2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one
Isoorientin
CAS: 4261-42-1
Molecular Formula: C21H20O11
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one - Names and Identifiers
| Name | Isoorientin |
| Synonyms | Isoorientin HOMOORIENTIN IsoorientinI Homoorientin lespecapittoside HoMoorientin, froM PolygonuM orientale 2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one 6-(β-D-Glucopyranosyl)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one (1S)-1,5-anhydro-1-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-D-glucitol 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]chromone |
| CAS | 4261-42-1 |
| InChI | InChI=1/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1 |
| InChIKey | ODBRNZZJSYPIDI-VJXVFPJBSA-N |
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one - Physico-chemical Properties
| Molecular Formula | C21H20O11 |
| Molar Mass | 448.38 |
| Density | 1.759±0.06 g/cm3(Predicted) |
| Melting Point | 245-246°C |
| Boling Point | 856.7±65.0 °C(Predicted) |
| Specific Rotation(α) | +18°（4.8mg/mL，methanol） |
| Flash Point | 303.2°C |
| Solubility | DMSO : ≥ 100 mg/mL (223.03 mM) |
| Vapor Presure | 2.9E-31mmHg at 25°C |
| Appearance | Yellow powder |
| Color | yellow |
| pKa | 5.90±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.767 |
| MDL | MFCD00017433 |
| Physical and Chemical Properties | Yellow powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from bamboo leaves, Prunella vulgaris, Dianthus. |
| In vitro study | Isoorientin is a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa. PANC-1 and PATU-8988 cells are grown for 24 hours in the presence of Isoorientin (0, 20, 40, 80, and 160 μM), and a CCK8 solution is added. The cell viability decreases significantly at the concentrations of 20, 40, 80, and 160 μM. After the cells are cultured with Isoorientin (0, 20, 40, 80, and 160 μM for PANC-1; 0, 20, 40, 80, 160, and 320 μM for PATU-8988) for 24 hours, the expression of p-AMPK and AMPK is assessed by Western blotting. After the Isoorientin treatment, the p-AMPK expression is increased. Then, in the shRNA group, the concentration of 80 μM is used to detect the effects of Isoorientin. The expression levels of AMPK and p-AMPK are much lower in the shRNA group than in the wild-type PC cells (WT) and the group that is transfected with a negative control lentivirus (NC). |
| In vivo study | Animals treated with Isoorientin at 10 mg/kg and 20 mg/kg body weight have a statistically significant reduction in paw edema, with a mean peak thickness of 1.19±0.05 mm and 1.08±0.04 mm, respectively. This indicated that Isoorientin significantly attenuates paw edema compared with the control group. |
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29389090 |
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one - Reference
| Reference Show more | 1. Yanan He Zijun Liu Gang. Optimization of extraction process of isoorientin from Humulus scandens by response surface methodology [J]. Northern horticulture 2020 000(007):124-131. 2. Yang Yanmei. Determination of seven index components in seven species of Gentiana macrophylla by UPLC [J]. Chinese herbal medicine 2016 Vol.47Issue(11): -1973. 3. Lu Youyuan, Zhang wavelet, Yang Yanmei, etc. Study on quality regionalization of Gentiana macrophylla [J]. Chinese Journal of Traditional Chinese Medicine, 2016, 41(017):3132-3138. 4. Zhang Yong, Feng Yuting, Ma Ninghui, etc. Comprehensive Evaluation of extraction technology of bamboo leaves [J]. Chinese Journal of Experimental prescriptions, 2018, 3 (17). 5. Yang Yanmei, Ma Xiaohui, LV Peilin, etc. A comparative study of 7 index components between wild and cultivated Gentiana straminea [J]. China Pharmacy, 2016, 27(19):2618-2621. 6. Luo Linyun, Yang Yanmei, Jin Ling. A comparative study on the contents of seven index components of Gentiana macrophylla from Qinghai province and Gansu province [J]. Chinese Journal of Hospital Pharmacy, 2017, 37(008):717-721. 7. Yang Yanmei, Huang Dedong, Lu, you Yuan, etc. Study on UPLC fingerprint of Gentiana xanthoides [J]. Chinese herbal medicines, 2016, 39(008):1734-1737. 8. Guo Jing, Wang Haoran, Shen Zhouyuan, Zhang Tong, Yuan Xiurong, Ding Yue. Analysis of antioxidant components in three kinds of bamboo leaves [J]. Chinese patent medicine 2019 41(11):2688-2694. 9. Wang Wei, He Ping, Jiang Xiaoming. Anti-inflammatory and antioxidant effects of luteolin and its flavonoid glycosides [J]. Food Science, 2020,41(17):208-215. 10. Zhang, G. , et al. "Antinoiceptive effect of isoorientin against neuropathic pain induced by the chronic constraint injury of the scientific nerve in mice." International Immunology 75(2019):105753-.DOI: 10.1016/j. Intimp.2019, 105753 11. Wang, Chu-Yang, et al. "Isolation of wheat mutants with higher grain phenolics to enhance anti-oxidant potential." Food chemistry 303 (2020): 125363.https://doi.org/10.1016/j.foodchem.2019.125363 12. [IF=5.279] Yong Sun et al."Qualitative and Quantitative Analysis of Phenolics in Tetrastigma hemsleyanum and Their Antioxidant and Antiproliferative Activities."J Agr Food Chem. 2013;61(44):10507-10515 13. [IF=7.514] Chu-Yang Wang et al."Isolation of wheat mutants with higher grain phenolics to enhance anti-oxidant potential."Food Chem. 2020 Jan;303:125363 14. [IF=5.396] Mingfang Tao et al."Flavonoids from the mung bean coat promote longevity and fitness in Caenorhabditis elegans."Food Funct. 2021 Aug;12(17):8196-8207 15. [IF=2.19] Sheng-xiang Yang et al."Extraction of flavonoids from Cyclocarya paliurus (Juglandaceae) leaves using ethanol/salt aqueous two-phase system coupled with ultrasonic."J Food Process Pres. 2020 Jun;44(6):e14469 16. [IF=2.863] Xiaokang Liu et al."Spectrum-effect relationship between ultra-high-performance liquid chromatography fingerprints and antioxidant activities of Lophatherum gracile Brongn."Food Science & Nutrition. 2022 Feb 22 17. [IF=3.373] Yiyuan Luo et al."Quality evaluation of Tetrastigma hemsleyanum different parts based on quantitative analysis of 42 bioactive constituents combined with multivariate statistical analysis."PHYTOCHEMICAL ANALYSIS. 2022 Apr 05 18. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 19. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 |
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one - Reference Information
| biological activity | Isoorientin is an effective COX-2 inhibitor with an IC50 value of 39 μM. |
| target | COX-2 39 μM (IC 50 ) |
| in vitro study | Isoorientin is a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa. PANC-1 and PATU-8988 cells are grow for 24 hours in the presence of Isoorientin (0, 20, 40, 80, and 160 μ m), and a CCK8 solution is added. the cell viability decreases significantly at the concentrations of 20, 40, 80, and 160 μ m. after the cells are cultured with Isoorientin (0, 20, 40, 80, and 160 μ m for PANC-1; 0, 20, 40, 80, 160, and 320 μ m for PATU-8988) for 24 hours, the expression of p-AMPK and AMPK is assessed by Western blotting. after the Isoorientin treatment, the p-AMPK expression is increased. Then, in the shRNA group, the concentration of 80 μ m is used to detect the effects of Isoorientin. the expression levels of AMPK and p-AMPK are much lower in the shRNA group than in the wild-type PC cells (WT) and the group that is transfected with a negative control lentivirus (NC). |
| in vivo study | Animals treated with Isoorientin at 10 mg/kg and 20 mg/kg body weight have a statistically significant reduction in paw edema, with a mean peak thickness of 1.19±0.05 mm and 1.08±0.04 mm, respectively. This indicated that Isoorientin significantly attenuates paw edema compared with the control group. |
| chemical properties | yellow powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from bamboo leaves, Prunella vulgaris, and Dianthus. |
| use | isoorientin has anti-myocardial ischemia effect. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: hepatoprotective effect, antiviral activity, anti-peroxidation effect, anxiety relief effect. |
Last Update：2024-04-10 22:29:15
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