Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring.

This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO(3)-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ(10,11)- and Δ(11,12)-isomers, respectively.

Crotalaria medicaginea associated with horse deaths in northern Australia: new pyrrolizidine alkaloids.

Crotalaria medicaginea has been implicated in horse poisoning in grazing regions of central-west Queensland, which resulted in the deaths of more than 35 horses from hepatotoxicosis in 2010. Liver pathology was suggestive of pyrrolizidine alkaloidosis, and we report here the isolation of two previously uncharacterized pyrrolizidine alkaloids from C. medicaginea plant specimens collected from pastures where the horses died.

Daphnane- and tigliane-type diterpenoid esters and orthoesters from Pimelea elongata.

Investigation of Pimelea elongata ("Lakebed Pimelea") afforded 18 tigliane- and daphnane-type diterpenes (1-18). Eight of these were new compounds: four (1-3, 5) tigliane esters and four (7, 8, 10, 11) daphnane orthoesters. The 10 known compounds were 12-O-decanoylphorbol-13-acetate (4), P.

Pimelotides A and B, diterpenoid ketal-lactone orthoesters with an unprecedented skeleton from Pimelea elongata.

A detailed investigation of the minor phytochemical components of Pimelea elongata foliage led to the discovery of two new diterpenoid daphnane ketal-lactone orthoesters with an unprecedented skeleton, pimelotides A (1) and B (2). Their structures and relative configurations were elucidated by NMR spectroscopy.

Chemistry of Glossodoris nudibranchs: specific occurrence of 12-keto scalaranes.

With the aim of establishing whether the oxidation of the tricyclic carbon skeleton of scalaradial (1) is specific to Glossodoris mollusks, the chemical investigation of specimens of Glossodoris pallida from two distinct geographical areas (China and Guam) and of Glossodoris vespa and Glossodoris averni from Eastern Australia was performed. 12-Deacetoxy-12-oxo-scalaradial (4), recently reported from another Glossodoris nudibranch, was the main metabolite of G. pallida from China, G.

Mooloolabenes A-E, norsesterterpenes from the Australian sponge Hyattella intestinalis.

Five new norsesterterpenes, mooloolabenes A-E (1-5), and the new sesterterpene mooloolaldehyde (6), related to the scalarane family of compounds, were isolated from an acetone extract of the Australian sponge Hyattella intestinalis. Structural elucidation, including relative stereochemical assignment, was based on spectroscopic analysis. All compounds tested showed cytotoxic activity against the P388 cell line.

Spongian diterpenes from Australian Nudibranchs: an anatomically guided chemical study of Glossodoris atromarginata.

An Australian population of the nudibranch mollusk Glossodoris atromarginata has been found to contain furanoditerpenes of the spongian series. Spongia-13(16),14-dien-3-one (1) and 3alpha-acetoxy-19-hydroxyspongia-13(16),14-dien-2-one [corrected] (2) were isolated for the first time from a natural source, along with a series of known diterpenes (3-7). Anatomical dissection of the animals revealed the relative distribution and chemical variation of secondary metabolites.