Introduction：Basic information about Afzelin CAS 482-39-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Afzelin Basic information
| Product Name: | Afzelin |
| Synonyms: | AFZELIN;KAEMPFEROL 3-O-GLUCORHAMNOSIDE;KAEMPFEROL 3-O-RHAMNOSIDE;2-(4-Hydroxyphenyl)-4-oxo-5,7-dihydroxy-4H-1-benzopyran-3-yl α-L-rhamnopyranoside;3-(α-L-Rhamnopyranosyloxy)-5,7,4'-trihydroxyflavone;3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Kaempferol 3-rhamnoside;KaeMpferin |
| CAS: | 482-39-3 |
| MF: | C21H20O10 |
| MW: | 432.38 |
| EINECS: | |
| Product Categories: | |
| Mol File: | 482-39-3.mol |
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Afzelin Chemical Properties
| Melting point | 172-174 °C (decomp)(Solv: water (7732-18-5)) |
| Boiling point | 765.6±60.0 °C(Predicted) |
| density | 1.70±0.1 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Store in freezer, under -20°C |
| solubility | Soluble in methan |
| form | powder |
| pka | 6.20±0.40(Predicted) |
| color | Yellow |
| Major Application | metabolomics
vitamins, nutraceuticals, and natural products |
| Cosmetics Ingredients Functions | SKIN CONDITIONING - EMOLLIENT
SKIN PROTECTING
ANTIOXIDANT |
| InChIKey | SOSLMHZOJATCCP-AEIZVZFYSA-N |
| SMILES | OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)=C(C3=CC=C(O)C=C3)O4)=O)C4=C1 |
Safety Information
| WGK Germany | WGK 3 |
| Storage Class | 11 - Combustible Solids |
Afzelin Usage And Synthesis
| Description | Afzelin (Synonyms: Kaempferol-3-O-rhamnoside) is a flavonoid isolated from Thesium chinense Turcz. and widely distributed in Korea and China. It has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis Induced cardiotoxicity and scopolamine -induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin. |
| Uses | Kaempferol 3-O-α-L-Rhamnoside is found in Cornus macrophylla and has shown to have antibacterial activity against Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals. |
| Definition | ChEBI: Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). |
| in vivo | Afzelin (5, 10 mg/kg/day; po; 20 days) attenuates DOX toxicity-induced cardiac injury in a concentration-dependent manner. Afzelin exerts cardioprotective effects by upregulating p-AMP-activated protein kinase α (AMPKα) and Sirtuin1 (SIRT1) levels[2].
Afzelin (0.1-10 mg/kg/day; po; for 5 days) reduces the asthma phenotype by downregulating the GATA-binding protein 3 transcription factor (GATA3) in mouse models of asthma. Afzelin inhibits GATA3 and reduces Th2 cytokines, while GATA3 is the main regulator of Th2 cytokine differentiation and production[3].
Afzelin (100 ng/μL vis icv; 3 times a week for 1 month) ameliorates synaptic plasticity and cognitive/memory behaviors in mice given Scopolamine (HY-N0296)[4].
| Animal Model: | C57BL/6 Mouse[2] | | Dosage: | 5 mg/kg/day, 10 mg/kg/day | | Administration: | Oral gavage for 20 days, while C57BL/6 mouse were treated with 4 mg/kg/d (ip, injected at day 1, 7, 14) DXO for 3 doses. | | Result: | Attenuated DOX-induced cardiac damage and reduced serum levels of alanine aminotransferase and pro-inflammatory cytokines.
Also upregulated the expression of p-AMP-activated protein kinase α (AMPKα) and Sirtuin1 (SIRT1).| Animal Model: | Asthma murine model sensitized by ovalbumin (OVA)[3] | | Dosage: | 0.1, 1 and 10 mg/kg | | Administration: | PO; once daily from day 19 to day 23 | | Result: | Suppressed eosinophil infiltration, allergic airway inflammation, airway hyperresponsiveness, OVA-specific IgE and Th2 cytokine secretion.| Animal Model: | Scopolamine induced mouse model[4] | | Dosage: | 100 ng/μL | | Administration: | ICV, administered into the third ventricle of the hypothalamus; 3 time per week for 1 month | | Result: | Resulted the restoration of the cholinergic systems and molecular signal transduction via CREB-BDNF pathways.
Led to improved neurocognitive and neuroprotective effects on synaptic plasticity and behaviors partly through the increase in CREB-BDNF signaling.
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| | References | [1] SO-YOUNG OH. Central administration of afzelin extracted from Ribes fasciculatum improves cognitive and memory function in a mouse model of dementia.[J]. Scientific Reports, 2021: 9182. DOI:10.1038/s41598-021-88463-6.
[2] LEI XIA. Afzelin induces immunogenic cell death against lung cancer by targeting NQO2.[J]. BMC Complementary Medicine and Therapies, 2023, 23 1: 381. DOI:10.1186/s12906-023-04221-3.
[3] EVA RACHMI. Identification of afzelin potential targets in inhibiting triple-negative breast cancer cell migration using reverse docking.[J]. Porto biomedical journal, 2020, 5 6: e095. DOI:10.1097/j.pbj.0000000000000095.
[4] SIMPLICE JOEL NDENDOUNG TATSIMO. Antimicrobial and antioxidant activity of kaempferol rhamnoside derivatives from Bryophyllum pinnatum.[J]. BMC Research Notes, 2012, 5: 158. DOI:10.1186/1756-0500-5-158.
[5] YOUNG-KYOON KIM. Isolation of flavonol rhamnosides fromloranthus tanakae and cytotoxic effect of them on human tumor cell lines[J]. Archives of Pharmacal Research, 2004, 27 1: 44-47. DOI:10.1007/BF02980044.
[6] VINIT RAJ. Antiviral activities of 4H-chromen-4-one scaffold-containing flavonoids against SARS–CoV–2 using computational and in vitro approaches[J]. Journal of Molecular Liquids, 2022, 353: Article 118775. DOI:10.1016/j.molliq.2022.118775.
[7] BORBáLA VERMES . The synthesis of afzelin, paeonoside and kaempferol 3-O-β-rutinoside[J]. Phytochemistry, 1976, 15 8: Pages 1320-1321. DOI:10.1016/0031-9422(76)85106-0. |
Afzelin Preparation Products And Raw materials |
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