthamine alkaloids, namely 3-acetoxynorzoanthamine (1) and 3-acetoxyzoanthamine (2), have been isolated from the zoantharian Zoanthus cf. pulchellus collected off the coast of the Santa Elena Peninsula, Ecuador, together with three known derivatives: zoanthamine, norzoanthamine, and 3-hydroxynorzoanthamine. The chemical structures of 1 and 2 were determined by interpretation of their 1D and 2D NMR data and comparison with literature data. This is the first report of zoanthamine-type alkaloids from Zoanthus cf. pulchellus collected in the Tropical Eastern Pacific. The neuroinflammatory activity of all the isolated compounds was evaluated in microglia BV-2 cells and high inhibitory effects were observed in reactive oxygen species (ROS) and nitric oxide (NO) generation.
Assuntos
Alcaloides/química , Alcaloides/farmacologia , Antozoários/química , Azepinas/química , Azepinas/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Inflamação/tratamento farmacológico , Quinolinas/química , Quinolinas/farmacologia , Animais , Espectroscopia de Ressonância Magnética/métodos , Microglia/efeitos dos fármacos , Óxido Nítrico/metabolismo , Espécies Reativas de Oxigênio/metabolismo , EstereoisomerismoRESUMO
Zoantharians represent a group of marine invertebrates widely distributed from shallow waters to the deep sea. Despite a high diversity and abundance in the rocky reefs of the Pacific Ocean, very few studies have been reported on the diversity of this group in the Tropical Eastern Pacific coasts. While molecular techniques recently clarified some taxonomic relationships within the order, the taxonomy of zoantharians is still highly challenging due to a lack of clear morphological characters and confusing use of different data in previous studies. Our first insight into the zoantharian diversity at El Pelado Marine Protected Area - Ecuador led to the identification of six species: Terrazoanthus patagonichus; Terrazoanthus sp.; Antipathozoanthus hickmani; Parazoanthus darwini; Zoanthus cf. pulchellus; and Zoanthus cf. sociatus. A metabolomic approach using UHPLC-HRMS was proven to be very efficient as a complementary tool in the systematics of these species and specialized metabolites of the ecdysteroid and alkaloid families were identified as key biomarkers for interspecific discrimination. These results show good promise for an application of this integrative approach to other zoantharians.
RESUMO
Despite a large occurrence, especially over the Pacific Ocean, the chemical diversity of marine invertebrates belonging to the order Zoantharia is largely underexplored. For the two species of the genus Antipathozoanthus no chemical study has been reported so far. The first chemical investigation of Antipathozoanthus hickmani collected at the Marine Protected Area "El Pelado", Santa Elena, Ecuador, led to the isolation of four new ecdysteroid derivatives named ecdysonelactones. The structures of ecdysonelactones A-D (1-4) were determined based on their spectroscopy data, including 1D and 2D NMR and HRMS. The four compounds of this family of ecdysteroids feature an unprecedented γ-lactone fused at the C-2/C-3 position of ring A. These derivatives exhibited neither antimicrobial nor cytotoxic activities.
Assuntos
Antozoários/química , Ecdisteroides/química , Animais , Ecdisteroides/farmacologia , Equador , Lactonas/química , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Oceano PacíficoRESUMO
The first chemical study of the common species Terrazoanthus onoi, present off the coast of Ecuador, led to the identification of a new family of 2-aminoimidazole alkaloids named terrazoanthines A-C (1-3). Homologues 1 and 2 feature an unprecedented 6-(imidazol-5-yl)benzo[d]imidazole. Acyl substitution pattern and complete configurational assignments were deduced from comparison between experimental and theoretical 13C NMR and ECD data, respectively. These compounds may represent key derivatives in the biosynthesis of zoanthoxanthins.