1. Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)
- Author
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Till F. Schäberle, Fontje Kaligis, Robert Bara, Nils Böhringer, Stefan Kehraus, Gert Wörheide, Cora Hertzer, Heike Wägele, Dirk Erpenbeck, Gabriele M. König, and Publica
- Subjects
Stereochemistry ,Doriprismatica stellata ,01 natural sciences ,Full Research Paper ,lcsh:QD241-441 ,03 medical and health sciences ,Doridoidea ,lcsh:Organic chemistry ,Gastropoda ,scalarane ,lcsh:Science ,030304 developmental biology ,0303 health sciences ,biology ,nudibranchia ,010405 organic chemistry ,Chemistry ,sesterterpene ,Organic Chemistry ,biology.organism_classification ,Arthrobacter crystallopoietes ,Spongia ,0104 chemical sciences ,dictyoceratida ,antibacterial ,Sponge ,Chromodorididae ,lcsh:Q ,Dictyoceratida - Abstract
Investigations on the biochemical relationship between Doriprismatica stellata (Chromodorididae, Doridoidea) nudibranchs, their egg ribbons, and the associated dietary sponge Spongia cf. agaricina (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 Doriprismatica and scalarane-containing dictyoceratid sponges of the Spongiidae family. The results also indicate that D. stellata passes the scalarane metabolite on to its egg ribbons, most likely for protective purposes. The scalarane showed antibacterial activity against the Gram-positive bacteria Arthrobacter crystallopoietes (DSM 20117) and Bacillus megaterium (DSM 32).
- Published
- 2020