The chemical and chemo‐ecological studies on Weizhou nudibranch Glossodoris atromarginata

Abstract

A detailed chemical investigation of the nudibranch Glossodoris atromarginata collected from Weizhou Island, South China Sea, yielded a new spongian‐type diterpene 1, together with the four known‐related compounds 2–5. The structure of the new compound 1 was elucidated by the detailed spectroscopic analysis, the comparison of the spectroscopic data with the known diterpene isoagatholactone, and the 13C chemical shift calculation. In addition, evidence for the absolute stereochemistry of the known compound 2 was, for the first time, provided by the application of time‐dependent density functional theory electronic circular dichroism calculation.

Antibacterial scalarane fromDoriprismatica stellatanudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary spongeSpongiacf.agaricina(Demospongiae, Dictyoceratida)

“…agaricina . This, among other investigations on Doriprismatica atromarginata [ 38 , 41 , 44 – 45 50 ] and D. sedna [ 39 ], supports the idea of a stenophagous dietary relationship between nudibranchs of the genus Doriprismatica and scalarane-containing dictyoceratid sponges of the families Thorectidae and Spongiidae. This relationship is further reflected by their shared specialized metabolite 12-deacetoxy-4-demethyl-11,24-diacetoxy-3,4-methylenedeoxoscalarin, as proven in this study.…”

“…Chemotaxonomic approaches have shown that chromodorid nudibranchs of the genera Chromodoris , Doriprismatica , Felimare , Felimida , Glossodoris/Casella , and Goniobranchus sequester and reuse spongian-type furanoterpenoids, diterpenoids, and sesquiterpenoids, or scalarane-type sesquiterpenoids and sesterterpenoids from their sponge prey [ 23 , 37 – 45 ]. However, confusion in the chemotaxonomy of Chromodorididae arose by multiple changes in the species names, including splitting and synonymizations, and the inclusion of species that have since been discovered to be members of other genera.…”

“…Members of Glossodoris/Casella and Doriprismatica represent such a case of complex systematic challenges and complicated taxonomic histories [ 49 ]. Previous work on Doriprismatica (former Glossodoris ) sedna [ 39 ] and Doriprismatica (former Glossodoris or Casella ) atromarginata [ 38 , 41 , 44 – 45 50 ], reported the isolation of scalaranes, homoscalaranes, norscalaranes, spongian diterpenoids and furanoditerpenoids. A dietary origin of these molecules was inferred and attributed to dictyoceratid sponges of the genera Hyrtios and Carteriospongia (Thorectidae), as well as Hyattella and Spongia (Spongiidae).…”

Bioactive Compounds from Marine Heterobranchs

“…As taxonomical studies progress, many Chromodoris and Glossodoris species have been renamed, such as Goniobranchus , Ardeadoris , Doriprismatica , Felimare, and Felimida , respectively [ 171 , 175 , 179 , 180 , 181 , 182 , 183 , 184 , 185 ]. Goniobranchus collingwoodi presents six spongian-16-one diterpenes in the mantle, and the extract of the whole body displayed deterrence against the allopatric palaemonid shrimp P. serenus [ 185 ].…”

“…Doriprismatica (Glossodoris) atromarginata presents furanoditerpenoids and scalarane sesterterpenes from its dietary sponges Spongia ( Hyatella ) sp. and Hyrtios spp., and these compounds display ichthyotoxicity against the mosquito fish, G. affinis —particularly, the activity of 12-deacetoxy-12-oxodeoxoscalarin ( 136 ) is noticeable [ 92 , 175 , 180 , 378 , 379 , 380 , 381 , 382 , 383 , 384 , 385 , 386 ]. Other NPs from chromodoridids were analyzed for ichthyotoxicity against G. affinis , including homoscalarane and scalarane compounds from Felimida (Glossodoris) dalli , Glossodoris rufomarginata , Glossodoris pallida , Glossodoris vespa , and Ardeadoris (Glossodoris) averni , and 12-deacetyl-23-acetoxy-20-methyl-12- epi- scalaradial ( 135 ) was the most potent of them [ 175 , 183 , 383 ].…”