Synthesis and Evaluation of Dioleoyl Glyceric Acids Showing Antitrypsin Activity

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  • Habe Hiroshi
    Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST)
  • Fukuoka Tokuma
    Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST)
  • Sato Shun
    Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST)
  • Kitamoto Dai
    Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST)
  • Sakaki Keiji
    Research Institute for Innovations in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST)

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Previously, Lešová et al. reported the isolation and identification of metabolite OR-1, showing antitrypsin activity, produced during fermentation by Penicillium funiculosum. The structure of OR-1 was a mixture of glyceric acid (GA), esterified with C14-C18 fatty acids, and oleic acid (C18:1) as the most predominant fatty acid (Folia Microbiol. 46, 21–23, 2001). In this study, dioleoyl D-GA and dioleoyl L-GA were synthesized via diesterification with oleoyl chloride, and their antitrypsin activities were evaluated using both a disk diffusion method and spectral absorption measurements. The results show that both compounds and their equivalent mixtures possess antitrypsin activities; however, their IC50 values (approximately 2 mM) are much higher than that of OR-1 (4.25 μM), suggesting that dioleoyl GA does not play a major role in the OR-1 antitrypsin activity.

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