Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters

Mainini, F.; Contini, Alessandro; Nava, Donatella; Corsetto, Paola Antonia; Rizzo, Angela Maria; Agradi, E.; Pini, Elena

doi:10.1007/s11746-013-2314-0

Cited by 27 publications

(25 citation statements)

References 30 publications

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“…All n-3 PUFA-phenol esters tested in literature showed radical scavenging activity in the DPPH radical assay [10,12,14,17,33,36]. It is worthy of note that even though the structures contain an easily oxidizable PUFA, the lipidic part appears to be protected from oxidation by conjugation with phenolic residue.…”

Section: Antioxidant and Anticarbonyl Stress Activitymentioning

confidence: 96%

“…For more complex polyphenolic structures like epigallocatechine-3-O-gallate (EGCG) 1 [31e33], epigallocatechin (EGC) 2 [34,35], quercetin 3 [36], phloroglucinol 15 or resveratrol 17 [37], two different strategies are used: with or without phenolic protection. On the one hand, uncontrolled acylation leading to the introduction of the FAs on several phenolic functions have been reported for quercetin and EGCG.…”

Section: Chemical Synthesismentioning

confidence: 99%

“…On the one hand, uncontrolled acylation leading to the introduction of the FAs on several phenolic functions have been reported for quercetin and EGCG. Penta, tetra and tri-esters of quercetin (3) were obtained using acyl chloride of ALA [36]. Unsaturated acyl chlorides/ phenols molar ratio modulation allowed Mainini et al to obtain preferentially pentaesters (74%) when using phenolic/FA in a 1 to 10 ratio or a mixture of tetra and triesters (45 and 15%, respectively) at 1/ 4 ratio.…”

Section: Chemical Synthesismentioning

confidence: 99%

“…At the difference with ester or amide linkages between the phenolic compound and the PUFA part, non hydrolysable bounds have been obtained [38] [18][19]29] (dopamine and analogues) 11 [26,29,67] (vanillyl amine) 14 [17] ( [28] (Farinosone C analogue) 21 [20] (juglone) 22 [23] (shikonin) Dox-hyd-PUFA: 24a Dox-3-ami-PUFA: 24b (doxorubicin) [25,[63][64][65] 23 [27] (podophyllotoxin analogue) DDPT 15 [37] (phloroglucinol) 4'-PUFA:17a [22,37] 3-DHA: 17b (resveratrol) 18 [21] (trimethoxy anilide) 19 [24,66] (diisopropylphenol) 3 5 4' 3 3 2 [34][35] (EGC) 3 [36] (quercetin) 4 [15] (naringin) 5 [10][11][13][14][15] (rutin) 6 [12] (phloridzin) 7 [12] (isoquercitrin) 8 [38] 9 [30] 10 [ linker [39]. Since pH in tumor cells is lower than in healthy tissue, the hydrazone bond, stable at pH 7.4, is rapidly cleaved at lower pH in cancerous cells.…”

Section: Chemical Synthesismentioning

confidence: 99%

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Omega-3 polyunsaturated lipophenols, how and why?

et al. 2016

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Polyphenols and n-3 polyunsaturated fatty acids (PUFAs) are two classes of natural compounds, which have been highlighted in epidemiological studies for their health benefits. The biological activities of those two families of metabolites on oxidation, inflammation, cancer, cardiovascular and degenerative diseases have been reported in vitro and in vivo. On the other hand, chemical bonding between the two structures leading to n-3 lipophenol derivatives (or phenolipids) has been studied in numerous works over the last decade, and some examples could also be found from natural sources. Interest in lipophilization of phenolic structures is various and depends on the domain of interest: in food industry, the development of lipidic antioxidants could be performed to protect lipidic food matrix from oxidation. Whereas, on pharmaceutical purpose, increasing the lipophilicity of polar phenolic drugs could be performed to improve their pharmacological profile. Moreover, combining both therapeutic aspects of n-3 PUFAs and of polyphenols in a single lipophenolic molecule could also be envisaged. An overview of the synthesis and of the natural sources of n-3 lipophenols is presented here, in addition to their biological activities which point out in several cases the benefit of the conjugated derivatives.

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Section: Antioxidant and Anticarbonyl Stress Activitymentioning

confidence: 96%

Section: Chemical Synthesismentioning

confidence: 99%

Section: Chemical Synthesismentioning

confidence: 99%

Section: Chemical Synthesismentioning

confidence: 99%

See 2 more Smart Citations

Omega-3 polyunsaturated lipophenols, how and why?

et al. 2016

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“…The chemical esteriication of lavonoids with some faty acids was provided by [37] and its product exhibited lipophilic, antiradical and antioxidant properties. In works reported by Zhong and Shahidi [38,39] on epigallocatechin gallate (EGCG), the predominant catechin in tea was structurally modiied by esteriication with faty acids, including stearic acid (SA), docosapentaenoic acid (DPA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).…”

Section: Chemical Synthesis Of Phenolic Lipidsmentioning

confidence: 99%

Synthesis and Characterization of Phenolic Lipids

Roby¹

2017

Phenolic Compounds - Natural Sources, Importance and Applications

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Omega-3 polyunsaturated faty acids (ω3 PUFAs) from ish oils promote well-established health and antiaging beneits that justify their use as functional ingredients in dietary supplements, healthy foods, and nutraceutical products. Dietary supply is needed because human metabolism exhibits limited to synthesize ω3 PUFAs. However, the practical use of such lipids as food ingredients is often limited due to their high susceptibility to oxidation, which is responsible for the undesirable of-lavor and odor of rancid oils, associated with the loss of nutritional value. Produced phenolic lipids were a good solution for all these problems. These phenolic lipids are preferentially produced by enzymatic bioprocesses that exhibit high selectivity toward polyfunctional substrates and mild reaction conditions compared with chemical synthesis pathways. This chapter presents the acylation of phenolic compounds and lipids using enzyme under various operating conditions. In conclusion, the acylation of lipids with natural phenolic compounds resulted in the formation of a lipophilic ester that should be able to stabilize the oil, fats, and emulsions against oxidation. Acylation of lipids to phenolic compounds that have antioxidant properties thus protects the lipids from oxidation, and the phenolic lipid derivatives carry the combined health beneicial properties of lipids and the phenolic molecules.

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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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Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters

Cited by 27 publications

References 30 publications

Omega-3 polyunsaturated lipophenols, how and why?

Omega-3 polyunsaturated lipophenols, how and why?

Synthesis and Characterization of Phenolic Lipids

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

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