Phytochemical analysis and extraction/isolation and characterization of a new furanocoumarin from Heracleum maximum

Furanocoumarins are a class of naturally occurring compounds found in many plants and contain a furan ring fused with a coumarin (benzo-α-pyrone) either in a linear or angular fashion leading to Psoralen or Angelicin types of furanocoumarins. Heracleum maximum, a plant native to North America is known to contain several furanocoumarins. This plant has been used in traditional medicine by Native Americans to prevent and treat several ailments like tuberculosis, influenza, cholera and small pox. Prior research from our lab has shown that Heracleum maximum ethanolic seed extract is toxic to brine shrimp.The objective of this study was to do a phytochemical analysis of the Heracleum seed extract and identify the toxic compound(s).The powdered seeds were extracted with hexane and water separately, using continuous extraction and the aqueous extract was lyophilized to give a solid whereas the hexane extract was concentrated to yield a green liquid (with some solid separating out). The solid (hexane extract) was filtered and recrystallized with hexane/ether. Preparative TLC on the solid obtained from the hexane extract led to the isolation of a previously unreported furanocoumarin from this species called Heratomin, which was characterized by NMR. Phytochemical analysis of the aqueous and hexane extract and extraction/isolation and characterization of the new compound from this plant will be discussed.