Anthelmintic activity of selected neolignans and semisynthetic derivatives from Styrax suberifolius

Abstract

The plant metabolite, equiselignan B (2), isolated from the fruits of Styrax suberifolius was used to generate a semisynthetic library. Extraction and purification studies yielded large quantities (∼70 mg) of 2, a new glycoside, suberifolioside A (1), and the previously described neolignan egonol (3). The planer structure of 1 was established following 1D/2D NMR and MS analyses, and its absolute configuration was determined by X-ray diffraction studies. Acid hydrolysis of 1 yielded an additional amount of scaffold 2 (436 mg) that was subsequently converted into seven new ether derivatives (4–10) and two new ester derivatives (11–12) using commercially available alkyl halides and acyl chlorid..