Abstract
Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid 16-epi-irciformonin G (4), along with three known metabolites (−)-sponalisolide B (5), 18-nor- 3,17-dihydroxy-spongia-3,13(16),14-trien-2-one (6), and cholesta-7-ene-3β,5α-diol-6-one (7). The biosynthetic pathway for the molecular skeleton of 1 and related compounds was postulated for the first time. Anti-inflammatory activity of these metabolites to inhibit superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophil cells and cytotoxicity of these compounds toward three cancer cell lines and one human dermal fibroblast cell line were assayed. Compound 1 was found to significantly reduce the superoxide anion generation and elastase release at a concentration of 10 μM, and compound 5 was also found to display strong inhibitory activity against superoxide anion generation at the same concentration. Due to the noncytotoxic activity and the potent inhibitory effect toward the superoxide anion generation and elastase release, 1 and 5 can be considered to be promising anti-inflammatory agents.
Highlights
Marine sponges have been considered to be an important source for the discovery of
The chemical investigation of an unidentified
On the basis of the above findings, we propose that 1 can be derived from an intermediate spongian 9, which was biosynthesized from the mevalonic acid pathway, after oxygenation of the six-membered ring A and a subsequent ring contraction and formation of a fivemembered carbocycle, as illustrated in Scheme 1
Summary
Marine sponges have been considered to be an important source for the discovery of. 1. Marine sponges have been considered to be an important source for the discovery sponges have been shown to exhibit a variety of biological activities, such as antimicroof structurally diverse bioactive secondary metabolites [1]. [33,34,35],spongian sesquiterpene quinones [36,37], led to the discovery of ascalarane series of furanoterpenes diterpenoids [27,28,29,30,31,32], along with other kinds of metabolites, for example, sterols [38,39,40].
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