Chemistry of Two Distinct Aeolid Spurilla Species: Ecological Implications

Abstract

The lipophilic extracts of two marine aeolid nudibranch molluscs of the genus Spurilla collected in distinct geographical areas have been chemically analyzed. The Et O extracts of the nudibranchs were dominated by the presence of usual fatty acids and sterols and contained terpenoid compounds 1 - 3 as minor metabolites. Spurillin A (1) and spurillin B (3) were new molecules whereas cis-γ-monocyclofarnesol (2) was already reported in the literature as a synthesis product. Interestingly, bursatellin (4), previously isolated from anaspidean molluscs of the genus Bursatella, was found in the butanol extract of both Spurilla species. Compounds 1 - 4 were not detected in the extracts of the sea-anemone preys collected together with the molluscs.

Terpenoids in Marine Heterobranch Molluscs

“…The aeolid Spurilla sp. from Argentina presents spurillin B together with other compounds [183]. In pleurobranchoids, Pleurobranchaea meckelii from the Mediterranean possesses two labdane aldehyde diterpenes in the mantle [189], which are similar to those of the pulmonate Trimusculus reticulatus (see below).…”

“…The species Phyllodesmium longicirrum from Australia presents cembranoid diterpenes obtained from its prey, the soft coral Sarcophytum trochelioforum [182]. The chemical study of Spurilla aeolids led to the finding of terpenoid compounds, spurillin A (43) ( Figure 6) from the mediterranean S. neapolitana, and (−)-cis-γ-monocyclofarnesol from the argentinian Spurilla sp., together with other compounds [183]. Tochuina tetraquetra from British Columbia presents two previously known cembrane diterpenoids, rubifolide (44) and pukalide (45) (Figure 6), together with some sesquiterpenes, obtained from the soft coral Gersemia rubiformis, with unknown role [156].…”

Marine natural products

“…gave the farnesol derivative 1407, previously known as a synthetic product, and diterpene spurillin B 1408. 625 Both mollusc samples contained the known laevorotatory alkaloid bursatellin. None of the four metabolites were detected in extracts of sea anemones Aiptasia diaphana or Parabunodactis imperfecta that S. neapolitana or Spurilla sp., respectively, were associated with in the wild.…”

High-value compounds from the molluscs of marine and estuarine ecosystems as prospective functional food ingredients: An overview

“…Spurilla neapolitana from Bay of Naples afforded cyclohexenyl terpenoid, named as spurillin A 182 , whereas Spurilla sp. from Patagonian collection was reported with a farnesol derivative 183 and diterpene spurillin B 184 ( Ciavatta et al, 2017 ). The methylsarcoate analog 185 , 2R secogorgosterol 186 , bisepoxide 187 , isobisglaucumlides B-C 188 – 189 and isosarcophine 190 were isolated from Phyllodesmium longicirrum ( Bogdanov et al, 2017 ).…”