Abstract
Ten new briarane diterpenoids, briaviolides A–J (1–10), together with six known briaranes, solenolides A and D, excavatolide A, briaexcavatolide I, 4β-acetoxy-9-deacetystylatulide lactone and 9-deacetylstylatulide lactone, were isolated from the Taiwanese soft coral, Briareum violacea. Their structures were determined on the basis of spectroscopic data (1H- and 13C-NMR, 1H–1H COSY, HSQC, HMBC and NOESY), HR-MS and chemical methods. The absolute configuration of briaviolide A (1) was determined by X-ray crystallographic analysis. Compounds 5, 9 and derivative 11 showed moderate inhibitory activities on superoxide-anion generation and elastase release by human neutrophils in response to N-formyl-methionyl-leucyl-phenylalanine/Cytochalasin B (fMLP/CB).
Highlights
The briarane diterpenoids [1] continue to attract the attention of natural product chemists because of their structural complexity and interesting biological activities, such as anti-inflammatory [2], antiviral [3], cytotoxic [4,5,6], antifouling [7,8], immuno-modulatory [9], insecticidal [10] and reversal of multidrug resistance [11]
Cells were activated by fMLP (100 nM)/CB (0.5 μg/mL), and changes in absorbance at 405 nm were monitored continuously for elastase release
The results are expressed as the percentage of the initial rate of elastase release in the formyl-methionyl-leucyl-phenylalanine/ Cytochalasin B (fMLP/CB)-activated, test compound-free (DMSO) control system
Summary
The briarane diterpenoids [1] continue to attract the attention of natural product chemists because of their structural complexity and interesting biological activities, such as anti-inflammatory [2], antiviral [3], cytotoxic [4,5,6], antifouling [7,8], immuno-modulatory [9], insecticidal [10] and reversal of multidrug resistance [11]. The structures of these diterpenoids are characterized by a highly oxygenated bicyclo[8.4.0]tetradecane skeleton that is frequently attached with a γ-lactone moiety. The in vitro anti-inflammatory activities of new compounds (1–10) and new derivative 11 were tested for their inhibition of elastase release and superoxide-anion generation from human neutrophils
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