| Identification | Back Directory | [Name]
KAEMPFEROL 3-O-GLUCORHAMNOSIDE | [CAS]
482-39-3 | [Synonyms]
AFZELIN
KaeMpferin
Afzeloside
Kaempferol 3-rhamnoside
KAEMPFEROL 3-O-RHAMNOSIDE
Kaempferol 3-O-α-L-Rhamnoside
KAEMPFEROL 3-O-GLUCORHAMNOSIDE
KAEMPFERIN; KAEMPFEROL-3-RHAMNOSIDE
Afzelin/Kaempferol 3-o-glucorhamnoside
3-(α-L-Rhamnopyranosyloxy)-5,7,4'-trihydroxyflavone
2-(4-Hydroxyphenyl)-4-oxo-5,7-dihydroxy-4H-1-benzopyran-3-yl α-L-rhamnopyranoside
3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-Mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)- | [Molecular Formula]
C21H20O10 | [MDL Number]
MFCD00210589 | [MOL File]
482-39-3.mol | [Molecular Weight]
432.38 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
Afzelin (Synonyms: Kaempferol-3-O-rhamnoside) is a flavonol glycoside that 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: A glycosyloxyflavone that is kaempferol attached to a alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. | [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.
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| 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. |
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