Chemo-enzymatic synthesis, in vitro antioxidant activities and positive effects on oil-in-water emulsion Stabilization of phenolic acid-esterified phosphatidylcholines
Abstract
The industrial application of phenolic acids (PAs) is significantly limited by their low solubility and poor bioavailability in lipid-rich systems. Lipophilization via esterification of PAs with lipid matrices offers a promising approach to address these challenges. In this study, an efficient lipase-chemical catalytic method was developed for synthesizing phenolic acid-esterified phosphatidylcholines (PA-EPCs) from PAs and phosphatidylcholine (PC). Three derivatives-caffeic acid-esterified phosphatidylcholines (CA-EPC), ferulic acid-esterified phosphatidylcholines (FA-EPC), and p-hydroxycinnamic acid-esterified phosphatidylcholines (p-HCA-EPC)-were successfully obtained with isolated yields of 67.5 %, 84.5 %, and 85.3 %, respectively. Their structures were confirmed by 1H/13C NMR and ESI-MS analyses. Compared with unmodified PC, PA-EPCs, especially CA-EPC, showed significantly enhanced in vitro antioxidant activity, as demonstrated by assays of lipid peroxide value, DPPH/ABTS radical scavenging capacity, and ferric reducing antioxidant power (FRAP). Due to the incorporation of PC into PAs, PA-EPCs exhibited enhanced lipophilicity, which significantly improved the stability of oil-in-water (O/W) emulsions. This improvement was evidenced by higher emulsifying activity indices, smaller droplet sizes, more homogeneous distribution, and a slower increase in thiobarbituric acid reactive substances (TBARs) over time. Collectively, these findings indicate that PA-EPCs possess remarkable potential as effective antioxidants and emulsifiers in food, cosmetic, and pharmaceutical industries.
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BibTeX
@article{li2026chemoenzymatic,
title = {{Chemo-enzymatic synthesis, in vitro antioxidant activities and positive effects on oil-in-water emulsion Stabilization of phenolic acid-esterified phosphatidylcholines}},
author = {Hong Li and Xintian Qiao and Ran Ding and Zihao Guo and Desong Zhu and Lu Zhang and Ruiling Shen and Tao Wei},
journal = {Journal of Oleo Science},
year = {2026},
month = sep,
doi = {10.5650/jos.ess25285},
url = {https://www.jstage.jst.go.jp/article/jos/75/9/75_jos.ess25285/_article},
note = {CC BY},
}
RIS
TY - JOUR
TI - Chemo-enzymatic synthesis, in vitro antioxidant activities and positive effects on oil-in-water emulsion Stabilization of phenolic acid-esterified phosphatidylcholines
AU - Hong Li
AU - Xintian Qiao
AU - Ran Ding
AU - Zihao Guo
AU - Desong Zhu
AU - Lu Zhang
AU - Ruiling Shen
AU - Tao Wei
PY - 2026
DA - 2026/09/01
JO - Journal of Oleo Science
DO - 10.5650/jos.ess25285
UR - https://www.jstage.jst.go.jp/article/jos/75/9/75_jos.ess25285/_article
AB - The industrial application of phenolic acids (PAs) is significantly limited by their low solubility and poor bioavailability in lipid-rich systems. Lipophilization via esterification of PAs with lipid matrices offers a promising approach to address these challenges. In this study, an efficient lipase-chemical catalytic method was developed for synthesizing phenolic acid-esterified phosphatidylcholines (PA-EPCs) from PAs and phosphatidylcholine (PC). Three derivatives-caffeic acid-esterified phosphatidylcholines (CA-EPC), ferulic acid-esterified phosphatidylcholines (FA-EPC), and p-hydroxycinnamic acid-esterified phosphatidylcholines (p-HCA-EPC)-were successfully obtained with isolated yields of 67.5 %, 84.5 %, and 85.3 %, respectively. Their structures were confirmed by 1H/13C NMR and ESI-MS analyses. Compared with unmodified PC, PA-EPCs, especially CA-EPC, showed significantly enhanced in vitro antioxidant activity, as demonstrated by assays of lipid peroxide value, DPPH/ABTS radical scavenging capacity, and ferric reducing antioxidant power (FRAP). Due to the incorporation of PC into PAs, PA-EPCs exhibited enhanced lipophilicity, which significantly improved the stability of oil-in-water (O/W) emulsions. This improvement was evidenced by higher emulsifying activity indices, smaller droplet sizes, more homogeneous distribution, and a slower increase in thiobarbituric acid reactive substances (TBARs) over time. Collectively, these findings indicate that PA-EPCs possess remarkable potential as effective antioxidants and emulsifiers in food, cosmetic, and pharmaceutical industries.
SN - 1347-3352
SN - 1345-8957
ER -