Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer reviewed journal
Publication Acceptance Date: 1/23/2006
Publication Date: 4/3/2006
Citation: Kenar, J.A. 2006. Reaction chemistry of gossypol and its derivatives. Journal of the American Oil Chemists' Society. 83(4):269-302. Interpretive Summary: Gossypol is a naturally occurring, highly colored yellow pigment found in the pigment glands of cotton plants. Initially, gossypol was perceived as an unwanted component of cotton meal and oil processing. It was not until its anti-tumor and male infertility activity was discovered that it was considered a value-added natural product possessing useful properties. These serendipitous discoveries created much excitement, and an enormous amount of research on gossypol has ensued. Since then the main focus of gossypol research has been to prepare suitable gossypol derivatives for medicinal applications. This review summarizes current knowledge about gossypol and the many varied reactions the gossypol molecule can undergo. The information will be of interest to researchers working on gossypol, and will then generate new insights and ideas regarding the transformations and uses of this interesting molecule.
Technical Abstract: The reaction chemistry pertaining to gossypol, a toxic pigment found in cottonseed is critically reviewed. Gossypol has been known for well over a hundred years and the dichotomy between its toxicity to man and nonruminant animals and its unique biological activities as antifertility, anticancer, and plant defense agent places gossypol in an unusual position. On one hand researchers are currently working diligently to produce glandless strains of cottonseed devoid of gossypol to provide high quality cottonseed products without the gossypol’s associated toxicity. In contrast, researchers are using gossypol’s binaphthyl structure, functionality, and unique biological activities to make gossypol a potentially important value-added natural product. The research to understand gossypol’s reaction chemistry, in conjunction with reports on gossypol’s antifertility and anticancer properties, has opened future research opportunities for gossypol research and its utilization.