Naringenin chalcone
(Synonyms: 柚皮素查耳酮) 目录号 : GC38972
A flavonoid with diverse biological activities
Cas No.:73692-50-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Naringenin chalcone is a flavonoid that has been found in the skin of red tomatoes and has diverse biological activities.1,2,3 It inhibits the proliferation of SENCAR mouse skin transformed (SST) cells and SENCAR mouse skin transformed tumor (SST-T) cells (IC50s = 92 and 184 ?g/ml).1 Naringenin chalcone (50 ?g/animal) reduces the number of papillomas in a mouse model of skin carcinogenesis induced by phorbol 12-myristate 13-acetate . Topical administration of naringenin chalcone reduces ear edema in a mouse model of TPA-induced inflammation.2 Naringenin chalcone (0.8 mg/kg) reduces airway hyperresponsiveness, bronchoalveolar lavage fluid (BALF) eosinophil infiltration, and lung mucus production in a mouse model of ovalbumin-induced allergic asthma.3
1.Yagura, T., Motomiya, T., Ito, M., et al.Anticarcinogenic compounds in the Uzbek medicinal plant, Helichrysum maracandicumJ. Nat. Med.62(2)174-178(2008) 2.Escribano-Ferrer, E., Regué, J.Q., Garcia-Sala, X., et al.In vivo anti-inflammatory and antiallergic activity of pure naringenin, naringenin chalcone, and quercetin in miceJ. Nat. Prod.82(2)177-182(2019) 3.Iwamura, C., Shinoda, K., Yoshimura, M., et al.Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cellsAllergol. Int.59(1)67-73(2010)
| Cas No. | 73692-50-9 | SDF | |
| 别名 | 柚皮素查耳酮 | ||
| Canonical SMILES | OC(C=C1)=CC=C1/C=C/C(C2=C(C=C(O)C=C2O)O)=O | ||
| 分子式 | C15H12O5 | 分子量 | 272.25 |
| 溶解度 | DMF: 15 mg/ml,DMSO: 10 mg/ml,Ethanol: 1 mg/ml,PBS (pH 7.2): slightly soluble | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.6731 mL | 18.3655 mL | 36.7309 mL |
| 5 mM | 0.7346 mL | 3.6731 mL | 7.3462 mL |
| 10 mM | 0.3673 mL | 1.8365 mL | 3.6731 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Flavonoids Naringenin chalcone, naringenin, dihydrotricin, and tricin are lignin monomers in papyrus
Plant Physiol 2022 Jan 20;188(1):208-219.PMID:34662399DOI:10.1093/plphys/kiab469.
Recent studies demonstrate that several polyphenolic compounds produced from beyond the canonical monolignol biosynthetic pathways can behave as lignin monomers, participating in radical coupling reactions and being incorporated into lignin polymers. Here, we show various classes of flavonoids, the chalconoid Naringenin chalcone, the flavanones naringenin and dihydrotricin, and the flavone tricin, incorporated into the lignin polymer of papyrus (Cyperus papyrus L.) rind. These flavonoids were released from the rind lignin by Derivatization Followed by Reductive Cleavage (DFRC), a chemical degradative method that cleaves the β-ether linkages, indicating that at least a fraction of each was integrated into the lignin as β-ether-linked structures. Due to the particular structure of tricin and dihydrotricin, whose C-3' and C-5' positions at their B-rings are occupied by methoxy groups, these compounds can only be incorporated into the lignin through 4'-O-β bonds. However, Naringenin chalcone and naringenin have no substituents at these positions and can therefore form additional carbon-carbon linkages, including 3'- or 5'-β linkages that form phenylcoumaran structures not susceptible to cleavage by DFRC. Furthermore, Nuclear Magnetic Resonance analysis indicated that Naringenin chalcone can also form additional linkages through its conjugated double bond. The discovery expands the range of flavonoids incorporated into natural lignins, further broadens the traditional definition of lignin, and enhances the premise that any phenolic compound present at the cell wall during lignification could be oxidized and potentially integrated into the lignin structure, depending only on its chemical compatibility. This study indicates that papyrus lignin has a unique structure, as it is the only lignin known to date that integrates such a diversity of phenolic compounds from different classes of flavonoids. This discovery will open up new ways to engineer and design lignins with specific properties and for enhanced value.
Bioavailability of Naringenin chalcone in humans after ingestion of cherry tomatoes
Int J Vitam Nutr Res 2020 Oct;90(5-6):411-416.PMID:30961461DOI:10.1024/0300-9831/a000574.
Chalcones are a type of flavonoids characterized by an α-β unsaturated structural element which may react with thiol groups to activate pathways such as the Nrf2-Keap-1 system. Naringenin chalcone is abundant in the diet but little is known about its bioavailability. In this work, the bioavailability of Naringenin chalcone from tomatoes was investigated in a group of healthy men (n=10). After ingestion of 600 grams of tomatoes providing a single dose of 17.3 mg Naringenin chalcone, 0.2 mg of naringenin, and 195 mg naringin plasma levels of free and conjugated naringenin and Naringenin chalcone (glucuronide and sulfate) were analyzed by UHPLC-QTOF-MS at 0.5, 1, 3, and 6 h post-consumption. Plasma levels of conjugated naringenin increased to about 12 nmol/L with a maximum at about 3 h. Concentrations of free naringenin hardly elevated above baseline. Plasma levels of free and conjugated Naringenin chalcone significantly increased. A maximum of the conjugated chalcone was reached at about 3 h after ingestion with an average concentration of about 0.5 nmol/L. No free chalcone was detectable at baseline but low amounts of the unconjugated compound could be detected with an average maximum of 0.8 nmol/L at about 1 h after ingestion. The data demonstrate that Naringenin chalcone is bioavailable in humans from cherry tomatoes as a dietary source. However, availability is poor and intramolecular cyclisation as well as extended metabolism likely contribute to the inactivation of the reactive alpha-beta unsaturated reactive center as well as the excretion of the biologically active molecule, respectively.
Protonated Forms of Naringenin and Naringenin chalcone: Proteiform Bioactive Species Elucidated by IRMPD Spectroscopy, IMS, CID-MS, and Computational Approaches
J Agric Food Chem 2023 Mar 8;71(9):4005-4015.PMID:36849438DOI:10.1021/acs.jafc.2c07453.
Naringenin (Nar) and its structural isomer, Naringenin chalcone (ChNar), are two natural phytophenols with beneficial health effects belonging to the flavonoids family. A direct discrimination and structural characterization of the protonated forms of Nar and ChNar, delivered into the gas phase by electrospray ionization (ESI), was performed by mass spectrometry-based methods. In this study, we exploit a combination of electrospray ionization coupled to (high-resolution) mass spectrometry (HR-MS), collision-induced dissociation (CID) measurements, IR multiple-photon dissociation (IRMPD) action spectroscopy, density functional theory (DFT) calculations, and ion mobility-mass spectrometry (IMS). While IMS and variable collision-energy CID experiments hardly differentiate the two isomers, IRMPD spectroscopy appears to be an efficient method to distinguish naringenin from its related chalcone. In particular, the spectral range between 1400 and 1700 cm-1 is highly specific in discriminating between the two protonated isomers. Selected vibrational signatures in the IRMPD spectra have allowed us to identify the nature of the metabolite present in methanolic extracts of commercial tomatoes and grapefruits. Furthermore, comparisons between experimental IRMPD and calculated IR spectra have clarified the geometries adopted by the two protonated isomers, allowing a conformational analysis of the probed species.
Naringenin chalcone improves adipocyte functions by enhancing adiponectin production
Mol Cell Endocrinol 2010 Jul 29;323(2):208-14.PMID:20363289DOI:10.1016/j.mce.2010.03.020.
Naringenin chalcone is a flavonoid contained in tomato peel. In this study, we investigated its effects on adipocyte functions related to metabolic processes, including adipocytokine production. Naringenin chalcone promoted the gene expression (8.0-fold, p<0.001) and protein secretion (2.2-fold, p<0.001) of adiponectin from 3T3-L1 adipocytes. Reporter gene assays revealed that naringenin enhanced the activity of peroxisome proliferator-activated receptor gamma. DNA microarray experiments and Gene Ontology analysis revealed that Naringenin chalcone also up-regulated the genes associated with mitochondrial energy metabolism, reflecting its insulin-sensitizing effects. Conversely, genes in categories such as those for cell adhesion were down-regulated. The expression of one adiponectin receptor, AdipoR2, was also increased (1.8-fold, p<0.01), suggesting that Naringenin chalcone could activate the adiponectin pathway through the elevation of both the ligand and its receptor. These results indicate that Naringenin chalcone is a potent tomato flavonoid that improves adipocyte metabolic functions and exerts insulin-sensitizing effects by activating an adiponectin-related pathway.
Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells
Allergol Int 2010 Mar;59(1):67-73.PMID:20035147DOI:10.2332/allergolint.09-OA-0118.
Background: Some polyphenols possess anti-allergic activities. Naringenin chalcone is one of the polyphenols that is present in the skin of red tomatoes. In this study, we investigated the effect of Naringenin chalcone in allergic responses in vivo using an experimental mouse model system of allergic asthma. Methods: Allergic airway inflammation was induced in mice by sensitization and challenge with ovalbumin. Naringenin chalcone was orally administrated every day during the course of the experiment. Airway hyperreactivity, the eosinophilic infiltration in the bronchioalveolar lavage fluid and Th2 cytokine production from splenic CD4 T cells were assessed. Results: Eosinophilic airway inflammation, airway hyperreactivity and Th2 cytokine production from CD4 T cells were significantly suppressed in mice that were treated with Naringenin chalcone. Hyperproduction of mucus was slightly reduced. Conclusions: The results of this study suggest that Naringenin chalcone suppresses asthmatic symptoms by inhibiting Th2 cytokine production from CD4 T cells. Thus, Naringenin chalcone may be a useful supplement for the suppression of allergic symptoms in humans.