Isoliquiritin apioside
(Synonyms: 芹糖异甘草苷) 目录号 : GC39095
Isoliquiritin apioside (ISLA, ILA), a component isolated from Glycyrrhizae radix rhizome (GR), significantly decreases PMA-induced increases in matrix metalloproteinase (MMP) activities and suppresses PMA-induced activation of mitogen-activated protein kinase (MAPK) and NF-κB. Isoliquiritin apioside possesses anti-metastatic and anti-angiogenic abilities in malignant cancer cells and ECs, with no cytotoxicity.
Cas No.:120926-46-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isoliquiritin apioside (ISLA, ILA), a component isolated from Glycyrrhizae radix rhizome (GR), significantly decreases PMA-induced increases in matrix metalloproteinase (MMP) activities and suppresses PMA-induced activation of mitogen-activated protein kinase (MAPK) and NF-κB. Isoliquiritin apioside possesses anti-metastatic and anti-angiogenic abilities in malignant cancer cells and ECs, with no cytotoxicity.
[1] Aeyung Kim, Jin Yeul Ma. Front Pharmacol. 2018 Dec 10;9:1455.
| Cas No. | 120926-46-7 | SDF | |
| 别名 | 芹糖异甘草苷 | ||
| Canonical SMILES | O=C(C1=C(C=C(O)C=C1)O)/C=C/C(C=C2)=CC=C2O[C@H](O[C@H](CO)[C@@H](O)[C@@H]3O)[C@]3([H])O[C@H]4[C@@H]([C@](CO)(O)CO4)O | ||
| 分子式 | C26H30O13 | 分子量 | 550.51 |
| 溶解度 | Soluble in DMSO | 储存条件 | -20°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.8165 mL | 9.0825 mL | 18.165 mL |
| 5 mM | 0.3633 mL | 1.8165 mL | 3.633 mL |
| 10 mM | 0.1816 mL | 0.9082 mL | 1.8165 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Isoliquiritin apioside relieves intestinal ischemia/reperfusion-induced acute lung injury by blocking Hif-1α-mediated ferroptosis
Int Immunopharmacol 2022 Jul;108:108852.PMID:35597117DOI:10.1016/j.intimp.2022.108852.
Isoliquiritin apioside (IA), a critical ingredient of Glycyrrhizae radix et rhizoma, has been unveiled to possess remarkable pharmacological activity against oxidative stress and inflammation. However, the potential roles of IA in intestinal ischemia/reperfusion (I/R)-induced acute lung injury (ALI) have not been reported yet. In the present study, we explored the effects of IA on I/R-induced ALI, and also clarified the possible mechanisms. To mimic intestinal I/R-induced ALI, the mice were subjected to 60 min of intestinal ischemia via clamping of the superior mesenteric artery followed by 60 min of reperfusion. IA was administered orally (20 mg/kg/day and 50 mg/kg/day) for 7 consecutive days before intestinal I/R. Lung epithelial MLE-2 cells were subjected to hypoxia for 2 h and regeneration for 3 h to mimic in vitro ALI. The results showed that IA administration prevented intestinal I/R-induced lung injury, inflammation and edema. Also, IA administration decreased the level of ferroptosis in murine lung tissues challenged with intestinal I/R. In terms of mechanism, IA administration inhibited the protein upregulation of Hif-1α and HO-1 in mice with ALI. In vitro experiments further demonstrated that IA treatment could inhibit the mRNA and protein levels of Hif-1α in hypoxia/regeneration (H/R)-induced MLE-2 cells in a concentration-dependent manner. Hif-1α stabilizer molidustat itself also significantly promoted ferroptosis of MLE-2 cells. And Hif-1α activation increased the mRNA levels of Ptgs2 and Acsl4 but decreased the mRNA level of Gpx4 in H/R-induced MLE-2 cells treated with IA. Taken together, our study unveiled IA could protect against intestinal I/R-induced ALI by decreasing lung epithelial ferroptosis in a Hif-1α-dependent manner.
Isoliquiritin apioside Suppresses in vitro Invasiveness and Angiogenesis of Cancer Cells and Endothelial Cells
Front Pharmacol 2018 Dec 10;9:1455.PMID:30618749DOI:10.3389/fphar.2018.01455.
Several components isolated from Glycyrrhizae radix rhizome (GR), including glycyrrhizin, liquiritin, and liquiritigenin, have been shown to induce cancer cell death and inhibit cancer metastasis. Isoliquiritin apioside (ISLA), a component isolated from GR, has been effective for treating tetanic contraction and genotoxicity. However, the effects of ISLA on the metastasis and angiogenesis of malignant cancer cells and endothelial cells (ECs) have not been reported. In this study, we found that up to 100 μM ISLA did not affect cell proliferation but efficiently suppressed the metastatic ability of HT1080 cells, as assessed by scratch-wound migration, Transwell® migration, scratch-wound invasion, Transwell® invasion, and three-dimensional spheroid invasion. ISLA significantly decreased phorbol 12-myristate 13-acetate (PMA)-induced increases in matrix metalloproteinase (MMP) activities and suppressed PMA-induced activation of mitogen-activated protein kinase as well as NF-κB, which are involved in cancer metastasis. In addition, ILSA treatment reduced the production of pro-angiogenic factors in HT1080 cells, including MMP-9, placental growth factor, and vascular endothelial growth factor under normoxia as well as hypoxia conditions, by impairing the hypoxia-inducible factor-1α pathway. We also found that the abilities of human umbilical vein ECs to migrate across the Transwell® and to form tube-like structures were significantly reduced by ISLA treatment. Moreover, using the chorioallantoic membrane assay, vessel formation with or without vascular endothelial growth factor was significantly suppressed by ISLA. These results suggested that ISLA possesses anti-metastatic and anti-angiogenic abilities in malignant cancer cells and ECs, with no cytotoxicity. ISLA may therefore be a safe and effective lead compound to develop anti-cancer drug for limiting the spread of primary tumors to distant organs to form secondary tumors.
HPLC method determination of Isoliquiritin apioside and isoliquiritin in rat plasma for application in pharmacokinetic study after an oral administration of zhigancao extract
J Anal Methods Chem 2012;2012:364013.PMID:23365791DOI:10.1155/2012/364013.
A sensitive HPLC method was developed for the quantitative determination of Isoliquiritin apioside (ILA) and isoliquiritin (IL) in rat plasma. After protein precipitation with acetonitrile, chloroform was used to separate lipid-soluble impurities from the plasma samples and remove acetonitrile. A chromatography was carried out on Diamonsil C18 (150 × 4.6 mm; 5 μm) analytical column, using a mobile phase consisting of water (containing phosphoric acid 0.1%, v/v); acetonitrile (72 : 28, v/v) at a flow rate of 1.0 mL/min. The wavelength-switching technology was performed to determine ILA and IL at 360 nm and wogonoside (internal standard, IS) at 276 nm. The calibration curves of ILA and IL were fairly linear over the concentration ranges of 0.060-3.84 μg/mL (r = 0.9954) and 0.075-4.80 μg/mL (r = 0.9968), respectively. The average extract recoveries of ILA, IL, and IS were all over 80%. The precision and accuracy for all concentrations of quality controls and standards were within 15%. The lower limit of quantification (LLOQ) was 0.060 μg/mL for ILA and 0.075 μg/mL for IL. The method was used in pharmacokinetic study after an oral administration of Zhigancao extract to rats.
Evaluation of antigenotoxic activity of Isoliquiritin apioside from Glycyrrhiza glabra L
Toxicol In Vitro 2009 Jun;23(4):680-6.PMID:19490840DOI:10.1016/j.tiv.2009.01.019.
Prevention of manifestation of events characteristic of carcinogenesis is being emphasized a rational strategy to combat cancer. Reactive oxygen species (ROS) play an important role in tumor initiation through oxidative damage of DNA. In search for lead molecules in cancer chemoprevention from natural products, a fraction 'Rlicca' isolated from Glycyrrhiza glabra was studied for modulatory effect against hydrogen peroxide and 4-nitroquinoline-N-oxide induced genotoxicity in Escherichiacoli PQ37 using SOS chromotest and in human peripheral blood lymphocytes using the Comet assay. The fraction 'Rlicca' at a concentration of 191 microM decreased the SOS inducing potency (SOSIP) of hydrogen peroxide (1.0mM) and NQO (20 microg/ml) by 83.72% and 68.77%, respectively. In the human blood lymphocytes, 'Rlicca' reduced the tail moment induced by hydrogen peroxide (25 microM) and NQO (5 microg/ml) by 88.04% and 76.64%, respectively, using the Comet assay. The spectroscopic data of 'Rlicca' fraction revealed it to be Isoliquiritin apioside, a chalcone oligoglycoside. This is the first report of Isoliquiritin apioside with marked potential to combat oxidative stress-induced genotoxicity.
Saponin and sapogenol. L. On the constituents of the roots of Glycyrrhiza uralensis Fischer from Xinjiang, China. Chemical structures of licorice-saponin L3 and Isoliquiritin apioside
Chem Pharm Bull (Tokyo) 1993 Sep;41(9):1567-72.PMID:8221970DOI:10.1248/cpb.41.1567.
From the air-dried roots of Glycyrrhiza uralensis Fischer collected in Xinjiang province, China ("Shinkyo-Kanzo" in Japanese), a new oleanene-type triterpene oligoglycoside named licorice-saponin L3 and a new chalcone oligoglycoside named Isoliquiritin apioside were isolated together with glycyrrhizin, 18 alpha-glycyrrhizin, apioglycyrrhizin, araboglycyrrhizin, licorice-saponins A3, E2, G2, and H2, and six known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of licorice-saponin L3 and Isoliquiritin apioside were elucidated as 3 beta-[alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1--> 2)-beta-D-glucuronopyranosyloxy]-22 beta-acetoxy-24-hydroxyolean-12-en-30-oic acid (1) and 4-O-[beta-D-apiofuranosyl(1-->2)-beta-D- glucopyranosyl]isoliquiritigenin (6), respectively.