Abstract
Chemical analysis of a marine sponge, Cacospongia sp. (CMB-03404), obtained during deep sea commercial fishing activities off the southern coast of Australia, yielded an unprecedented family of sesterterpene α-methyl-γ-hydroxybutenolides, cacolides A–L (1–12), together with biosynthetically related norsesterterpene carboxylic acids, cacolic acids A–C (13–15). Structures were assigned on the basis of detailed spectroscopic analysis with comparisons to known natural products and biosynthetic considerations. In addition to revealing new chemical diversity, this study provided a valuable platform for comparing and contrasting the capabilities of the traditional dereplication technologies of HPLC-DAD, HPLC-MS and NMR, with those of the emerging HPLC-MS/MS approach known as global natural products social molecular networking (GNPS), as applied to marine sponge sesterterpene tetronic acids.
Highlights
Marine sponges (Phyla: Porifera) are a rich source of chemically diverse natural products
A case in point are the sesterterpene tetronic acids encountered in the Family: Irciniidae, Genera: Ircinia, Psammocinia and Sarcotragus [1]
We describe an unprecedented family of sponge sesterterpenes, cacolides A–L (1–12)
Summary
Marine sponges (Phyla: Porifera) are a rich source of chemically diverse natural products. A case in point are the sesterterpene tetronic acids encountered in the Family: Irciniidae, Genera: Ircinia, Psammocinia and Sarcotragus [1]. The rapid pace of marine natural product discovery over the last four decades has included many accounts of Irciniidae sesterterpene tetronic acids, including from Australian Ircinia [5,6], Psammocinia [6,7,8,9,10] and Sarcotragus spp. Dereplication strategies seek to analyse crude extracts/fractions, to achieve the early detection and de-prioritization of known chemistry, such as sponge sesterterpene tetronic acids, to ensure effective use of scientific resources. Many marine natural products researchers use these strategies to deprioritize such extracts at an early stage in the discovery process, in favour of extracts with a higher probability of returning new chemistry.
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