Antioxidant Activities of Dihydromyricetin Derivatives with Different Acyl Donor Chain Lengths Synthetized by Lipozyme TL IM

Dihydromyricetin (DHM) is a phytochemical with multiple bioactivities. However, its poor liposolubility limits its application in the field. In this study, DHM was acylated with different fatty acid vinyl esters to improve its lipophilicity, and five DHM acylated derivatives with different carbon chain lengths (C2-DHM, C4-DHM, C6-DHM, C8-DHM, and C12-DHM) and different lipophilicity were synthesized. The relationship between the lipophilicity and antioxidant activities of DHM and its derivatives was evaluated with oil and emulsion models using chemical and cellular antioxidant activity (CAA) tests. The capacity of DHM derivatives to scavenge 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical (ABTS+•) was similar to that of DHM, except for C12-DHM. The antioxidant activity of DHM derivatives was lower than that of DHM in sunflower oil, while C4-DHM exhibited better antioxidant capacity in oil-in-water emulsion. In CAA tests, C8-DHM (median effective dose (EC50) 35.14 μmol/L) exhibited better antioxidant activity than that of DHM (EC50: 226.26 μmol/L). The results showed that in different antioxidant models, DHM derivatives with different lipophilicity had various antioxidant activities, which has guiding significance for the use of DHM and its derivatives.

[1]  Dekui Zhang,et al.  Molecular mechanism and therapeutic significance of dihydromyricetin in nonalcoholic fatty liver disease. , 2022, European journal of pharmacology.

[2]  Dejian Huang,et al.  Highly Efficient Regioselective Acylation of Dihydromyricetin Catalyzed by Lipase in Nonaqueous Solvents , 2022, Processes.

[3]  Dejian Huang,et al.  Antioxidant activities of chlorogenic acid derivatives with different acyl donor chain lengths and their stabilities during in vitro simulated gastrointestinal digestion. , 2021, Food chemistry.

[4]  Song Zhu,et al.  Antioxidant activities of lipophilic (−)-epigallocatechin gallate derivatives in vitro and in lipid-based food systems , 2021 .

[5]  Xingguo Wang,et al.  Interactions between α-tocopherol and γ-oryzanol in oil-in-water emulsions. , 2021, Food chemistry.

[6]  C. Akoh,et al.  Comparison of antioxidant activities of selected phenolic compounds in O/W emulsions and bulk oil. , 2021, Food chemistry.

[7]  R. Elias,et al.  Effect of alkyl chain length on the antioxidant activity of alkylresorcinol homologues in bulk oils and oil-in-water emulsions. , 2021, Food chemistry.

[8]  Song Zhu,et al.  Lipase-catalyzed highly regioselective synthesis of acylated chlorogenic acid , 2020 .

[9]  I. Norton,et al.  The use of natural antioxidants to combat lipid oxidation in O/W emulsions , 2020, Journal of Food Engineering.

[10]  P. Villeneuve,et al.  Synthesis and evaluation of antioxidant activities of novel hydroxyalkyl esters and bis-aryl esters based on sinapic and caffeic acids. , 2020, Journal of agricultural and food chemistry.

[11]  Jun Sun,et al.  Evaluation of antioxidant modification on the functional and structural properties of EWP conjugates , 2020, RSC advances.

[12]  Qingzhe Jin,et al.  Physical properties and cellular antioxidant activity of vegetable oil emulsions with different chain lengths and saturation of triglycerides , 2020, LWT.

[13]  J. Bernatonienė,et al.  Flavonoids as Anticancer Agents , 2020, Nutrients.

[14]  R. Pegg,et al.  The cellular antioxidant and anti-glycation capacities of phenolics from Georgia peaches. , 2020, Food chemistry.

[15]  Xin‐an Zeng,et al.  Dihydromyricetin: A review on identification and quantification methods, biological activities, chemical stability, metabolism and approaches to enhance its bioavailability , 2019, Trends in Food Science & Technology.

[16]  S. Losada-Barreiro,et al.  Control of antioxidant efficiency of chlorogenates in emulsions: modulation of antioxidant interfacial concentrations. , 2019, Journal of the science of food and agriculture.

[17]  F. Shahidi,et al.  Antioxidant activity of resveratrol ester derivatives in food and biological model systems. , 2018, Food chemistry.

[18]  Guanglei Zhao,et al.  Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro , 2018, Microbial Cell Factories.

[19]  Zhi Wang,et al.  Regioselective acylation of resveratrol catalyzed by lipase under microwave , 2018, Green Chemistry Letters and Reviews.

[20]  R. K. Saxena,et al.  Efficient regioselective acylation of quercetin using Rhizopus oryzae lipase and its potential as antioxidant. , 2016, Bioresource technology.

[21]  J. Stanslas,et al.  Lipase-catalyzed acylation of quercetin with cinnamic acid , 2016 .

[22]  D. Mcclements,et al.  What Makes Good Antioxidants in Lipid-Based Systems? The Next Theories Beyond the Polar Paradox , 2015, Critical reviews in food science and nutrition.

[23]  G. Cabello,et al.  Boosting Antioxidants by Lipophilization: A Strategy to Increase Cell Uptake and Target Mitochondria , 2013, Pharmaceutical Research.

[24]  C. Bravo-Díaz,et al.  Modeling chemical reactivity in emulsions , 2013 .

[25]  D. Mcclements,et al.  An investigation of the versatile antioxidant mechanisms of action of rosmarinate alkyl esters in oil-in-water emulsions. , 2012, Journal of agricultural and food chemistry.

[26]  F. Shahidi,et al.  Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants. , 2011, Journal of agricultural and food chemistry.

[27]  P. Villeneuve,et al.  Chain length affects antioxidant properties of chlorogenate esters in emulsion: the cutoff theory behind the polar paradox. , 2009, Journal of agricultural and food chemistry.

[28]  Jie Zeng,et al.  Characterization and antioxidant activity of dihydromyricetin–lecithin complex , 2009 .

[29]  Rui Hai Liu,et al.  Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements. , 2007, Journal of agricultural and food chemistry.

[30]  Anne M. Drolet,et al.  Use of polyamide oxidative fluorescence test on lipid emulsions : contrast in relative effectiveness of antioxidants in bulk versus dispersed systems , 1989 .

[31]  F. Shahidi,et al.  Antiglycation activity of lipophilized epigallocatechin gallate (EGCG) derivatives. , 2016, Food chemistry.