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Chemical Structure| 480-41-1 Chemical Structure| 480-41-1
Chemical Structure| 480-41-1

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Naringenin could suppess ERK2 activity and decrease stability of FRA1. It is a predominant flavanone derived from plant food with antioxidant effect.

Synonyms: NSC 34875; S-Dihydrogenistein; Salipurol

4.5 *For Research Use Only !

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Commey, Leslie ; Mechref, Yehia ; Burow, Mark ; Mendu, Venugopal ;

Abstract: The peanut seed coat acts as a physical and biochemical barrier against Aspergillus flavus infection; however, the nature of the inhibitory chemicals in the peanut seed coat in general is not known. This study identified and characterized peanut seed coat metabolites that inhibit A. flavus growth and aflatoxin contamination. Selected peanut accessions grown under well-watered and water-deficit conditions were assayed for A. flavus resistance, and seed coats were metabolically profiled using liquid chromatography mass spectrometry. Kyoto Encyclopedia of Genes and Genome phenylpropanoid pathway reference analysis resulted in the identification of several seed coat metabolic compounds, and ten selected metabolites were tested for inhibition of A.flavus growth and aflatoxin contamination. Radial growth bioassay demonstrated that inhibited A. flavus growth (98.7%) and reduced the aflatoxin contamination estimate from 994 to 1 μg/kg. Scanning electron micrographs showed distorted hyphae and conidiophores in cultures of 2,5-dihydroxybenzaldehyde-treated A. flavus, indicating its potential use for field application as well as seed coat metabolic engineering.

Keywords: aflatoxin, A. flavus ; metabolomics ; seed coat ; liquid chromatography mass spectrometry (LC-MS) ; radial growth bioassay ; secondary metabolites

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Nasanjargal Dorjjugder ; Goro Taguchi ;

Abstract: Flavonoid 7-O-glucosides exhibit various biological activities; however, some are not abundant in nature. Therefore, a method to produce flavonoid 7-O-glucosides was investigated. Escherichia coli expressing tobacco-derived glucosyltransferase (Ec-NtGT2) converted several flavonoids (apigenin, luteolin, quercetin, kaempferol, and naringenin) to their 7-O-glucosides with conversion rates of 67–98%. In scaled-up production, Ec-NtGT2 yielded 24 mg/L of apigenin 7-O-glucoside, 41 mg/L of luteolin 7-O-glucoside, 118 mg/L of quercetin 7-O-glucoside, 40 mg/L of kaempferol 7-O-glucoside, and 75 mg/L of naringenin 7-O-glucoside through sequential administration of substrates in 4–9 h. The conversion rates of apigenin, luteolin, quercetin, kaempferol, and naringenin were 97%, 72%, 77%, 98%, and 96%, respectively. These results indicated that Ec-NtGT2 is a simple and efficient bioconversion system for the production of flavonoid 7-O-glucosides.

Keywords: Escherichia coli bioconversion ; Flavonoid 7-O-glucoside ; Flavonoid ; 7-O-glucosyltransferase ; Sequential administration

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Dorjjugder, Nasanjargal ; Hatano, Mayu ; Taguchi, Goro ;

Abstract: Objectives: To produce flavonol and flavone 6-C-glucosides by bioconversion using recombinant Escherichia coli expressing a C-glucosyltransferase from wasabi (WjGT1). Results: Escherichia coli expressing WjGT1 (Ec-WjGT1) converted flavones (apigenin and luteolin) and flavonols (quercetin and kaempferol) into their 6-C-glucosides in M9 minimal media supplemented with glucose, and released these products into the culture media. Ec-WjGT1 system also converts a flavanone (naringenin) into its C-glucoside at a conversion rate of 60% in 6 h. For scale-up production, apigenin, kaempferol, and quercetin were sequentially fed into the Ec-WjGT1 system at concentrations of 20-50 µM every 15-60 min, and the system was then able to produce isovitexin, kaempferol 6-C-glucoside, and quercetin 6-C-glucoside at an 89-99% conversion rate. Conclusions: The Ec-WjGT1 system quickly and easily produces flavone and flavonol 6-C-glucosides at high conversion rates when using sequential administration to avoid precipitation of substrates.

Keywords: C-glucosyltransferase ; Escherichia coli bioconversion ; Flavonol C-glucoside

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Product Details of Naringenin

CAS No. :480-41-1
Formula : C15H12O5
M.W : 272.25
SMILES Code : O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3
Synonyms :
NSC 34875; S-Dihydrogenistein; Salipurol
MDL No. :MFCD00870553
InChI Key :FTVWIRXFELQLPI-ZDUSSCGKSA-N
Pubchem ID :439246

Safety of Naringenin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Naringenin

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 480-41-1 ]
  • Downstream synthetic route of [ 480-41-1 ]

[ 480-41-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 480-41-1 ]
  • [ 578-74-5 ]
References: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034.
 

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