2008 Annual Report 1a.Objectives (from AD-416) To develop improved methods to separate cottonseed glands from cottonseed and facilitate large-scale isolation of gossypol. To develop novel gossypol chemistries to improve analytical methods and to support bioactivity studies. To provide gossypol analytical services or support as needed. 1b.Approach (from AD-416) Cottonseed will be milled to free pigment glands. Glands will be recovered with a vibratory table. Gossypol will be isolated from the separated glands and characterized. Chemical modification will be studied to improve analytical detection of the compound and to improve biological activity. 3.Progress Report The purpose of the agreement is to support chemical studies on compound gossypol, a component of the cotton plant that is responsible for limiting the use of cottonseed and cottonseed meal as an ingredient in animal feed. During the prior year, we synthesized a group of methoxy-derivatives of gossypol starting from a mixture of the methoxy-gossypol parent compounds. The separation of these compounds was achieved with large-scale liquid chromatography. After collecting the individual compounds, each compound was recovered by a combination of evaporation and precipitation steps. All of the isolated products were characterized for ultraviolet-visible light absorbance and proton nuclear magnetic resonance spectroscopy. The characterization of these compounds will continue into the next year. The progress is monitored via periodic emails and phone conversations.