A New Series of Diterpenes from Australian Spongia Species

Abstract

Great Barrier Reef sponges of the genus Spongia have yielded eight closely related tetracyclic furanoditerpenes. The structures, assigned on the basis of spectral methods, have been confirmed by a single-crystal X-ray analysis of one of the metabolites and the relative stereochemical features have been defined. The absolute configuration of this metabolite was determined by circular dichroism, which allowed the relationship between the eight new compounds to be determined.

Novel Anti‐Inflammatory Spongian Diterpenes from the New Zealand Marine SpongeChelonaplysilla violacea

“…Spongian diterpenes are so named as many of the early examples were isolated from the Dictyoceratid genus Spongia. [1] Many of the reported spongian diterpenes possess highly oxygenated and rearranged carbon skeletons, examples include tetrahydroaplysulfurin-1 (1) [2Ϫ4] and cadlinolide B (2). [4] In the course of our NMR-directed sponge extract screening program, an extract of C. violacea collected using SCUBA at Stephens Island, Marlborough Sounds, New Zealand, was found to contain several compounds of interest.…”

Spongian Diterpenes from the Sponge <i>Hyattella</i> aff. <i>intestinalis</i>

“…Among the known spongians we isolated, we referred compound 1, which absolute configuration was elucidated by observing positive Cotton effect (290 nm, Δε +1.95) of its triacetate. 8) Although the specific rotation value of our compound 1 ([α] D +37) did not agree well with the reported ([α] D +142.5), 8) it is likely to have the same configuration due to the same sign. As both compounds 1 and 7 showed positive Cotton effect (285 nm, Δε +1.27; 286 nm, Δε +0.85), the results suggest the absolute configuration of 7 as in Fig.…”

“…By separating the extracts, we obtained a series of spongianclass diterpenes. Spongian diterpenes were first reported in 1979 as unique metabolites of a sponge, 8) and since then a number of spongians have been reported. [9][10][11][12][13][14] Recent reports include new cyototoxic spongians 15) and rediscovery of spongiatriol (1) as a moderate apoptosis inducer and an inhibitor of nuclear factor-kappaB (NF-κB) activation.…”

Spongiatriol Inhibits Nuclear Factor Kappa B Activation and Induces Apoptosis in Pancreatic Cancer Cells

“…While we found various known compounds with this activity, their response could be ascribed to their previously described mode of actions as protein synthesis inhibitors, DNA intercalators or inhibitors of topoisomerase II. Spongiatriol, a marine furanoditerpenoid that was first isolated in the 1970s [11], was found to be active in the assays and did not have a reported mechanism of action that explained the inhibition of NFκB. Therefore, we undertook studies to better understand its effects in pancreatic cancer cell lines.…”