TY - JOUR
T1 - Microwave-Assisted Synthesis and Ionic Liquids: Green and Sustainable Alternatives toward Enzymatic Lipophilization of Anthocyanin Monoglucosides
AU - Guimarães, Marta
AU - Mateus, Nuno
AU - De Freitas, Victor
AU - Branco, Luis C.
AU - Cruz, Luís
N1 - The authors thank Dr. Ze ' lia Azevedo for the MS analysis and Dr. Ana Silva for facilitating the use of a microwave reactor. This work was supported by the Associate Laboratory for Sustainable Chemistry, Clean Processes and Technologies LAQV. The latter is financed by national funds from UIDB/50006/2020.
This work was also supported by the project PTDC/OCE-ETA/31250/2017 funded by FCT and FEDER. L.C. gratefully acknowledges the research FCT contract.
PY - 2020/7/15
Y1 - 2020/7/15
N2 - Anthocyanins recycling and transformations into novel compounds have been of great interest of the scientific community to improve the circular economy and enhance their technological applications. The enzymatic acylation of anthocyanins into lipophilic derivatives by conjugation with fatty acids emerged as one of the approaches; however, the literature describes only the use of organic solvents and conventional heating. In this work, the production of cyanidin-3-glucoside-octanoic acid conjugate combining ionic liquids (ILs), microwave (MW) irradiation, and Candida antarctica lipase B as a biocatalyst was attempted for the first time. Overall, the use of MW irradiation could reduce drastically the reaction time, allowing the formation of an acylated product with similar concentrations to the conventional method. On the other hand, the study of the lipophilic conjugate synthesis using different ILs showed that their composition is crucial to achieve the desired enzymatic reaction, and in this case, the combination of an imidazolium derivative as the cation with the triflate as the anion was suitable for the production of this derivative. These promising results achieved through the combination of greener alternatives to those reported in the literature are a starting point for further developments to produce this kind of anthocyanin derivatives exploring such sustainable and ecofriendly conditions.
AB - Anthocyanins recycling and transformations into novel compounds have been of great interest of the scientific community to improve the circular economy and enhance their technological applications. The enzymatic acylation of anthocyanins into lipophilic derivatives by conjugation with fatty acids emerged as one of the approaches; however, the literature describes only the use of organic solvents and conventional heating. In this work, the production of cyanidin-3-glucoside-octanoic acid conjugate combining ionic liquids (ILs), microwave (MW) irradiation, and Candida antarctica lipase B as a biocatalyst was attempted for the first time. Overall, the use of MW irradiation could reduce drastically the reaction time, allowing the formation of an acylated product with similar concentrations to the conventional method. On the other hand, the study of the lipophilic conjugate synthesis using different ILs showed that their composition is crucial to achieve the desired enzymatic reaction, and in this case, the combination of an imidazolium derivative as the cation with the triflate as the anion was suitable for the production of this derivative. These promising results achieved through the combination of greener alternatives to those reported in the literature are a starting point for further developments to produce this kind of anthocyanin derivatives exploring such sustainable and ecofriendly conditions.
KW - ionic liquids
UR - http://www.scopus.com/inward/record.url?scp=85088180306&partnerID=8YFLogxK
U2 - 10.1021/acs.jafc.0c02599
DO - 10.1021/acs.jafc.0c02599
M3 - Article
C2 - 32609499
AN - SCOPUS:85088180306
SN - 0021-8561
VL - 68
SP - 7387
EP - 7392
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
IS - 28
ER -