Carbonylation Modification of Epicatechin and Its Activities of UV Absorption and Antioxidant

LEI Xiang; ZHANG Minfeng; LIN Hui; WANG Lili; ZHENG Deyong

doi:10.13305/j.cnki.jts.2024.03.002

PDF(359 KB)

Journal of Tea Science ›› 2024, Vol. 44 ›› Issue (3) : 493-500. DOI: 10.13305/j.cnki.jts.2024.03.002

Research Paper

Carbonylation Modification of Epicatechin and Its Activities of UV Absorption and Antioxidant

LEI Xiang^1,2, ZHANG Minfeng¹, LIN Hui¹, WANG Lili¹, ZHENG Deyong^1,3,*

Author information +

History +

Abstract

In order to enhance the UV absorption characteristic of epicatechin derivatives and improve their solubility in non-polar solvents such as oils and fats, 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin was synthesized from epicatechin and p-hydroxybenzoic acid using methane sulfonic acid as solvent and catalyst. The target products were separated by column chromatography, and the purity was verified by high performance liquid chromatography (HPLC), and the structure of the target products were verified by UV-vis, FT-IR, ¹H NMR, ¹³C NMR, LC-MS spectroscopy. The UV absorption characteristic of 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin and its ability to scavenge ABTS⁺·, DPPH· and O^2-· were evaluated. The results show that the synthesized 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin had similar UV absorption and comparable molar absorptivity to OMC, the commonly used UV absorber, and is expected to be an excellent UV absorber in the UVB band. 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin had good antioxidant activity in vitro, and its antioxidant capacity in vitro was higher than that of VC and slightly lower than that of epicatechin, which is expected to be used for cosmetic applications.

Key words

carbonylation / cosmetic / epicatechin / modification / UV absorption

Cite this article

EndNote

Ris (Procite)

Bibtex

Download Citations

LEI Xiang, ZHANG Minfeng, LIN Hui, WANG Lili, ZHENG Deyong. Carbonylation Modification of Epicatechin and Its Activities of UV Absorption and Antioxidant[J]. Journal of Tea Science. 2024, 44(3): 493-500 https://doi.org/10.13305/j.cnki.jts.2024.03.002

References

[1] 冯娇, 刘光荣, 朱文驿, 等. 具有防晒功能的植物源成分研究进展[J]. 日用化学品科学, 2018, 41(1): 40-44.
Feng J, Liu G R, Zhu W Y, et al.Research progress on sunscreen ingredients from plants[J]. Detergent & Cosmetics, 2018, 41(1): 40-44.
[2] 张志敏. 防晒产品中的抗氧化剂[J]. 日用化学品科学, 2010, 33(8): 49-50.
Zhang Z M.Antioxidant cocktail could complement sunscreen use[J]. Detergent & Cosmetics, 2010, 33(8): 49-50.
[3] 刘苗. 负载白藜芦醇纳米结构脂质载体防晒凝胶的制备及其防晒效果评价[D]. 西安: 中国人民解放军空军军医大学, 2018.
Liu M.The preparation and protective effect of resveratrol-loaded nanostractured lipid carrier sunscreen gel [D]. Xi'an: Air Force Military Medical University, 2018.
[4] 刘静, 周莉君, 袁明, 等. 油茶籽油抗氧化和防紫外辐射活性分析及多酚类物质提取研究[J]. 中国油脂, 2017, 42(10): 130-133.
Liu J, Zhou L J, Yuan M, et al.Antioxidation and anti-ultraviolet radiation activities of oil-tea camellia seed oil and extraction of polyphenols[J]. China Oils and Fats, 2017, 42(10): 130-133.
[5] 黄琳, 马烁, 赵华, 等. 茶多酚提取及其在日用化学品中的应用进展[J]. 精细石油化工, 2022, 39(1): 64-67.
Huang L, Ma S, Zhao H, et al.Research progress on extraction of tea polyphenols and their application in daily chamical products[J]. Speciality Petrochemicals, 2022, 39(1): 64-67.
[6] 王巧娥, 唐安斌, 马志红, 等. 含不同脂肪链脂溶性茶多酚的合成及其抗氧化活性研究[J]. 精细化工, 2002, 19(2): 86-89.
Wang Q E, Tang A B, Ma Z H, et al.Synthesis of liposoluble tea polyphenols with varying aliphatic groups and their antioxidation activity[J]. Fine Chemicals, 2002, 19(2): 86-89.
[7] 邵卫梁, 胡天喜, 杭晓敏, 等. 不同酯化程度的脂溶性茶多酚抗氧化和抗脂质过氧化研究[J]. 安徽医药, 2006, 10(12): 904-907.
Shao W L, Hu T X, Hang X M, et al.Study on the quality index of the lipid tea polyphenols based on their effects of antioxidation and anti-lipid preoxidation in different esterification degree[J]. Anhui Medical and Pharmaceutical Journal, 2006, 10(12): 904-907.
[8] Dutta S, Basak A, Dasgupta S.Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: importance of hydroxyl groups[J]. Bioorganic Medicinal Chemistry, 2010, 18(17): 6538-6546.
[9] 卢聪聪. 茶多酚的化学改性和脂溶性茶多酚分离分析[D]. 上海: 上海交通大学, 2008.
Lu C C.Chemical modification on tea polyphenols and study on lipid-soluble tea polyphenols [D]. Shanghai: Shanghai Jiao Tong University, 2008.
[10] 张芳芳, 李太衬, 姜恒, 等. 甲烷磺酸催化合成7-羟基-4-甲基香豆素[J]. 工业催化, 2009, 17(11): 70-72.
Zhang F F, Li T C, Jiang H, et al.Synthesis of 7-hydroxy-4-methylcoumarin catalyzed by methanesulfonic acid[J]. Industrial Catalysis, 2009, 17(11): 70-72.
[11] 张玉银, 丛琳, 李雪竹. 浅析无机防晒剂及其防晒机理与安全问题[J]. 当代化工研究, 2020, 1(8): 35-36.
Zhang Y Y, Cong L, Li X Z.Analysis of inorganic sunscreen and its sunscreen mechanism and safety[J]. Modern Chemical Research, 2020, 1(8): 35-36.
[12] 陈华铮, 朱凯. 两种柑橘类精油及其主要成分的抑菌和抗氧化活性[J]. 林产化学与工业, 2021, 41(4): 17-22.
Chen H Z, Zhu K.Antibacterial and antioxidant activities of two citrus essential oils and their main components[J]. Chemistry and Industry of Forest Product, 2021, 41(4): 17-22.
[13] 龚海波, 焦丰龙, 胡蓓娟, 等. 一种池蝶蚌多糖的分离纯化、表征特性及体外抗氧化活性[J]. 南昌大学学报(理科版), 2017, 41(2): 166-170.
Gong H B, Jiao F L, Hu B J, et al.Purification, characterization and antioxidant activities in vitro of polysccharides from Hyriopsis schlegelii[J]. Journal of Nanchang University (Natural Science), 2017, 41(2): 166-170.
[14] 潘百明, 苏辉兰, 梁昌祥, 等. 紫茄超氧化物歧化酶的提取及其活性测定[J]. 食品工业, 2020, 41(2): 143-146.
Pan B M, Su H L, Liang C X, et al.SOD extraction and activity determination from purple eggplant[J]. The Food Industry, 2020, 41(2): 143-146.
[15] Hu J X, Gao J Y, Zhao Z J, et al.Response surface optimization of polysaccharide extraction from Galla Chinensis and determination of its antioxidant activity in vitro[J]. Food Science and Technology, 2021, 41(1): 188-194.
[16] 吴剑龙, 胡学森, 马林. 多羟基二苯甲酮的抗氧化性能研究[J]. 中山大学学报(自然科学版), 2010, 49(s1): 70-74.
Wu J L, Hu X S, Ma L.The study of antioxidant activity of polyhydroxybenzophenones[J]. Acta Scientiarum Naturalium Universitatis Sunyatseni, 2010, 49(s1): 70-74.