Lipase mediated synthesis of rutin fatty ester: Study of its process parameters and solvent polarity

Chandrasekar, Vaisali; Belur, Prasanna D.; Iyyaswami, Regupathi

doi:10.1016/j.foodchem.2017.03.168

Cited by 21 publications

(16 citation statements)

References 39 publications

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“…In a previous paper, a semisynthetic derivative of quercetin, 2-(2,2-diphenylbenzo[d] [1,3] dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl oleate, was synthesized according to Steglich conditions and validated as a potential insulin secretagogue agent G-protein-coupled receptor 40 ligand [3]. In this context, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl oleate, quercetin-3-oleate, was synthesized avoiding the preventive catechol protection but considering several literature observations [7], considering that Candida antartica Lipase B ® -the most used acylating enzyme-was not able to produce esters of quercetin [8]. In a typical optimized experiment, one equivalent of quercetin, and one equivalent of oleic acid were added to PPL and acetone.…”

Section: Resultsmentioning

confidence: 99%

Quercetin-3-oleate

Carullo

Aiello

2018

Molbank

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Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in recent years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, esterification seems to be the preferred modification. Ester derivatives may be able to reduce the bioavailability problems connected to polyphenols. On the other hand, the presence of esterase enzymes in the body guarantees ester hydrolysis, which in turn frees the two molecules that make it up. Lipase-catalyzed esterifications gave birth to several derivatives of flavonoids glycosides, in green conditions. In this short paper, pancreatic porcine lipase was firstly used as a cheap bio-catalyst, to synthesize oleoyl derivatives of quercetin in aglycone form. The results demonstrated how the enzyme is able to promote a regioselective acylation on C-3 position, with high yields and easy purification processes.

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Section: Resultsmentioning

confidence: 99%

Quercetin-3-oleate

Carullo

Aiello

2018

Molbank

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“…In this context, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl oleate, quercetin-3-oleate, was synthesized avoiding the preventive catechol protection but considering several literature observations [7], considering that Candida antartica Lipase B ® (the most used acylating enzyme) was not able to produce esters of quercetin [8]. In a typical optimized experiment, 1 equivalent of quercetin, 1 equivalent of oleic acid were added of PPL and acetone.…”

Section: Resultsmentioning

confidence: 99%

Bio-Catalytic Synthesis of Quercetin-3-Oleate

Carullo¹,

Aiello²

2018

Preprint

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Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in the last years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, the esterification seems to be the preferred. Ester derivatives could be able to reduce the bioavailability problems connected to polyphenols. On the other hand, the presence of the esterase enzymes in the body guarantees the ester hydrolysis, which in turn frees the two molecules that make it up. Lipase-catalyzed esterifications afforded several derivatives of flavonoids glycosides, in green conditions. In this short note, pancreatic porcine lipase was firstly used as a cheap bio-catalyst, to synthesize oleoyl derivatives of quercetin in aglycone form. Results demonstrated how the enzyme acyl regioselective in position C-3, with high yields and easy purification processes.Keywords: keyword 1; keyword 2; keyword 3 (List three to ten pertinent keywords specific to the article; yet reasonably common within the subject discipline.)

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“…The purity of the product was analysed using HPLC‐ESI‐MS system by a method described by Vaisali et al . (). Ethyl acetate was then allowed to evaporate under vacuum by rotary evaporator.…”

Section: Methodsmentioning

confidence: 97%

“…Preparation and purification of lipophilic rutin fatty ester Ester derivative of rutin was prepared by esterification with decanoic acid in acetone, catalysed by immobilised Candida antartica lipase as described by Vaisali et al (2017). After the reaction, enzyme molecules were separated from the mixture by filtration.…”

Section: Methodsmentioning

confidence: 99%

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Effectiveness of rutin and its lipophilic ester in improving oxidative stability of sardine oil containing trace water

Chandrasekar

Belur

Iyyaswami

2017

Int J of Food Sci Tech

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Summary Poor oxidative stability exhibited by n‐3 polyunsaturated fatty acid rich sardine oil is a major challenge for its utilisation in industry. Considering the fact that water is always present in bulk oil in trace amounts during storage, an effort was made to understand and compare the effectiveness of rutin and its corresponding lipophilic ester in enhancing oxidative stability of refined sardine oil containing trace water (0.16% w/w). Peroxide value, conjugated diene value, p‐anisidine value and thiobarbituric acid reactive substances (TBARS) value were determined during 20 days storage. Rutin fatty ester showed 50% reduction in primary oxidation and 42.46% reduction in secondary oxidation, whereas rutin showed 20.6% and 20.43% reduction in primary and secondary oxidation, respectively, by the end of 20 days storage. Thus, it is clearly established that rutin fatty ester is more effective than hydrophilic rutin in sardine oil containing trace water, which contradicts the polar paradox theory.

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Lipase mediated synthesis of rutin fatty ester: Study of its process parameters and solvent polarity

Cited by 21 publications

References 39 publications

Quercetin-3-oleate

Quercetin-3-oleate

Bio-Catalytic Synthesis of Quercetin-3-Oleate

Effectiveness of rutin and its lipophilic ester in improving oxidative stability of sardine oil containing trace water

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