A Rapid and Practical Catalytic Esterification for the Preparation of Caffeic Acid Esters

Xie, Dongsheng; Yang, Fulun; Xie, Jin; Zhang, Man; Liu, Wenlu; Fu, Lei

doi:10.3184/174751914x14146000527920

Cited by 5 publications

(4 citation statements)

References 30 publications

(48 reference statements)

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“…The structural modification, especially enzymatic esterification, is an effective means to improve lipophilicity. Many hydrophilic bioactive compounds have been lipophilized, including EGCG, cinnamic, caffeic acids, ascorbic acid, genistein [22][23][24][25][26], and expanding their application in a more lipophilic system.…”

Section: Lipophilicity Of Legcgmentioning

confidence: 99%

Lipophilized Epigallocatechin Gallate Derivative Exerts Anti-Proliferation Efficacy through Induction of Cell Cycle Arrest and Apoptosis on DU145 Human Prostate Cancer Cells

Zhang

Chen

et al. 2019

Nutrients

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Epigallocatechin gallate (EGCG) is the predominant tea polyphenol and it exhibits a hydrophilic character. The lipophilized EGCG derivative (LEGCG) was synthesized by enzymatic esterification of EGCG with lauric acid to enhance its bioactivity. The tetralauroyl EGCG was confirmed by high-performance liquid chromatography-tandem mass spectrometry and further identified as 3 , 5 , 3 , 5 -4-O-lauroyl EGCG by 1 H and 13 C nuclear magnetic resonance. The anti-proliferation effect of LEGCG on DU145 human prostate carcinoma cells was evaluated by MTT assay. In addition, the underlying molecular mechanism by which LEGCG exerts anti-proliferation efficacy was elucidated by flow cytometry and immunoblot analysis. Results suggested that LEGCG exhibited a dose-dependent anti-proliferation effect on DU145 cells by G0/G1 phase arrest and induction of apoptosis. LEGCG induced cell cycle arrest via p53/p21 activation, which down-regulated the cyclin D1 and CDK4 expression. In addition, LEGCG induced apoptosis by increasing the Bax/Bcl-2 ratio, the cytochrome c release, and the caspases cleavage on DU145 cells. The results provide theoretical support to prevent prostate cancer with LEGCG.Nutrients 2020, 12, 92 2 of 10 cancer affects [16]. Therefore, we hypothesized that LEGCG has the potential to prevent prostate cancer. In the present study, enzymatic esterification of EGCG was implemented. The high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) and 1 H and 13 C nuclear magnetic resonance (NMR) were used to determine the chemical structures of LEGCG.The inhibitory effect and the underlying mechanism of LEGCG on DU145 cells were investigated by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay, flow cytometry, and immunoblot analysis. Materials and Methods MaterialsEGCG, MTT, and propidium iodide (PI) were purchased from Sigma-Aldrich Co. (St. Louis, MO., USA). Annexin V-FITC/PI kit was from Biolegend (San Diego, CA, USA). Cyclin D1, CDK 4, p21, p27, p53, Bax, Bcl-2, cytochrome c, cleaved caspase-9, cleaved caspase-3, and GAPDH antibodies were from Cell Signaling Technology (Danvers, MA, USA). Preparation of Crude EGCG DerivativeLEGCG was prepared according to the literature [17]. Briefly, EGCG and lauric acid were mixed at a mole ratio of 1:1 in ethanol, and then 5% of Lipozyme TLIM (5% w/w) was added. The mixture was heated at 45 • C for 12 h in a screw-capped glass bottle. The reaction was terminated by the removal of the enzyme through filter paper, and the product was concentrated to get crude LEGCG.

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Section: Lipophilicity Of Legcgmentioning

confidence: 99%

Lipophilized Epigallocatechin Gallate Derivative Exerts Anti-Proliferation Efficacy through Induction of Cell Cycle Arrest and Apoptosis on DU145 Human Prostate Cancer Cells

Zhang

Chen

et al. 2019

Nutrients

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“…Many hydrophilic bioactive compounds have been lipophilized for use in a lipophilic system [ 32 , 33 , 34 ]. The log P values of parent EGCG and EGCG stearyl derivatives are shown in Table 2 (0.69 ± 0.08 and 3.49 ± 0.34, respectively) ( p < 0.05).…”

Section: Resultsmentioning

confidence: 99%

Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems

et al. 2021

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Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the molar ratio of vinyl stearate: EGCG as 3:1, an enzyme amount of 4.0% (ratio of substrate mass), and a reaction temperature and time of 50 °C and 96 h, respectively, achieving 65.2% EGCG conversion. HPLC–MS and NMR were used to determine the structure of EGCG stearyl derivative (3″,5″-2-O-stearyl-EGCG). The lipophilicity of EGCG stearyl derivatives (3.49 ± 0.34) was higher (5.06 times) than that of the parent EGCG (0.69 ± 0.08). Furthermore, EGCG stearyl derivatives had excellent lipid oxidation compared with BHT, BHA, and parent EGCG. The POVs of soybean oil with EGCG stearyl derivatives (18.17 ± 0.92 mEq/kg) were significantly reduced (by 62.5%) at 21 d compared with those of EGCG (48.50 ± 1.23 mEq/kg). These results indicate that EGCG derivatives have broad antioxidant application prospects in lipophilic environments/high-fat food.

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“…Many hydrophilic bioactive compounds can be lipophilized, and their applications in more lipophilic systems have been expanded (Jakovetic et al., 2013; Xie et al., 2014; Zengin, 2011). The lipophilic properties of EGCG lauroyl derivatives were evaluated by their logP value, and the value of logP was positively correlated with the lipophilicity of the compounds.…”

Section: Resultsmentioning

confidence: 99%

Structural characterization and antioxidant property of enzymatic‐transesterification derivatives of (−)‐epigallocatechin‐3‐O‐gallate and vinyl laurate

Jiang

Wang

Huang

et al. 2021

Journal of Food Science

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(−)‐Epigallocatechin‐3‐O‐gallate(EGCG) was enzymatically modified to enhance the lipophilicity and the antioxidant property. The determination of optimal reaction conditions are as follows: Lipase DF “Amano” 15 and acetone were used as catalyst and solvent, respectively. Equal molar of EGCG and vinyl laurate (1:1); lipase addition of 6.0% (w/w of total substrates); reaction temperature of 50°C and reaction time of 96 h, which obtained the conversion rate of EGCG at 80.1%. The structure of EGCG lauroyl derivatives were 5″‐O‐lauroyl‐EGCG, 3″,5″‐2‐O‐lauroyl‐EGCG, and 5′,3″,5″‐3‐O‐lauroyl‐EGCG, identified by high‐performance liquid chromatography‐mass spectrometry (HPLC–MS) and nuclear magnetic resonance (NMR). Compared with the logP of precursor EGCG (0.69 ± 0.03), the logP of EGCG lauroyl derivatives was 1.37 ± 0.19, 2.27 ± 0.33, and 3.28 ± 0.37, increasing by 0.98, 2.28, and 3.75 times, respectively (p < 0.05), suggesting the grafted fatty acid chains make EGCG derivatives more lipophilic, and the lipid solubility gradually increased as the number of substituents increased. Furthermore, EGCG lauroyl derivatives had excellent lipid oxidation than that of EGCG. The POVs (peroxide values) of soybean oil with mono‐, di‐, tri‐lauroyl EGCG were significantly reduced by 42%, 47%, and 57% than that of EGCG at 21 days, respectively, indicating the antioxidative inhibition of these derivatives decreased with the increase in substituents. This indicates that these derivatives have broad prospects of the antioxidant application while improving their solubility properties in lipophilic environments/high‐fat food. Practical Application: The lipophilic esterification reaction of EGCG catalyzed by new catalytic lipase DF “Amano” 15 was carried out in a non‐aqueous solvent.Various reaction factors on a higher conversion rate of EGCG lauroyl derivatives were evaluated. The lipophilicity and antioxidant properties of EGCG lauroyl derivatives were much excellent than that of parent EGCG.

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A Rapid and Practical Catalytic Esterification for the Preparation of Caffeic Acid Esters

Cited by 5 publications

References 30 publications

Lipophilized Epigallocatechin Gallate Derivative Exerts Anti-Proliferation Efficacy through Induction of Cell Cycle Arrest and Apoptosis on DU145 Human Prostate Cancer Cells

Lipophilized Epigallocatechin Gallate Derivative Exerts Anti-Proliferation Efficacy through Induction of Cell Cycle Arrest and Apoptosis on DU145 Human Prostate Cancer Cells

Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems

Structural characterization and antioxidant property of enzymatic‐transesterification derivatives of (−)‐epigallocatechin‐3‐O‐gallate and vinyl laurate

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