Cytotoxic cembranoids from the gorgonian pseudopterogorgia bipinnata

Wright, Amy E.; Burres, Neal S.; Schulte, Gayle K.

doi:10.1016/s0040-4039(00)99421-8

Cited by 50 publications

(76 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The 2,3 J CH cross peaks observed in the HMBC spectrum between the acetyl carbonyl carbon at δ C 169.7 (C-23) and the hydrogens of the methyl group at δ H 2.13 (s, H-24) and the methine at 6.18 (s, H-7), as well as between the carbon signal at δ C 73.6 (C-8) and the hydrogens at δ H 6.18 (s, H-7), 1.75 (dd, J = 15.0 and 6.0 Hz, H-9b) and 1.41 (s, H-19) confirmed the 7-acetoxyl, 8-hydroxyl substitution pattern. The relative stereochemistry of 4 was deduced based on the coupling constants between H-9b, H-10 and H-11, 1 H-1 H NOESY (300 MHz, CDCl 3 ) data and comparison with literature observations obtained for related compounds 33 .…”

Section: Isolation and Structure Elucidation Of Diterpenesmentioning

confidence: 99%

“…The assignment of the hydroxyl carbon bearing at C-8 was also corroborated by HMBC correlations between δ C 71.6 (C-8) with δ H 5.35 (H-7) and 1.54 (H-19). As for the diterpene 4, the relative stereochemistry of 5 was proposed on the basis of 1 H-1 H coupling constants, by 1 H-1 H NOESY experiments (300 MHz, CDCl 3 ) and comparison with literature data 27,29,33 .…”

Section: Isolation and Structure Elucidation Of Diterpenesmentioning

confidence: 99%

“…Fractions B and C were rich in furanocembranolide diterpenes, a class of natural products comprising over 16 diterpenoids which has been exclusively isolated from octocorals 21,[27][28][29][33][34][35][36][37][38] . Only three of these compounds have been previously investigated as icthyodeterrents ( Figure 2) [11][12][13][14] .…”

Section: Palatability Field Assaysmentioning

confidence: 99%

See 2 more Smart Citations

Chemical defenses of the endemic Brazilian gorgonian Lophogorgia violacea Pallas (Octocorallia, Gorgonacea)

Epifanio¹,

Maia²,

Fenical³

2000

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

O mecanismo de defesa contra predadores no octocoral brasileiro Lophogorgia violacea foi investigado através de ensaios de preferência alimentar em campo frente a predadores. Os ensaios de palatabilidade com o extrato bruto da gorgônia demonstraram que seus metabólitos secundários possuem atividade deterrente significativa frente a peixes generalistas. O fracionamento do extrato bruto, guiado pelos ensaios em campo, revelou que uma mistura complexa de furanocembranolídeos é a responsável pela defesa química de L. violacea. O diterpeno lophotoxina (1) foi a principal substância isolada, seguida por outras duas similares, deoxilophotoxina (2) e 13-acetoxi-11β,12β-epoxipukalídeo (3), além de dois furanocembranolídeos inéditos na literatura, 7-acetoxi-8-hidroxilophotoxina (4) e 3-metoxi-8-hidroxilophotoxina (5). A lophotoxina (1), uma importante neurotoxina, originalmente isolada de L. rigida do Pacífico, demonstrou ser a mais potente dentre as substâncias fagoinibidoras presentes no extrato bruto. Por outro lado, os outros quatro furanocembranolídeos isolados também parecem contribuir, de maneira aditiva, para a atividade total observada. Estes resultados corroboram estudos prévios, confirmando que furanocembranolídeos são uma classe de substâncias de defesa frente ao consumo por peixes em ambientes tropicais e temperados.The chemical defenses of the Brazilian gorgonian octocoral Lophogorgia violacea Pallas have been investigated using feeding preference experiments performed in situ with an ecologically relevant, natural assemblage of predatory fishes. Feeding experiments incorporating the crude extract of the animal into palatable foods showed that the organic constituents of L. violacea provide a powerful chemical deterrence toward consumption by generalist fish carnivores. Bioassayguided fractionation of the extract and evaluation of the fractions and purified compounds obtained in the same in situ assay revealed that a complex mixture of furanocembranolides was responsible for the overall feeding deterrence observed. The most potent feeding deterrent identified was lophotoxin (1), followed by two previously reported and structurally related compounds, deoxylophotoxin (2), and 13-acetoxy-11β,12β-epoxypukalide (3), as well as two new furanocembranolides: 7-acetoxy-8-hydroxylophotoxin (4) and 3-methoxy-8-hydroxylophotoxin (5). Lophotoxin (1), a neurotoxin originally isolated from the Pacific gorgonian L. rigida, was the most potent feeding deterrent among the furanocembranolides isolated. However, the four other related furanocembranolides (2-5) appear to contribute, in an additive manner, to the overall deterrent effects observed. These results add to earlier studies providing further evidence that compounds of this structural class provide effective chemical defenses against fish predators in both temperate and tropical environments.

show abstract

Section: Isolation and Structure Elucidation Of Diterpenesmentioning

confidence: 99%

Section: Isolation and Structure Elucidation Of Diterpenesmentioning

confidence: 99%

Section: Palatability Field Assaysmentioning

confidence: 99%

See 1 more Smart Citation

Chemical defenses of the endemic Brazilian gorgonian Lophogorgia violacea Pallas (Octocorallia, Gorgonacea)

Epifanio¹,

Maia²,

Fenical³

2000

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…In addition, these natural products typically feature a butenolide moiety encompassing C10-C12, as well as C20, which is why they were isolated from the same gorgonian specimen [131][132][133][134]. A new similar diterpene, rubifolide (459), has been isolated from the soft coral Gersemia rubiformis [135].…”

Section: Furanocembranoidsmentioning

confidence: 99%

Cembrane Diterpenes Chemistry and Biological Properties

Yang¹,

Zhou²,

Lin³

et al. 2012

COC

View full text Add to dashboard Cite

Cembrane-type diterpenoids are a large and structurally varied group of natural products isolated from both terrestrial and marine organisms. The present paper reviews all the metabolites of cembrane diterpenes, reported up to 2010. The natural products discussed in this review can be divided into several different structural families featuring a variety of ring sizes and oxidation patterns. The currently known biological activities will be presented as well.

show abstract

“…Son muchos los compuestos con actividades anticancerígenas y citotóxicas aislados de gorgóneos, especialmente derivados diterpé-nicos (Donovan & Clardy 1982, Wright et al 1989, Rodríguez & Dhasmana 1993, Ortega et al 2002, Wei et al 2004. Por consiguiente, se puede atribuir a los grupos terpenoidales, detectados en los extractos crudos de los octocorales, entre otros metabolitos bioactivos, la actividad letal mostrada por éstos y sus fracciones.…”

Section: Cuadro 5 Actividad Antimicrobiana De Las Fracciones Solublesunclassified

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

RBT

View full text Add to dashboard Cite

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.

show abstract

Cytotoxic cembranoids from the gorgonian pseudopterogorgia bipinnata

Cited by 50 publications

References 4 publications

Chemical defenses of the endemic Brazilian gorgonian Lophogorgia violacea Pallas (Octocorallia, Gorgonacea)

Chemical defenses of the endemic Brazilian gorgonian Lophogorgia violacea Pallas (Octocorallia, Gorgonacea)

Cembrane Diterpenes Chemistry and Biological Properties

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

Contact Info

Product

Resources

About