Influence of the chain length of the fatty acids present in different oils and the pore diameter of the support on the catalytic activity of immobilized lipase for ethyl ester production

Marcucci, Sílvio Miguel Parmegiani; Araki, Carina Akemi; Silva, Lidiane S. da; Zanin, Gisella Maria; Arroyo, Pedro Augusto

doi:10.1007/s43153-021-00132-3

Cited by 10 publications

(5 citation statements)

References 54 publications

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“…Consequently, excessive chain length can lead to steric hindrance, impeding access to the enzyme's active site [41]. Marcucci et al reported the production of ethyl esters using fatty acids of different chain lengths found in oil and found that the highest yield was obtained with 16-carbon palmitic acid [42] solubility (lipophilicity) [35]. In this section, acylation with fatty acids was performed to improve the lipid solubility of puerarin, and enzymatic reactions were performed with fatty acids of various chain lengths to select the acyl donor with the highest conversion.…”

Section: Effects Of Different Acyl Donors On the Conversion Of Puerar...mentioning

confidence: 99%

“…Consequently, excessive chain length can lead to steric hindrance, impeding access to the enzyme's active site [41]. Marcucci et al reported the production of ethyl esters using fatty acids of different chain lengths found in oil and found that the highest yield was obtained with 16-carbon palmitic acid [42] improve the lipid solubility of puerarin, and enzymatic reactions were performed with fatty acids of various chain lengths to select the acyl donor with the highest conversion.…”

Section: Effects Of Different Acyl Donors On the Conversion Of Puerar...mentioning

confidence: 99%

“…Consequently, excessive chain length can lead to steric hindrance, impeding access to the enzyme's active site [41]. Marcucci et al reported the production of ethyl esters using fatty acids of different chain lengths found in oil and found that the highest yield was obtained with 16-carbon palmitic acid [42] The acylation process involves either esterification or transesterification, depending on the type of acyl donor employed. The esterification of flavonoids with fatty acid generates water as a by-product, whereas the transesterification of flavonoids with fatty acid ester generates alcohol as a by-product.…”

Section: Effects Of Different Acyl Donors On the Conversion Of Puerar...mentioning

confidence: 99%

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Enhanced Enzymatic Synthesis of Puerarin Palmitate with Different Acyl Donors for Lipid Solubility Improvement

Lee,

Shin,

Bae

et al. 2024

IJMS

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Puerarin is a flavonoid known as a natural antioxidant found in the root of Pueraria robata. Its antioxidant, anticancer, and anti-inflammatory effects have attracted attention as a potential functional ingredient in various bioindustries. However, puerarin has limited bioavailability owing to its low lipid solubility and stability. Acylation is proposed as a synthesis method to overcome this limitation. In this study, lipase-catalyzed acylation of puerarin and various acyl donors was performed, and the enzymatic synthetic condition was optimized. Under the condition (20 g/L of Novozym 435, palmitic anhydride, 1:15, 40 °C, tetrahydrofuran (THF)), the synthesis of puerarin ester achieved a significantly high conversion (98.97%) within a short time (3 h). The molecule of the synthesized puerarin palmitate was identified by various analyses such as liquid chromatography–mass spectrometry (LC–MS), Fourier-transform infrared spectroscopy (FT-IR), and carbon-13 nuclear magnetic resonance (13C NMR). The lipid solubility and the radical scavenging activity were also evaluated. Puerarin palmitate showed a slight decrease in antioxidant activity, but lipid solubility was significantly improved, improving bioavailability. The high conversion achieved for puerarin esters in this study will provide the foundation for industrial applications.

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Section: Effects Of Different Acyl Donors On the Conversion Of Puerar...mentioning

confidence: 99%

“…Consequently, excessive chain length can lead to steric hindrance, impeding access to the enzyme's active site [41]. Marcucci et al reported the production of ethyl esters using fatty acids of different chain lengths found in oil and found that the highest yield was obtained with 16-carbon palmitic acid [42] improve the lipid solubility of puerarin, and enzymatic reactions were performed with fatty acids of various chain lengths to select the acyl donor with the highest conversion.…”

Section: Effects Of Different Acyl Donors On the Conversion Of Puerar...mentioning

confidence: 99%

“…Consequently, excessive chain length can lead to steric hindrance, impeding access to the enzyme's active site [41]. Marcucci et al reported the production of ethyl esters using fatty acids of different chain lengths found in oil and found that the highest yield was obtained with 16-carbon palmitic acid [42] The acylation process involves either esterification or transesterification, depending on the type of acyl donor employed. The esterification of flavonoids with fatty acid generates water as a by-product, whereas the transesterification of flavonoids with fatty acid ester generates alcohol as a by-product.…”

Section: Effects Of Different Acyl Donors On the Conversion Of Puerar...mentioning

confidence: 99%

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Enhanced Enzymatic Synthesis of Puerarin Palmitate with Different Acyl Donors for Lipid Solubility Improvement

Lee,

Shin,

Bae

et al. 2024

IJMS

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“…[23] Additionally, the chain length of the fatty acid in the oil is another parameter that affects the biocatalyst activity in the reaction due to the shape of the lipase active site. [25] Thus, the objective of this study was to evaluate the use of lipase immobilized on mesoporous silica SBA-15 and pore-expanded SBA-15 with the tin-modified surface, which were previously synthesized and characterized, [26] for ethyl ester production. The study focused on evaluating the following parameters: pore diameter of the biocatalyst used in the reaction, the effect of soybean oil type, the influence of the water and ethanol-to-oil molar ratio, the mass percentage of the biocatalyst, temperature, and presence of glycerol in the reactions.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ethyl ester production with immobilized lipase in tin modified SBA‐15: Effect of the support characteristic and reaction conditions

et al. 2023

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This study investigated the use of immobilized lipase in SBA‐15 and pore‐expanded SBA‐15 surface modified with tin, denoted as SnS23B (mean pore size of 21.6 nm) and SnS8B (with mean pore size of 9.6 nm), respectively, to produce ethyl esters. The effects of various reaction parameters, including biocatalyst type, oil (refined and degummed soybean oil), water addition, oil‐to‐ethanol molar ratio, immobilized lipase concentration, agitation speed, reaction temperature, and glycerol addition, were examined. The optimal conditions were found to be the use of SnS23B as the biocatalyst, degummed soybean oil as the substrate, 1% (w/w oil) water, 1:3 oil‐to‐ethanol molar ratio, 5% (w/w oil) immobilized lipase, 800 rpm agitation speed, and 25°C reaction temperature. The presence of glycerol negatively impacted the reaction. Under the optimal conditions, the mass percent of ethyl ester obtained was 98.2% ± 0.16. The immobilized lipase showed stability, as no lipase activity was detected upon removing the biocatalyst from the reaction. However, the biocatalyst lost 50% of its activity after 10 successive reactions, likely due to thermal deactivation and lipase inhibition caused be the adsorption of glycerol and other chemical species. Attenuated total reflectance analysis supported this hypothesis.

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Biofuel Production: An Ecofriendly Way to Produce Sustainable Energy

Datta,

Ghosal,

Biswas

et al. 2024

Environmental Science and Engineering

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Influence of the chain length of the fatty acids present in different oils and the pore diameter of the support on the catalytic activity of immobilized lipase for ethyl ester production

Cited by 10 publications

References 54 publications

Enhanced Enzymatic Synthesis of Puerarin Palmitate with Different Acyl Donors for Lipid Solubility Improvement

Enhanced Enzymatic Synthesis of Puerarin Palmitate with Different Acyl Donors for Lipid Solubility Improvement

Ethyl ester production with immobilized lipase in tin modified SBA‐15: Effect of the support characteristic and reaction conditions

Biofuel Production: An Ecofriendly Way to Produce Sustainable Energy

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