Graduate Thesis Or Dissertation
 

Novel icosanoids from the red marine alga Farlowia mollis

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  • Farlowia mollis is a marine red alga that grows in the intertidal region along the coast of Oregon. We began studying the chemistry of this alga after a survey of Oregon seaweeds revealed possibly interesting chemistry and antimicrobial activity in its crude organic extract. Over the past three years the biomedicinal potential of nearly 100 species of Oregon seaweeds has been explored in the Oregon seaweed survey. The survey screens the aqueous and organic extracts of different algal collections for antimicrobial activity, brine shrimp toxicity and interesting chemical metabolites as judged by thin layer chromatography. Farlowia mol1is was one of 17 different species of algae that were identified as promising for further study. The natural products of Farlowia mollis include three unique diol-containing fatty acids whose structures were determined by a combination of spectroscopic techniques, including 2D-NMR, mass spectrometry, and IR, UV and circular dichroic spectroscopy. These structures are very similar to several mammalian icosanoids which possess a wide range of biological activities. We decided to test these seaweed compounds for biological activity in common with several mammalian icosanoids, specifically for their ability to stimulate superoxide anion production in human neutrophils. It appears that the "farlowdiols" are moderate inhibitors of super oxide anion production in cells stimulated with formyl-methionylleucyl- phenylalanine. Other biological activities of the "farlowdiols" include mild inhibition of the dog kidney Na⁺/K⁺ ATPase and of the enzyme 5-lipoxygenase. The biological roles of the "farlowdiols" in the alga Farlowia mollis are not known, however, several other icosanoids have recently been isolated from other red algae, and have identical or similar structures to several biologically active mammalian icosanoids. These icosanoids may play important hormonal and bioregulatory roles in the algae, and may aid research in understanding the roles that icosanoids play in asthma, inflammation and other disease states.
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