Marine isocyanides and related natural products structure, biosynthesis and ecology

This review highlights structural and biosynthetic work on a group of nitrogen-functionalised terpenes that are almost exclusively found in marine invertebrates and the animals that feed on them. The chemical functionality reviewed includes isocyanides, isothiocyanates, formamides, thiocyanates, isocyanates, and dichloroimines. The literature through mid 2003 is reviewed and there are 143 citations.

Sperm ultrastructure of the Actinocyclidae (Mollusca, Nudibranchia) and homology of the terminal region of nudibranch sperm

Sperm ultrastructure is examined and described for the actinocyclidid nudibranchs Actinocyclus verrucosus, Hallaxa iju and Hallaxa indecora. Although general characteristics were consistent with previously described heterobranch observations, present investigations revealed ultrastructural synapomorphies for the family based on the morphology of the terminal region of the spermatozoon. In actinocyclidids, the axonemal microtubules penetrate for some distance beyond the annulus, and the annular accessory body elongates to completely seal the terminal region. Chromodoris also has an annular accessory body that completely seals the axoneme and terminal region, but it does not extend far beyond the annulus, and it is possible that these states were derived independently. Cytochemical staining confirmed that there was no glycogen present in the posterior region of the sperm for H. indecora or Chromodoris kuniei. However, representatives of other chromodoridid genera (Noumea, Risbecia) have an axoneme that penetrates through the entire annular complex, after which it is sheathed by a glycogen deposit. Similarities in the acrosomal complex support the proposed sister group relationship between the Actinocyclidae and Chromodorididae.

Basal chromodorid sperm ultrastructure (Nudibranchia, Gastropoda, Mollusca)

The relationship between three genera considered basal in the Chromodorididae (Cadlina, Tyrinna, Cadlinella) has not yet been resolved by traditional morphological means. Here we examined the sperm ultrastructure of Tyrinna nobilis, Tyrinna evelinae, Cadlina flavomaculata and Cadlina cf. nigrobranchiata, with the expectation of finding phylogenetically informative characters. No Tyrinna or Cadlina species showed sperm similarities to Cadlinella. Both Cadlina species and Tyrinna nobilis (but not T. evelinae) exhibited coarse striations in the acrosomal pedestal. The putative fibers that occurred between the coarse striations of the pedestal are condensed into a layer in Cadlina and Tyrinna, but not in other species that also have coarse striations (Gymnodoris), and may constitute evidence for a close relationship. Tyrinna evelinae possessed fine acrosomal striations, which was shared with other Chromodorididae, Actinocyclidae and the cryptobranchs Rostanga and Aphelodoris. We also examined the sperm ultrastructure of 'Chromodoris' ambiguus, an animal which has shown molecular affinities to species of Cadlina, and not Chromodoris. The sperm of 'C'.' ambiguus did not exhibit the typical Cadlina characteristics, but also showed important differences to other investigated Chromodoris species.

Diversity of Symbiodinium dinoflagellate symbionts from the Indo-Pacific sea slug Pteraeolidia ianthina (Gastropoda : Mollusca)

The aeolid nudibranch Pteraeolidia ianthina hosts symbiotic dinoflagellates in the same way as many reef-building corals. This widespread Indo-Pacific sea slug ranges from tropical to temperate waters, and offers a unique opportunity to examine a symbiosis that occurs over a large latitudinal gradient. We used partial 28S and 18S nuclear ribosomal (nr) DNA to examine the genetic diversity of the Symbiodinium dinoflagellates contained within F ianthina. We detected Symbiodinium from genetic clades A, B, C and D. P. ianthina from tropical regions (Singapore, Sulawesi) host Symbiodinium clade C or D or both; those from the subtropical eastern Australian coast (Heron Island, Mon Repo, Moreton Bay, Tweed Heads) host Symbiodinium clade C, but those from the temperate southeastern Australian coastline (Port Stephens, Bare Island) host clade A or B or both. The Symbiodinium populations within 1 individual nudibranch could be homogeneous or heterogeneous at inter- or intra-clade levels (or both). Our results suggested that the Pteraeolidia-Symbiodinium symbiosis is flexible and favours symbiont phylotypes best adapted for that environment. This flexibility probably reflects the function of the symbiont clade in relation to the changing environments experienced along the latitudinal range, and facilitates the large geographic range of P. ianthina.

Spongian Diterpenes from Australian nudibranchs: An anatomically guided chemical study of Glossodoris atromarginata

An Australian population of the nudibranch mollusk Glossodoris atromarginata has been found to contain furanoditerpenes of the spongian series. Spongia-13(16),14-dien-3-one (1) and 3 beta-acetoxy-19-hydroxyspongia-13(16),14-dien-2-one (2) were isolated for the first time from a natural source, along with a series of known diterpenes (3-7). Anatomical dissection of the animals revealed the relative distribution and chemical variation of secondary metabolites. Structural studies have provided a basis for chemical comparisons between populations from different geographic locations.