Xylella fastidiosa (Xf) is a plant-pathogenic bacterium that grows within the xylem of infected plants; infection with Xf prevents the uptake of water, resulting in drying of leaves and fruit, and eventually killing the plant. In grapevines, this infection is known as Pierce's Disease. Observations of infected vineyards reveal that some individual plants are able to resist the attack of Xf, while others are not. Since the grapevines are genetically identical, we know that the reason that some plants escape and others do not cannot be a genetic factor. A comparison of fungi isolated from the xylem sap of healthy grapevines with those isolated from infected grapevines yielded a fungus, Cochliobolus sp., that inhibited the growth of Xf in vitro. Bioassay-guided isolation of an organic extract of Cochliobolus sp. led us to identify the natural product radicinin as the active metabolite. The solubility of radicinin in water is meager at best, and modification of the secondary alcohol group through sulfonation should increase the water solubility for use as treatment for infected grapevines. We report progress toward the sulfonation and counterion exchange of radicinin, and the water-solubility of the resulting analog.

Synthesis of a water-soluble radicinin derivative for use as an antibacterial agent in grapevines

251st National Meeting (2016)

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