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An undescribed tricyclic spiroketal compound clathriketal was purified from the solvent extract of the Microcionidae sponge  Clathria prolifera , and was characterised as 7-(hydroxymethyl)-13-methoxy-3,11-dimethyl-4-oxo-octahydrospiro[chromene-9,13-pyran]-11-yl propionate by spectroscopic experiments. Clathriketal exhibited significant anti-hyperglycemic property by attenuating serine protease dipeptidyl peptidase-IV (IC 50  0.37 mM), and its activity was comparable with the standard diprotin A (IC 50  0.31 mM). The spiroketal also exhibited significant inhibitory potentials against carbolytic enzymes  α -glucosidase (IC 50  0.43 mM) and  α -amylase (IC 50  0.41 mM). Superior antioxidant properties of clathriketal against the oxidants, 2, 2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid and 2, 2-diphenyl-1-picrylhydrazyl (IC 50  ∼1.2 mM) also reinforced its promising anti-hyperglycemic activity. Considerably greater topological surface area (91.29) coupled with lesser steric parameters of clathriketal, as elucidated from the structure-activity relationship analyses could further ascribe the improved ligand-receptor interactions resulting in its prospective anti-hyperglycemic activity. Molecular docking analysis of clathriketal with dipeptidyl peptidase-IV recorded lesser binding energy (–9.63 kcal/mol), which further corroborated its prospective antihyperglycemic activity.

Clathriketal, a new tricyclic spiroketal compound from marine sponge Clathria prolifera attenuates serine exopeptidase dipeptidyl peptidase-IV