Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties

Schulte, Gary R.; Scheuer, Paul J.; McConnell, Oliver J.

doi:10.1002/hlca.19800630805

Cited by 118 publications

(51 citation statements)

References 9 publications

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“…The former is the smaller of the two genera, and only one species has been studied by natural products chemists. This is what is now called Risbecia godefroyana, in which Schulte et al (1980) found two furanosesquiterpenoids of the kind that characterize Hypselodoris (Fig. 9); in this case they are derived from the sponge Dysidea fragilis (Ceractinomorpha: Dictyoceratica: Dysideidae).…”

Section: Nudibranchia: Dendronotacea and Arminaceamentioning

confidence: 99%

“…Gosliner and Johnson (1999) have found that there are two distinct clades, one of which is largely limited to the Indopacific, the other to the Atlantic and Eastern Pacific. Data on the former group seem to be limited to Hypselodoris maridadilus (Schulte et al 1980;Schulte & Scheuer 1982) which contains furanosesquiterpenes called nakafurans, derived from the sponge Dysidea fragilis. Nakafurans have been reported from other chromodorids.…”

Section: Nudibranchia: Dendronotacea and Arminaceamentioning

confidence: 99%

See 1 more Smart Citation

Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranchs (Mollusca: Gastropoda: Opisthobranchia)

Cimino¹,

Ghiselin²

1999

Chemoecology

122

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An evolutionary scenario incorporating recent advances in phylogenetic research begins with an opisthobranch-pulmonate common ancestor that was herbivorous and had some diet-derived chemical defense. The Nudibranchia and their closest relatives, the Notaspidea, form a lineage the ancestors of which had switched to feeding upon sponges and deriving protection from metabolites contained in them. Subsequently there have been repeated shifts in food and defensive metabolites, and trends are evident in the ability to detoxify, sequester and utilize metabolites from food, as well as to synthesize defensive compounds de no6o. The Notaspidea display a minor adaptive radiation that foreshadows a more extensive one in the various lineages of nudibranchs. This review emphasizes changes that have occurred within the Holohepatica, or dorid nudibranchs (order Doridacea). Their sister-group, the Cladohepatica, consists of three other orders, Dendronotacea, Arminacea, and Aeolidiacea, in which there has been a shift from sponges to Cnidaria as food. The Dendronotacea often feed upon Octocorallia, which combine spicules, chemical defense, and stinging capsules and thereby suggest a transition from feeding on sponges. A previous diet of Octocorallia is suggested by the defensive use of prostaglandins in the dendronotacean Tethys fimbria, which eats crustaceans. A shift to bryozoans in some Arminacea is accompanied by use of different metabolites. Dorid nudibranchs evidently began as sponge-feeders, but some lineages have shifted to a variety of other food organisms, and others have specialized in the kind of sponges they feed on and how they do it. There have been shifts to bryozoans (Ectoprocta) and ascidians (Chordata: Urochordata) that track metabolites rather than the taxonomy of the food. There is a crude correlation between the genealogy and the defensive metabolites of the sponge-feeding dorids.De no6o synthesis is well documented in this order and the metabolites are appropriately positioned so as to have an adaptive effect. The hypothesis that the capacity for de no6o synthesis was acquired by gene transfer across lineages is rejected, partly on the basis of different chirality of metabolites in the nudibranchs and their food organisms. Instead it is proposed that there has been a preadaptive phase followed by evolution in a retrosynthetic mode, with selection favoring enzymes that enhance the yield of end products that are already present in the food.

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Section: Nudibranchia: Dendronotacea and Arminaceamentioning

confidence: 99%

Section: Nudibranchia: Dendronotacea and Arminaceamentioning

confidence: 99%

Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranchs (Mollusca: Gastropoda: Opisthobranchia)

Cimino¹,

Ghiselin²

1999

Chemoecology

122

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“…G. hikeurensis and G. cincta look very alike and are brown. Glossodoris nudibranchs typically feed on sponges in the order Dictyoceratida (Schulte et al 1980, Okuda P1 Scheuer 1985. The Dictyoceratida are among several orders of the class Desmospongiae that possess a fibrous rather than a mineral skeleton (Bergquist 1980) tions of the sponge and nudibranch exlst at a depth of 20 to 30 m on a pinnacle known as Sponge Mound in Apra Harbor, Guam (Fig.…”

Section: Study Organisms and Sitesmentioning

confidence: 99%

Chemical defenses of three Glossodoris nudibranchs and their dietary Hyrtios sponges

Rogers¹,

Paul²

1991

Mar. Ecol. Prog. Ser.

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Dorid nudibranchs prey upon sponges, tunicates, and bryozoans which generally contain high levels of secondary metabolites. On Guam, the nudibranch Glossodoris pallida was found in Apra Harbor exclusively on a variety of Hyrt~os erecta sponge containing a high concentration of the secondary metabollte scalaradial. Glossodoris hjkeurensis and G. cincta preyed upon a second variety of H. erecta from Cocos Lagoon which did not contaln scalaradial, but rather had high concentrations of heteronemin, a secondary metabolite that was not found in the variety of H. erecta from Apra Harbor. In laboratory tests, G. pallida strongly preferred H. erecta from Apra Harbor while G. hikeurensis and G. cincta preferred H erecta from Cocos Lagoon. H. erecta from Apra Harbor contained 3 major secondary rnetabolites, scalaradial, deoxyscalarin, and scalarin, as well as several minor metabolites. G. pallida sequestered only 2 of these metabolites, scalaradial and deoxyscalarin. H. erecta from Cocos Lagoon contained primarily heteronemin, whereas its predators G. l~ikeurensis and G. cincta contained heteronemin and episcalaradial. Results of feeding deterrence assays with extracts and isolated metabolites differed when tested toward different predators, indicating that these secondary metabolites may be deterrent toward some but not all potential predators Organlc extracts of the Hyrtios sponges were deterrent at half of natural concentrations in some laboratory and field feeding assays while organic extracts of nudibranchs were never deterrent at half of natural concentrations. Heteronemin deterred feeding by fishes in most assays; however, scalaradial did not deter feeding by predatory fishes in most fleld or laboratory assays and was only deterrent at high concentrations in one assay. Minor metabolites or synergistic effects among sponge metabolltes may play a key role in determining feeding deterrence for these sponges. Glossodoris nudibranchs probably excrete or alter some secondary metabolites from their diets.

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“…The metabolites from the sponges were shown to be taken up and transferred to specialized repugnatorial glands, the mantle dermal formations (MDF's) located along the rim of the mantle near the head and gills (Fontana et al 1994). The only species of Risbecia, now called R. godeffroyana, that has been studied by natural product chemists was found to contain dietary furanosesquiterpenoids (Schulte et al 1980). Little is known about the Ceratosoma secondary metabolism that seems to be similar to that of Hypselodoris and Risbecia even though the reported results could seem ambigous.…”

Section: Introductionmentioning

confidence: 99%

Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn

et al. 2005

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Two Furanosesquiterpene Marine Metabolites with Antifeedant Properties

Cited by 118 publications

References 9 publications

Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranchs (Mollusca: Gastropoda: Opisthobranchia)

Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranchs (Mollusca: Gastropoda: Opisthobranchia)

Chemical defenses of three Glossodoris nudibranchs and their dietary Hyrtios sponges

Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn

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