Cytotoxic Furanoditerpenes from the Sponge Spongia tubulifera Collected in the Mexican Caribbean

Two new spongian furanoditerpenes, 3β-hydroxyspongia-13(16),14-dien-2-one (1) and 19-dehydroxy-spongian diterpene 17 (2), along with five known terpenes, the spongian furanoditerpenes 9-nor-3-hydroxyspongia-3,13(16),14-trien-2-one (3), 3β,19 dihydroxyspongia-13(16),14-dien-2-one (epispongiadiol) (4) and spongian diterpene 17 (5), the furanoditerpene ambliol C (6), and the sesterterpene scalarin (7), were isolated from the methanolic extract of the sponge Spongia tubulifera, collected in the Mexican Caribbean. The planar structures of the new compounds were elucidated by 1D/2D NMR and IR spectroscopic analysis, high resolution electrospray mass spectrometry (HRESIMS), and comparison of their spectral data with those reported in the literature. Absolute configurations were determined by comparison of the experimental electronic circular dichroism (ECD) spectrum with those calculated by time-dependent density functional theory (TDDFT). Compounds 1, 4, and 6 displayed weak cytotoxic activity against different human tumour cell lines.

Chromolactol, an Oxygenated Diterpene from the Indo-Pacific Nudibranch Goniobranchus coi: Spectroscopic and Computational Studies

A rearranged spongian diterpene chromolactol was obtained from the mantle extract of the Indo-Pacific nudibranch Goniobranchus coi. The structure of chromolactol, either 1a or 1b, which was investigated by extensive NMR experiments and by data comparison as well as by molecular modelling studies and density functional calculations, has a different relative configuration of the 2,8-dioxabicyclo-[3.3.0]-octane ring compared with the co-metabolite norrisolide (2). A biosynthetic pathway leading to the preferred diastereomer of chromolactol (1a) is presented.

Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp

Chemical investigation of the marine sponge Spongia sp., collected from the Fiji Islands resulted in the isolation of three new furanoditerpenoids 1-3, along with the known compounds epispongiatriol (4) and 17,19-dihydroxyspongia-13(16),14-dien-2,3-dione (5) While 1 is a new spongian diterpene with a modified oxidation pattern, compounds 2 and 3 represent two new ring A-contracted spongians, displaying a novel and unprecedented nor-spongian carbon skeleton. Despite their labile nature the structures could be established through a combined strategy including complete analysis of spectroscopic data (NMR, MS), molecular modeling and quantum-mechanical calculations.