Celenamides A and B, linear peptide alkaloids from the sponge Cliona celata

Stonard, Richard J.; Andersen, Raymond J.

doi:10.1021/jo01306a029

Cited by 77 publications

(30 citation statements)

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“…The crude sponge metabolites were extracted, acetylated, and the acetylated residue fractionated on a column of silica gel G as previously described (1). Pure pentacetylcelenamide C (12; 12 mg, -0.003% wet weight) and nonacetylcelenarnide D (13; 10 mg, -0.002% wet weight) were obtained as noncrystalline solids following repeated silica ptlc (20 x 20 cm, 1.0 mm) using chloroform-methanol (14: 1) as the developing solvent.…”

Section: Methodsmentioning

confidence: 99%

Linear peptide alkaloids from the sponge Clionacelata (Grant). Celenamides C and D

Stonard¹,

Andersen²

1980

Can. J. Chem.

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. Can. J. Chem. 58,2121Chem. 58, (1980. Celenam~des C (7) and D (8), two novel alkaloids closely related to peptide alkaloids found in higher plants, have been isolated as their penta (12) and nonacetyl (13) derivatives, respectively, from acetylated extracts of the sponge Cliona celata (Grant). The structure elucidation of 7 and 8 is described. On a isolt deux nouveaux alcaloi'des les ctlenamides C (7) et D (8) qui s'apparentent beaucoup aux alcaloi'des peptidiques que I'on trouve dans les plantes superieures. On les obtient sous forme de dtrives penta (12) et non acttyles (13) a partir des extraits acetyles de I'tponge Cliona celata (Grant). On decrit la determination de la structure des composes 7 et 8.

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Section: Methodsmentioning

confidence: 99%

Linear peptide alkaloids from the sponge Clionacelata (Grant). Celenamides C and D

Stonard¹,

Andersen²

1980

Can. J. Chem.

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“…Samples were prepared by dissolving 10 mg of the N-alkenylamide in 700 µl of deuterated solvent (DMSOd 6 or DMSO-d 6 -CD 3 CN). All 2D EXSY data were acquired at 300 MHz using a NOESY sequence with the States et al phase-cycling method to generate pure absorption phase spectra.…”

Section: Spectramentioning

confidence: 99%

N‐Alkenyl amide rotational barriers by 2D EXSY NMR

Aguirre

Somanathan

Hellberg

et al. 2003

Magnetic Reson in Chemistry

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“…Many of these compounds have potent pharmacological activities, including anti-tumor, anti-fungal, anti-viral, and anti-bacterial effects (e.g. Schmitz & Gopichand 1978, Stonard & Andersen 1980, Kashman et al 1989. Although the synthesis of these unusual compounds may ultimately be traced to endosymbiotic microorganisms for some sponge species (e.g.…”

Section: Introductionmentioning

confidence: 99%

Defenses of Caribbean sponges against predatory reef fish. I. Chemical deterrency

Pawlik¹,

Chanas²,

Toonen³

et al. 1995

Mar. Ecol. Prog. Ser.

368

361

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Laboratory feeding assays employing the common Canbbean wrasse Thalassoma bifasciatum were undertaken to determine the palatability of food pellets containing natural concentrations of crude organic extracts of 71 species of Caribbean demosponges from reef, mangrove, and grassbed habitats. The majority of sponge species (69%) yielded deterrent extracts, but there was considerable inter-and intraspecific vanability in deterrency. Most of the sponges of the aspiculate orders Verongida and Dictyoceratida yielded highly deterrent extracts, as did all the species in the orders Homosclerophorida and Axinellida. Palatable extracts were common among species in the orders Hadromerida, Poecilosclerida and Haplosclerida. Intraspecific variability was evident, suggesting that, for some species, some individuals (or portions thereof) may be chemically undefended. Reef sponges generally yielded more deterrent extracts than sponges from mangrove or grassbed habitats, but 4 of the 10 most common sponges on reefs yielded palatable extracts (Callyspongia vaginalis, Mycale laevis, Niphates erecta, Iotrochota birotulata), including those most commonly eaten by sponge-eating reef fish. The presence of symbiotic zoanthid cnidarians of the genus Parazoanthus in the tissues of otherwise palatable sponges had little effect on the deterrency of tissue extracts, indicating that these commensal polyps do not confer a chemical defense by association There was no relationship between sponge color and deterrency, suggesting that sponges are not aposematic and that color variation is the result of other factors. There was also no relationship between the toxicity of sponge extracts (as determined in previous studies) and deterrency, confirming the invalidity of previous assessments of chemical defense based on toxicity. Although chemical antipredatory defenses are important strategies for most Caribbean sponges, some common species appear to rely on other tactics.

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Celenamides A and B, linear peptide alkaloids from the sponge Cliona celata

Cited by 77 publications

References 0 publications

Linear peptide alkaloids from the sponge Clionacelata (Grant). Celenamides C and D

Linear peptide alkaloids from the sponge Clionacelata (Grant). Celenamides C and D

N‐Alkenyl amide rotational barriers by 2D EXSY NMR

Defenses of Caribbean sponges against predatory reef fish. I. Chemical deterrency

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