Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin

Lo, Stephen; Leung, Euphemia; Fedrizzi, Bruno; Barker, David

doi:10.3390/molecules26061608

Cited by 8 publications

(11 citation statements)

References 28 publications

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“…Additionally, our group had also reported studies on fatty acyl modifications to flavonoid structures and their effects on bioactivity. In these studies, it was found that by selectively acylating specific hydroxy positions of both luteolin [ 32 ] and quercetin [ 31 ], these products displayed improved antiproliferative activity against both HCT116 and MDA-MB-231 cancer cells. It was also found that the radical scavenging activity did not change, which was a good indication that the modifications did not reduce their antioxidant activities.…”

Section: Resultsmentioning

confidence: 99%

“…The were some considerations around the method for derivatizing the compounds in the extract. Since our reported studies identified three acylated flavonoids (which are octanoyl, lauroyl and palmitoyl derivatives of both luteolin or quercetin) as having better antiproliferative activity, it was decided that the corresponding acylating agents would be used [ 31 , 32 ]. The differences between previous studies and the present study that would affect the acylation approach were also considered.…”

Section: Resultsmentioning

confidence: 99%

“…The aim of the study was to develop a process whereby bioactive polyphenolics could be sourced from grape pomace, used as starting materials and modified into products with improved health-promoting properties. This work drew inspiration from previously reported studies conducted by our research group, which presented findings on the use of a simple method for extracting polyphenolics from grape pomace [ 30 ] and the structural modifications to flavonoids that led to improved bioactivity [ 31 , 32 ]. It was proposed that the integration of these methods could be a feasible process to achieve the study aim.…”

Section: Introductionmentioning

confidence: 99%

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Attempts to Create Products with Increased Health-Promoting Potential Starting with Pinot Noir Pomace: Investigations on the Process and Its Methods

Pilkington

Barker

et al. 2022

Foods

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A process for using grape (Pinot noir) pomace to produce products with improved health-promoting effects was investigated. This process integrated a solid–liquid extraction (SLE) method and a method to acylate the polyphenolics in the extract. This report describes and discusses the methods used, including the rationale and considerations behind them, and the results obtained. The study begins with the work to optimize the SLE method for extracting higher quantities of (+)-catechin, (−)-epicatechin and quercetin by trialing 28 different solvent systems on small-scale samples of Pinot noir pomace. One of these systems was then selected and used for the extraction of the same flavonoids on a large-scale mass of pomace. It was found that significantly fewer quantities of flavonoids were observed. The resultant extract was then subject to a method of derivatization using three different fatty acylating agents. The antiproliferative activities of these products were measured; however, the resulting products did not display activity against the chosen cancer cells. Limitations and improvements to the methods in this process are also discussed.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Attempts to Create Products with Increased Health-Promoting Potential Starting with Pinot Noir Pomace: Investigations on the Process and Its Methods

Pilkington

Barker

et al. 2022

Foods

Self Cite

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“…Therefore, sinularin shows higher • OH scavenging activity than dihydrosinularin. [32] is another in vitro antioxidant detection method. In Figure 2, the ABTS scavenging activity of sinularin dramatically increases to 50% at 15 μM and reaches a plateau of 60% activity above 250 μM.…”

Section: Hydroxyl ( • Oh) Radical Scavenging Activitymentioning

confidence: 99%

“…The scavenging effect for ABTS was assessed as mentioned [32,44]. 7.4 mM ABTS •+ /2.6 mM persulfate solution was equally mixed and reacted with sinularin or dihydrosinularin (dissolved in ethanol) in the darkness for 15 min.…”

Section: Abts •+ Radical Scavenging Activitymentioning

confidence: 99%

Comparison of Antioxidant and Anticancer Properties of Soft Coral-Derived Sinularin and Dihydrosinularin

Wang

Lin

et al. 2021

Molecules

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Marine natural products are abundant resources for antioxidants, but the antioxidant property of the soft corals-derived sinularin and dihydrosinularin were unknown. This study aimed to assess antioxidant potential and antiproliferation effects of above compounds on cancer cells, and to investigate the possible relationships between them. Results show that sinularin and dihydrosinularin promptly reacted with 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS), and hydroxyl (•OH), demonstrating a general radical scavenger activity. Sinularin and dihydrosinularin also show an induction for Fe+3-reduction and Fe+2-chelating capacity which both strengthen their antioxidant activities. Importantly, sinularin shows higher antioxidant properties than dihydrosinularin. Moreover, 24 h ATP assays show that sinularin leads to higher antiproliferation of breast, lung, and liver cancer cells than dihydrosinularin. Therefore, the differential antioxidant properties of sinularin and dihydrosinularin may contribute to their differential anti-proliferation of different cancer cells.

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Research Progress on Quercetin's Biological Activity and Structural Modification Based on Its Antitumor Effects

Guo,

Zeng,

Sun

et al. 2023

ChemistrySelect

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Quercetin is a naturally existing flavonoid with numerous physiological effects, including antitumor activity. It functions as an antitumor agent by inducing apoptosis and inhibiting tumor cell development, preventing tumor cell invasion and metastasis, and reversing tumor multidrug resistance. Quercetin has limited therapeutic usefulness due to its low water solubility, poor oral absorption, and low bioavailability. New quercetin derivatives are being developed and manufactured via a variety of methods to address inadequacies and for utilization in disease prevention and therapy. The synthesis and anticancer effects of quercetin derivatives, as well as the structure‐activity relationship of quercetin derivatives, were explored, and the unique dosage forms of these derivatives were summarized to serve as a reference for future quercetin research and development.

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Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin

Cited by 8 publications

References 28 publications

Attempts to Create Products with Increased Health-Promoting Potential Starting with Pinot Noir Pomace: Investigations on the Process and Its Methods

Attempts to Create Products with Increased Health-Promoting Potential Starting with Pinot Noir Pomace: Investigations on the Process and Its Methods

Comparison of Antioxidant and Anticancer Properties of Soft Coral-Derived Sinularin and Dihydrosinularin

Research Progress on Quercetin's Biological Activity and Structural Modification Based on Its Antitumor Effects

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