Chemical defense of crinoids by polyketide sulphates

Rideout, John A.; Smith, Narelle B.; Sutherland, M. D.

doi:10.1007/bf01963951

Cited by 69 publications

(34 citation statements)

References 6 publications

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“…Numerous marine organisms are known to contain toxins (Halstead, 1970(Halstead, , 1978Rideout et al, 1979). Many soft corals (Coelenterata: Alcyonacea) possess an extensive range of unique organic molecules, the majority of which fall into the terpene class of compounds (Tursch et al, 1978;Coll et al, 1980;Coll, 1981).…”

Section: Introductionmentioning

confidence: 99%

Chemical Defences in Soft Corals (Coelenterata: Octocorallia) of the Great Barrier Reef: A Study of Comparative Toxicities

Coll¹,

Barre²,

Sammarco³

et al. 1982

Mar. Ecol. Prog. Ser.

136

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We have tested 136 specimens of soft corals (Coelenterata. Alcyonacea) for toxicity by exposing Gambusia affinis (Vertebrata, Pisces) to aqueous extracts of coral macerate and assessing mortality. Sixty-eight corals were examined in detail utilizing behavioral responses of fish as well as mortality rates to establish relative toxicities among and within coral genera. The responses exhibited by the fish ranged from rapid mortality through slow mortality and varying levels of narcotisation to negligible effects. With respect to individual soft corals, the fish exhibited varying patterns of response through time, and were sorted into 9 distinct groups via multivariate computer analyses according to similarity of these behavioral patterns. Only 2 of the genera tested, Lemnalia and Sarcophyton, were restricted to the most toxic set of groups. A number of genera such as Lobophytum, Sinularia, Nephthea, and Cespitularia had representatives which spanned the entire spectrum of responses from highly toxic to non-toxic. The wide range of toxicity determined for the specimens examined and the fact that approximately 50 % of all specimens were toxic suggests that chemical defences against predation are common in the Alcyonacea of the central region of the Great Barrier Reef. Toxicity, however, occurs significantly less frequently in this group than in those examined from the northern Great Barrier Reef in an earlier study.

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Section: Introductionmentioning

confidence: 99%

Chemical Defences in Soft Corals (Coelenterata: Octocorallia) of the Great Barrier Reef: A Study of Comparative Toxicities

Coll¹,

Barre²,

Sammarco³

et al. 1982

Mar. Ecol. Prog. Ser.

136

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“…Antifeedant Activity of Ptilometric Acid (2) and Its Sulfate (1) in Fish It has been reported that quinone pigments, especially the sulfate forms, provide a chemical mechanism against predatory fish for some species of crinoids. 9) In this study, ptilometric acid 6-O-sulfate (1) showed concentrationdependent antifeedant activity in fish, but ptilometric acid (2) was ineffective (Table 3). Antifeedant activities of 2-butanoyl-3,6,8-trihydroxy-1,4-naphtoquinone (4) and its sulfate (3) could not be measured because of the small sample size.…”

Section: -Carboxylic Acid 6-o-sulfate)mentioning

confidence: 57%

“…Various reports on the quinone pigments of crinoids have been published. 1) At present, the following four groups of polyketidederived pigments, linear and angular naphthopyrones, [2][3][4] 4-acylanthraquinones, [5][6][7] 3-alkylanthraquinones, 6,8) and diametric bianthrones (bianthraquinones and phenanthroperylenequinones) 9,10) are known to occur in crinoids. Some of the quinone pigments in crinoid are present in sulfate form.…”

mentioning

confidence: 99%

New Quinone Sulfates from the Crinoids <i>Tropiometra afra macrodiscus</i> and <i>Oxycomanthus japonicus</i>

et al. 2002

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“…However, secondary metabolites such as quinones may also play a role in chemical defense. Hypericin and gymnochromes are well known for their biological activity (8,24), and antifeedant activities against fish have been reported for structurally related anthraquinone pigments from comatulids (27,28). Previous observations on two extant isocrinids, Endoxocrinus parrae and Neocrinus decorus, suggested that stalked crinoids lack chemical defense against fish predation, supporting the hypothesis that restriction of stalked crinoids to deep-water habitats may have resulted from the Mesozoic radiation of durophagous fishes in shallow seas (29).…”

Section: Resultsmentioning

confidence: 77%

Persistent and widespread occurrence of bioactive quinone pigments during post-Paleozoic crinoid diversification

Wolkenstein

2015

Proc. Natl. Acad. Sci. U.S.A.

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Secondary metabolites often play an important role in the adaptation of organisms to their environment. However, little is known about the secondary metabolites of ancient organisms and their evolutionary history. Chemical analysis of exceptionally well-preserved colored fossil crinoids and modern crinoids from the deep sea suggests that bioactive polycyclic quinones related to hypericin were, and still are, globally widespread in post-Paleozoic crinoids. The discovery of hypericinoid pigments both in fossil and in presentday representatives of the order Isocrinida indicates that the pigments remained almost unchanged since the Mesozoic, also suggesting that the original color of hypericinoid-containing ancient crinoids may have been analogous to that of their modern relatives. The persistent and widespread occurrence, spatially as well as taxonomically, of hypericinoid pigments in various orders during the adaptive radiation of post-Paleozoic crinoids suggests a general functional importance of the pigments, contributing to the evolutionary success of the Crinoidea.crinoids | molecular preservation | marine natural products | polyketides | liquid chromatography-mass spectrometry

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Chemical defense of crinoids by polyketide sulphates

Cited by 69 publications

References 6 publications

Chemical Defences in Soft Corals (Coelenterata: Octocorallia) of the Great Barrier Reef: A Study of Comparative Toxicities

Chemical Defences in Soft Corals (Coelenterata: Octocorallia) of the Great Barrier Reef: A Study of Comparative Toxicities

New Quinone Sulfates from the Crinoids <i>Tropiometra afra macrodiscus</i> and <i>Oxycomanthus japonicus</i>

Persistent and widespread occurrence of bioactive quinone pigments during post-Paleozoic crinoid diversification

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