Isorhamnetin 3-O-galactoside
(Synonyms: 异鼠李素-3-O-半乳糖苷; Cacticin) 目录号 : GC36338Isorhamnetin 3-O-galactoside (Cacticin) 是从 Artemisia capillaris Thunberg 中分离出的一种黄酮苷,通过增强抗氧化防御系统和减少炎症信号通路来改善 CCl4-诱导的肝损伤。Isorhamnetin 3-O-galactoside (Cacticin) 具有抗血栓和抗炎作用。
Cas No.:6743-92-6
Sample solution is provided at 25 µL, 10mM.
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Isorhamnetin 3-O-galactoside (Cacticin), a flavonoid glycoside isolated from Artemisia capillaris Thunberg, which ameliorates CCl4-induced hepatic damage by enhancing the anti-oxidative defense system and reducing the inflammatory signaling pathways. Isorhamnetin 3-O-galactoside (Cacticin) has antithrombotic and anti-inflammatory activities[1][2][3].
[1]. Kim DW, et al. Isorhamnetin-3-O-galactoside Protects against CCl4-Induced Hepatic Injury in Mice. Biomol Ther (Seoul). 2012 Jul;20(4):406-12. [2]. Kim TH, et al. Anti-inflammatory activities of isorhamnetin-3-O-galactoside against HMGB1-induced inflammatory responses in both HUVECs and CLP-induced septic mice. J Cell Biochem. 2013 Feb;114(2):336-45. [3]. Ku SK, et al. Antithrombotic and profibrinolytic activities of isorhamnetin-3-O-galactoside and hyperoside. Food Chem Toxicol. 2013 Mar;53:197-204.
Cas No. | 6743-92-6 | SDF | |
别名 | 异鼠李素-3-O-半乳糖苷; Cacticin | ||
Canonical SMILES | O=C1C(O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)=C(C3=CC=C(O)C(OC)=C3)OC4=CC(O)=CC(O)=C14 | ||
分子式 | C22H22O12 | 分子量 | 478.4 |
溶解度 | DMSO : 100 mg/mL (209.03 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
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1 mM | 2.0903 mL | 10.4515 mL | 20.903 mL |
5 mM | 0.4181 mL | 2.0903 mL | 4.1806 mL |
10 mM | 0.209 mL | 1.0452 mL | 2.0903 mL |
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Anthocyanins and other flavonoids as flower pigments from eleven Centaurea species
Nat Prod Commun 2015 Mar;10(3):447-50.PMID:25924526doi
Anthocyanins and other flavonoids were isolated from the flowers of eleven Centaurea species, C. macrocephala, C. rupestotilis and C. suaveolens, which produce yellow flowers, and C. achtarovii, C. dealbata, C. montana, C. nigra, C. scabiosa, C. simplicicaulis, C. hypoleuca and C. triumfetti, which have cyanic flowers. Four anthocyanins, cyanidin 3,5-di-O-glucoside, cyanidin 3-O-(6"-malonylglucoside)-5-O-glucoside, cyanidin 3-O-(6"-succinylglucoside)-5- O-glucoside and cyanidin glycoside, were detected in the cyanic flowers of seven Centaurea species. Of these anthocyanins, the first two were found as major anthocyanins. In the cyanic species, four other flavonoids, apigenin 7-O-glucuronide-4'-O-glucoside, malonylated apigenin 7,4'-di-O-glucoside, apigenin 7-0- glucuronide and kaempferol glycoside, were also isolated. On the other hand, nine flavonols and four flavones were isolated from the three yellow-flowered species, and identified as quercetagetin, quercetagetin 7-O-glucoside, quercetagetin 3'-methyl ether 7-O-glucoside, patuletin, patuletin 7-O-glucoside, quercetin 7-O-glucoside, kaempferol 3-methyl ether, kaempferol 3-methyl ether 4'-O-glucuronide and Isorhamnetin 3-O-galactoside, and apigenin, apigenin 7- O-glucuronide, luteolin 7-O-glucoside and apigenin 6,8-di-C-glucoside (vicenin-2). Of these flavonoids, the former five flavonols are "yellow flavonols", and it was shown that their flower colors are due to these compounds.
The flavonoid constitunts of Leucaena leucocephala. Growing in Egypt, and their biological activity
Afr J Tradit Complement Altern Med 2013 Nov 2;11(1):67-72.PMID:24653555doi
Background: Leucaena leucocephala is native to Southern Mexico and Northern Central America, but is now naturalized throughout the tropics. The phyto-chemical data of L. leucocephala revealed the presence of terpenes, flavonoids, coumarins and sterols. Various parts of L. leucocephala have been reported to have medicinal properties. Materials and methods: Flavonoids were isolated from the aerial parts of L. leucocephala. Antioxidant activity of the extracts and the isolated compounds was evaluated using (DPPH), as well as their cytotoxic activity using a single tumor [Ehrlish ascites carcinoma cells]. Results: The flavonoidal constituents isolated from chloroform, ethyl acetate and n-butanol fractions of the aqueous alcoholic extract of aerial parts of Leucaena leucocephala were identified as Caffeic acid, Isorhamnetin, Chrysoeriol, Isorhamnetin 3-O-galactoside, Kaempferol-3-O-rubinoside, Quercetin-3-O-rhamnoside and Luteolin-7-glucoside. Chemical structures of the isolated compounds were identified by TLC, PC and spectral techniques (UV, (1)H-NMR and MS). The ethyl acetate fraction and the isolated flavonoidal compounds showed high antioxidant activity compared to Trolox (standard antioxidant compound). The different fractions and isolated compounds of Leucaena leucocephala exhibited no cytotoxic activity against Ehrlich-ascitis carcinoma cell line at the tested concentrations. Conclusion: This is the first record of the flavonoids in the aerial parts of Leucaena leucocephala (L.) except Quercetin-3-O-rhamnoside.
Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. "Brettacher") by HPLC-PDA and HPLC-APCI-MS/MS
Phytochem Anal 2002 Mar-Apr;13(2):87-94.PMID:12018028DOI:10.1002/pca.630.
Extracts of apple fruits (Malus domestica cv. "Brettacher") were analysed by HPLC with photodiode array detection. An unknown peak was monitored displaying the same retention time as isorhamnetin 3-O-glucoside. Preliminary identification of the isorhamnetin aglycone was performed by comparison of UV spectral data of the unknown compound with a reference substance. Using atmospheric pressure chemical ionisation mass spectrometry in the negative ion mode, the presence of an isorhamnetin glycoside was supported by loss of 162 amu from the pseudomolecular ion (m/z 477). MS2 product ion analysis of the parent ion m/z 477 provided a fragmentation pattern identical to the reference. Collision-induced dissociation of the aglycone (m/z 315) in the MS3 product ion analysis allowed the differentiation of rhamnetin and isorhamnetin, and unambiguous assignment by comparison with standard compounds. A second isorhamnetin glycoside eluting prior to the glucoside was tentatively identified as Isorhamnetin 3-O-galactoside. To the best of our knowledge, this is the first report of isorhamnetin glycosides in apple fruit extracts. Results are discussed with respect to chemotaxonomic relevance within the genera Malus and Pyrus, and especially in consideration of the control of the authenticity of apple products.
Inhibition of 5-lipoxygenase and skin inflammation by the aerial parts of Artemisia capillaris and its constituents
Arch Pharm Res 2011 Sep;34(9):1561-9.PMID:21975819DOI:10.1007/s12272-011-0919-0.
The aerial parts of Artemisia capillaris Thunberg (Compositae) have been used in Chinese medicine as a liver protective agent, diuretic, and for amelioration of skin inflammatory conditions. This study was conducted to establish the scientific rationale for treating skin inflammation and to find active principles from A. capillaris. To accomplish these goals, the 70% ethanol extract of the aerial parts of A. capillaris (AR) was prepared and its 5-lipoxygenase (5-LOX) inhibitory action was studied since 5-LOX products are known to be involved in several allergic and skin inflammatory disorders. AR showed potent inhibitory activity against 5-LOX-catalyzed leukotriene production by ionophore-induced rat basophilic leukemia-1 cells, with an IC(50) of < 1.0 μg/mL. Nine major compounds, scopoletin, scopolin, scoparone, esculetin, quercetin, capillarisin, isorhamnetin, 3-O-robinobioside, Isorhamnetin 3-O-galactoside and chlorogenic acid, were isolated from A. capillaris, and their effects were examined to identify the active principle(s). Several coumarin and flavonoid derivatives were found to be 5-LOX inhibitors. In particular, esculetin and quercetin were potent inhibitors, with IC(50) values of 6.6 and 0.7 μM, respectively. Against arachidonic acid-induced ear edema in mice, AR, and esculetin strongly inhibited edematic response. AR and esculetin also inhibited delayed-type hypersensitivity response in mice. In conclusion, AR and some of their major constituents are 5-LOX inhibitors, and these in vitro and in vivo activities may contribute to the therapeutic potential of AR in skin inflammatory disorders in traditional medicine.