Melilotoside Derivatives from Artemisia splendens (Asteraceae)

A combination of solid-phase-extraction (SPE) and reversed-phase preparative high-performance liquid chromatography (prep-HPLC) of the methanolic extract of the aerial parts of Artemisia splendens (common name: “Asia Minor Wormwood”), an endemic Iranian species, afforded Z- and E-melilotosides (1 and 2), Z- and E-4-methoxy-melilotosides (3 and 4), and a new dimer, bis-ortho-Z-melilotoside (5, named: splendenoside). Whilst the structures of these compounds (1-5) were elucidated unequivocally by spectroscopic means, the in vitro free-radical-scavenging property of 1-5 was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. This is the first report on the occurrence of any melilotoside derivatives in the genus Artemisia.