6-Hydroxyflavone
(Synonyms: 6-羟基黄酮) 目录号 : GC38142
6-Hydroxyflavone 是一种天然存在的黄酮化合物，具有抗炎作用。6-Hydroxyflavone 对牛血红蛋白 (BHb) 糖基化具有抑制作用。6-Hydroxyflavone 能激活 AKT、ERK 1/2、JNK 信号通路，有效促进成骨细胞分化。6-Hydroxyflavone 能抑制 LPS 诱导的 NO 的产生。
Cas No.:6665-83-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
6-Hydroxyflavone is a naturally occurring flavone, with anti-inflammatory activity. 6-Hydroxyflavone exhibits inhibitory effect towards bovine hemoglobin (BHb) glycation. 6-Hydroxyflavone can activate AKT, ERK 1/2, and JNK signaling pathways to effectively promote osteoblastic differentiation. 6-Hydroxyflavone inhibits the LPS-induced NO production[1] [2].
[1]. Das S, et al. Characterization of non-covalent binding of 6-hydroxyflavone and 5,7-dihydroxyflavone with bovine hemoglobin: Multi-spectroscopic and molecular docking analyses. J Photochem Photobiol B. 2018 Jan;178:40-52. [2]. Lai CH, et al. Effects of 6-Hydroxyflavone on Osteoblast Differentiation in MC3T3-E1 Cells. Evid Based Complement Alternat Med. 2014;2014:924560. [3]. Wang X, et al. 6-Hydroxyflavone and derivatives exhibit potent anti-inflammatory activity among mono-, di- and polyhydroxylated flavones in kidney mesangial cells. PLoS One. 2015 Mar 19;10(3):e0116409.
| Cas No. | 6665-83-4 | SDF | |
| 别名 | 6-羟基黄酮 | ||
| Canonical SMILES | O=C1C=C(C2=CC=CC=C2)OC3=CC=C(O)C=C13 | ||
| 分子式 | C15H10O3 | 分子量 | 238.24 |
| 溶解度 | DMSO: 125 mg/mL (524.68 mM) | 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 | 4.1974 mL | 20.9872 mL | 41.9745 mL |
| 5 mM | 0.8395 mL | 4.1974 mL | 8.3949 mL |
| 10 mM | 0.4197 mL | 2.0987 mL | 4.1974 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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The flavonoid 6-Hydroxyflavone prevention of cisplatin-induced nephrotoxicity
Histol Histopathol 2020 Oct;35(10):1197-1209.PMID:32909617DOI:10.14670/HH-18-251.
In this study, the flavonoid, 6-Hydroxyflavone was investigated for its renal protective activity in the cisplatin rat model of nephrotoxicity. Male Sprague-Dawley rats weighing 200-250 g were included in the study. 6-Hydroxyflavone was daily administered at 25 and 50 mg/kg (i.p.), while ascorbic acid was used as a positive control and injected (i.p.) at 50 mg/kg for 15 days. The nephrotoxicity was evoked with a single cisplatin injection at 7.5 mg/kg on the tenth day of treatment. The renal function and levels of oxidative stress markers were assessed. Each tissue slide of different groups was observed under a compound microscope attached with a digital camera. Cisplatin significantly decreased the overall body weight with an increase in serum creatinine and urea and production of severe histopathological and oxidative stress in the kidneys. The daily treatment with 6-Hydroxyflavone significantly attenuated the cisplatin associated detrimental changes in the body weight, and serum levels of creatinine and urea at both 25 mg/kg (P<0.05) and 50 mg/kg (P<0.01). The 6-Hydroxyflavone treatment also preserved the renal histoarchitecture from the toxicological influence of cisplatin as evident from a significant reduction in the severity of histopathological changes in the renal tissues. Moreover, 6-Hydroxyflavone also reduced the cisplatin-induced lipid peroxidation and corrected the renal antioxidant status. A similar protective effect was observed with the positive control, ascorbic acid (50 mg/kg). These findings show that the flavonoid 6-Hydroxyflavone has potential nephroprotective properties and can be used for the management of chemotherapy associated renal disturbances.
6-Hydroxyflavone and derivatives exhibit potent anti-inflammatory activity among mono-, di- and polyhydroxylated flavones in kidney mesangial cells
PLoS One 2015 Mar 19;10(3):e0116409.PMID:25790236DOI:10.1371/journal.pone.0116409.
Inflammatory responses by kidney mesangial cells play a critical role in the glomerulonephritis. The anti-inflammatory potential of nineteen mono-, di- and polyhydroxylated flavones including fisetin, quercetin, morin, tricetin, gossypetin, apigenin and myricetin were investigated on rat mesangial cells with lipopolysaccharide (LPS) as the inflammatory stimuli. 6-Hydroxyflavone and 4',6-dihydroxyflavone exhibited high activity with IC50 in the range of 2.0 μM, a much better inhibition potential in comparison to the well-studied polyhydroxylated flavones. Interestingly, the anti-inflammatory activity was not due to direct quenching of NO radicals. Investigation on derivatives with methylation, acetylation or sulfation of 6-hydroxyl group revealed that 6-methoxyflavone was the most potent with an IC50 of 192 nM. Mechanistic study indicated that the anti-inflammatory activity of 6-methoxyflavone arose via the inhibition of LPS-induced downstream inducible NO synthase in mesangial cells. The identification of 6-Hydroxyflavone and 6-methoxyflavone with potent anti-inflammatory activity in kidney mesangial cells provides a new flavone scaffold and direction to develop naturally derived products for potential nephritis prevention and treatment.
Functional mechanism of tracheal relaxation, antiasthmatic, and toxicological studies of 6-Hydroxyflavone
Drug Dev Res 2019 Mar;80(2):218-229.PMID:30394554DOI:10.1002/ddr.21484.
Previously, we described tracheal rat rings relaxation by several flavonoids, being 6-Hydroxyflavone (6-HOF) the most active derivative of the series. Thus, its mechanism of action was determined in an ex vivo tracheal rat ring bioassay. The anti-asthmatic effect was assayed in in vivo OVAlbumin (OVA)-sensitized guinea pigs. Finally, the toxicological profile of 6-HOF was studied based on Organization of Economic Cooperation and Development guidelines with modifications. 6-HOF-induced relaxation appears to be related with receptor-operated calcium channel and voltage-operated calcium channel blockade as the main mechanism of action, and also through the production of relaxant second messengers NO and cGMP. Molecular docking supports that 6-HOF acts as calcium channel blocker and by activation of nitric oxide synthase. In addition, the in vivo anti-asthmatic experiments demonstrate the dose-dependent significant anti-allergic effect of 6-HOF induced by OVA, with best activity at 50 /kg. Finally, toxicological studies determined a LD50 > 2,000 mg/kg and, after 28 day of treatment with 6-HOF (50 mg/kg) by intragastric route, mice did not exhibit evidence of any significant toxicity. In conclusion, experiments showed that 6-HOF exerts significant relaxant activity through calcium channel blockade, and possibly, by NO/cGMP-system stimulation on rat trachea, which interferes with the contraction mechanism of smooth muscle cells in the airways. In addition, the flavonoid shows potential anti-asthmatic properties in an anti-allergic pathway. Furthermore, because the pharmacological and safety evidence, we propose this flavonoid as lead for the development of a novel therapeutic agent for the treatment of asthma and related respiratory diseases.
Characterization of non-covalent binding of 6-Hydroxyflavone and 5,7-dihydroxyflavone with bovine hemoglobin: Multi-spectroscopic and molecular docking analyses
J Photochem Photobiol B 2018 Jan;178:40-52.PMID:29102848DOI:10.1016/j.jphotobiol.2017.10.021.
Flavonoids are biologically imperative compounds used as anti-oxidants, anti-cancer, anti-bacterial agents etc. The current work reports comprehensive binding studies of two important flavonoids, 6-Hydroxyflavone and 5,7-dihydroxyflavone (chrysin) with bovine hemoglobin (BHb) at 298K and 308K, in aqueous medium using UV-vis spectroscopy, steady state fluorescence, circular dichroism (CD) measurements, Fourier Transform infrared spectroscopy (FT-IR) and molecular docking studies. Both 6-Hydroxyflavone and chrysin can quench the intrinsic fluorescence intensity of BHb via static quenching mechanism. The values of binding constant (Kb) for BHb-chrysin complex (3.177±0.992×104M-1, at 298K) was found to be greater than that of BHb-6-hydroxyflavone complex (2.874±0.863×104M-1, at 298K) and the Kb values decreased with the rise in temperature. The thermodynamic parameters indicated that hydrophobic forces and H-bonding play crucial role in BHb-6-hydroxyflavone complexation whereas electrostatic interaction plays the major role in the binding of BHb and chrysin. The binding distances from donor BHb to the acceptor ligands (6-Hydroxyflavone and chrysin) were estimated using the Föster's theory and the possibility of non-radiative energy transfer from BHb to 6-Hydroxyflavone/chrysin was observed. The ligands, 6-Hydroxyflavone and chrysin induced conformational change around Trp residues in BHb as confirmed by synchronous and 3D fluorescence results. CD and FT-IR studies indicated that the % α-helicity of BHb was enhanced due to 6-Hydroxyflavone/chrysin binding. Both the flavonoids showed remarkable inhibitory effect towards BHb glycation. Hydrophobic probe (8-anilino-1-naphthalenesulfonic acid, ANS) displacement and molecular docking studies revealed that the ligands bind within the hydrophobic pocket of BHb.
Effects of 6-Hydroxyflavone on Osteoblast Differentiation in MC3T3-E1 Cells
Evid Based Complement Alternat Med 2014;2014:924560.PMID:24795772DOI:10.1155/2014/924560.
Osteoblast differentiation plays an essential role in bone integrity. Isoflavones and some flavonoids are reported to have osteogenic activity and potentially possess the ability to treat osteoporosis. However, limited information concerning the osteogenic characteristics of hydroxyflavones is available. This study investigates the effects of various hydroxyflavones on osteoblast differentiation in MC3T3-E1 cells. The results showed that 6-Hydroxyflavone (6-OH-F) and 7-hydroxyflavone (7-OH-F) stimulated ALP activity. However, baicalein and luteolin inhibited ALP activity and flavone showed no effect. Up to 50 μ M of each compound was used for cytotoxic effects study; flavone, 6-OH-F, and 7-OH-F had no cytotoxicity on MC3T3-E1 cells. Moreover, 6-OH-F activated AKT and serine/threonine kinases (also known as protein kinase B or PKB), extracellular signal-regulated kinases (ERK 1/2), and the c-Jun N-terminal kinase (JNK) signaling pathways. On the other hand, 7-OH-F promoted osteoblast differentiation mainly by activating ERK 1/ 2 signaling pathways. Finally, after 5 weeks of 6-OH-F induction, MC3T3-E1 cells showed a significant increase in the calcein staining intensity relative to merely visible mineralization observed in cells cultured in the osteogenic medium only. These results suggested that 6-OH-F could activate AKT, ERK 1/2, and JNK signaling pathways to effectively promote osteoblastic differentiation.