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

• Main Authors: Takuya Kubo, Hiroo Takagi, Tomoharu Sano, James S. Metcalf, Geoffrey A. Codd, Louise F. Morrison, Kunimitsu Kaya
• Format: Article
• Language: English
• Published: MDPI AG 2006-07-01
• Series: Molecules
• Subjects: biosurfactant; cyanobacterium; Aphanizomenon flos-aquae; fatty acids; 2-hydroxyethanephosphonate; 2-acyloxyethanephosphonate; C-P linkage; surface tension; toxicity; critical micelle concentration (CMC).
• Online Access: http://www.mdpi.com/1420-3049/11/7/539/
• ISSN: 1420-3049

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.