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  • Chemistry  (1)
  • cembranoid  (1)
  • competition  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Variability of terpene content in the soft coralSinularia flexibilis (Coelenterata: Octocorallia), and its ecological implications (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2285-2296 
    Details
    ISSN: 1573-1561
    Keywords: Allelopathy ; diterpenes ; soft corals ; Sinularia flexibilis ; Coelenterata ; Octocorallia ; variability ; competition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Colonies of the soft coralSinularia flexibilis (Quoy & Gaimard) (Coelenterata, Octocorallia) were collected at Lizard Island (14°40′S and 145°28′E) Research Station. Extraction of the corals and quantitative chemical analysis for the three major diterpene components, flexibilide, dihydroflexibilide, and sinulariolide, afforded average ratios of 4∶3∶1 respectively. Colonies, sized on the basis of the sterile stalk circumference, were analyzed for possible correlations between size and chemical composition. The major metabolite, flexibilide, was inversely correlated with colony size, while sinulariolide concentration showed a direct correlation. The concentration of dihydroflexibilide was independent of colony size. Samples were further analyzed with respect to site of collection. Colonies were collected at three distinct reefal sites. One was characterized by large monospecific stands ofParites cylindrica, a second was a sandy bottom site with a mixed community of soft corals and occasional scleractinians, while the third site was a very diverse reef community with many species of scleractinian corals.Sinularia flexibilis was well represented at each site, and the concentration of flexibilide and sinulariolide varied significantly among sites. The concentration of flexibilide was significantly higher at the third, highly competitive site, while the concentration of sinulariolide was highest at thePorites-dominated site. Dihydroflexibilide levels were independent of site. It seems likely that concentrations of flexibilide, a highly cytotoxic molecule involved in interference competition, and sinulariolide, a known algicide probably responsible for colony maintenance, may be influenced by their environments.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00979664
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  • 2
    Electronic Resource
    Electronic Resource
    Pukalide, a widely distributed octocoral diterpenoid, induces vomiting in fish (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 2697-2704 
    Details
    ISSN: 1573-1561
    Keywords: Key Words ; Vomiting ; emesis ; terpenoid ; cembranoid ; octocoral ; pukalide ; fish
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Tissue and extractable metabolites from the subtropical gorgonianLeptogorgia virgulata (Coelenterata: Anthozoa: Octocorallia: Gorgonacea) induce vomiting in a variety of fish species. To elucidate the chemical bases of this phenomenon, experiments were undertaken with purified pukalide, a cembranoid diterpene that comprises as much as 0.1–0.5% of the wet tissue weight ofL. virgulata. When incorporated into artificial foods at concentrations corresponding to the levels found inL. virgulata, pukalide induced emesis when delivered orally to killifish (Fundulus heteroclitus). The threshold dose for pukalide-induced emesis was 0.05 mg/g fish body weight. Control pellets devoid of pukalide did not induce vomiting. The emetic effect of pukalide was dose-dependent, as fish ingesting more than 0.100 mg pukalide/ g body weight exhibited a significantly higher incidence of vomiting than fish ingesting lower doses of pukalide (G=5.5,df=1,P〈0.025). The elapsed time between ingestion of pukalide-containing pellets and emesis was significantly longer in fish that ingested marginally emetic doses of pukalide (Kruskal-WallisH=4.00, significant withP〈0.05). Although not markedly unpalatable to fish, pukalide may function in nature as a defensive toxin by inducing emesis and learned aversion in potential octocoral predators.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00980701
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  • 3
    Electronic Resource
    Electronic Resource
    The mass spectra of some C-19 modified 5α-cholestane derivatives (1970)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 4 (1970), S. 373-382 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectra of twenty-seven C-19 modified cholestane derivatives have been determined, and have been compared with the mass spectra of similar compounds reported1 in the cholesteryl series. In the spectra of 2α,19-dihydroxy-5α-cholestane (la), initial loss of the 10β-hydroxymethyl group was observed followed by loss of water, whereas with the 2α-methoxy and 2α-acetoxy derivatives (Ib, Ic), loss of the 2α-substituent as methanol and acetic acid respectively, preceded the elimination of the 10β-hydroxymethyl group. Loss of the 10β-hydroxymethyl group was also observed in Δ1-, Δ2- and 2-oxo derivatives (VI, Va and VII), whilst loss of both the 1 substituent and the 10β-hydroxymethyl group from the molecular ion was observed with the 1α-ol (IIa) and the 1β-yl-chloride (III).In a series of 19-acetoxy derivatives loss of acetic acid [M - 60] from the 19-acetoxy group, involving abstraction of a sterically favourable hydrogen, always occurred, although this was usually accompanied by loss of the 10β-acetoxymethyl residue [M - 73].The mass spectra of a series of 10β-carboxylic acids and their methyl esters were more complex with three or more fragmentation patterns being observed. 1,3-Diaxial interactions, similar to those observed in chemical reactions, were observed in the mass spectra of three 2β-oxygenated-19-substituted compounds.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210040140
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    Paper (German National Licenses)
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