(2E)-3-[4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]phenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one
Isoliquiritin apioside
CAS: 120926-46-7
Molecular Formula: C26H30O13
(2E)-3-[4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]phenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one - Names and Identifiers
(2E)-3-[4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]phenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one - Physico-chemical Properties
| Molecular Formula | C26H30O13 |
| Molar Mass | 550.51 |
| Density | 1.63 |
| Boling Point | 901°C at 760mmHg |
| Specific Rotation(α) | (c, 0.6 in EtOH)-92.9 |
| Solubility | Soluble in DMSO, soluble in methanol |
| Appearance | Pale yellow or yellow powder |
| Storage Condition | 2-8℃ |
| MDL | MFCD20487832 |
| Physical and Chemical Properties | White powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from licorice. |
(2E)-3-[4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]phenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one - Reference
| Reference Show more | 1. Zhou Yuemei, Feng Chao, Shi Yuhua, et al. Study on HPLC fingerprint of licorice extract and determination of multi-index components [J]. China Modern Applied Pharmacy, 2020, v.37(09):26-31. 2. Cai Shuhui, Zhao huachong, Jia Meng, Zhao Xiaoli, Chi Yumei, Zhang Wen, Wang Honglan, Di Liuqing. Quality Evaluation of roasted licorice based on HPLC fingerprint and multi-component quantitative analysis [J]. Chinese Journal of Traditional Chinese Medicine, 2021,46(01):118-124. 3. Yang, Ruocong, et al. "Chemical composition and pharmacologic mechanism of Qingfei Paidu division and Ma Xing Shi Gan division against Coronavirus Disease 2019 (COVID-19): in silico and experimental study." Pharmacologic research 157 (2020): 104820.h 4. Luo, Hui-Long, et al. "A systematic quality control method of Huangqi decoction: simultaneous determination of eleven flavonoids and seven triterpenoid saponins by UHPLC-MS." Analytical Methods 6.13 (2014): 4593-4601. 5. Yang, Zhenzhong, et al. "Deciphering bioactive compounds of complex natural products by tandem mass spectral molecular networking combined with an aggregation-induced emission based probe ." Journal of Pharmaceutical Analysis (2020).https://doi.org/10.1016/ 6. [IF=5.455] Fei Fuhuan et al."Rapid screening and identification of bioactive compounds specifically binding to beta 2-adrenoceptor from San-ao decoction using affinity magnetic fine particles coupled with high-performance liquid chromatography-mass spectrometry."Ch 7. [IF=2.896] Hui-Long Luo et al."A systematic quality control method of Huangqi decoction: simultaneous determination of eleven flavonoids and seven triterpenoid saponins by UHPLC-MS."Anal Methods-Uk. 2014 Jun;6(13):4593-4601 8. [IF=5.893] Ruocong Yang et al."Chemical composition and pharmacological mechanism of Qingfei Paidu Decoction and Ma Xing Shi Gan Decoction against Coronavirus Disease 2019 (COVID-19): In silico and experimental study."Pharmacol Res. 2020 Jul;157:104820 9. [IF=5.81] Cui Lihua et al."Chaihu Guizhi Ganjiang Decoction Ameliorates Pancreatic Fibrosis via JNK/mTOR Signaling Pathway."Front Pharmacol. 2021 Jun;0:1369 10. [IF=4.769] Zhenzhong Yang et al."Deciphering bioactive compounds of complex natural products by tandem mass spectral molecular networking combined with an aggregation-induced emission based probe."J Pharm Anal. 2020 Nov;: 11. [IF=3] Lu-Lin CHEN et al."Identification of constituents in Gui-Zhi-Jia-Ge-Gen-Tang by LC-IT-MS combined with LC-Q-TOF-MS and elucidation of their metabolic networks in rat plasma after oral administration."Chin J Nat Medicines. 2019 Nov;17:803 12. [IF=2.629] Li Tingting et al."Quality Assessment of Licorice Based on Quantitative Analysis of Multicomponents by Single Marker Combined with HPLC Fingerprint."Evid-Based Compl Alt. 2021;2021:8834826 13. [IF=1.885] Xia Wenxin et al."Study on the Spectrum-Effect Relationship of the Traditional Effect of Saponins in Glycyrrhiza uralensis Fisch."Int J Anal Chem. 2021;2021:6617033 14. [IF=3.645] Shuaishuai Fan et al."Comprehensive characterization and identification of chemical constituents in Yangwei decoction using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry."Jo |
(2E)-3-[4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]phenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one - Reference Information
| Plant Source: | licorice |
| Introduction | licorice is the leguminous plant Glycyrrhiza uralensifisch. Glycyrrhiza inflata or Glycyrrhiza glabra the dried roots and rhizomes. In Chinese Pharmacopoeia 2010 edition (1), sweet, flat; Return to heart, lung, spleen, stomach. With Spleen qi, detoxification, Expectorant Cough, relief of pain, to reconcile the efficacy of various drugs. Mainly produced in Inner Mongolia, Gansu, Xinjiang, Shaanxi, northeast, Shanxi and other regions. The main active ingredients were saponins and flavonoids. The main representative components of the flavonoids in the genus liquiritin are liquiritin, liquiritin, liquiritin, isoliquiroside, liquiritin, and isoliquiritigenin, liquiritin, liquiritin and other representative of the licorice flavonoids, with anti-myocardial ischemia and inhibit the proliferation of AIDS Virus. |
| effect | Anti-myocardial ischemia and inhibition of proliferation of AIDS Virus |
| detection | pharmacological research reports based on related components of licorice, the quality of licorice can not be fully reflected by the content index of liquiritin and glycyrrhizic acid, because other flavonoids in licorice also have obvious effect. The contents of liquiritin, liquiritin, isoliquiroside, isoliquiroside and glycyrrhizic acid in Glycyrrhiza were determined by high performance liquid chromatography (HPLC), which reflected the material basis of licorice efficacy. The mobile phase and detection wavelength were investigated, and the methanol-water, acetonitrile-water and acetonitrile -1%~ 3% acetic acid water systems were compared, the separation effect of acetonitrile-water was better than that of methanol-water system, and the separation effect was further improved after adding acetic acid. Finally, acetonitrile -3% acetic acid water system was selected as the mobile phase. The DAD detector is used to scan the sample at full wavelength, and the detection results of each wavelength are compared. It is found that the components generally have large absorption at the selected wavelength in this experiment. Finally, 254nm is selected to detect the sample. |
| preparation | Take 5.0 of dried licorice, the extract was refluxed twice with 8 times and 6 times the amount of 95% ethanol aqueous solution for 1H each time. The extracts were combined twice, concentrated to a certain concentration under reduced pressure, and then placed on a column equipped with D101 macroporous resin, eluted with water and 40%, 95% ethanol, respectively, and 40% ethanol eluate was collected, after concentration under reduced pressure to the appropriate concentration, semi-preparative liquid chromatography, acetonitrile-water (10: 90 → 100: 0) gradient elution to give compound 1(3.9mg), 2(4.6mg), 3(3.3mg) and 4(3.0mg). The 95% ethanol eluent was collected and further separated by ODS medium pressure column chromatography using 55% methanol and pure methanol solvent. The pure methanol eluate was collected and concentrated under reduced pressure and lyophilized to give a dry powder (28g). 0.43g of the dry powder was dissolved in methanol and separated by semi-preparative liquid chromatography. Acetonitrile-water gave apigenin (2.7mg). |
| Use | Anti-myocardial ischemia, inhibition of AIDS Virus proliferation. |
Last Update：2024-04-09 21:11:58
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