Naringenin chalcone
(Synonyms: 柚皮素查耳酮) 目录号 : GC38972
Naringenin chalcone是一种口服抗过敏化合物，具有降低人胎盘CYP19A1活性的作用，IC50值为2.6μmol/L。
Cas No.:73692-50-9
Sample solution is provided at 25 µL, 10mM.
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Naringenin chalcone functions as an anti-allergic compound that can be taken orally and has shown effectiveness in reducing human placental CYP19A1 activity with an IC50 value of 2.6μmol/L[1]. Naringenin chalcone is a flavonol biosynthesis intermediate that converts into Naringenin through spontaneous metabolism by chalcone isomerase and serves as a common research subject for anti-inflammatory studies[2].
In vitro, Naringenin chalcone treatment (100µmol/L; 48h) significantly promoted the apoptosis of U87MG human glioblastoma cells, inhibited chromatin condensation, DNA fragmentation and membrane blistering of the cells, and upregulated the expression of all PI3K-related proteins[3]. Naringenin chalcone inhibited the histamine release from rat peritoneal mast cells with IC50 value of 68μg/ml for 24h[4]. After treating 3T3-L1 cells with 100µmol/L Naringenin chalcone for 24h, the genes related to mitochondrial energy metabolism were upregulated and the metabolic function of the cells was improved[5].
In vivo, Naringenin chalcone treatment (80mg/kg/day; p.o.) for 24 days significantly inhibited tumor weight and tumor volume in xenograft tumor model of nude mice[3]. After oral administration of Naringenin chalcone (20mg/kg) to male Sprague-Dawley rats for 24 hours, the level of Naringenin chalcone 2 '-O-β -D-glucuronide in the rat serum increased, inhibiting histamine release[6]. Oral administration of Naringenin chalcone (0.8mg/kg/day) for 23 days can alleviate allergic respiratory tract inflammation in the experimental mouse model of allergic asthma[7].
References:
[1] Wang Y, Pan P, Li X, et al. Food components and environmental chemicals of inhibiting human placental aromatase[J]. Food and Chemical Toxicology, 2019, 128: 46-53.
[2] Kolot C, Rodriguez-Mateos A, Feliciano R, et al. Bioavailability of naringenin chalcone in humans after ingestion of cherry tomatoes[J]. International Journal for Vitamin and Nutrition Research, 2019.
[3] Zhang S, Jiang Z F, Pan Q, et al. Anti-cancer effect of naringenin chalcone is mediated via the induction of autophagy, apoptosis and activation of PI3K/Akt signalling pathway[J]. Bangladesh Journal of Pharmacology, 2016, 11(3): 684-690.
[4] Yamamoto T, Yoshimura M, Yamaguchi F, et al. Anti-allergic activity of naringenin chalcone from a tomato skin extract[J]. Bioscience, biotechnology, and biochemistry, 2004, 68(8): 1706-1711.
[5] Escribano-Ferrer E, Queralt Regue J, Garcia-Sala X, et al. In vivo anti-inflammatory and antiallergic activity of pure naringenin, naringenin chalcone, and quercetin in mice[J]. Journal of natural products, 2019, 82(2): 177-182.
[6] Yoshimura M, Sano A, Kamei J I, et al. Identification and quantification of metabolites of orally administered naringenin chalcone in rats[J]. Journal of agricultural and food chemistry, 2009, 57(14): 6432-6437.
[7] Iwamura C, Shinoda K, Yoshimura M, et al. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells[J]. Allergology International, 2010, 59(1): 67-73.
Naringenin chalcone是一种口服抗过敏化合物，具有降低人胎盘CYP19A1活性的作用，IC50值为2.6μmol/L[1]。Naringenin chalcone是一种黄酮醇生物合成中间体，通过查尔酮异构酶自发代谢转化为柚皮素，是抗炎研究的常用研究对象[2]。
在体外，Naringenin chalcone处理（100µmol/L; 48h）可显著促进U87MG人胶质母细胞瘤细胞的凋亡，抑制细胞染色质凝聚、DNA断裂和膜起泡，上调所有PI3K相关蛋白的表达[3]。Naringenin chalcone处理24小时可抑制大鼠腹膜肥大细胞的组胺释放，IC50值为68μg/ml[4]。100µmol/L Naringenin chalcone处理3T3-L1细胞24小时后，细胞线粒体能量代谢相关基因上调，细胞代谢功能得到改善[5]。
在体内，Naringenin chalcone处理（80mg/kg/day; p.o.）24天后可显著抑制裸鼠异种移植瘤模型的肿瘤重量和肿瘤体积[3]。口服Naringenin chalcone（20mg/kg）24小时后，雄性SD大鼠血清中柚皮素查尔酮2'-O-β-D-葡糖苷含量升高，Naringenin chalcone可抑制组胺释放[6]。口服Naringenin chalcone（0.8mg/kg/day）23天可减轻实验性哮喘小鼠模型的过敏性呼吸道炎症[7]。
| Cell experiment [1]: | |
Cell lines | 3T3-L1 cells |
Preparation Method | 3T3-L1 cells grew in Dulbecco's Modified Eagle Medium (DMEM) which included 10% fetal bovine serum (FBS). Cells began differentiation into adipocytes two days post-confluence when differentiation medium composed of DMEM with 10% FBS and 0.5mmol/L 3-isobuthyl-1-methylxantine along with 1μmol/L dexamethasone and 10μg/ml insulin was added together with specific Naringenin chalcone concentrations (25, 50, 100μmol/L) on day 0. On the second day, 3T3-L1 cells moved to adipocyte-growing medium (DMEM with 10% FBS and 5μg/ml insulin) and received various Naringenin chalcone concentrations (25, 50, 100μmol/L), which was replenished every 48 hours. Use dimethyl sulfoxide to serve as the vehicle control for Naringenin chalcone at a 0.1% concentration. The culture medium was gathered on day 8 to measure adiponectin secretion during differentiation days 6 to 8 using enzyme-linked immunosorbent assay (ELISA). Extract total RNA for use in quantitative reverse transcription-polymerase chain reaction (RT-PCR) and DNA microarray analysis. |
Reaction Conditions | 25, 50, 100μmol/L; 0-8 days |
Applications | Naringenin chalcone stimulated adiponectin gene expression and protein secretion in 3T3-L1 cells while simultaneously boosting genes involved in mitochondrial energy metabolism. |
| Animal experiment [2]: | |
Animal models | BALB/c nude mice |
Preparation Method | BALB/c nude mice received an intraperitoneal injection of 100μg of Ovalbumin (OVA) bound to 1mg of alum on day 0 followed by another dose on day 7. The mice received aerosolized OVA dissolved in saline at 10mg/mL concentration through inhalation for 30 minutes by means of a supersonic nebulizer on both day 21 and day 23. During the entire experimental period the mice received 0.8mg/kg of Naringenin chalcone through oral delivery using a 0.5% carboxymethyl cellulose sodium salt solution at a volume of 5mL/kg of body weight each day. Use a 0.5% carboxymethyl cellulose sodium salt solution lacking Naringenin chalcone as the placebo treatment. The metabolites of Naringenin chalcone maintained a half-life of 5.5±1.7 hours in rat blood while approximately 60% of the administered compound was absorbed. After 48 hours from the final OVA challenge the mice underwent asphyxiation before the lungs of mice received a 10% (v/v) formalin PBS buffer infusion to enable tissue fixation. The lung samples underwent sectioning and staining with either hematoxylin and eosin (H&E) reagents or periodic acid-Schiff (PAS) reagent before examination under a light microscope at ×100 magnification to identify pathological changes. Determine the number of infiltrated mononuclear cells in the peribronchiolar regions through direct counting in four separate fields for each slide. |
Dosage form | 0.8mg/kg/day for 23 days; p.o. |
Applications | Naringenin chalcone significantly inhibited eosinophilic airway inflammation, airway hyperresponsiveness and Th2 cytokine production by CD4+ T cells in the experimental mouse model, resulting in a slight reduction in mucus overproduction. |
References: | |
| 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 |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度： mg/ml；
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2.
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Quality Control & SDS
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- Purity: >98.00%
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