Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E

Abstract

The chemical investigation of the marine sponge Dysidea sp., which was collected from Bohol province in the Philippines, resulted in the identification of 15 new scalarane-type sesterterpenoids (1–14, 16), together with 15 known compounds. The chemical structures of the new compounds were elucidated based on NMR spectroscopy and HRMS. The structure of 12-epi-phyllactone D/E (15) isolated during this study was originally identified in 2007. However, careful inspection of our experimental 13C NMR spectrum revealed considerable discrepancies with the reported data at C-9, C-12, C-14, and C-23, leading to the correction of the reported compound to the C-12 epimer of 15, phyllactone D/E. The biological properties of compounds 1–16 were evaluated using the MDA-MB-231 cancer cell line. Compound 7, which bears a pentenone E-ring, exhibits significant cytotoxicity with a GI50 value of 4.21 μM.

Keywords

• <i>Dysidea</i>
• sesterterpenoid
• scalarane
• marine sponge
• marine natural product
• anticancer activity