Polymethoxyflavones in peel of Citrus reticulata ‘Chachi’ and their biological activities

Duan, Li; Li, Dou; Yu, Ke-Yun; Guo, Long; Chen, Baizhong; Li, Ping; Liu, E‐Hu

doi:10.1016/j.foodchem.2017.05.018

Cited by 87 publications

(54 citation statements)

References 26 publications

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“…13 C-NMR (101 MHz, CDCl 3 ) δ 182.95(C-4), 163.91(C-2), 152.98(C-7), 152.48(C-4’), 149.53(C-3’), 149.39(C-9), 145.75(C-5), 136.58(C-6), 132.95(C-8), 123.70(C-1’), 120.14(C-6’), 111.29(C-5’), 108.80(C-2’), 106.99(C-10), 103.98(C-3), 62.05, 61.71, 61.11, 56.12, 56.00 (5 × OMe) ( Figure S5 ). These data were consistent with the literature reported previously [ 42 ], so it was identified as 5-hydroxy-6,7,8,3’,4’-pentamethoxyflavone, and the purity detected by UPLC was 98.1%.…”

Section: Resultssupporting

confidence: 92%

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

Zhao

Zhou

2018

Molecules

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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.

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Section: Resultssupporting

confidence: 92%

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

Zhao

Zhou

2018

Molecules

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“…Fraction K2 (20.0 g) was subjected to silica gel column chromatography (70-230 mesh, 1.5 x 90 cm) using increasing polarity of the mixture of nhexane-EtOAc (100:0 to 0:100) to give one hundred fractions of 150 mL each. Fractions of similar compounds were combined, based on their TLC profiles to give five sets (S1 (1-29), S2 (30)(31)(32)(33)(34)(35), S3 (39-41), S4 (46)(47)(48)(49)(50)(51)(52)(53), S5 (63-66), S6 (68-72), S7 (84-87) and S8 (90-100)). The S1 series, mainly an extract rich in weakly polar compounds, was subjected to column chromatography on silica gel (70-230 mesh, 1.5 x 100 cm) eluting with a gradient mixture of n-hexane-EtOAc of increasing polarity (100:0 to 0:100) to lead to compound (1) (0.06 g) using n-hexane-EtOAc (19:1) as elution solvent.…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…Based on all these data and by comparison with those described in the literature, the structure of compound (5) has been attributed to 5, 6, 7, 3′, 4′-pentamethoxyflavone or Sinensetin. Isolated for the first time from roots of Khaya senegalensis and previously roots of Citrus reticulata [46,47].…”

Section: Chemical Analysismentioning

confidence: 99%

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)

Nganso¹,

Tchana²,

Kahouo³

et al. 2020

SJC

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This present study investigates the in vitro inhibitory effect and antimicrobial activity of secondary metabolites isolated from the roots of Khaya senegalensis, a plant of the Meliaceae family. Khaya senegalensis is widely used in traditional medicine for the treatment of various illnesses such as: fever, stomach ache, diarrhea, dysentery and anemia. The chemical study of the extract with CH 2 Cl 2-MeOH (1:1) led to the isolation of five compounds: Alphitolic acid (1); Epigouanic acid (2); Methyl angolensate (3); Rohituca-3 (4) and 5, 6, 7, 3′, 4′-pentamethoxyflavone or Sinensetin (5). Alphitolic acid (1), Rohituca-3 (4) and 5, 6, 7, 3′, 4′-pentamethoxyflavone or Sinensetin (5) were isolated from the roots of this plant for the first time. The structures of the isolated compounds have been elucidated on the basis of spectroscopic analysis and a comparison of their spectral data with those reported in the literature. The results of the antibiogram tests showed that the strain of Escherichia coli is sensitive to all the antibiotics tested except Ceftazidime, a Cephalosporin. The Staphylococcus aureus strain is resistant to almost all the antibiotics tested except Amikacin, an aminoglycoside. This is because the enzymes diffuse through the inter and intraspecific transmission of genes through a plasmid. The antibiogram made it possible to establish the sensitivity profile of the strains tested with regard to certain antibiotics. The antimicrobial tests carried out showed that the inhibitory effect of the compounds isolated from Khaya senegalensis on the four bacterial strains tested at the concentration of 25 mg/mL positively influenced at least one of the microbial strains. However, compounds 1, 2 and 3 did not show any bacterial growth inhibitory activity against Proteus vulgaris. MIC obtained for microbiological tests varied between 0.097 and 0.195 mg/mL for the most sensitive strains of Escherichia coli and Pseudomonas aeruginosa, which revealed the highest antibacterial powers. Furthermore, these results therefore show a great variability in the bacteriostatic qualities of the compounds with respect to the different strains. The two Grampositive strains of Staphylococcus aureus are more sensitive than the other Gram-negative bacterial strains tested. From the antibacterial activity, it appears that the compounds isolated from this plant have a bactericidal activity against Escherichia coli and Pseudomonas aeruginosa. This bactericide could justify their use in herbal medicine against bacterial infections.

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“…Researchers have reported that tangerine peel presents high nutritional value due to the presence of phenolic compounds and flavonoids (Moulehi et al, 2012;Putnik et al, 2017;Singanusong, Nipornram, Tochampa, & Rattanatraiwong, 2015). Pharmacological studies of C. reticulata peel have demonstrated several biological activities such as antiinflammatory, antioxidant, antitumor, antimicrobial, and anti-atherosclerosis properties (Duan et al, 2017;Mandal & Mandal, 2016).…”

Section: Introductionmentioning

confidence: 99%

Ultrasound extraction of bioactive compounds from Citrus reticulata peel using electrolyzed water

Soquetta

Tonato

Quadros

et al. 2019

J Food Process Preserv

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The aim of this study was to evaluate the use of acid electrolyzed water, basic electrolyzed water, and slightly acidic electrolyzed water (AEW, BEW, and SAEW, respectively) as solvents in ultrasound (US) to extract bioactive compounds from Citrus reticulata. The influence of the intensity (17–85 W/cm2) and pulse cycles (0.5–1.0 dimensionless) was investigated in relation to the extraction of total phenolics (TP), total flavonoids (TF), and antioxidant activity (FRAP). The extract obtained with US + SAEW presented the highest values for TP (4,324.32 mg GAE.100/g of tangerine peel) and FRAP (663.69 µmol TEAC.100/g of tangerine peel). The highest TF content was found for US + AEW (691.76 mg EQ.100/g of tangerine peel). Response surface methodology showed that higher US intensities improved the extraction of phenolic compounds. Regarding the flavonoid compounds, the highest extractions were obtained at the central points (intensity (51 W/cm2) and cycle (0.75). The results showed that US and electrolyzed water successfully extracted bioactive compounds from tangerine peel; the processing time was also reduced by around 87.5%. These results were higher than those in the literature regarding conventional extraction techniques. Practical applications The combination of unconventional techniques (ultrasound and electrolyzed water as solvent) is characterized as a new methodology for the extraction of bioactive compounds from tangerine peel. This technique is environmental friendly due to the use of fruit residues, as well as the absence of organic solvents, and lower levels of energy use. The extract provided a higher content of total phenolics and total flavonoids than conventional methods. The extract can be incorporated into foods to provide nutritional quality and antioxidant properties. This technique is easily incorporated at the industrial level and is low cost after the purchase of the relevant equipment.

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Polymethoxyflavones in peel of Citrus reticulata ‘Chachi’ and their biological activities

Cited by 87 publications

References 26 publications

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

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

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)

Ultrasound extraction of bioactive compounds from Citrus reticulata peel using electrolyzed water

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Polymethoxyflavones in peel of Citrus reticulata ‘Chachi’ and their biological activities

Cited by 87 publications

References 26 publications

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

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

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of &lt;i&gt;Khaya Senegalensis&lt;/i&gt; (Desr.) A. Juss. (Meliaceae)

Ultrasound extraction of bioactive compounds from Citrus reticulata peel using electrolyzed water

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Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)