Journal of Agricultural and Food Chemistry
Article
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FAG−MFA yield (%)
= 99.14 + 15.08X1 + 8.41X2 + 16.43X3 + 24.21X4
− 14.14X12 − 11.95X2 − 10.77X3 − 3.42X4
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2
2
2
− 14.14X1X2 − 11.95X1X3 − 10.77X1X4 + 3.42X2X3
− 12.68X2X4 + 4.50X3X4
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Optimum Conditions and Model Verification. Reaction
conditions were optimized using RSM as follows: (1) for the
transesterification of GMF with SBO in [C12mim]PF6, enzyme
concentration 45 mg/mL, 90 °C, GMF/SBO 1:2.5 (mol/mol),
and 11 h. Under these optimal conditions, GMF conversion
and FAG yield were 94.3 0.7% and 83.8 1.0%, respectively;
(2) for the esterification of GMF with MFA in [C10mim]PF6,
enzyme concentration 20 mg/mL, 90 °C, GMF/MFA 1:2
(mol/mol), and 8 h. Under these optimal conditions, high
GMF conversion (98.9 0.9%) and FAG yield (88.9 0.6%)
were achieved, which are both higher than that of using SBO
and the previous reports of using GMF to synthesize FAGs.44
Furthermore, either SBO or MFA as acyl donor can remarkably
improve the lipophilic FAG yields compared to previous
reactions that using EF/FA/VF in shorter reaction time.15−22
In conclusion, FAGs, the lipophilic feruloyl structure lipids,
were successfully synthesized by the enzymatic reaction of
GMF with different acyl donors (SBO and MFA) in IL systems.
For the esterification of GMF with MFA, higher FAG selectivity
(0.90) was obtained; and for the transesterification of GMF
with SBO, relative high FAG selectivity (0.89) was also ob-
tained. The low reaction rate, using SBO as acyl donor, was
attributed to the steric hindrance of SBO. Although, using MFA
as acyl donor, GMF conversion (98.9 0.9%) and FAG yield
(88.9 0.6%) were both higher than those (94.3 0.7% and
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83.8
1.0%) of SBO, SBO is still a good choice for FAG
preparation considering the price of raw materials and the more
convenient use of SBO.
AUTHOR INFORMATION
■
Corresponding Author
67758022.
Notes
The authors declare no competing financial interest.
The authors gratefully acknowledge financial support from
Program for Science & Technology Innovation Talents in
Universities of Henan Province (15HASTIT030), and Funding
Scheme for Young Teachers Cultivating Program in Henan
University of Technology.
ABBREVIATIONS USED
■
SBO, soybean oil; MFA, mixed fatty acids; GMF, glyceryl
monoferulate; GDF, glyceryl diferulate; FMAG, feruloylated
monoacylglycerols; FDAG, feruloylated diacylglycerols; FAGs,
feruloylated acylglycerols (FMAG + FDAG); EF, ethyl ferulate;
FA, ferulic acid
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synthesis of ferulate esters. J. Am. Oil Chem. Soc. 2000, 77, 513−519.
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two consecutive enzyme synthesis of feruloylated monoacyl-and
diacyl-glycerols in a solvent-free system. Biotechnol. Lett. 2007, 29,
1947−1950.
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