4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy-
eupatilin
CAS: 22368-21-4
Molecular Formula: C18H16O7
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Names and Identifiers
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Physico-chemical Properties
| Molecular Formula | C18H16O7 |
| Molar Mass | 344.32 |
| Melting Point | 236-238 °C |
| Boling Point | 583.6±50.0 °C(Predicted) |
| Solubility | Soluble in DMSO, hot methanol, chloroform methanol mixed solvent, insoluble in petroleum ether and other solvents. |
| Appearance | Yellow needle crystal |
| Storage Condition | 2-8℃ |
| MDL | MFCD13194819 |
| Physical and Chemical Properties | The chemical properties are soluble in DMSO, hot methanol, chloroform methanol mixed solvent, and insoluble in petroleum ether and other solvents. Derived from the dried leaves of Artemisia argyi Levl. et Vant. |
| Use | Uses for content determination/identification/pharmacological experiments. Pharmacological Efficacy: heat pain, warm by hemostasis, the treatment of gastric ulcer and the role of antispasmodic, can regulate blood sugar |
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Reference
| Reference Show more | 1. Cao Li, Lu, Jin, Qing, Ye, Xin, et al. Simultaneous determination of kaempferol-cyanidin-isoadenophorin in different brands of moxa and moxa stick by HPLC [J]. Chinese pharmacist 2018 v.21(08):73-75 80. 2. Gong Min, Lu, Jin, Qing, Xiao, Yushu. Determination of total flavonoids and three main aglycones in Artemisia argyi from different habitats [J]. China pharmacist 2019 22(05):174-176 183. 3. Wang Xinger, Zhao Lu, Ye Junwei, et al. Study on the effect of moxa powder extract and its compound preservative on cherry tomato and grape. 4. Hu Qian, Li Jing, Liu Jia, Cao Yan. Antioxidant activity of total flavonoids from Artemisia argyi in vitro and in vivo [J]. Science and Technology of food industry, 2021,42(06):304-309. 5. [IF = 2.967] Wei-Feng Zhong et al."Eupatilin indents human renal cancer cell apoptopsis via ROS-mediated MAPK and PI3K/signaling AKT pathways." Oncol Lett. 2016 Oct;12(4):2894-2899 6. [IF = 4.411] Min Li et al."Study of the Variation of Phenolic Acid and Flavonoid Content from Fresh Artemisiae argyi Folium to Moxa Wool."Molecules. 2019 Jan;24(24):4603 7. [IF=4.36] Qian Hu et al."Antioxidant capacity of flavonoids from Folium Artemisiae Argyi and the molecular mechanism in Caenorhabditis elegans."J Ethnopharmacol. 2021 Oct;279:114398 8. [IF=2.632] Zhao Wu et al."Eupatilin regulates proliferation and cell cycle of cervical cancer by regulating hedgehog signalling pathway."Cell Biochem Funct. 2020 Jun;38(4):428-435 |
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Introduction
Zelanlin is also called isocyanin. Isocyanin (Eupatilin) is a kind of flavonoid with pharmacological activity. It is extracted from mugwort (Asteraceae) and used for mucosal protection. It has anti-inflammatory properties and is widely used in the treatment of gastritis and peptic ulcer. It has antioxidant effect on gastric mucosal damage and can enhance the regeneration of damaged mucosa. Isoplanflavin was identified as having anti-tumor effects: Isoplanflavin inhibits angiogenesis in gastric cancer cells by blocking the expression of signal transduction molecules and vascular endothelial growth factor (VEGF) and activation of transcription factor 3. Isoplanflavin can be used as a chemoprevention and anti-metastasis agent for human gastric cancer.
Last Update：2024-04-10 22:29:15
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Uses and synthesis methods
| in vitro study |
Eupatilin is a PPARα agonist. Eupatilin (10, 30, 100 μM) suppresses IL-4 expression and degranulation in RBL-2H3 cells. Eupatilin (50-100 μM) slightly reduces cell viability of HaCaT cells. Eupatilin (10, 30, 50, 100 μM) increases PPARα transactivation and expression in HaCaT cells. Eupatilin (10, 30, 50 μM) also suppresses TNFα-induced MMP-2/-9 expression in HaCaT cells. Furthermore, Eupatilin inhibits TNFα-induced p65 translocation, I κBα Phosphorylation, AP-1 and MAPK signaling via PPARα. Eupatilin (10-50 μM) shows no cytotoxic effects on ARPE19 cells. Eupatilin (10, 25, 50 μM) elevates cell viability from oxidative stress, and inhibits H 2 O 2 -induced ROS production in ARPE19 cells. Moreover, Eupatilin (50 μM) inbibits H 2 O 2 -induced cells apoptosis and promotes the activation of PI3K/Akt pathway in RPE cells.
|
| in vivo study |
Eupatilin (1.5% or 3.0%) restores PPARα mRNA expression, and improves atopic dermatitis (AD)-like symptoms in oxazolone-induced Balb/c mice. Eupatilin causes significant decrease in serum IgE, IL-4 levels, oxazolone-induced TNFα, IFNγ, IL-1β, TSLP, IL-33 and IL-25 mRNA expression in oxazolone-induced mice. Eupatilin also increases filaggrin and loricrin mRNA expression in oxazolone-induced mice. |
Last Update：2024-04-10 22:29:15
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Nature
| melting point | 236-238 °C |
| boiling point | 583.6±50.0 °C(Predicted) |
| density | 1.387±0.06 g/cm3(Predicted) |
| storage conditions | Keep in dark place,Sealed in dry,Store in freezer, under -20°C |
| acidity coefficient (pKa) | 6.47±0.40(Predicted) |
Last Update：2024-04-09 21:04:16
4H-1-Benzopyran-4-one, 2-(3,4-diMethoxyphenyl)-5,7-dihydroxy-6-Methoxy- - Uses and synthesis methods
| physical and chemical properties | pure product is yellow needle crystal, density: 1.387g/cm3, boiling point: 583.6 ℃, flash point: 214.7 ℃, melting point: 234-236 ℃, soluble in DMSO, hot methanol, chloroform methanol mixed solvent, insoluble in petroleum ether and other solvents. | |
| pharmacological effects | 1. Zelanlin has the effects of heat dissipation, pain relief, warming and hemostasis. 2. Inhibit tumor growth. 3. Zelanlin can be used to treat gastric ulcer and antispasmodic. 4. Regulate blood sugar content. 5. Minor energy of anti-mutagenic factors. |
|
| biological activity | Eupatilin is a lipophilic flavonoid compound separated from Artemisia plants. It is an agonist of PPARα and has anti-apoptosis, antioxidant and anti-inflammatory effects. | |
| Target |
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Last Update：2024-04-09 20:52:54
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