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Comparative Study of Interfacial and Biological Properties in d-Glycerate-Derived Surfactants

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Journal of the American Oil Chemists' Society

Abstract

The effects of hydrophobic chain length on the interfacial and biological properties of diacyl d-glyceric acid (d-GA) sodium salts were evaluated based on interfacial tension analyses, dynamic light scattering (DLS), and antitrypsin activity. Of the four synthesized d-GA-derived surfactants [dihexanoyl d-GA sodium salt (diC6GA-Na), dioctanoyl d-GA sodium salt (diC8GA-Na), didecanoyl d-GA sodium salt (diC10GA-Na), and dilauroyl d-GA sodium salt (diC12GA-Na)], only those with C6, C8, and C10 acyl chains were investigated because diC12GA-Na were insoluble at room temperature. Together with our previous results, surface tensions at the critical micelle concentration (CMC) were 33.9 mN/m for diC6GA-Na, 25.5 mN/m for diC8GA-Na, and 27.9 mN/m for diC10GA-Na. Evaluation of assembly size via DLS and optical microscopy revealed that diC8GA-Na and diC10GA-Na formed large associates with average sizes ranging from 50 to 200 μm at concentrations 4–5 times greater than their CMC, whereas diC6GA-Na did not form such associates. In tryptic hydrolysis studies using N α-benzoyl-dl-arginine-4-nitroanilide as a substrate, diC8GA-Na exhibited an inhibitory effect on trypsin (trypsin specific activity: 0.26 ± 0.045 U/mg-protein) greater than that of diC10GA-Na (0.39 ± 0.10 U/mg-protein), whereas diC6GA-Na did not show antitrypsin activity. These results show that diC8GA-Na was the most bioactive of the evaluated diacyl d-glycerate surfactants.

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Acknowledgements

This work was funded in part by KAKENHI No. 25850064.

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Author notes

  1. Hiroshi Habe

    Present address: Environmental Management Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), 16-1 Onogawa, Tsukuba, Ibaraki, 305-8569, Japan

Authors and Affiliations

  1. Research Institute for Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5-2, 1-1-1 Higashi, Tsukuba, Ibaraki, 305-8565, Japan

    Shun Sato, Dai Kitamoto & Hiroshi Habe

  2. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku, Tokyo, 162-8601, Japan

    Shota Nagata, Yutaka Takahashi & Yukishige Kondo

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  1. Shun Sato
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  2. Shota Nagata
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Correspondence to Hiroshi Habe.

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Sato, S., Nagata, S., Kitamoto, D. et al. Comparative Study of Interfacial and Biological Properties in d-Glycerate-Derived Surfactants. J Am Oil Chem Soc 94, 1393–1401 (2017). https://doi.org/10.1007/s11746-017-3032-9

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  • DOI: https://doi.org/10.1007/s11746-017-3032-9

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