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

Molecules

Kunimitsu Kaya²  Louise F. Morrison³  Geoffrey A. Codd³  James S. Metcalf³  Tomoharu Sano¹  Hiroo Takagi¹ 

[1] National Institute for Environmental Studies, 16-2 Onogawa, Tsukuba Ibaraki 305-8506, Japan, E-mails:;Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan, E-mail:;Division of Environmental and Applied Biology, School of Life Sciences, University of Dundee, Dundee DD1 4HN, UK. E-mails:

关键词: biosurfactant;    cyanobacterium;    Aphanizomenon flos-aquae;    fatty acids;    2-hydroxyethanephosphonate;    2-acyloxyethanephosphonate;    C-P linkage;    surface tension;    toxicity;    critical micelle concentration (CMC);   

DOI  :  10.3390/11070539

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
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