Enzymatic synthesis of new aromatic and aliphatic esters of flavonoids using<i>Candida antarctica</i>lipase as biocatalyst

Ardhaoui, M.; Falcimaigne, Aude; Engasser, Jean‐Marc; Moussou, Philippe; Pauly, G.; Ghoul, Mohamed

doi:10.1080/10242420400005796

Cited by 41 publications

(31 citation statements)

References 25 publications

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“…Many acylating agents have been tested in flavonoid esterification, such as aromatic or aliphatic organic acids, substituted or not (Tab.3). Special attention was attributed to fatty acid ester production (Katsoura et al, 2006;Mellou et al, 2005Mellou et al, , 2006Ardhaoui et al, 2004aArdhaoui et al, , 2004bArdhaoui et al, , 2004cEnaud et al, 2004;Gayot et al, 2003;Kontogianni et al, 2003). This approach enables to improve flavonoid solubility and stability in lipophilic systems.…”

Section: Acyl Donormentioning

confidence: 99%

“…2-Methylbutan-2-ol Ghoul et al, 2006;Ardhaoui et al, 2004aArdhaoui et al, , 2004bArdhaoui et al, , 2004cPassicos et al, 2004;Gayot et al, 2003Acetone Ghoul et al, 2006Mellou et al, 2005Mellou et al, , 2006Kontogianni et al, 2001Kontogianni et al, , 2003Ishihara et al, 2002Nakajima et al, 1999Nakajima et al, , 2003Danieli et al, 1997Acetonitrile Ghoul et al, 2006Nakajima et al, 1997Nakajima et al, , 1999 2-Methylpropan-2-ol Ghoul et al, 2006;Stevenson et al, 2006;Mellou et al, 2005;Moussou et al, 2004;Kontogianni et al, 2001Kontogianni et al, , 2003Otto et al, 2001Dioxane Ghoul et al, 2006Danieli et al, 1997Pyridine Danieli et al, 1990THF, DMSO, DMF Kontogianni et al, 2001, 2003Danieli et al, 1997 Binaric mixtures of solvents Ghoul et al, 2006;Gao et al, 2001;Nakajima et al, 1999;Danieli et al, 1997 Table 2. Organic solvents used in flavonoid acylation.…”

Section: Solvent Referencementioning

confidence: 99%

“…The choice of temperature depends on the enzyme and solvent used. The majority of authors performed flavonoid acylation at 60°C due to the best enzyme activity, good solubility of substrates and highest yields of resulting esters reached (Viskupicova et al, 2006Ghoul et al, 2006;Katsoura et al, 2006;Stevenson et al, 2006;Ardhaoui et al, 2004aArdhaoui et al, , 2004bArdhaoui et al, , 2004cMoussou et al, 2004;Passicos et al, 2004;Enaud et al, 2004;Gayot et al, 2003;Otto et al, 2001). Our results on the effect of temperature on naringin conversion are presented in Fig.2 and are in accordance with other authors (Viskupicova et al, 2006).…”

Section: Temperaturementioning

confidence: 99%

“…which is preferred due to its acceptance of a wide range of substrates, good catalytic activity and a high degree of regioselectivity Katsoura et al, 2006Katsoura et al, , 2007Ghoul et al, 2006;Mellou et al, 2005Mellou et al, , 2006Stevenson et al, 2006;Ardhaoui et al, 2004aArdhaoui et al, , 2004bArdhaoui et al, , 2004cPassicos et al, 2004;Moussou et al, 2004;Gayot et al, 2003;Ishihara et al, 2002;Kontogianni et al, 2001Kontogianni et al, , 2003Nakajima et al, 1999Nakajima et al, , 2003Gao et al, 2001;Otto et al, 2001;Danieli et al, 1997).…”

Section: Lipasesmentioning

confidence: 99%

“…To date, flavonoid transformation has been carried out in the temperature range 30 -100°C Katsoura et al, 2006;Stevenson et al, 2006;Mellou et al, 2005;Ardhaoui et al, 2004aArdhaoui et al, , 2004bArdhaoui et al, , 2004cMoussou et al, 2004;Passicos et al, 2004;Enaud et al, 2004;Gayot et al, 2003;Kontogianni et al, 2003;Ishihara et al, 2002;Gao et al, 2001;Otto et al, 2001;Nakajima et al, 1999;Danieli et al, 1990). The choice of temperature depends on the enzyme and solvent used.…”

Section: Temperaturementioning

confidence: 99%

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Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

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Section: Acyl Donormentioning

confidence: 99%

Section: Solvent Referencementioning

confidence: 99%

Section: Temperaturementioning

confidence: 99%

Section: Lipasesmentioning

confidence: 99%

Section: Temperaturementioning

confidence: 99%

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Strategies for the Biocatalytic Lipophilization of Phenolic Antioxidants

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Biosynthesis of Quercetin Palmitate Esters and Evaluation of their Physico‐Chemical Properties and Stability

Saik

Lim

Stanslas

et al. 2020

J Americ Oil Chem Soc

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Quercetin was acylated with palmitic acid, catalyzed by either Candida antarctica lipase B (CAL‐B) or Pseudomonas cepacia lipase C (PCL‐C) to produce quercetin palmitate esters. The effects of various operating factors including incubation temperature, reaction duration, and molar ratio of substrates on the bioconversion yield, initial rate of reaction, and regioselectivity of the reactions were investigated. Three new esters were identified: quercetin 4′‐palmitate (C31H40O8, 540 g mol−1), quercetin 3′,4′‐dipalmitate (C47H70O9, 778 g mol−1), and quercetin 7,3′,4′‐tripalmitate (C63H100O10, 1016 g mol−1). The effects of incubation temperature, reaction duration, and molar ratio of substrates on bioconversion yields varied across the conditions. However, the highest bioconversion yield of 27.72 ± 1.64% was obtained with PCL‐C, at day 7, incubation temperature of 60 °C, quercetin:palmitic acid molar ratio of 1:20. The initial rate of reaction was significantly higher with PCL‐C. However, regioselectivity was similar for both PCL‐C‐ and CAL‐B‐catalyzed reactions with acylation occurred successively at 4´‐OH, 3´‐OH, and 7‐OH. Thin‐layer chromatography analysis showed that the three quercetin palmitate esters possessed enhanced lipophilicity (134% higher than quercetin). Besides, in silico investigation showed that quercetin 4′‐palmitate had a higher partition coefficient (log P) value than the parent compounds, indicating improved solubility. During gastrointestinal tract simulation, quercetin palmitate esters were recovered in the range of 71.03% to 79.36% after digestion, which were significantly higher than quercetin at 40.43 ± 8.71%. Quercetin 4′‐palmitate was also found stable over 28 days of storage. Due to improved lipophilicity, solubility, and stability, quercetin 4′‐palmitate has the potential to be used in topical applications.

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Enzymatic synthesis of new aromatic and aliphatic esters of flavonoids usingCandida antarcticalipase as biocatalyst

Cited by 41 publications

References 25 publications

Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

Enzyme-Mediated Preparation of Flavonoid Esters and Their Applications

Strategies for the Biocatalytic Lipophilization of Phenolic Antioxidants

Biosynthesis of Quercetin Palmitate Esters and Evaluation of their Physico‐Chemical Properties and Stability

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