7-Methoxyflavone
(Synonyms: 7-甲氧基黄酮) 目录号 : GC48880
A flavone with diverse biological activities
Cas No.:22395-22-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
7-Methoxyflavone is a flavone that has been found in Z. brasiliensis and has diverse biological activities.1,2,3,4 It inhibits aromatase (IC50 = 1.9 µM in a cell-free assay) and LPS-induced nitric oxide (NO) production by 17.74% in RAW 264.7 macrophages when used at a concentration of 20 µM.1,2 7-Methoxyflavone activates androgen and/or glucocorticoid receptor transcriptional activity in a reporter assay and has antinociceptive effects in the acetic acid-induced writhing test in mice (ED50 = 82.5 µmol/kg).3,4
1.Ta, N., and Walle, T.Aromatase inhibition by bioavailable methylated flavonesJ. Steroid. Biochem. Mol. Biol.107(1-2)127-129(2007) 2.An, J.-Y., Lee, H.-H., Shin, J.-S., et al.Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE2 in LPS-induced RAW 264.7 cellsBioorg. Med. Chem. Lett.27(11)2613-2616(2017) 3.Nishizaki, Y., Ishimoto, Y., Hotta, Y., et al.Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assayBioorg. Med. Chem. Lett.19(16)4706-4710(2009) 4.da Silva, A.D.S., Cavalcante-Silva, L.H.A., da Matta, C.B.B., et al.Antinociceptive effect of 7-methoxyflavone isolated from Zornia brasiliensisNat. Prod. Res.27(18)1695-1699(2013)
| Cas No. | 22395-22-8 | SDF | |
| 别名 | 7-甲氧基黄酮 | ||
| Canonical SMILES | O=C1C=C(C2=CC=CC=C2)OC3=CC(OC)=CC=C13 | ||
| 分子式 | C16H12O3 | 分子量 | 252.3 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 15 mg/ml,Ethanol: 5 mg/ml | 储存条件 | -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 | 3.9635 mL | 19.8177 mL | 39.6354 mL |
| 5 mM | 0.7927 mL | 3.9635 mL | 7.9271 mL |
| 10 mM | 0.3964 mL | 1.9818 mL | 3.9635 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。
5-Hydroxy-7-methoxyflavone derivatives from Kaempferia parviflora induce skeletal muscle hypertrophy
Food Sci Nutr 2018 Nov 20;7(1):312-321.PMID:30680186DOI:10.1002/fsn3.891.
Skeletal muscle plays a critical role in locomotion and energy metabolism. Maintenance or enhancement of skeletal muscle mass contributes to the improvement of mobility and prevents the development of metabolic diseases. The extracts from Kaempferia parviflora rhizomes contain at least ten methoxyflavone derivatives that exhibit enhancing effects on ATP production and glucose uptake in skeletal muscle cells. In the present study, we investigated the effects of ten K. parviflora-derived methoxyflavone derivatives (six 5,7-dimethoxyflavone (DMF) derivatives and four 5-hydroxy-7-methoxyflavone (HMF) derivatives) on skeletal muscle hypertrophy. Murine C2C12 myotubes and senescence-accelerated mouse-prone 1 (SAMP1) mice treated with methoxyflavones were used as experimental models to determine the effects of HMF derivatives on myotube diameter and size and muscle mass. The four HMF derivatives, but not the six DMF derivatives, increased myotube diameter. The 5-hydroxyflavone, 7-Methoxyflavone, and 5,7-dihydroxyflavone had no influence on myotube size, a result that differed from HMF. Dietary administration of the mixture composed of the four HMF derivatives resulted in increase in the soleus muscle size and mass in SAMP1 mice. HMF derivatives also promoted protein synthesis in myotubes, and treatment with the intracellular Ca2+ chelator BAPTA-AM, which depletes intracellular Ca2+ levels, inhibited this promotion. Furthermore, BAPTA-AM inhibited HMF-promoted protein synthesis even when myotubes were incubated in Ca2+-free medium. These results indicate that HMF derivatives induce myotube hypertrophy and that both the 5-hydroxyl group and the 7-methoxy group in the flavones are necessary for myotube hypertrophy. Furthermore, these results suggest that HMF-induced protein synthesis requires intracellular Ca2+, but not extracellular Ca2+.
Antinociceptive effect of 7-Methoxyflavone isolated from Zornia brasiliensis
Nat Prod Res 2013;27(18):1695-9.PMID:23425114DOI:10.1080/14786419.2013.768988.
In this study, we investigated the antinociceptive effect of 7-Methoxyflavone (7MF) in mice using the following tests: acetic acid-induced writhing, glutamate- and formalin-induced nociception and hotplate. 7MF (30, 50, 100 and 300 μmol/kg, i.p.) reduced the number of writhes, with ID₅₀ = 82.5 ± 11.7 μmol/kg and E max = 58.4%. 7MF treatment (100 μmol/kg, i.p.) inhibited paw-licking time in the neurogenic phase of the formalin pain response (65.6%) and did not decrease the nociceptive response in the inflammatory phase. In addition, in glutamate-induced nociception, 7MF inhibited 26% of the nociceptive answer. On the other hand, 7MF did not increase the latency time of the animals in the hotplate test. These results suggest that 7MF has peripheral antinociceptive activity.
Investigation of the binding behavior of bioactive 7-Methoxyflavone to human serum albumin by coupling multi-spectroscopic with computational approaches
Spectrochim Acta A Mol Biomol Spectrosc 2023 Jan 15;285:121920.PMID:36201870DOI:10.1016/j.saa.2022.121920.
The natural flavonoids with bioactivity as secondary plant metabolites are mostly found in fruits, vegetables, tea and herbs, the distribution and bioavailability of which in vivo depends on the interaction and successive binding with carrier proteins in the systemic circulation. In this paper, the binding behavior of bioactive 7-Methoxyflavone (7-MF) with human serum albumin (HSA) was studied with the aid of the combination of multi-spectroscopic methods, molecular docking and molecular dynamic simulation. The results of multi-spectroscopic experiments revealed that 7-MF interacted with HSA predominantly via fluorescence static quenching and the microenvironment around the fluorophore Trp residues in HSA became more hydrophilicity with the binding of 7-MF. Thermodynamic analysis demonstrated that hydrogen bonds and van der Waals forces played a dominant role in stabilizing the HSA-7-MF complex. Moreover, the docking experiment and molecular dynamic simulation further confirmed that 7-MF could enter the active cavity of HSA and caused more stable conformation and change of secondary structure of HSA through forming hydrogen bond. The exploration of the mechanism of 7-MF binding to HSA lights a new avenue to understand the stability, transport and distribution of 7-MF and 7-MF may hold great potential to be extended as a promising alternative of dietary supplements or pharmaceutical agents.
Nervione, a new benzofuran derivative from Nervilia concolor
Nat Prod Res 2022 Oct;36(20):5148-5154.PMID:33970720DOI:10.1080/14786419.2021.1920585.
A new benzofuran derivative, nervione (1), was isolated from Nervilia concolor (Blume) Schltr. (Orchidaceae). Eight previously reported compounds were also isolated: 5,7-dimethoxyflavone (2), 3,5,7-trimethoxyflavone (3), 7-Methoxyflavone (4), 3,7-dimethoxy-5-hydroxyflavone (5), tetramethylscutellarein (4',5,6,7-tetramethoxyflavone) (6), 5,7-dimethoxy-4'-hydroxyflavone (7), rhamnetin (8), and 5,7-dihydroxy-3',4'-dimethoxyflavone (9). The structures were elucidated by 1D, 2D NMR, and HRESIMS spectroscopy in addition to the literature. The relative configuration of 1 was defined using DP4+ probability while its absolute configuration was defined by comparison of the ECD spectrum of 1 with those of previously reported compounds. All isolated compounds were evaluated for alpha-glucosidase inhibition, revealing weak or no activity.[Formula: see text].
Microbial metabolism. Part 6. Metabolites of 3- and 7-hydroxyflavones
Chem Pharm Bull (Tokyo) 2006 Mar;54(3):320-4.PMID:16508185DOI:10.1248/cpb.54.320.
Fermentation of 3-hydroxyflavone (1) with Beauveria bassiana (ATCC 13144) yielded 3,4'-dihdroxyflavone (3), flavone 3-O-beta-D-4-O-methylglucopyranoside (4) and two minor metabolites. 7-Hydroxyflavone (2) was transformed by Nocardia species (NRRL 5646) to 7-Methoxyflavone (5) whilst Aspergillus alliaceus (ATCC 10060) converted it to 4',7-dihydroxyflavone (6). Flavone 7-O-beta-D-4-O-metylglucopyranoside (7) and 4'-hydroxyflavone 7-O-beta-D-4-O-methylglucopyranoside (8) were the metabolic products of 7-hydroxyflavone (2) when fermented with Beauveria bassiana (ATCC 7159). One of the minor metabolites of 3-hydroxyflavone (1) was tentatively assigned a beta'-chalcanol structure (9). Compounds 4, 7 and 8 are reported as new compounds. Structure elucidation of the metabolites was based on spectroscopic data.