TY - JOUR
T1 - Synthesis and characterization of dioctanoyl glycerate as water-soluble trypsin inhibitor
AU - Sato, Shun
AU - Nagata, Shota
AU - Imura, Tomohiro
AU - Fukuoka, Tokuma
AU - Morita, Tomotake
AU - Takahashi, Yutaka
AU - Kondo, Yukishige
AU - Kitamoto, Dai
AU - Habe, Hiroshi
PY - 2016/3/1
Y1 - 2016/3/1
N2 - Glyceric acids (GAs) esterified with long acyl chains (> C16) exhibit antitrypsin activity (Folia Microbiol. 46, 21-23 (2001)). However, their hydrophobic nature, derived from the long acyl chains, has limited the number of studies on their physical and biological properties. To improve the water solubility of diacyl GAs, GA was esterified with octanoyl groups (C8), and its physical properties were investigated. Synthesized dioctanoyl GA was not water-soluble, whereas its sodium salt was. Surface tension measurements of dioctanoyl GA sodium salt (diC8GA-Na) in water revealed that the critical micelle concentration (CMC) was 0.82 mM, and surface tension at the CMC was 25.5 mN/m. Additionally, diC8GANa inhibited casein digestion by trypsin to a greater extent than dioleoyl GA. These data suggest that watersoluble diacyl GAs may have utility as surfactants and bioactive compounds.
AB - Glyceric acids (GAs) esterified with long acyl chains (> C16) exhibit antitrypsin activity (Folia Microbiol. 46, 21-23 (2001)). However, their hydrophobic nature, derived from the long acyl chains, has limited the number of studies on their physical and biological properties. To improve the water solubility of diacyl GAs, GA was esterified with octanoyl groups (C8), and its physical properties were investigated. Synthesized dioctanoyl GA was not water-soluble, whereas its sodium salt was. Surface tension measurements of dioctanoyl GA sodium salt (diC8GA-Na) in water revealed that the critical micelle concentration (CMC) was 0.82 mM, and surface tension at the CMC was 25.5 mN/m. Additionally, diC8GANa inhibited casein digestion by trypsin to a greater extent than dioleoyl GA. These data suggest that watersoluble diacyl GAs may have utility as surfactants and bioactive compounds.
KW - Antitrypsin activity
KW - Diacyl glyceric acid
KW - Glyceric acid
KW - Glycerol
KW - Surfactant
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U2 - 10.5650/jos.ess15189
DO - 10.5650/jos.ess15189
M3 - Article
C2 - 26876677
AN - SCOPUS:84959368574
SN - 1345-8957
VL - 65
SP - 251
EP - 256
JO - Journal of Oleo Science
JF - Journal of Oleo Science
IS - 3
ER -