A novel method for the synthesis of glyceryl monocaffeate by the enzymatic transesterification and kinetic analysis

Sun, Shangde; Hu, Bingxue

doi:10.1016/j.foodchem.2016.07.087

Cited by 33 publications

(31 citation statements)

References 31 publications

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“…Two main peaks (peak 2 and 5) were shown in Figure (A) with other trace compounds as by products shown in peak 1, 3, and 4. EC was readily characterized as peak 5 since the same retention time with EC standard (Figure S1A), which was consistent with he study of Sun & Hu (Sun & Hu, ). Peak 2 is another major product which could be deduced as MCG with a retention time of 9.30 min (Sun, Shan, Jin, Liu, & Wang, ).…”

Section: Resultssupporting

confidence: 86%

“…Peak 2 is another major product which could be deduced as MCG with a retention time of 9.30 min (Sun, Shan, Jin, Liu, & Wang, ). In a previous study, peak 1 and 2 were specified to 2‐MCG and 1‐MCG, respectively (Sun & Hu, ). However, further research should be carried out to confirm its transesterification position.…”

Section: Resultsmentioning

confidence: 99%

“…Besides, the different proton signals of 3‐OH (δH 4.65), 4‐OH (δH 4.91) also suggests the different glycerol ‐OH in the product. Therefore, the main product of transesterification was confirmed as 1‐MCG, which was possibly due to the steric hindrance (Sun & Hu, ).…”

Section: Resultsmentioning

confidence: 99%

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Antioxidant Profile of 1‐Monocaffeoyl Glycerol in Lipophobic/Lipophilic Media

Weng

Lin

et al. 2019

Journal of Food Science

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Oxidative stress has been generally considered as one trigger of organism imbalance, resulting in lipid peroxidation, DNA damage and protein oxidation, which could be relieved by antioxidant supplement or endogenous antioxidant system. In present study, 1‐monocaffeoyl glycerol (1‐MCG), an amphipathic caffeic acid natural derivative, was enzymatically synthesized by Lipozyme 435, and its antioxidant profile in both lipophilic and lipophobic media was evaluated. The 1‐MCG was identified by HPLC‐UV, HPLC‐ESI‐MS, and 1H/13C‐NMR. Subsequently, antioxidant assays in lipophilic (DPPH assay) and lipophobic (ABTS, ORAC, erythrocyte hemolysis, ROS, MDA, and GPx assays) systems were explored. The better and lasting DPPH· and ABTS+· inhibitions of 1‐MCG than caffeic acid (CA) were related to its better solubilities in ethanol/water media and electron transfer ability. ORAC results suggested the radical scavenging activities of 1‐MCG (5 to 40 µM) were higher than Trolox. Furthermore, the effectiveness of 1‐MCG against AAPH‐induced erythrocytes oxidation indicated that 1‐MCG can effectively inhibit hemolysis. ESEM was also applied to verify the hemolysis inhibition and morphology preservation abilities of 1‐MCG. Besides, results showed 1‐MCG was able to prevent ROS from invasion, reduce production of MDA, up‐regulated GPx activity, terminate lipid peroxidation, and maintain the integrity of the structure and function of erythrocytes. Practical Application As an amphiphilic caffeic acid derivative, 1‐monocaffeoyl glycerol was synthesized, purified, and identified. 1‐Monocaffeoyl glycerol could significantly eliminate radicals including DPPH·, ABTS+·, and AAPH in ethanol, water, and PBS system, respectively. 1‐Monocaffeoyl glycerol could protect erythrocyte from AAPH induced hemolysis.

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Section: Resultssupporting

confidence: 86%

Section: Resultsmentioning

confidence: 99%

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Antioxidant Profile of 1‐Monocaffeoyl Glycerol in Lipophobic/Lipophilic Media

Weng

Lin

et al. 2019

Journal of Food Science

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“…O carbonato de glicerol é tradicionalmente obtido por rotas químicas onerosas e apresenta vasta possibilidade de aplicações, tais como: componente de membranas de separação de gás, espumas de poliuretano, revestimentos, tintas e detergentes (WANG et al, 2011). A literatura relata a obtenção deste carbonato por via biotecnológica utilizando a transesterificação enzimática (JUNG et al, 2012).…”

Section: Introductionunclassified

“…Para CALB LC-OVERLOAD carregamento superior a 60 mg resultou em diminuição na conversão. Segundo a literatura a diminuição ou a constância dos valores de conversão com o aumento de carregamento de enzima imobilizada pode ser devido a problemas de aglomeração da lipase e dificuldade de difusão da enzima por substratos com maior carga enzimática(SUN & HU, 2017).…”

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GLICERÓLISE DE URÉIA CATALISADA POR LIPASE DE Candida antarctica B IMOBILIZADA

Azevedo¹,

Moreira²,

Oliveira³

et al. 2018

Blucher Chemical Engineering Proceedings

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RESUMO -O objetivo deste trabalho foi realizar a glicerólise de ureia catalisada por lipase de B de Candida antarctica imobilizada comercialmente (Novozyme 435) e imobilizada pela técnica de sol-gel seguida de ligação covalente com sobrecarga (CALB LC-OVERLOAD) utilizando o glutaraldeído como agente bifuncional. A conversão da glicerólise foi determinada através da quantificação do glicerol remanescente das amostras por UV-VIS. Diferentes solventes foram avaliados (metanol, etanol, tertbutanol e acetonitrila. A cinética da glicerólise da ureia catalisada por ambas as enzimas foi avaliada entre 6-144 h e o efeito do carregamento de enzima foi estudado. Com 48 h de reação, para Novozyme 435 o metanol mostrou-se o melhor solvente (40% de conversão do glicerol) e para CALB LC-OVERLOAD foram obtidas conversões entre 44, 45 e 50% utilizando etanol, metanol e acetonitrila como solventes, respectivamente. CALB LC-OVERLOAD converteu 40 % do glicerol em após 24 h de reação. O melhor carregamento de biocatalisador imobilizado foi de 60 mg em utilizando o metanol como solvente para ambas as enzimas.

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Enzymatic Synthesis and Antioxidant Activity of 1‐Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol

Meng

et al. 2018

J Americ Oil Chem Soc

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Caffeic acid (CA) as a strong antioxidant has lower solubility in nonpolar media, which limits its application in the food industry. To increase the lipophilicity of CA, 1-caffeoylglycerol (1-CG) was synthesized by lipasecatalyzed transesterification of alkyl caffeates in solvent-free system and its antioxidant capacity was investigated. Methyl caffeate was screened as the appropriate substrate from tested alkyl caffeates with a yield of 90.63%. Ethyl acetate was used for extracting 1-CG from enzymatic reactants and could be easily recycled. The produced 1-CG had 2.5-and 10-fold lower values of half maximal inhibitory concentration (IC 50 ) (10.86 and 3.99 μM) than butylated hydroxyanisole by 1,1-diphenyl-2-picrylhydrazyl radical scavenging and β-carotene-linoleic acid assays, respectively. Thus, 1-CG is an excellent antioxidant for application in the functional food industry. Using alkyl caffeates and glycerol as substrates to produce 1-CG catalyzed by immobilized lipase in a solvent-free system is a simple, selective, and safe bioprocess that can readily be achieved in the food industry, and the product 1-CG could be widely applied in food, nutraceutical, and biotechnological products.

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A novel method for the synthesis of glyceryl monocaffeate by the enzymatic transesterification and kinetic analysis

Cited by 33 publications

References 31 publications

Antioxidant Profile of 1‐Monocaffeoyl Glycerol in Lipophobic/Lipophilic Media

Antioxidant Profile of 1‐Monocaffeoyl Glycerol in Lipophobic/Lipophilic Media

GLICERÓLISE DE URÉIA CATALISADA POR LIPASE DE Candida antarctica B IMOBILIZADA

Enzymatic Synthesis and Antioxidant Activity of 1‐Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol

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