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A neutral Cu-based MOF for effective quercetin extraction and conversion from natural onion juice.

ABSTRACT: We report herein a new microporous neutral three-dimensional (3D) metal-organic framework [Cu₂(L)(DMF)(H₂O)]·guest (1·guest) composed of copper paddle-wheel and flexible tetracarboxylic acid linkers (DMF = N,N-dimethylformamide, H₄L = tetrakis[(6-carboxynaphthoxy)methyl]methane). Surprisingly, this MOF with neutral cavities can not only extract pure quercetin (QT) but also convert it into Cu-QT during the desorption process. It has been well characterized by UV-vis, IR, ESI-MS and TEM-EDS studies. Moreover, it can efficiently extract natural product QT from fresh QT-rich onion juice and rapidly convert it into Cu-QT with a relatively high conversion rate.

SUBMITTER: Xiang RQ

PROVIDER: S-EPMC9073668 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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A neutral Cu-based MOF for effective quercetin extraction and conversion from natural onion juice.

Xiang Rui-Qi RQ Niu Yan-Fei YF Han Jie J Lau Yat-Long YL Wu Hai-Hong HH Zhao Xiao-Li XL

RSC advances 20191021 58

We report herein a new microporous neutral three-dimensional (3D) metal-organic framework [Cu2(L)(DMF)(H2O)]·guest (1·guest) composed of copper paddle-wheel and flexible tetracarboxylic acid linkers (DMF = N,N-dimethylformamide, H4L = tetrakis[(6-carboxynaphthoxy)methyl]methane). Surprisingly, this MOF with neutral cavities can not only extract pure quercetin (QT) but also convert it into Cu-QT during the desorption process. It has bee ...[more]

PMID: 35528871

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Project description:Quorum sensing (QS) regulates bacterial gene expression and studies suggest quercetin, a flavonol found in onion, as a QS inhibitor. There are no studies showing the anti-QS activity of plants containing quercetin in its native glycosylated forms. This study aimed to evaluate the antimicrobial and anti-QS potential of organic extracts of onion varieties and its representative phenolic compounds quercetin aglycone and quercetin 3-β-D-glucoside in the QS model bacteria Chromobacterium violaceum ATCC 12472, Pseudomonas aeruginosa PAO1, and Serratia marcescens MG1. Three phenolic extracts were obtained: red onion extract in methanol acidified with 2.5% acetic acid (RO-1), white onion extract in methanol (WO-1) and white onion extract in methanol ammonium (WO-2). Quercetin 4-O-glucoside and quercetin 3,4-O-diglucoside were identified as the predominant compounds in both onion varieties using HPLC-DAD and LC-ESI-MS/MS. However, quercetin aglycone, cyanidin 3-O-glucoside and quercetin glycoside were identified only in RO-1. The three extracts showed minimum inhibitory concentration (MIC) values equal to or above 125 μg/ml of dried extract. Violacein production was significantly reduced by RO-1 and quercetin aglycone, but not by quercetin 3-β-D-glucoside. Motility in P. aeruginosa PAO1 was inhibited by RO-1, while WO-2 inhibited S. marcescens MG1 motility only in high concentration. Quercetin aglycone and quercetin 3-β-D-glucoside were effective at inhibiting motility in P. aeruginosa PAO1 and S. marcescens MG1. Surprisingly, biofilm formation was not affected by any extracts or the quercetins tested at sub-MIC concentrations. In silico studies suggested a better interaction and placement of quercetin aglycone in the structures of the CviR protein of C. violaceum ATCC 12472 than the glycosylated compound which corroborates the better inhibitory effect of the former over violacein production. On the other hand, the two quercetins were well placed in the AHLs binding pockets of the LasR protein of P. aeruginosa PAO1. Overall onion extracts and quercetin presented antimicrobial activity, and interference on QS regulated production of violacein and swarming motility.

Project description:BackgroundQuercetin is one of the most important bioflavonoids having positive effects on the biological processes and human health. Typically, it is extracted from plant matrices using conventional methods such as maceration, sonication, infusion, and Soxhlet extraction with high solvent consumption. Our study aimed to optimize the environmentally friendly carbon dioxide-based method for the extraction of quercetin from quince fruit with an emphasis on extraction yield, repeatability, and short extraction time.ResultsA two-step design of experiments was used for the optimization of the key parameters affecting physicochemical properties, including CO2/co-solvent ratio, co-solvent type, temperature, and pressure. Finally, gas expanded liquid combining CO2/ethanol/H2O in a ratio of 10/81/9 (v/v/v) provided the best extraction yield. Extraction temperature 66 °C and pressure 22.3 MPa were the most suitable conditions after careful optimization, although both parameters did not significantly affect the process. It was confirmed by experiments in various pressure and temperature conditions and statistical comparison of obtained data. The optimized extraction procedure at a flow rate of 3 mL/min took 30 min. The repeatability of the extraction method exhibited an RSD of 20.8%.ConclusionsThe optimized procedure enabled very fast extraction in 30 min using environmentally friendly solvents and it was successfully applied to 16 different plant samples, including 14 bulbs and 2 fruits from South Africa. The quercetin content in extracts was quantified using ultra-high performance liquid chromatography (UHPLC) with tandem mass spectrometry. UHPLC hyphenated with high-resolution mass spectrometry was used to confirm chemical identity of quercetin in the analyzed samples. We quantified quercetin in 11 samples of all 16 tested plants. The quercetin was found in Agapanthus praecox from the Amaryllidaceae family and its presence in this specie was reported for the first time.

Dataset Information

A neutral Cu-based MOF for effective quercetin extraction and conversion from natural onion juice.

Publications

A neutral Cu-based MOF for effective quercetin extraction and conversion from natural onion juice.

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