Defense allomones of some marine mollusks

Schulte, Gary R.; Scheuer, Paul J.

doi:10.1016/0040-4020(82)80034-3

Cited by 58 publications

(48 citation statements)

References 32 publications

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“…Schulte & Scheuer (1982) found spiniferin-2 ( Fig. 9), which had already been reported from a sponge, Pleraplysilla spinifera (Ceractinomorpha: Dendroceratida: Aplysillidae); the sponge also contains longifolin, which has been recovered from Hypselodoris 6illafranca (not Glossodoris gracilis) and Hypselodoris picta (not Glossodoris 6alenciennesi ).…”

Section: Nudibranchia: Dendronotacea and Arminaceamentioning

confidence: 98%

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: 98%

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

Cimino¹,

Ghiselin²

1999

Chemoecology

122

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“…The skin extracts of many dorid nudibranchs contain novel metabolites, some of which are believed to function as chemical antifeedants (1). Recently, two of us reported the isolation of triophamine from the dorid Triopha catalinae and showed 2 that this metabolite possesses the unique diacylguanidine structure shown in 1 (2).…”

Section: Introductionmentioning

confidence: 99%

A total synthesis of (±)-triophamine

Piers¹,

Chong²,

Gustafson³

et al. 1984

Can. J. Chem.

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(1984). Treatment of ethyl 2-pentynoate (14) with lithium (phenylthio)(tri-11-butylstannyl)cuprate (12) afforded, in 76% yield, ethyl (2)-3-(tri-n-butylstanny1)-2-pentenoate (15). On the other hand, when compound 14 was allowed to react with the (tri-rzbutylstanny1)copper reagent 13, ethyl (E)-3-(tri-11-buty1stannyl)-2-pentenoate (21) was produced in 83% yield. Reduction (diisobutylaluminum hydride, ether) of the esters 15 and 21 gave the alcohols 1 6 and 22, respectively. Treatment of each of the latter substances with pyridine -sulfur trioxide complex, followed by further reduction of the resultant intermediates with lithium aluminum hydride, provided the geometrically isomeric alkenylstannanes 17 and 23. Conjugate addition of (E)-3-lithio-2-pentene (18) (formed by transmetalation of 17) to compound 19 produced the olefinic trimethylhydrazide 20, which was converted (diisobutylaluminum hydride, ether; pyridinium dichramate, dimethylformamide) into the corresponding carboxylic acid 2. Subjection of compound 23 to a sequence of reactions identical with that used for the conversion of 17 into 2 provided the isomeric acid 3, which was identical (infrared, 'H nmr) with the natural acid derived from triophamine (I). Conversion of 3 into the p-nitrophenyl ester 26, followed by condensation of the latter substance with guanidine, afforded a chromatographically separable mixture of (*)-triophamine (1) and the corresponding diastereomer.EDWARD PIERS, J. MICHAEL CHONG, KIRK GUSTAFSON et RAYMOND J. ANDERSEN. Can. J. Chem. 62, 1 (1984). Le pentyne-2 oate d'ethyl (14) riagit avec le (ph6nylthio)-(tri-n-butylstanny1)cuprate de lithium (12) pour donner, avec un rendement de 76%, le (2)-(tri-11-buty1stannyl)-3 pentkne-2 oate d'ithyle (15). Par ailleurs, quand on fait riagir le composi 14 avec le reactif (tri-n-butylstannyl)cuivre (13), on obtient avec un rendemcnt de 83%, le (E)-(tri-n-butylstanny1)-3 penthe-2 oate d'ithyle (21). Par reduction des esters 15 et 21 (par l'hydrure de diisobutylaluminium dans I'ither), on obtient respectivement les alcools 16 et 22. Ces alcools, par une riaction avec le complexe de pyridine -trioxyde de soufre suivie de la reduction des intermediaires resultants par I'alanate de lithium, conduisent aux alkinylstannates 17 et 2 3 qui sont des isomkres giometriques. L'addition conjuguke du (2)-lithio-3 penthe-2 (18) (forme par la transmetallation du composC 17) sur le composi 19 conduit au trimithylhydrazide olifinique 20 que I'on transforme (hydrure de diisobutylaluminium, ither; dichromate de pyridium, dimithylformamide) en I'acide carboxylique correspondant (2). Le compost? 23, soumis la suite dc riaction qui permet de transformer le compose 17 en composi 2, donne I'acide isomkre 3 que I'on a identifie (ir et rmn du 'H) i I'acide nature1 provenant de la triophamine (I). La transformation du composi 3 en esterp-nitrophknyle (26), suivie de la condensation de I'ester sur la guanidine, donne un milange de (*)-triophamine (1) et du diastCrioisomkre correspondant que I'on peut skparer par chromatogra...

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“…More recently (Hagadone et al 1979), the mucus secreted by Phyllidia varicosa was found to contain terpenoid substances that prove repugnant or toxic to potential predators. Since then similar deterrent metabolites have been isolated from the mantle of many other dorid nudibranchs (for reviews see Schulte and Scheuer 1982, Faulkner and Ghiselin 1983, Faulkner 1984, Cimino et al 1986). …”

Section: Introductionmentioning

confidence: 98%

Studies on the defensive behaviour ofHypselodoris species (Gastropoda: Nudibranchia): Ultrastructure and chemical analysis of mantle dermal formations (MDFs)

1990

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Abstract. The mantle dermal formations (MDFs) ofHypselodoris webbi (D'orbigny, 1839), and H. cantabrica (Bouchet and Ortea, 1980) are globu|ar sub-epidermal structures located in the cephalic and caudal regions. Histologically they consist of an accumulation of vacuolate cells surrounded by a basal lamina and an outer muscular capsule. Chemical analysis of H. webbi MDFs reveals the presence of high concentrations of longifolin, a well known deterrent furanosesquiterpenoid that had been previously isolated from this species. In the present paper it is demonstrated that the great majority of longifolin accumulated in the mantle of H. webbi is stored in the MDF vacuolar cells. This finding strongly suggests that such structures act as chemical weapons against predation, mainly protecting vital organs such as the head, rhinophores and gills.

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Defense allomones of some marine mollusks

Cited by 58 publications

References 32 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)

A total synthesis of (±)-triophamine

Studies on the defensive behaviour ofHypselodoris species (Gastropoda: Nudibranchia): Ultrastructure and chemical analysis of mantle dermal formations (MDFs)

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