Afzelin
(Synonyms: 阿福豆苷,Kaempferol-3-O-rhamnoside) 目录号 : GC35262
A polyphenolic glycoside flavone with diverse biological activities
Cas No.:482-39-3
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
Afzelin is a polyphenolic glycoside flavone that has been found in B. pinnatum and has diverse biological activities.1,2,3 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals with an IC50 value of 6.44 μg/ml.1 Afzelin is active against S. aureus, P. aeruginosa, S. typhi, C. albicans, C. parapsilosis, and C. neoformans (MICs = 8, 16, 2, 16, 4, and 4 μg/ml, respectively). It inhibits the proliferation of A549, SKOV3, and SK-MEL-2 cells (EC50s = 40.6, 34.5, and 33.9 μg/ml, respectively).2 Afzelin (26 mg/kg per day) reduces the number of eosinophils, other inflammatory cells, and total cells, as well as the levels of IL-4, IL-5, and IL-13, in bronchoalveolar lavage fluid (BALF) in a mouse model of allergic asthma.3
1.Tatsimo, S.J.N., Tamokou, J.d.D., Havyarimana, L., et al.Antimicrobial and antioxidant activity of kaempferol rhamnoside derivatives from Bryophyllum pinnatumBMC Res. Notes5158(2012) 2.Kim, Y.-K., Kim, Y.S., Choi, S.U., et al.Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell linesArch. Pharm. Res.27(1)44-47(2004) 3.Chung, M.J., Pandey, R.P., Choi, J.W., et al.Inhibitory effects of kaempferol-3-O-rhamnoside on ovalbumin-induced lung inflammation in a mouse model of allergic asthmaInt. Immunopharmacol.25(2)302-310(2015)
| Cas No. | 482-39-3 | SDF | |
| 别名 | 阿福豆苷,Kaempferol-3-O-rhamnoside | ||
| Canonical SMILES | O=C1C(O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)=C(C3=CC=C(O)C=C3)OC4=CC(O)=CC(O)=C14 | ||
| 分子式 | C21H20O10 | 分子量 | 432.38 |
| 溶解度 | Ethanol: 50 mg/mL (115.64 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 | 2.3128 mL | 11.5639 mL | 23.1278 mL |
| 5 mM | 0.4626 mL | 2.3128 mL | 4.6256 mL |
| 10 mM | 0.2313 mL | 1.1564 mL | 2.3128 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。
Anti-Cancer Potential of Afzelin towards AGS Gastric Cancer Cells
Pharmaceuticals (Basel) 2021 Sep 25;14(10):973.PMID:34681197DOI:10.3390/ph14100973.
Afzelin demonstrates anti-inflammatory and anti-cancer properties. Our purpose was to assess its influence on apoptosis, Bax, caspases, MUC1, cancer-related carbohydrate antigens, enzymes participating in their formation, and galectin-3 in AGS gastric cancer cells. A total of 60 and 120 μM Afzelin was used in all experiments. Flow cytometry was applied to determine apoptotic response. Western blotting and RT PCR were used to detect the expression of mentioned factors. Flavonoid at higher concentration revealed slight apoptotic respond. Bax, caspase-3, -8, -9 increased upon Afzelin action. Stimulatory effect of the flavonoid on MUC1 cytoplasmic tail and extracellular domain in cell lysates and on MUC1 gene was revealed. MUC1 release into the culture medium was inhibited by the flavonoid. The 60 μM Afzelin dose stimulated GalNAcTL5 protein expression and inhibited C1GalT1. ST6GalNAcT mRNA was inhibited by both flavonoid doses. ST3GalT was inhibited by 120 μM Afzelin on protein and mRNA level. Lewisa/b protein was reduced by both Afzelin concentrations. FUT3 and FUT4 mRNA was inhibited by 120 μM dose of Afzelin. Galectin-3 protein increased in cell lysates and decreased in culture supernatant by 60 and 120 μM flavonoid. Galectin-3 gene expression was stimulated by two used concentrations of Afzelin in comparison to control. We conclude that Afzelin can be considered as the potential anti-cancer agent, supporting conventional cancer treatment.
Afzelin suppresses proinflammatory responses in particulate matter-exposed human keratinocytes
Int J Mol Med 2019 Jun;43(6):2516-2522.PMID:31017255DOI:10.3892/ijmm.2019.4162.
Particulate matter (PM), a widespread airborne contaminant, is a complex mixture of solid and liquid particles suspended in the air. Recent studies have demonstrated that PM induces oxidative stress and inflammatory reactions, and may cause certain skin diseases. Afzelin is a flavonoid isolated from Thesium chinense Turcz, which has anti‑inflammatory, anticancer and antibacterial properties. Therefore, the present study aimed to investigate if Afzelin affected inflammatory responses in human keratinocytes exposed to PM. HaCaT cells were treated with PM (25 µg/cm2) in the presence or absence of Afzelin (200 µM). Here, standard reference material 1649b was used as PM. Cell viability was assessed using the water‑soluble tetrazolium salt‑1 assay. The generation of reactive oxygen species (ROS) was measured using the dichloro‑dihydro‑fluorescein diacetate assay. Gene and protein expression were investigated using reverse transcription‑quantitative polymerase chain reaction and western blot analysis, respectively. Levels of secreted inflammatory cytokines were measured using ELISA. The results suggested that Afzelin inhibited PM‑induced proinflammatory cytokine mRNA expression and protein secretion in HaCaT cells. In addition, Afzelin suppressed PM‑induced intracellular ROS generation, and p38 mitogen‑activated protein kinase and transcription factor activator protein‑1 component c‑Fos and c‑Jun activation. The results indicated that Afzelin exerts anti‑inflammatory and antioxidant effects in PM‑exposed HaCaT. Afzelin may have potential for preventing PM‑induced inflammatory skin diseases.
Afzelin positively regulates melanogenesis through the p38 MAPK pathway
Chem Biol Interact 2016 Jul 25;254:167-72.PMID:27287415DOI:10.1016/j.cbi.2016.06.010.
Melanogenesis refers to synthesis of the skin pigment melanin, which plays a critical role in the protection of skin against ultraviolet irradiation and oxidative stressors. We investigated the effects of Afzelin on melanogenesis and its mechanisms of action in human epidermal melanocytes. In this study, we found that Afzelin increased both melanin content and tyrosinase activity in a concentration-dependent manner. While the mRNA levels of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein (TRP)-1 increased following Afzelin treatment, the mRNA levels of TRP-2 were not affected by Afzelin. Likewise, Afzelin increased the protein levels of MITF, TRP-1, and tyrosinase but not TRP-2. Mechanistically, we found that Afzelin regulated melanogenesis by upregulating MITF through phosphorylation of p38 mitogen-activated protein kinase (MAPK), independent of cyclic adenosine monophosphate (cAMP)-protein kinase A (PKA) signaling. Taken together, these findings indicate that the promotion of melanogenesis by Afzelin occurs through increased MITF gene expression, which is mediated by activation of p38 MAPK, and suggest that Afzelin may be useful as a protective agent against ultraviolet irradiation.
Afzelin ameliorates D-galactosamine and lipopolysaccharide-induced fulminant hepatic failure by modulating mitochondrial quality control and dynamics
Br J Pharmacol 2017 Jan;174(2):195-209.PMID:27861739DOI:10.1111/bph.13669.
Background and purpose: Fulminant hepatic failure (FHF) is a fatal clinical syndrome that results in excessive inflammation and hepatocyte death. Mitochondrial dysfunction is considered to be a possible mechanism of FHF. Afzelin, a flavonol glycoside found in Houttuynia cordata Thunberg, has anti-inflammatory and antioxidant properties. The present study elucidated the cytoprotective mechanisms of Afzelin against D-galactosamine (GalN)/LPS induced FHF, particularly focusing on mitochondrial quality control and dynamics. Experimental approach: Mice were administered Afzelin i.p. 1 h before receiving GalN (800 mg·kg-1 )/LPS (40 μg·kg-1 ), and they were then killed 5 h after GalN/LPS treatment. Key results: Afzelin improved the survival rate and reduced the serum levels of alanine aminotransferase and pro-inflammatory cytokines in GalN/LPS-treated mice. Afzelin attenuated the mitochondrial damage, as indicated by diminished mitochondrial swelling and mitochondrial glutamate dehydrogenase activity in GalN/LPS-treated mice. Afzelin enhanced mitochondrial biogenesis, as indicated by increased levels of PPAR-γ coactivator 1α, nuclear respiratory factor 1 and mitochondrial transcription factor A. Afzelin also decreased the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Furthermore, while GalN/LPS significantly increased the level of fission-related protein, dynamin-related protein 1, and decreased the level of fusion-related protein, mitofusin 2; these effects were attenuated by Afzelin. Conclusions and implications: Our findings demonstrated that Afzelin protects against GalN/LPS-induced liver injury by enhancing mitochondrial biogenesis, suppressing excessive mitophagy and balancing mitochondrial dynamics.
Evaluating the Sun Protection Factor of Cosmetic Formulations Containing Afzelin
Chem Pharm Bull (Tokyo) 2021 Nov 1;69(11):1039-1044.PMID:34456215DOI:10.1248/cpb.c21-00398.
Exposure to UV radiation damages the skin and increases the risk of skin cancer. Sunscreen is used to protect the skin from the harmful effects of UV radiation. However, the chemical UV filters used in sunscreen can show toxicity and cause allergic reactions. A safe sunscreen that includes a lower content of chemical UV filters and exerts an excellent effect on UV protection needs to be developed. The objective of this study was to investigate whether the addition of Afzelin to sunscreen could improve the sun protection factor (SPF). A synergistic effect between Afzelin and organic sunscreen agents including padimate O and oxybenzone was confirmed. Interestingly, 100% in vitro SPF-boosting was observed when Afzelin (0.05%) was applied with a standard SPF formulation containing organic sunscreens while Afzelin alone had no contribution to the SPF. In vivo SPF analysis of the standard SPF formulation showed an SPF value of 13.3 that increased to 20.1 when supplemented with Afzelin (0.05%). Additionally, Afzelin showed no skin irritation in a human trial. These results suggest that Afzelin is useful as a natural additive in sunscreen formulations and provides an SPF-boosting effect. Afzelin supplementation to the formulation showed the potential to reduce the use of synthetic photoprotectors, which could minimize the risk of synthetic agent toxicity.