Literature DB >> 17971725

A novel biosurfactant, 2-acyloxyethylphosphonate, isolated from waterblooms of Aphanizomenon flos-aquae.

Kunimitsu Kaya1, Louise F Morrison, Geoffrey A Codd, James S Metcalf, Tomoharu Sano, Hiroo Takagi, Takuya Kubo.   

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.

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Year:  2006        PMID: 17971725      PMCID: PMC6148651          DOI: 10.3390/11070539

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  10 in total

1.  Spiroidesin, a novel lipopeptide from the cyanobacterium Anabaena spiroides that inhibits cell growth of the cyanobacterium Microcystis aeruginosa.

Authors:  Kunimitsu Kaya; Aparat Mahakhant; Ladda Keovara; Tomoharu Sano; Takuya Kubo; Hiroo Takagi
Journal:  J Nat Prod       Date:  2002-06       Impact factor: 4.050

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Journal:  Nature       Date:  1959-09-19       Impact factor: 49.962

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Journal:  Biochemistry       Date:  1967-07       Impact factor: 3.162

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Authors:  M C Moschidis
Journal:  Z Naturforsch C J Biosci       Date:  1986-03

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Journal:  Anal Biochem       Date:  1968-09       Impact factor: 3.365

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Journal:  Biochim Biophys Acta       Date:  1972-07-07

7.  A procedure for detecting phosphonolipids on thin-layer chromatograms.

Authors:  L W Stillway; S J Harmon
Journal:  J Lipid Res       Date:  1980-11       Impact factor: 5.922

8.  A novel mechanism for resistance to the antimetabolite N-phosphonoacetyl-L-aspartate by Helicobacter pylori.

Authors:  B P Burns; G L Mendz; S L Hazell
Journal:  J Bacteriol       Date:  1998-11       Impact factor: 3.490

9.  Studies on Tetrahymena membranes: temperature-induced alterations in fatty acid composition of various membrane fractions in Tetrahymena pyriformis and its effect on membrane fluidity as inferred by spin-label study.

Authors:  Y Nozawa; H Iida; H Fukushima; K Oki; S Onishi
Journal:  Biochim Biophys Acta       Date:  1974-10-29

10.  Determination of the presence of ceramide aminoethylphosphonate and ceramide N-methylaminoethylphosphonate in marine animals by fast atom bombardment mass spectrometry.

Authors:  T Matsubara; M Morita; A Hayashi
Journal:  Biochim Biophys Acta       Date:  1990-02-23
  10 in total
  1 in total

1.  Purification and characterization of phosphonoglycans from Glycomyces sp. strain NRRL B-16210 and Stackebrandtia nassauensis NRRL B-16338.

Authors:  Xiaomin Yu; Neil P J Price; Bradley S Evans; William W Metcalf
Journal:  J Bacteriol       Date:  2014-02-28       Impact factor: 3.490

  1 in total

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