Steroidal Compounds from the Caribbean Octocoral Eunicea laciniata

D’Armas, Haydelba; Mootoo, Baldwin S.; Reynolds, William F.

doi:10.1021/np000315s

Cited by 19 publications

(18 citation statements)

References 10 publications

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“…The detailed analysis of other HMBC correlations and an agreement of the 13 C-NMR chemical shifts of 1 with the reported data led to assignment of 1 as 3βhydroxyergosta-5,24(28)-diene-7-one [12]. [14]. The HMBC cross peaks of H-19 (δ H 1.17) with C-1 (δ C 36.47)/C-5 (δ C 145.17)/C-9 (δ C 53.96)/C-10 (δ C 36.04) and H-6 (δ H 4.02) with C-4 (δ C 128.40)/C-8 (δ C 29.72)/C-10 (δ C 36.04) confirmed positions of the double bond at C-4/C-5 and the hydroxy group at C-6.…”

Section: Extraction and Isolationsupporting

confidence: 57%

Structure Elucidation of Four Steroids From the Soft Coral Sinularia Nanolobata

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et al. 2017

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Section: Extraction and Isolationsupporting

confidence: 57%

Structure Elucidation of Four Steroids From the Soft Coral Sinularia Nanolobata

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Thành

Cường

et al. 2017

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“…The fourth sec-methyl signal appeared as a broad singlet at δ H 0.98, assigned to H-21 by heteronuclear single quantum coherence (HSQC), HMBC, and COSY experiments, is also characteristic of a gorgosterol-type side chain possessing a cyclopropane ring. 21,22) Positions of the oxymethine group at C-3 and epoxy group at C-5/C-6 were identified by COSY cross-peaks of H 2 -1/H 2 -2/H-3/H 2 -4 as well as HMBC cross-peaks of H-19 (δ H 1.00) with C-1 (δ C 37.2), C-5 (δ C 62.9), C-9 (δ C 51.4), and C-10 (δ C 34.9) and H b -4 (δ H (Fig. 2) clearly confirmed the planar structure of 2.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Steroids from the Vietnamese Soft Coral Sinularia leptoclados

et al. 2017

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Fifteen steroids, including two new compounds, leptosteroid (1) and 5,6β-epoxygorgosterol (2), were isolated and structurally elucidated from the Vietnamese soft coral Sinularia leptoclados. Their cytotoxic effect against a panel of eight human cancer cell lines was evaluated using sulforhodamine B (SRB) method. Key words Sinularia leptoclados; Alcyoniidae; soft coral; steroid; cytotoxic activityThe phylum Cnidaria includes about 10000 species which are traditionally divided into three classes: Anthozoa, Hydrozoa, and Scyphozoa. The best-known representatives of the class Anthozoa are the gorgonians and soft corals among the subclass Octocorallia and the sea anemones and stony corals among the subclass Hexacorallia. Soft corals attracted considerable attention because of the wide range of their bioactive secondary metabolites. In these marine invertebrates, genus Sinularia (phylum Cnidaria, class Anthozoa, subclass Octocorallia, order Alcyonacea) is one of the most widely distributed soft corals and constitutes a dominant portion of the biomass in the tropical reef environment.1,2) Sinularia soft corals are a rich source of steroids and terpenoids. 2-5)As a part of our ongoing investigations on cytotoxic steroids from Vietnamese Sinularia soft corals, [6][7][8] this paper addressed the isolation, structure elucidation, and cytotoxic evaluation of fifteen steroids, including two new compounds, leptosteroid (1) and 5,6β-epoxygorgosterol (2), from the soft coral S. leptoclados. Results and DiscussionUsing various chromatographic separations, fifteen steroids (Fig. 1) were isolated from a methanol extract of the soft coral S. leptoclados. The known compounds, 7-oxogorgosterol (3), 6) crassumsterol (4), 9) 7β-hydroxygorgosterol (5), 10) sarcophytosterol (6), 11) 3β-hydroxyergosta-5-ene-7-one (7), 12) ergost-5-en-3β,7β-diol (8), 13) ergost-5-en-3β,7α-diol (9), 14,15) ergosta-5,24(28)-diene-3β-ol (10), 16) 3β-hydroxyergost a-5,24(28)-diene-7-one (11), 17,18) ergosta-5,22,24(28)-trien-3β-ol (12), 19) 3β,7β-dihydroxyergosta-5,24(28)-diene (13), 20) 3β,7α-di hydroxyergosta-5,24(28)-diene (14), 20) and 3β,4α-dihydroxyergosta-5,24(28)-diene (15), 7) were identified by detailed analysis of their one and two dimensional (1-and 2D)-NMR and MS data as well as comparison of them with those reported in the literatures.Leptosteroid (1) was isolated as a white powder with molecular formula of C 29 H 48 O 3 , determined by high-resolution electrospray ionization (HR-ESI)-MS at m/z 445.36819 [M+H]

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“…En lo referente a la biosíntesis de terpenos en moluscos, se han aislado diterpenos diacilglicéridos con importante actividad biológica en Austrodoris kerguelencis (Davies-Coleman & Faulkner 1991), posiblemente utilizados por este organismo como mecanismo de defensa. También se ha informado sobre la presencia de esteroles en moluscos (Pastoriza 1981) y en octocorales, siendo más destacados los derivados del gorgosterol en E. laciniata (D'Armas et al 2000); así como el acerosterol (John & Tinto 1993) y el 9,11-secogorgost-5-en-9-ona-3β,11-diol (Wayne & Clardy 1995), aislados de las especies P. acerosa y P. hummelinkii, respectivamente. Por otro lado, la presencia de saponinas fue detectada sólo en el extracto de Muricea sp., lo cual confirma que este género de gorgonio puede biosintetizar esta familia química de metabolitos, tal y como se ha informado para la especie M. fruticosa, de la cual se aislaron dos únicas saponinas aminogalactosas que contienen agliconas derivadas del pregnano, llamadas muricin-1 y muricin-2 (Bandurraga & Fenical 1983).…”

Section: Discussionunclassified

Metabolitos secundarios, letalidad y actividad antimicrobiana de los extractos de tres corales y tres moluscos marinos de Sucre, Venezuela

Ordaz¹,

D’Armas²,

Yañez³

et al. 2009

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Secondary metabolites, lethality and antimicrobial activity of extracts from three corals and three marine mollusks from Sucre, Venezuela. The study of biochemical activity of extracts obtained from marine organisms is gaining interest as some have proved to have efficient health or industrial applications. To evaluate lethality and antimicrobial activities, some chemical tests were performed on crude extracts of the octocorals Eunicea sp., Muricea sp. and Pseudopterogorgia acerosa and the mollusks Pteria colymbus, Phyllonotus pomum and Chicoreus brevifrons, collected in Venezuelan waters. The presence of secondary metabolites like alkaloids, unsaturated sterols and pentacyclic triterpenes in all invertebrates, was evidenced. Additionally, sesquiterpenlactones, saponins, tannins, cyanogenic and cardiotonic glycosides were also detected in some octocoral extracts, suggesting that biosynthesis of these metabolites is typical in this group. From the lethality bioassays, all extracts resulted lethal to Artemia salina (LC 50 <1.000μg/ml) with an increased of lethal activity with exposition time. P. pomum extract showed the highest lethality rate (LC 50 =46.8μg/ml). Compared to the octocorals, mollusks extracts displayed more activity and a greater action spectrum against different bacterial strains, whereas octocorals also inhibited some fungi strains growth. Staphylococcus aureus was the most susceptible to the antimicrobial power of the extracts (66.7%), whereas Pseudomonas aeruginosa, Candida albicans and Aspergillus niger were not affected. The antibiosis shown by marine organisms extracts indicates that some of their biosynthesized metabolites are physiologically active, and may have possible cytotoxic potential or as a source of antibiotic components. Rev. Biol. Trop. 58 (2): 677-688. Epub 2010 June 02.

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Steroidal Compounds from the Caribbean Octocoral Eunicea laciniata

Cited by 19 publications

References 10 publications

Structure Elucidation of Four Steroids From the Soft Coral Sinularia Nanolobata

Structure Elucidation of Four Steroids From the Soft Coral Sinularia Nanolobata

Cytotoxic Steroids from the Vietnamese Soft Coral <i>Sinularia leptoclados</i>

Metabolitos secundarios, letalidad y actividad antimicrobiana de los extractos de tres corales y tres moluscos marinos de Sucre, Venezuela

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