Isohamnetin
Isorhamnetin
CAS: 480-19-3
Molecular Formula: C16H12O7
Isohamnetin - Names and Identifiers
| Name | Isorhamnetin |
| Synonyms | C.I. 75680 Isohamnetin Isorhamnetin 3-Methylquercetin 3'-METHOXY-3,5,7,4'-TETRAHYDROXYFLAVONE 3'-METHOXY-3,4',5,7-TETRAHYDROXYFLAVONE IsorhaMnetin, froM Hippophae fhaMnoides L. 3,5,7-Trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-one 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)- sorhamnetin 3,5,7-Trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on |
| CAS | 480-19-3 |
| EINECS | 207-545-5 |
| InChI | InChI=1/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3 |
| InChIKey | IZQSVPBOUDKVDZ-UHFFFAOYSA-N |
Isohamnetin - Physico-chemical Properties
| Molecular Formula | C16H12O7 |
| Molar Mass | 316.26 |
| Density | 1.634±0.06 g/cm3(Predicted) |
| Melting Point | 307°C |
| Boling Point | 599.4±50.0 °C(Predicted) |
| Flash Point | 227.8°C |
| Solubility | Slightly soluble in water and methanol, soluble in mixed solvent of methanol and chloroform, soluble in DMSO. |
| Vapor Presure | 5.79E-15mmHg at 25°C |
| Appearance | Pale yellow needle crystal |
| Color | Light yellow to Amber to Dark green |
| BRN | 44723 |
| pKa | 6.31±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.74 |
| MDL | MFCD00017310 |
| In vitro study | Isorhamnetin is a plant flavonoid that occurs in fruits and medicinal herbs. Isorhamnetin binds directly to MEK1 in an ATP-noncompetitive manner and to PI3-K in an ATP-competitive manner. In vitro and ex vivo kinase assay data show that Isorhamnetin inhibits the kinase activity of MAP/ERK kinase (MEK) 1 and PI3-K and the inhibition is due to direct binding with Isorhamnetin. Isorhamnetin inhibits the Akt/mTOR and MEK/ERK signaling pathways, and promotes the activity of the mitochondrial apoptosis signaling pathway. The inhibitory effects of Isorhamnetin on breast cancer cells are determined using the CCK-8 method. Isorhamnetin inhibits the proliferation of numerous breast cancer cells (IC 50 , ~10 µM), including MCF7, T47D, BT474, BT-549, MDA-MB-231 and MDA-MB-468, whereas less inhibitory activity is observed in the MCF10A normal breast epithelial cell line (IC 50 , 38 µM). |
| In vivo study | Photographic data shows that Isorhamnetin treatment suppresses tumor development in mice. The average volume of tumors in untreated mice increases over time and reaches a volume of 623 mm 3 at 4 weeks post-inoculation; however, at this time, in mice treated with 1 or 5 mg/kg Isorhamnetin, the average tumor volume is only 280 or 198 mm 3 , respectively. At the end of the study, Isorhamnetin treatment (1 or 5 mg/kg) reduces tumor weight compared with the untreated control group. |
Isohamnetin - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S22 - Do not breathe dust. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
| RTECS | LK9275450 |
| HS Code | 29329990 |
Isohamnetin - Reference Information
| Plant source: | Seabuckthorn |
| overview | isorhamnetin (Isorhamnetin,Iso) is a flavonoid compound isolated and purified from medicinal plants such as ginkgo biloba and seabuckthorn, and is also widely found in flowers, fruits and leaves of many other plants. It has good anti-tumor, anti-myocardial hypoxia, ischemia, relieve angina pectoris, anti-arrhythmia, treat coronary heart disease and hypertension, scavenge oxygen free radicals, reduce serum cholesterol, protect cardiovascular, promote blood flow, etc. A variety of biological effects are widely used in clinical practice. |
| physical properties | yellow needle crystal (dilute methanol),mp312 ℃ (decomposition). UV λmax (MeOH) nm: 257,370;(MeOH/NaOMe): 272,330,427 (decomposition);(MeOH/ AlCl3): 267,304 (sh),360,428. IRvmax (KBr)cm-1: 3242,2940,1657,1616,1603,1560,1508,1244,1211,1167. EIMS m/z: 316,315,153,151. 1HNMR. (2015-09-06) Figure 1 shows isorhamnetin |
| plant source: | isorhamnetin can be extracted from the following plants: 1. Elaeagnaceae: the plant seabuckthorn Hippophae the fruit of fhamnoides l. 2. Asclepiadaceae (Asclepiadaceae): Taiwan eye tree lotus Dischidia formosana maxim. Whole grass. 3. Bignoniaceae (Bingoniaceae): Huangzhong flower Tecomastans H. B. K. flower. 4. Euonymus (Celastraceae): Wild. leaves, the Maytenus emarginata of Meadeng wood. 5. Compositae (Compositae): Arnica longifolia D.C.Eaton flower; Artemisia annua L Artemisia leaves, stems: Artemisia annua Artemisia capillaris Thunb. 6. Cucurbitaceae (Cucurbitaceae): Gynostemma yixingense C. Y. Wu et S. K. Chen's overground part. 7. Leguminosae (Leguminosae): Sophora japonica Sophora?japonica L. flower buds; Red clover Trifolium pratense L. petals. 8. Sapindus family (Sapindaceae): Chesangzi Dodonaea viscosa (L.) Jacq. Flowers. 9. Tamarix family (Tamaricaceae): Lour, Tamarix chinensis of Xihe Willow. Branches. 10. Taxus family (Taxaceae): Taxus brevifolia Taxus brevifolia Nutt. Leaves. 11. linden tree family (Tiliaceae): scum leaf Microcos paniculata L.12. cattail family (Typhaceae): long bract cattail typha angustata Bory et Chaub.; Typha angustifolia L.13. Umbelliferae (Umbelliferae): Wall. ex DC. var. giraldii Wolff, Bupleurum longicaule of Bupleurum in Qinling Mountains; Oenanthe javanica of cress. 14. Tribulus terrestris family (Zygophyllaceae): Nitraria tangutorum Bolor seeds. |
| pharmacological activity | 1. crown expansion. Increase coronary blood flow. 2. Inhibit platelet aggregation. 3. Anti-hemostatic effect. Inhibit the effect of certain hemostatic components. 4. Anti-liver toxicity components. It has an inhibitory effect on CCl4 and GalN-induced hepatocyte poisoning in rats. 5.V9Z: Regulate the reproductive ability of male plants. 6. Reduce cholesterol concentration in rat serum and liver. 7. Anti-lipid peroxidation. Reduce the amount of thiobarbituric acid reactive substance TBARS in rat liver. 8. Anti-tumor effect, isorhamnetin mainly inhibits tumor cell proliferation, induces cell apoptosis, inhibits signal transduction, etc., Isorhamnetin has a significant anti-breast cancer effect, and its mechanism of action is related to inhibiting cell proliferation pathway and promoting cell apoptosis. |
| extraction and synthesis method | extraction method of isorhamnetin in seabuckthorn pomace The principle of ultrasonic extraction of isorhamnetin is that ultrasound produces cavitation between the solvent and the sample, resulting in the formation, growth, blasting and compression of bubbles in the solution, which is helpful for solute diffusion and improves the mass transfer rate of the target from the solid phase to the liquid phase. Ultrasonic method can greatly shorten the extraction time, improve the rate of effective ingredients and the utilization rate of raw materials. The best process for accurately weighing about 1.0g of seabuckthorn pomace → adding extract → ultrasonic extraction → filtration → filtrate constant volume → isorhamnetin seabuckthorn pomace is as follows: under the condition of 50 ℃, ultrasonic frequency 40 kHz, ultrasonic extraction twice with the extract with V ethyl acetate: V 95% ethanol 4:6, 1 h each time, and the solid-liquid ratio is 1:25. The content of isorhamnetin extracted by this method can reach 5.09 mg · g-1. Chemical synthesis method: quercetin (Ⅰ) is used as the starting material to obtain quercetin pentaacetate (Ⅱ) and 4 ',7-di-O-benzyl quercetin (Ⅲ),4',7-di-O-benzyl quercetin triacetate (Ⅳ) and 4 ',7-di-O-benzyl -3'-methyl quercetin (Ⅴ) intermediates, respectively. Compound (Ⅴ) is subjected to benzylation reaction to obtain isorhamnetin (Ⅵ). |
| biological activity | Isorhamnetin is a flavonoid compound extracted from the Chinese herbal medicine Hippophae rhamnoides (Hippophae rhamnoides L.). Isorhamnetin can inhibit skin cancer by directly inhibiting MEK1 and PI3K. |
Last Update：2024-04-09 20:52:54
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