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Molecules 2006, 11(7), 539-548; doi:10.3390/11070539
Article

A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae

1,* , 2
, 2,* , 2
, 3
, 3
 and 1
1 Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan 2 Division of Environmental and Applied Biology, School of Life Sciences, University of Dundee, Dundee DD1 4HN, UK 3 National Institute for Environmental Studies, 16-2 Onogawa, Tsukuba Ibaraki 305-8506, Japan
* Authors to whom correspondence should be addressed.
Received: 16 June 2006 / Revised: 18 July 2006 / Accepted: 18 July 2006 / Published: 22 July 2006
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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.
Keywords: biosurfactant; cyanobacterium; Aphanizomenon flos-aquae; fatty acids; 2-hydroxyethanephosphonate; 2-acyloxyethanephosphonate; C-P linkage; surface tension; toxicity; critical micelle concentration (CMC). biosurfactant; cyanobacterium; Aphanizomenon flos-aquae; fatty acids; 2-hydroxyethanephosphonate; 2-acyloxyethanephosphonate; C-P linkage; surface tension; toxicity; critical micelle concentration (CMC).
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Kaya, K.; Morrison, L.F.; Codd, G.A.; Metcalf, J.S.; Sano, T.; Takagi, H.; Kubo, T. A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae. Molecules 2006, 11, 539-548.

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