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A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae
Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan
Division of Environmental and Applied Biology, School of Life Sciences, University of Dundee,
Dundee DD1 4HN, UK
National Institute for Environmental Studies, 16-2 Onogawa, Tsukuba Ibaraki 305-8506, Japan
* Authors to whom correspondence should be addressed.
Received: 16 June 2006; in revised form: 18 July 2006 / Accepted: 18 July 2006 / Published: 22 July 2006
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).
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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.
Kaya K, Morrison LF, Codd GA, Metcalf JS, Sano T, Takagi H, Kubo T. A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae. Molecules. 2006; 11(7):539-548.
Kaya, Kunimitsu; Morrison, Louise F.; Codd, Geoffrey A.; Metcalf, James S.; Sano, Tomoharu; Takagi, Hiroo; Kubo, Takuya. 2006. "A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae." Molecules 11, no. 7: 539-548.