Amorfrutin A
(Synonyms: Amorfrutin 1) 目录号 : GC40636
An antidiabetic natural product
Cas No.:80489-90-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Amorfrutin A is an isoprenoid-substituted benzoic acid natural product found in the fruit of A. fruticosa and G. foetida that exhibits antidiabetic effects. It binds to PPARγ with a Ki of 0.236 µM and activates a PPARγ gene reporter assay with an EC50 value of 0.458 µM. In high-fat diet-induced obese (DIO) mice, amorfrutin A (100 mg/kg/day) enhanced glucose tolerance and insulin sensitivity, while decreasing plasma triglycerides, free fatty acids, insulin, and glucose concentrations. Amorfrutin A inhibits TNF-α-induced expression of a number of inflammatory genes such as COX-2, IL-1β, MCP-1, MIP-2, MIP-3α, MMP-9, and IL-8 through inhibition of both NF-κB and PPARγ activity with efficacy at 5-20 µM.
| Cas No. | 80489-90-3 | SDF | |
| 别名 | Amorfrutin 1 | ||
| Canonical SMILES | OC(C(C(O)=C(C/C=C(C)/C)C(OC)=C1)=C1CCC2=CC=CC=C2)=O | ||
| 分子式 | C21H24O4 | 分子量 | 340.4 |
| 溶解度 | DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble | 储存条件 | Store at -20°C |
| 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 | 2.9377 mL | 14.6886 mL | 29.3772 mL |
| 5 mM | 0.5875 mL | 2.9377 mL | 5.8754 mL |
| 10 mM | 0.2938 mL | 1.4689 mL | 2.9377 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。
Amorfrutin A inhibits TNF-α induced JAK/STAT signaling, cell survival and proliferation of human cancer cells
Immunopharmacol Immunotoxicol 2017 Dec;39(6):338-347.PMID:28879797DOI:10.1080/08923973.2017.1371187.
Context: Amorfrutin A is a natural product isolated from the fruits of Amorpha fruticosa L. and has been shown to exhibit multiple bioeffector functions. In the present study, we investigated whether Amorfrutin A exerts anticancer effects by inhibiting STAT3 activation in cervical cancer cells. Objective: To investigate the effectiveness of Amorfrutin A as a treatment of cancer, and determine the underlying pharmacological mechanism of action. Materials and methods: HeLa, SK-Hep1, MDA-MB-231 and HCT116 cells were used in this study. Major assays were luciferase reporter assay, MTT, Western blot analysis, immunofluorescence assay, reverse transcription-PCR (RT-PCR), flow cytometric analysis, EdU labeling and immunofluorescence, xenografted assay. Results: Amorfrutin A significantly inhibited tumor necrosis factor-α (TNF-α)-induced phosphorylation and nuclear translocation of STAT3 in human cervical carcinoma cells. Amorfrutin A also inhibited activation of the upstream kinases Janus-activated kinase 1 (JAK1), JAK2 and Src signaling pathways. Furthermore, Amorfrutin A increased the expression of p53, p21, p27, induced cell cycle arrest in the G1 phase as well as decreased levels of various oncogene protein products. In vivo studies further confirmed the inhibitory effect of Amorfrutin A on the expression of STAT3 proteins, leading to a decrease growth of HeLa cells in a xenograft tumor model. Discussion and conclusions: The results indicated that Amorfrutin A is a potent inhibitor of STAT3 and provide new perspectives into the mechanism of its anticancer activity.
Amorfrutin A inhibits TNF-α-induced NF-κB activation and NF-κB-regulated target gene products
Int Immunopharmacol 2014 Jul;21(1):56-62.PMID:24785328DOI:10.1016/j.intimp.2014.04.016.
The nuclear factor-κB (NF-κB) transcription factors control many physiological processes including inflammation, immunity, apoptosis, and angiogenesis. In our search for NF-κB inhibitors from natural resources, we identified Amorfrutin A as an inhibitor of NF-κB activation from the fruits of Amorpha fruticosa L. In present study, this compound significantly inhibited the TNF-α-induced expression of NF-κB reporter gene. Further analysis revealed that Amorfrutin A was a potent inhibitor of NF-κB activation by the suppression of TNF-α-induced inhibitor of κBα (IκBα) degradation, p65 nuclear translocation, and DNA-binding activity of NF-κB. We also demonstrated that pretreatment of cells with this compound prevented the TNF-α-induced expression of NF-κB target genes, such as antiapoptosis (cIAP-1 and FLIP), proliferation (COX-2 and cyclinD1), invasion (MMP-9), angiogenesis (VEGF), and major inflammatory cytokines (TNF-α, IL-8, and MCP1). Furthermore, our results suggest that Amorfrutin A potentiates TNF-α-induced apoptosis. Taken together, Amorfrutin A could be a valuable candidate for the intervention of NF-κB-dependent pathological conditions such as inflammation.
Directed C-H Bond Functionalization: A Unified Approach to Formal Syntheses of Amorfrutin A, Cajaninstilbene Acid, Hydrangenol, and Macrophyllol
J Org Chem 2018 Oct 5;83(19):12327-12333.PMID:30211554DOI:10.1021/acs.joc.8b02116.
Formal syntheses of natural products Amorfrutin A, cajaninstilbene acid, hydrangenol, and macrophyllol have been accomplished on the basis of successive C-H bond functionalization of ready-stock benzoic acids. This concise strategy involves transition-metal-catalyzed directed C-H olefination, C-H hydroxylation, and acid-mediated C-H prenylation as key steps.
Unified total synthesis of amorfrutins A and C via the Claisen rearrangement
Biosci Biotechnol Biochem 2019 Sep;83(9):1635-1641.PMID:31130067DOI:10.1080/09168451.2019.1618699.
A concise, unified total synthesis of the two prenylated aromatic polyketides amorfrutins A and C, which exhibit various medicinally important biological profiles such as antimicrobial, PPARγ modulating and quorum sensing inhibitory activities, has been achieved from commercially available 3,5-dimethoxybenzaldehyde in 38% and 10% overall yields through nine and ten steps, respectively. The key transformation for the synthesis of Amorfrutin A was the Claisen rearrangement of a mono-O-(1,1-dimethylallyl)resorcinol derivative to install the C3-prenyl substituent, while that for the synthesis of amorfrutin C was the double Claisen rearrangement of a di-O-(1,1-dimethylallyl)resorcinol derivative to introduce the two prenyl groups at the C3 and C5 positions all at once.
Isolation and purification of prenylated phenolics from Amorpha fruticosa by high-speed counter-current chromatography
J Sep Sci 2015 Aug;38(16):2924-9.PMID:26041477DOI:10.1002/jssc.201500224.
Prenylated phenolics such as amorfrutins are recently identified potent anti-inflammatory and antidiabetic natural products. In this work, high-speed counter-current chromatography was investigated for the isolation and purification of prenylated phenolics from the fruits of Amorpha fruticosa by using a two-phase solvent system composed of n-hexane/ethanol/water (5:4:1, v/v). As a result, 14.2 mg of 5,7-dihydroxy-8-geranylflavanone, 10.7 mg of Amorfrutin A and 17.4 mg of amorfrutin B were obtained from 200 mg of n-hexane-soluble crude extract in one step within 250 min. The purities of 5,7-dihydroxy-8-geranylflavanone, amorfrutins A and B were 95.2, 96.7 and 97.1%, respectively, as determined by ultra high performance liquid chromatography. The structural identification was performed by mass spectrometry and (1) H and (13) C NMR spectroscopy. The results indicated that the established method is an efficient and convenient way to purified prenylated phenolics from A. fruticosa extract.