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

Abstract

<jats:p>Investigations on the biochemical relationship between <jats:italic>Doriprismatica stellata</jats:italic> (Chromodorididae, Doridoidea) nudibranchs, their egg ribbons, and the associated dietary sponge <jats:italic>Spongia</jats:italic> cf. <jats:italic>agaricina</jats:italic> (Demospongiae, Porifera) led to the isolation of the structurally new scalarane-type sesterterpene 12-deacetoxy-4-demethyl-11,24-diacetoxy-3,4-methylenedeoxoscalarin, with an unprecedented position of the cyclopropane ring annelated to the ring A. Unlike other scalaranes, which are most often functionalized at C-12 of ring C, it bears two acetoxy groups at C-11 and C-24 instead. The compound was present in all three samples, supporting the dietary relationship between chromodorid nudibranchs of the genus <jats:italic>Doriprismatica</jats:italic> and scalarane-containing dictyoceratid sponges of the Spongiidae family. The results also indicate that <jats:italic>D. stellata</jats:italic> passes the scalarane metabolite on to its egg ribbons, most likely for protective purposes. The scalarane showed antibacterial activity against the Gram-positive bacteria <jats:italic>Arthrobacter crystallopoietes</jats:italic> (DSM 20117) and <jats:italic>Bacillus megaterium</jats:italic> (DSM 32).</jats:p>

Marine natural products

“…agaricina and also the nudibranch's egg ribbons, where presumably it plays some biological/ecological role. 640 The degraded sterol 1410 was isolated from a Vietnamese collection of Dendrodoris fumata 641 and dendrillane terpenoids 1411 and 1412 from Australian specimens of Goniobranchus coi . 642 Room temperature line broadening in the 1 H NMR spectrum of 1411 was investigated by VT-NMR and attributed to conformational changes in the cycloheptane ring.…”

Bioactive Scalarane‐Type Sesterterpenoids from Marine Sources

“…It suggested antibacterial activities against the Gram‐positive Arthrobacter crystallopoietes and B. megaterium . It reduced bacterial growth to 0.4 % at 205.6 μM, 11.0 % at 102.8 μM, and 14.0 % at 51.4 μM in comparison to the negative control [58] …”

Recent advances on marine mollusk-derived natural products: chemistry, chemical ecology and therapeutical potential

“…109 In the next year, they performed a systematic investigation 110 134) and 12a,20-dioxyspongian-16-one dipropionate (135) from the mantle extract. In 2015, nine spongian diterpenes, furanoterpenes (136)(137)(138)(139)(140)(141)(142)(143)(144), were isolated from the nudibranch Doriprismatica (formerly Glossodoris) atromarginata. 111 In 2016, ve diterpenes (145-149), each with a highly oxygenated spongian framework, were discovered and characterized from the nudibranch Goniobranchus splendidus and the diterpene 7ahydroxydendrillol-3 (150) was identied from the nudibranch Ardeodoris egretta.…”

“…Sesterterpenes are a rare terpene class, accounting for less than 2% of all known terpenoids. 141 Although only a few research reports regarding their biosynthesis, 142,143 their frequent occurrence in marine organisms is striking and sponges are considered the prime source of these terpenoids. 144 A total 14 sesterterpenes was reported from three genera of the nudibranch mollusks Curnon, Glossodoris, and Doriprismatica.…”