Scalarane and homoscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli: chemical and biological properties.

A series of homoscalarane and scalarane compounds (2-7) have been isolated from two distinct species of Pacific Glossodoris nudibranchs. The structure and elucidation of the relative stereochemistry of the new metabolites 2 and 3 were obtained by spectroscopic methods. Compound 2 was ichthyotoxic at 0.1 ppm against Gambusia affinis and showed moderate activity (IC(50) 18 microM) to inhibit mammalian phospholipase A(2).

A new species of Trapania (Nudibranchia: Goniodorididae) from the Pacific coast of Central America.

A new marine gastropod species of the genus Trapania Pruvot-Fol, 1931, is described from Cabo Blanco, Puntarenas, Costa Rica and from Islas Secas, Panamá. Trapania inbiotica sp. nov. has a white body with red patches, white rhinophores with some little red patches, yellow appendages with partially red bases. The radula is composed of 28 rows of teeth. Each tooth has a large conical cusp with 21-24 denticles. Two or three of those denticles on the inner side of the cusp are smaller than the others. There are also 1-3 small denticles on the outside of the cusp. The jaw elements are very irregular.

Defensive allomones in three species ofHypselodoris (gastropoda: Nudibranchia) from the Cantabrian sea.

ThreeHypselodoris species,H. villafranca, H. cantabrica, and H. tricolor, have been studied in order to further investigate the defensive strategies of Chromodorididae mollusks from Iberian coasts. All animals possess large amounts of furanosesquiterpenoids, probably derived from their diet of sponges. The products are transferred and stored in specific sites of the mantle (mantle dermal formations, MDFs) to be used as chemical deterrents against predators. Chemical analysis of CantabrianHypselodoris species has led to the characterization of eight sesquiterpenoids. Among these, six have been found previously in both sponges and nudibranchs, while two are new natural products.Hypselodoris species cooccurring in the same area contained comparable mixtures of sesquiterpenoids. However, two populations ofH. cantabrica from different sites of the Cantabrian sea showed different metabolic patterns. All sesquiterpenoids induce feeding deterrence inCarassius auratus and two are also toxic toGambusia affinis.

4-acetylaplykurodin B and aplykurodinone B, two ichthyotoxic degraded sterols from the Mediterranean mollusk Aplysia fasciata.

Two ichthyotoxic lactones, 4-acetylaplykurodin B [1] and aplykurodinone B [2], were isolated from the external parts of the body of the mollusk Aplysia fasciata. Their structures, determined by spectroscopic and chemical means, are closely related to aplykurodin B [3] previously isolated from Aplysia kurodai. The interconversion of delta- and gamma-lactones in the aplykurodin derivatives has been also investigated.

Ichthyotoxic diterpenoids from the Cantabrian nudibranch Chromodoris luteorosea.

Five spongian diterpenoids 2, 3, 6-8, previously found in sponges and nudibranchs from very distinct geographical areas, have been isolated from the Cantabrian nudibranch Chromodoris luteorosea. The terpenoids are mainly localized along the border of the mantle of the mollusk. All the diterpenoids are toxic to Gambusia affinis.

Defensive strategy of twoHypselodoris nudibranchs from Italian and Spanish coasts.

Hypselodoris nudibranchs from different geographic areas (Spain and Italy) have been studied in order to investigate their general defensive strategy. Longifolin (1) and nakafuran-9 (2) are the main ichthyodeterrent allomones used by the mollusks to avoid predation. Evidence of their dietary origin is presented and the very effective strategy against predators, which includes secretion of allomones into the mucus and their storage into specific mantle dermal formations (MDFs), is also discussed.