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United States Department of Agriculture

Agricultural Research Service

Title: Naturally occurring esterification reactions with Bryostatin

item Abadi, Giso
item Manning, Thomas
item Philips, Dennis
item Groundwater, Paul
item Noble, Lyn
item Potter, Thomas

Submitted to: Natural Product Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/1/2007
Publication Date: 1/8/2008
Publication URL: http://DOI: 10.1080/14786410701642466
Citation: Abadi, G., Manning, T., Philips, D., Groundwater, P., Noble, L., Potter, T.L. 2008. Naturally occurring esterification reactions with Bryostatin. Natural Product Research. 22(10):865-878.

Interpretive Summary: Bryostatin is a natural product isolated from a tiny colonial animal, Bugula neritina, indigenous to the Gulf of Mexico. The compound has shown promise as a pharmaceutical agent and has been used in clinical trials in the treatment of breast, prostate, and kidney cancers, leukemia and Alzheimer's disease. Like many natural products bryostatin is susceptible to chemical reactions such as rearrangement and hydrolysis. These reactions may inactive the drug making treatments ineffective. To advance to potential for bryostatin use an understanding of factors which promote rearrangement, degradation, and other reactions during and its extraction, storage and administration is needed. In this study we examined how various extraction conditions may contribute to bryostatin hydrolysis and esterification. Results provided insight into procedures that will likely enhance the compound's stability during extraction.

Technical Abstract: Bryostatin structures share a commonality of a central bryophan ring, but each differs due to two groups (R1 and R2) that are attached to the bryophan ring via ester bonds. This research examines the impact that conditions such as UV light, acidic and basic conditions can have on the bryostatin structure in the presence of octanoic acid and water. Mass Spectrometry measurements suggest that bryostatin can easily rearrange into various structures under natural conditions by reacting with carboxylates that are ubiquitous in nature. A second set of measurements suggest bryostatin can be hydrolyzed by water, a reaction that has significant implications in both medicinal applications and extraction procedures.

Last Modified: 10/17/2017
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