Scalaradial, a Sesterterpenoid Metabolite from the Marine Sponge Cacospongia mollior

ent-Isocopal-12-ene-15,16-dialdehyde fromSpongia officinalis

“…It corresponds to a radius of curvature close to 13 ,~. Similar bending has been observed in the correlated structures of 12-deacetoxyscallaradial (De Rosa et al, 1994), scalaradial (Puliti et al, 1995), as well as of scalarolide and scalarin (Cambie et al, 1999), and helps to improve intramolecular interactions.…”

“…In both molecules the C12---C13 bond distances 1.332(5) and 1.338 (5),~ are typical of a localized double bond. The presence of axial and isooriented methyl groups gives rise to distortions in the geometry of the tricyclic skeleton similar to those observed in other correlated structures (Croft et al, 1983;Cimino, De Rosa et al, 1987;De Rosa et al, 1994;Puliti et al, 1995;Cambie et al, 1999). In particular, the longest bond distances occur in the molecular backbone marked by the atoms C4, C5, C10, C9 and C8.…”

“…In fact, the distance between carbonyl groups, depending on the orientation of the CHO substituent at the saturated C14 atom, is selective for the ability to form a covalent bond with receptors (Cimino, Sodano & Spinella, 1987). Another restrictive factor for the biological activity of these molecules is the presence, in the nearby C7 position, of a bulky substituent that can hinder the surface complementarity between metabolite and receptor (De Rosa et al, 1994;Puliti et al, 1995). Fig.…”

“…As a consequence, these substances are endowed with a wide pharmacological potential. The crystal structure determination of the title compound, (I), first studied by Cimino et al (1982), is part of the research in progress concerning structural elucidations and biological properties of natural compounds (Puliti et al, 1992(Puliti et al, , 1995De Rosa et al, 1994, 1995Ciavatta et al, 1997;Puliti & Mattia, 1999). In particular, the structure-activity relationship is important in the unsaturated 1,4-dialdehydes (polygodial type) because a few studies have focused on the specific relation between the stereochemistry of the aldehyde groups and biological activity, antifeedant and hot-tasting effects, especially (Cimino, Sodano & Spinella, 1987, and references therein).…”

The inactivation of phospholipase A2 by scalaradial: a biomimetic study by electrospray mass spectrometry

“…Scalaradial (SLD, 1 ) is a marine tetracyclic sesterterpenoid, firstly isolated from Cacospongia Mollior , that is widely occurring, along with related derivatives, in sponges belonging to the Cacospongia genus 1–10. It contains, as a remarkable structural feature, a pair of aldehyde groups.…”