Abstract
Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.
Highlights
Chemical investigations on marine invertebrates have disclosed structural diversity in the terpenoid and steroid constituents of octocorals [1]
We isolated a series of cembrane-diterpenoids [32] and steroids [29,31,33] from the Formosan soft corals Klyxum flaccidum, some of which have been found to possess cytotoxic and anti-inflammatory activities
In this paper we report the isolation, structure determination, and bioactivity of four new cembrane-derived diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), flaccidodioxide
Summary
Chemical investigations on marine invertebrates have disclosed structural diversity in the terpenoid and steroid constituents of octocorals [1]. Has shown a wealth of unique secondary metabolites, including cembrane- and eunicellin-based diterpenoids, and steroids. In this context, we isolated a series of cembrane-diterpenoids [32] and steroids [29,31,33] from the Formosan soft corals Klyxum flaccidum, some of which have been found to possess cytotoxic and anti-inflammatory activities. In this paper we report the isolation, structure determination, and bioactivity of four new cembrane-derived diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), flaccidodioxide (3), and flaccidodiol (4), and three known compounds, sarcophytol T (5) [34], flaccidoxide-13-acetate (6) [35], and 14-O-acetylsarcophytol B (7) [36]. The anti-inflammatory activities that occur due to the inhibition of superoxide anion (O2 − ) generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-challenged human neutrophils, were evaluated
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