Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems
Cyanidin-3-<i>O</i>-glucoside (C3G) was used as a substrate for enzymatic acylation, and different compounds (methyl <i>n</i>-octanoate and methyl salicylate) were selected as acyl donors. Structural analysis (UV–Vis, FTIR, and HPLC) revealed the successful integration of met...
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2025-04-01
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| author | Ziwei Ye Mingyun Liu Jingmei Lyu Han Rong Lujing Gan |
| author_facet | Ziwei Ye Mingyun Liu Jingmei Lyu Han Rong Lujing Gan |
| author_sort | Ziwei Ye |
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| description | Cyanidin-3-<i>O</i>-glucoside (C3G) was used as a substrate for enzymatic acylation, and different compounds (methyl <i>n</i>-octanoate and methyl salicylate) were selected as acyl donors. Structural analysis (UV–Vis, FTIR, and HPLC) revealed the successful integration of methyl ester compounds into the structural units of C3G. The thermostability and photostability of acylated C3Gs, particularly those with methyl salicylate as the acyl donor, exhibited significant improvements. The molecular geometries of the different anthocyanins were optimized using computational chemistry, and energy level calculations were performed by using Density Functional Theory (DFT) to identify the antioxidant active site. Then, the antioxidant properties of C3G and acylated C3Gs (O-C3G and S-C3G) were studied in both aqueous and lipid systems. In aqueous systems, acylated C3Gs exhibited higher antioxidant properties than C3G in DPPH radical scavenging and hydroxyl radical scavenging assays, with cyanidin-3-<i>O</i>-glucoside salicyl acyl product (S-C3G) demonstrating the highest activity. However, the antioxidant properties varied in lipid systems. In lipid systems, acylated C3Gs displayed better antioxidant properties than C3G in POV and TBARS assays, with cyanidin-3-<i>O</i>-glucoside <i>n</i>-octanoate acid acyl product (O-C3G) showing better antioxidant properties compared to that in aqueous systems. |
| format | Article |
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| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-e7b9efe2489d4b609d26e95dce31cec62025-08-20T02:59:08ZengMDPI AGMolecules1420-30492025-04-01309201510.3390/molecules30092015Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid SystemsZiwei Ye0Mingyun Liu1Jingmei Lyu2Han Rong3Lujing Gan4School of Materials and Environment, Beijing Institute of Technology, Zhuhai 519088, ChinaSchool of Materials and Environment, Beijing Institute of Technology, Zhuhai 519088, ChinaSchool of Materials and Environment, Beijing Institute of Technology, Zhuhai 519088, ChinaSchool of Materials and Environment, Beijing Institute of Technology, Zhuhai 519088, ChinaSchool of Materials and Environment, Beijing Institute of Technology, Zhuhai 519088, ChinaCyanidin-3-<i>O</i>-glucoside (C3G) was used as a substrate for enzymatic acylation, and different compounds (methyl <i>n</i>-octanoate and methyl salicylate) were selected as acyl donors. Structural analysis (UV–Vis, FTIR, and HPLC) revealed the successful integration of methyl ester compounds into the structural units of C3G. The thermostability and photostability of acylated C3Gs, particularly those with methyl salicylate as the acyl donor, exhibited significant improvements. The molecular geometries of the different anthocyanins were optimized using computational chemistry, and energy level calculations were performed by using Density Functional Theory (DFT) to identify the antioxidant active site. Then, the antioxidant properties of C3G and acylated C3Gs (O-C3G and S-C3G) were studied in both aqueous and lipid systems. In aqueous systems, acylated C3Gs exhibited higher antioxidant properties than C3G in DPPH radical scavenging and hydroxyl radical scavenging assays, with cyanidin-3-<i>O</i>-glucoside salicyl acyl product (S-C3G) demonstrating the highest activity. However, the antioxidant properties varied in lipid systems. In lipid systems, acylated C3Gs displayed better antioxidant properties than C3G in POV and TBARS assays, with cyanidin-3-<i>O</i>-glucoside <i>n</i>-octanoate acid acyl product (O-C3G) showing better antioxidant properties compared to that in aqueous systems.https://www.mdpi.com/1420-3049/30/9/2015cyanidin-3-<i>O</i>-glucosideenzymatic acylationstabilityantioxidant properties |
| spellingShingle | Ziwei Ye Mingyun Liu Jingmei Lyu Han Rong Lujing Gan Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems Molecules cyanidin-3-<i>O</i>-glucoside enzymatic acylation stability antioxidant properties |
| title | Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems |
| title_full | Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems |
| title_fullStr | Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems |
| title_full_unstemmed | Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems |
| title_short | Influence of Enzymatic Acylation on the Stability and Antioxidant Properties of Cyanidin-3-<i>O</i>-Glucoside in Both Aqueous and Lipid Systems |
| title_sort | influence of enzymatic acylation on the stability and antioxidant properties of cyanidin 3 i o i glucoside in both aqueous and lipid systems |
| topic | cyanidin-3-<i>O</i>-glucoside enzymatic acylation stability antioxidant properties |
| url | https://www.mdpi.com/1420-3049/30/9/2015 |
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