Xenobe Research Institute

Karanjin

Flavonoids are widely distributed in plants functioning both as pigments and as means of chemical defense. In recent years, interest in the chemical biology of flavonoids has intensified in part due to the complex structural diversity within this class of natural product. This, combined with their generally-low cytotoxicity and unique activity, we have begun efforts to develop an understanding the pathways regulated by these materials. Karanjin represents one member of a large class of benzofuran flavonoids. It has been identified in well over 50 plant species. While karanjin is an established ascaracide and insecticide, little is know about its cellular function and molecular targets. In collaboration with a team at the Salk Institute, efforts are now underway that combine chemical synthesis with fluorescent and affinity analyses to evaluate the role and function of these materials using a worm model (C. elegans). We have developed a synthesis of karanjin that permits the attachment of IAF labels at diverse positions on the karanjin scaffold. This route was first conducted at the milligram scale delivering an alloxyterminated IAF probe. Unfortunately, the synthesis of this material suffered from a low yielding cross metathesis reaction. This program has been terminated in 2011.