Abstract
A novel biosurfactant, 2-acyloxyethylphosphonate, was isolated from waterblooms of Aphanizomenon flos-aquae. Its structure was elucidated by chemical degradation and HRFABMS, GC/EI-MS and 1D- and 2D-NMR spectral analyses. The surfactant contained one mole of 2-hydroxyethylphosphonate and one mole of fatty acid, with hexadecanoic acid accounting for 84.1% of the total fatty acid content. The structure was confirmed by synthesis of 2-oleoyloxyethylphosphonate from ethylene oxide, phosphorus acid and oleic acid chloride. Considering the isolated surfactant molecule as hexadecanoyloxyethylphosphonic acid (mw. 364), the critical micelle concentration (CMC) was about 22 mM.
Highlights
Cyanobactyeria, which form water blooms in eutrophic lakes and reservoirs, can produce various kinds of bioactive compounds [1,2]
The biosurfactant 2-acyloxyethanesulfonate was readily soluble in alkaline aqueous solution, methanol, ethanol and chloroform and was not hydrolyzed with acid and alkaline phosphatases
The data presented here suggest that the C-P linkage in the biosurfactant is resistant to phosphatases
Summary
Cyanobactyeria (blue-green algae), which form water blooms in eutrophic lakes and reservoirs, can produce various kinds of bioactive compounds [1,2]. During investigations into bioactive compounds from blooms of the cyanobacterium Aphanizomenon flos-aquae collected from Balgavies Loch in Scotland, we have found a novel 2-hydroxyethylphosphonate-containing biosurfactant and here present its isolation and structure elucidation. After the extraction of fatty acid methyl esters from the methanolysate, the phosphonic acid-containing aqueous solution was condensed under reduced pressure, and analyzed by LC-MS.
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