Clathriolide from marine demosponge Clathria (Thalysias) vulpina (Lamarck, 1814): previously undescribed macrocylic lactone with attenuating potential against angiotensin converting enzyme.

Angiotensin-I converting enzyme catalyses the rate-determined step of the conversion of angiotensin-I to angiotensin-II that narrows the blood vessels, and angiotensin-I converting enzyme inhibitors were recognised as important medications for hypertension-related diseases. Chemical investigation of angiotensin-I converting enzyme inhibitors from marine demospongiae Clathria (Thalysias) vulpina (family Microcionidae), resulted in a previously undescribed 22-membered macrocyclic lactone derivative, named as clathriolide. The studied compound showed potential angiotensin converting enzyme attenuation property (IC50 0.41 mM), which was comparable with the standard captopril (IC50 0.36 mM). Clathriolide revealed significantly greater antioxidant potentials against free radical species (IC50 < 1 mM) in comparison with the standard α-tocopherol (IC50 > 1.5 mM). Superior electronic characteristics (topological polar surface area > 100) coupled with relatively smaller binding energy and docking score of clathriolide with the aminoacyl residues of angiotensin-I converting enzyme (-11.5 and -12.2 kcal/mol, respectively) described its potential inhibitory property against angiotensin-I converting enzyme.