EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
·
2023
·Vol. 125
·期 10
·2300015
·
IF 2.7
Juan Tian,Guilin Peng,Xiaodi Qu,Yunping Yao,Changmo Li
Thiamine (VB 1 ) is an essential water-soluble vitamin that is necessary in our daily diet. However, its instability when exposed to external factors poses a limitation on its application in the food industry. To address this issue and increase its application in fat-rich food systems, this study developed liposoluble VB 1 microcapsules via freeze-drying, utilizing β-cyclodextrin as a wall material and polyglycerol fatty acid ester as an emulsifying agent. The VB 1 microcapsules were characterized in terms of their particle size distribution, morphology, solubility, and stability in soybean oil, as well as their in vitro bioaccessibility. The results showed that the average particle size of VB 1 microcapsules was 83.73 μm with a nonuniform, somewhat wrinkled spherical structure. The solubility of the VB 1 microcapsules in soybean oil was increased to 142.86 mg kg –1 . The retention rates of VB 1 in soybean oil was found to be above 95% after 48 h of UV irradiation and 96.44% after heating for 7 days at 60°C. The presence of VB 1 microcapsules did not significant impact on the oxidation stability of soybean oil. The bioaccessibility of VB 1 in soybean oil was 82.81%. This work provides a useful and novel direction for the application of VB 1 in high-fat diets. Practical applications: VB 1 is one of the B-group vitamins that assists in maintaining normal glucose metabolism. However, it is readily inactivated when exposed to UV radiation, certain pH conditions, and other factors. In this work, the VB 1 microcapsules prepared by freeze-drying exhibited high liposolubility, stability, and bioaccessibility, rendering them suitable for applications in oil-based systems. This work not only provides a new delivery system to facilitate VB 1 supplementation in humans, but also helps to elucidate its application prospect of VB 1 in fat-rich foods, such as edible oil, butter, margarine, rich-fat dressings, and so on, thus improves the application value of VB 1 .
研究领域:
食品科学
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营养学
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DOI
高影响因子
Frontiers in Bioengineering and Biotechnology
·
2022
·
IF 6.064
Yang Rongling,Wang Yu,Zhao Xiangjie,Tong Zheng,Zhu Qianlin,He Xiaoxi,Wang Zhaoyu,Luo Hongzhen,Fang Fang
Salidroside, the main bioactive compound isolated from the plant source of Rhodiola rosea L, possesses broad-spectrum pharmacological activities, but suffers from the low cell membranes permeability and alimentary absorption due to its high polarity. Therefore, a whole-cell catalytic strategy for the synthesis of salidroside esters was explored to improve its lipophilicity. The results showed that Aspergillus oryzae demonstrated the highest biocatalytic activity among the microbial strains tested. For the synthesis of salidroside caprylate, the optimum conditions of reaction medium, Aspergillus oryzae amount, molar ratio of vinyl caprylate to salidroside and reaction temperature were acetone, 30 mg/ml, 10°C and 40°C, respectively. Under these conditions, the initial reaction rate was 15.36 mM/h, and substrate conversion and regioselectivity all reached 99%. Moreover, the results indicated that although various 6′-monoesters derivatives of salidroside were exclusively obtained with excellent conversions (96%–99%), the reaction rate varied greatly with different chain-length acyl donors. This study details an efficient and cost-effective biocatalytic approach for the synthesis of salidroside esters by using Aspergillus oryzae as a catalyst for the first time. Considering the whole cell catalytic efficiency and operational stability, this strategy may provide a new opportunity to develop green industrial processes production for ester derivatives of salidroside and its analogues.
研究领域:
药理学
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生物化学
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工业微生物学
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DOI
PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2024
·
IF 7
Hai-Xia Xu,Na-Na Zheng,Yu-Cong Zou,Qing-Feng Zhang
A lipophilic piceid lipoate (PIL) was synthesized by enzymatic method to enhance the antioxidant activity of piceid and improve its state in oil system. The highest substrate conversion of 93.71 % was obtained in γ-valerolactone using Novozym 435 as a catalyst, with a piceid/lipoic acid ratio of 1:15 (mM/mM), an enzyme dosage of 40 mg/mL, and 4 Å molecular sieves at 400 mg/mL. The lipophilicity and antioxidant activity of piceid and PIL were evaluated, which found the introduction of α-lipoic acid markedly increased the lipophilicity and antioxidant activity of piceid. The oxidation inhibition rate of PIL in bulk oil was nearly 2.0 and 1.9 times higher than piceid and butylated hydroxytoluene, indicating that PIL is a promising antioxidant for oil-based foods. The antioxidant micro-mechanisms of PIL were revealed by computational simulations, which found the lipoic acid moiety in PIL molecule enhanced its free radical scavenging capacity and improved its solubility, dispersion, and migration in bulk oil.
研究领域:
食品科学
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生物化学
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产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2023
·
IF 8.8
Xuejing Liu,Yaoyao Zhang,Shangde Sun
Caffeic acid (CA), as a potential green antioxidant, plays an important role in food processing. However, the low liposolubility of CA limits its applications. To overcome this issue, CA is normally modified by introducing a lipophilic group, such as alkyl alcohols, resulting in the formation of alkyl caffeate, which can significantly enhance the liposolubility of CA. In this study, a binuclear ionic liquid , 1,1-bis(2-pyrrolidinone) sulfate ([C 3 (Hnhp) 2 ][HSO 4 ] 2 ), is successfully synthesized and characterized by FT-IR and 1 H NMR. The physico-chemical properties of [C 3 (Hnhp) 2 ][HSO 4 ] 2 , including the density, viscosity, thermal stability and Brønsted acidity, were analyzed. As a novel catalyst for the esterification of CA with model dodecanol , its catalytic performance was investigated and optimized by response surface methodology. Under the optimal conditions, a 95.42 ± 1.01% yield of dodecanol caffeate was achieved. Moreover, the [C 3 (Hnhp) 2 ][HSO 4 ] 2 exhibits excellent stability and reusability, making it a highly promising catalyst for the synthesis of various lipophilic alkyl caffeates.
研究领域:
食品科学
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有机化学
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绿色化学
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DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2023
·Vol. 103
·期 7
·3489-3500
·
IF 4.1
Yihang Liu,Qingzhi Wang,Chen Liu,Haonan Yang,Li Jia,Litao Zhao,Fayong Gong,Chen Tan,Hongxun Tao,Wen-Sen He
BACKGROUND Oxidation is a major problem for oils and fats, which can be mitigated by antioxidants. Rutin has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. In this study, an efficient enzymatic synthesis route of lipophilic rutin ester was established using oleic acid as an acyl donor, and the antioxidant potential of rutin oleate was evaluated for the first time by proton ( 1 H) nuclear magnetic resonance (NMR) spectroscopy. RESULTS The synthesized product was finally identified as rutin oleate by Fourier transform infrared, high-performance liquid chromatography–mass spectrometry, and 1 H, carbon-13, and DEPT-135 NMR analyses, and the acylation site was the 4‴-OH of the rhamnose group in the rutin molecule. The maximum conversion was over 93% after 48 h of reaction using Novozym 435 as catalyst under the best conditions among these tests. The conversion of rutin ester decreased with the increase of carbon chain length and the number of carbon–carbon double bonds of the fatty acid molecule. Most importantly, rutin oleate exhibited antioxidant capacity comparable to butylated hydroxytoluene and its counterparts (rutin and oleic acid) at low temperatures (60° C), but had a significant advantage at high temperatures (120° C). CONCLUSION The antioxidant activity of rutin was significantly enhanced by lipase-mediated esterification with oleic acid. Therefore, rutin oleate could be further developed as a novel antioxidant for use in oil‑ and fat-based foods. © 2023 Society of Chemical Industry.
研究领域:
食品科学
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生物化学
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分析化学
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DOI
PubMed
高影响因子
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
·
2024
·
IF 1.8
Xin Yu,Xinyi Yang,Junqing Qian,Hui Guo
Mangiferin is one of the main bioactive ingredients in leaves of Mangifera indica . But the poor liposolubility and low bioavailability restrict its application. This study aimed to esterify mangiferin with lipase to improve its lipophilicity, and evaluate its antioxidant activity and hypoglycemic properties. Four fatty acids (palmitic acid, lauric acid, stearic acid, oleic acid) were selected for enzymatic esterification with mangiferin by single-factor experiments. Under the following optimum reaction conditions of tetrahydrofuran (THF): tert -amyl alcohol (2:1) was used as solvent, water activity was 0.31, TLIM lipase was 45 mg mL –1 , The ratio of mangiferin to fatty acid was 1:50, and the substrates were pretreated by ultrasonic for 0.5 h, then reacted at 55°C for 21 h, the resulting conversion rates of mangiferin-esterified derivatives exceeded 70.0%. Lipophilicity, antioxidant, and PTP1B inhibitory activity of mangiferin-esterified derivatives were determined. The results demonstrated that compared with mangiferin, the ability to scavenge DPPH radicals decreased by about 9%, but the lipophilicity was increased by 10–30 times, and the lipid antioxidant capacity was also improved significantly. Moreover, the inhibitory activity of protein tyrosine phosphatase 1B (PTP1B) exhibited minimal alteration. This indicates that esterification can not only improve the lipophilicity of mangiferin, but also improve its lipid antioxidant capacity. Practical Applications : In the study, a series of mangiferin-esterified derivatives were synthesized and their lipophilicity, antioxidant properties, and PTP1B inhibitory activity were determined. The results indicated that, compared with the untreated mangiferin, the mangiferin-esterified derivatives exhibited superior lipid antioxidant and hypoglycemic activities. Furthermore, the enzymatic esterification method employed in this study offered greater economic and environmental advantages when compared to chemical catalysis. Therefore, the preparation of mangiferin derivatives through enzymatic esterification were deemed feasible with potential application value for enhancing lipid antioxidant capacity in high-fat foods.
研究领域:
食品科学
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生物化学
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DOI
高影响因子
CRYSTENGCOMM
·
2019
·Vol. 21
·期 34
·5095-5105
·
IF 3.382
Xia-Lin Dai,Alexander P. Voronin,Wei Gao,German L. Perlovich,Tong-Bu Lu,Jia-Mei Chen
5-Fluorouracil (5FU) is a BCS class III drug with good aqueous solubility and poor permeability, which severely limits its transdermal permeation through the stratum corneum. Herein, four cocrystals of 5FU with a series of isomeric hydroxybenzoic acids, including salicylic acid (2 : 1), 3-hydroxybenzoic acid (1 : 1) and 4-hydroxybenzoic acid (forms I and II, 1 : 1) were prepared and subjected to membrane permeation. They exhibited significantly improved membrane permeability due to the lipid solubility enhancement caused by cocrystallization. Solid-state DFT computations followed by Bader analysis based on single crystal structures were carried out to quantify the pattern of non-covalent interactions in the cocrystals. The lattice energy values were estimated as a sum of energies of non-covalent intermolecular interactions, which show a negative correlation with the lipid solubility of 1 : 1 cocrystals. This study has important implications for the use of the cocrystallization approach to improve the permeability of transdermal drugs.
研究领域:
药学
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理论化学
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药物递送
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DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2025
·
IF 6.2
Jun Hu,Chujie Liang,Jinchao Xiao,Mu Chen,Kuanchen Huang,Yue Li,Shulin Deng,Xusheng Li,Jianxia Sun,Weibin Bai
Anthocyanins are widely used water-soluble pigments with various activities, which are attributed to their flavylium salt and polyhydroxy structure. However, this also leads to low lipid solubility and stability. Acylation modification has always been an attempt by researchers to improve it. In this study, two site-specific acylated anthocyanins, cyanidin-3-O-(2″-acetyl)-glucoside (C3AG) and malvidin-3-O-(2″-acetyl)-glucoside (M3AG), were prepared by optimizing the removal conditions of the protecting group through the general anthocyanin total synthesis route established in the early stage. The accurate positioning of the acylation is determined by MS/MS and 2D NMR. By comparing the oil–water partition coefficient, antioxidant activity, color, and thermal stability of the two acylated anthocyanins, it was found that the 2″ acylated anthocyanin achieved better lipid solubility and stability, but the antioxidant activity showed variability. These results together prove that these acylated anthocyanins have been optimized in application scenarios with little impact on the original activity. Therefore, this work not only provides a reference method for the acylation modification of anthocyanins but also promotes their application in the food and cosmetics industries.
研究领域:
食品科学
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化妆品科学
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植物化学
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DOI
PubMed
高影响因子
JOURNAL OF FOOD SCIENCE
·
2021
·Vol. 86
·期 5
·1714-1725
·
IF 3.167
Hai-Mei Li,Ting-Ting Xu,Qing-Xia Peng,Yong-Sheng Chen,Hua Zhou,Yu-Yun Lu,Ri-An Yan
Rutin (3′,4′,5,7-tetrahydroxy-flavone-3-rutinoside) was enzymatically acylated with benzoic acid and its esters (methyl benzoate and vinyl benzoate) using Thermomyces lanuginosus lipase (Lipozyme TLIM). The acylation reaction was optimized by varying the reaction medium, reaction temperature, acyl donor, substrate molar ratio, and reaction time. The highest conversion yield (76%) was obtained in tert -amyl alcohol (60 °C, 72 hr) using vinyl benzoate (molar ratio of 1:10) as acyl donor. The acylation occurred at the 2′′′-OH and 4′′′-OH of the rhamnose unit and the 2′′-OH position of the glucose moieties. Three novel rutin acylated derivatives (compounds 1 – 3 ) were purified and characterized by HR-MS and 1D and 2D NMR spectroscopy. We found that acylation significantly improved lipophilicity, capacity to inhibit lipid peroxidation, anticancer capacity and substantially maintained the antioxidant activity of rutin. This research provides important insights in the acylation of flavonoids with different glycosyl moieties. Practical Application In this study, three novel rutin derivatives were successfully synthesized and the highest conversion yield (76%) was obtained by reacting the rutin and vinyl benzoate at molar ratio of 1:10 in tert -amyl alcohol for 72 hr at 60 °C. Introducing a benzoic acid substituent into rutin molecule significantly improved their lipophilicity and inhibition of lipid peroxidation in lipophilic system. Furthermore, this study demonstrated that acylation significantly improved anticancer capacity and substantially maintained the antioxidant activity.
研究领域:
食品科学
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生物化学
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药物化学
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DOI
PubMed
高影响因子
Food & Function
·
2024
·Vol. 15
·期 11
·5785-5796
·
IF 5.1
Li-sha Hao,Meng-meng Zhang,Xiao-Feng Li,Xuan Xin,Guang-lei Zhao
In this study, we developed a multi-site acylation strategy to improve the lipophilicity and cellular uptake of troxerutin, a natural flavonoid with many health-promoting bioactivities. By clarifying the acylation properties of troxerutin catalyzed by lipases from different sources, a series of troxerutin ester derivatives acylated at different sites was synthesized, including troxerutin dipropyl (TDP), tripropyl (TTP), tetrapropyl (TEP), dibutyl (TDB), monohexyl (TMH), monooctyl (TMO) and monodecyl (TMD) esters. Interestingly, the troxerutin esters acylated at multiple sites with shorter fatty chains (TDP, TTP and TEP) had similar lipophilicity to the mono-acylated esters bearing longer fatty chains (TMH, TMO and TMD, respectively) and meanwhile demonstrated surprisingly lower cytotoxicity than that of the long fatty-chain mono-esters. In particular, the multi-acylated esters with shorter fatty chains showed remarkably higher cellular uptake than the mono-esters with long fatty chains. In vitro gastrointestinal digestion suggested that the multi-acylated esters of troxerutin were more resistant to gastrointestinal degradation than the mono-esters. These results indicated that multi-site acylation with short fatty chains could be an effective alternative to introducing one-site mono-acylation for the modification of troxerutin and other flavonoid compounds.
研究领域:
生物化学
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药理学
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食品科学
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产品关联
DOI
PubMed
高影响因子
CHEMOSPHERE
·
2022
·
IF 8.943
Xueke Liu,Yaofeng Fang,Xiaoran Ma,Peize Li,Peng Wang,Zhiqiang Zhou,Donghui Liu
Although chlordane-related compounds (CHLs) have been regulated, a variety of CHLs are still identified and detected in wild birds and eggs. Embryo is one of fragile periods and is very susceptible to toxic effects of pollutants. In this study, the fate of CHLs during embryo development and degradation of CHLs in neonatal chick were investigated. During embryo development, CHLs were mainly distributed to the liver and muscle, in which trans -nonachlor and an octachlorochlordane (MC5) were hardly metabolized and showed the high persistence, implying a greater risk to birds’ offspring . CHLs with the lower K ow were found to be higher uptake efficiency in embryo, implying contaminants with the lower lipophilicity may contribute to their transport to embryo. Furthermore, the effects of CHLs on the metabolome of neonatal chicks was evaluated. The ether lipid metabolism and glycerophospholipid metabolism were found to be significantly affected, which may disturb the angiogenesis and endothelial cell migration in embryogenesis . Taken together, the lipophilicity of contaminants might be a main factor influencing their transport to embryo, and metabolomics results improve understanding of the effects of CHLs on embryo.
研究领域:
环境科学
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毒理学
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代谢组学
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DOI
PubMed
高影响因子
RSC Advances
·
2021
·Vol. 11
·期 29
·17611-17621
·
IF 3.361
Yanfei Liu,Shuo Long,Shanshan Zhang,Yifu Tan,Ting Wang,Yuwei Wu,Ting Jiang,Xiaoqin Liu,Dongming Peng,Zhenbao Liu
Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.
研究领域:
药理学
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有机化学
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自由基生物学
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）