Cembrane and pseudopterane diterpenoids of the octocoral Pseudopterogorgia acerosa

Chan, W. R.; Tinto, Winston F.; Laydoo, Richard S.; Manchand, Percy S.; Reynolds, William F.; McLean, Stewart

doi:10.1021/jo00005a022

Cited by 35 publications

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“…52, 58-63, 627-631, 640-644 [24,29,179,184] Eunicea pinta 333-340 [104] Eunicea knighti 163-165 [63] Eunicea mammosa 161, 162, 203, 321-332 [62,[100][101][102][103] Eunicea succinea 158-160, 202, 311-320, 620 [61,98,99] Eunicea tourniforti 36-39 [19] Leptogorgia sp. 482-487, 519 [147,148] Leptogorgia alba 473, 474 [138] Leptogorgia laxa 155, 156 [59] Leptogorgia setacea 475, 476 [142] Lophogorgia peruana 157, 462-471, 526 [60,[137][138][139][140]143] Pseudopterogorgia sp. 532 [159] Pseudopterogorgia bipinnata 531, 619 [158] Pseudopterogorgia kallos 527-530 [134] Gorgonacea Plexaura flexuvsa 557 [163] Sea pen Gyrophyllum sibogae 66, 67 [31] Pseudopterogorgia acerosa 477 [143] Tetralophuzia setifomis 106 […”

Section: Resultsmentioning

confidence: 99%

“…482-487, 519 [147,148] Leptogorgia alba 473, 474 [138] Leptogorgia laxa 155, 156 [59] Leptogorgia setacea 475, 476 [142] Lophogorgia peruana 157, 462-471, 526 [60,[137][138][139][140]143] Pseudopterogorgia sp. 532 [159] Pseudopterogorgia bipinnata 531, 619 [158] Pseudopterogorgia kallos 527-530 [134] Gorgonacea Plexaura flexuvsa 557 [163] Sea pen Gyrophyllum sibogae 66, 67 [31] Pseudopterogorgia acerosa 477 [143] Tetralophuzia setifomis 106 […”

Section: Resultsmentioning

confidence: 99%

“…Pukalide (472), isolated from the soft coral Sinularia abrupt, is a diterpenoid with a cembrane skeleton, bearing butenolide, epoxide, isopropenyl, and an unprecedented , -disubstituted furan--carboxylate function [141]. Thirteen highly oxygenated cembranolides, which are structurally similar to pukalide, were isolated including 13-acetoxypukalide (473), pukalide aldehyde (474) [138], 11b,12b-epoxypukalide (475), and unnamed furanocembranoid (476) [142], acerosolide (477) [143], sethukarailin (478), sethukarailide (479) [144], danielid (480), 3 -ethoxyfuranocembranoid (481) [145], unnamed furanocembranoid (482) [146], leptodiol(483), acetate of leptodiol(484), 8-epiLopholide (485) [147]. Three furanocembranolides, (Z)-deoxypukalide (486), (E)-deoxypukalide (487), and isopukalide (488) were isolated from Leptogorgia spp.…”

Section: Furanocembranoidsmentioning

confidence: 99%

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Cembrane Diterpenes Chemistry and Biological Properties

Yang¹,

Zhou²,

Lin³

et al. 2012

COC

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Furanocembranoidsmentioning

confidence: 99%

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Cembrane Diterpenes Chemistry and Biological Properties

Yang¹,

Zhou²,

Lin³

et al. 2012

COC

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“…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%

“…Furanocembranolides have been previously isolated from several species of the orders Alcyonacea (Sinularia abrupta, S. polydactyla, S. dissecta and Gersemia rubiformis) and Gorgonacea (Lophogorgia alba, L. cuspidata, L. rigida, L. chilensis, Leptogorgia setacea, Pseudopterogorgia acerosa and Phyllogorgia dilatata) 21,[27][28][29][33][34][35][36][37][38] . To date, compounds 2, 4 and 5 have only been found in Lophogorgia species.…”

Section: Palatability Field Assaysmentioning

confidence: 99%

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

Epifanio¹,

Maia²,

Fenical³

2000

J. Braz. Chem. Soc.

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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.

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Cnidaria and Ctenophora–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Membrane Constituents and Secondary Metabolites of Hexacorallia (Anthozoa) Fatty Acids, Oxylipins, and Acetylenic Derivatives Sterols and Ecdysteroids Terpenes Carotenoids of Sea Anemones Aromatic Derivatives Ceramides and Lipidic α‐Amino Acids Examples of Nitrogenous Pigments: Zoanthoxanthins and Calliactine Palytoxins ( PTXs ) Mycosporines Betaines, Phosphobetaines, Purines, and Other Nitrogen‐Containing Derivatives Zoanthamine Alkaloids Cytolysins, Neuropeptides, and Other Venoms of Sea Anemones Venoms and Other Metabolites of Medusozoa Some Data on the Cubozoa and Other Jellyfish Bioluminescence of Jellyfish and Other Cnidaria Some Results on the Secondary Metabolites of Other Hydrozoa Ctenophora

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Cembrane and pseudopterane diterpenoids of the octocoral Pseudopterogorgia acerosa

Cited by 35 publications

References 0 publications

Cembrane Diterpenes Chemistry and Biological Properties

Cembrane Diterpenes Chemistry and Biological Properties

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

Cnidaria and Ctenophora–2

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