Dataset Information

Simultaneous Separation and Purification of Five Polymethoxylated Flavones from "Dahongpao" Tangerine (Citrus tangerina Tanaka) Using Macroporous Adsorptive Resins Combined with Prep-HPLC.

ABSTRACT: In this study, a preparative separation method was established to simultaneously isolate the polymethoxylated flavones (PMFs) from the peel of "Dahongpao" tangerine using macroporous adsorptive resins (MARs) combined with prep-HPLC. The total PMFs were enriched using MARs to remove most sugars, water-soluble pigments, and flavanones, and the eluents obtained were analyzed by ultra-performance liquid chromatography (UPLC) to determine the PMF composition. The separation and purification of PMFs were carried out by using a mass spectrometry-guided prep-HPLC with a gradient elution of acetonitrile-water (v/v), simultaneously. The purity of these PMFs was determined by UPLC, and their chemical structures were confirmed by electrospray ionization mass spectrometry (ESI-MS-MS), ultraviolet (UV), and nuclear magnetic resonance (NMR). Using the present method, five PMFs, including 5,6,7,4'-tetramethoxyflavone (1), nobiletin (2), tangeretin (3), sinensetin (4), and 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone (5), can be purified simultaneously, and the purity of the compounds obtained were 95.3%, 99.7%, 99.5%, 98.9%, and 98.1%, respectively. The method reported here is simple, rapid, and efficient, and it can be used to separate PMFs from citrus fruit peels and, potentially, other plant materials.

SUBMITTER: Li Z

PROVIDER: S-EPMC6222627 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Publications

Simultaneous Separation and Purification of Five Polymethoxylated Flavones from "Dahongpao" Tangerine (<i>Citrus tangerina</i> Tanaka) Using Macroporous Adsorptive Resins Combined with Prep-HPLC.

Li Zhenqing Z Zhao Ziyan Z Zhou Zhiqin Z

Molecules (Basel, Switzerland) 20181016 10

In this study, a preparative separation method was established to simultaneously isolate the polymethoxylated flavones (PMFs) from the peel of "Dahongpao" tangerine using macroporous adsorptive resins (MARs) combined with prep-HPLC. The total PMFs were enriched using MARs to remove most sugars, water-soluble pigments, and flavanones, and the eluents obtained were analyzed by ultra-performance liquid chromatography (UPLC) to determine the PMF composition. The separation and purification of PMFs w ...[more]

PMID: 30332822

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Project description:Antioxidants play a vital role in the human body by defending cells from damage caused by free radicals, highly reactive products of oxidation reactions. A major source of antioxidants is fruits and vegetables. Aronia mitschurinii, a breed created at the end of the 19th century by crossbreeding wild Aronia melanocarpa and Russian Mountain Ash, produces fruits with one of the highest known content of hydrophilic antioxidants. Aronia fruit contains a potent blend of anthocyanins, polyphenols, and flavonoids. The most popular way of consuming the fruit is through juicing. Yet, due to very high concentrations of tannins in the juice, very few food-related applications have been developed. Resin extraction of antioxidants provides an alternative for utilizing valuable phytochemicals from crops for applications in the food industry as nutraceutical supplements and more. To increase the market value of the plant, it is important to determine what resins can extract the optimum concentration of antioxidants from aronia juice, pulp, and whole berries. We have shown that macroporous resins such as Amberlite XAD 1180N, Amberlite XAD 7HP, Amberlite XAD 761, and Amberlite FPX66, which have been reported to be effective in extracting the anthocyanins and polyphenols from other fruit juices, skins of red grapes, and the wild breed, are also effective for use in juice, pulp, and whole fruits of Aronia mitchurinii. However, the extremely high content of antioxidants presents a challenge to obtaining high recovery; a notable change in the juice/resin ratio is required to obtain a higher recovery value. Our results showed that Amberlite FPX66 was the best at extracting anthocyanins, polyphenols, and flavonoids from aronia juice. A separate experiment conducted to determine how to optimize the efficiency of FPX66 extraction revealed that increasing the resin/juice ratio increased the percent recovery of anthocyanins from aronia juice. Moreover, we have compared recovery between juice, pulp, and whole aronia berries and batch versus column extraction.

Project description:Polymethoxylated flavones (PMFs) from citrus fruits are reported to present anticancer potential. However, there is a lack of information regarding their effect on cancer stem cell (CSC) populations, which has been recognized as responsible for tumor initiation, relapse, and chemoresistance. In this study, we evaluated the effect of an orange peel extract (OPE) and its main PMFs, namely, nobiletin, sinensetin, tangeretin, and scutellarein tetramethylether in targeting cell proliferation and stemness using a 3D cell model of colorectal cancer composed of HT29 cell spheroids cultured for 7 days in stirred conditions. Soft agar assay, ALDH1 activity, and relative quantitative gene expression analysis of specific biomarkers were carried out to characterize the stemness, self-renewal, and mesenchymal features of HT29 cell spheroids. Then, the impact of OPE and PMFs in reducing cell proliferation and modulating cancer stemness and self-renewal was assessed. Results showed that, when compared with monolayer cultures, HT29 cell spheroids presented higher ALDH1 activity (81.97% ± 5.27% compared to 63.55% ± 17.49% for 2D), upregulation of CD44, PROM1, SOX9, and SNAI1 genes (1.83 ± 0.34, 2.54 ± 0.51, 2.03 ± 0.15, and 6.12 ± 1.59 times) and high self-renewal capability (352 ± 55 colonies compared to 253 ± 42 for 2D). Incubation with OPE (1 mg/mL) significantly inhibited cell proliferation and modulated cancer stemness and self-renewal ability: colony formation, ALDH1 activity, and the expression of cancer stemness biomarkers PROM1 and LGR5 were significantly reduced (0.66 ± 0.15 and 0.51 ± 0.14 times, respectively). Among all PMFs, tangeretin was the most efficient in targeting the CSC population by decreasing colony formation and the expression of PROM1 and LGR5. Scutellarein tetramethylether was shown to modulate markers of mesenchymal/metastatic transition (increasing CDH1 and reducing ZEB1 and SNAI1) and nobiletin was capable of downregulating PROM1 and SNAI1 expression. Importantly, all PMFs and OPE were shown to synergistically interact with 5-fluorouracil, improving the antiproliferative response of this drug.

Dataset Information

Simultaneous Separation and Purification of Five Polymethoxylated Flavones from "Dahongpao" Tangerine (Citrus tangerina Tanaka) Using Macroporous Adsorptive Resins Combined with Prep-HPLC.

Publications

Simultaneous Separation and Purification of Five Polymethoxylated Flavones from "Dahongpao" Tangerine (<i>Citrus tangerina</i> Tanaka) Using Macroporous Adsorptive Resins Combined with Prep-HPLC.

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