Luteolin 5-O-glucoside
(Synonyms: 木犀草素-5-O-葡萄糖苷) 目录号 : GC61015Luteolin5-O-glucoside来自Cirsiummaackii,具有抗炎活性。Luteolin5-O-glucoside抑制LPS诱导的NO生成和t-BHP诱导的ROS生成。Luteolin5-O-glucoside作用于巨噬细胞,还抑制iNOS和COX-2表达。
Cas No.:20344-46-1
Sample solution is provided at 25 µL, 10mM.
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Luteolin 5-O-glucoside, a major flavonoidfrom Cirsium maackii, possesses anti-inflammatory activity. Luteolin 5-O-glucoside inhibits LPS-induced NO production and t-BHP-induced ROS generation. Luteolin 5-O-glucoside suppresses the expression of iNOS and COX-2 in macrophages[1].
Luteolin 5-O-glucoside, at a non-toxic concentration, inhibits LPS-induced NO production and t-BHP-induced ROS generation in a dose-dependent manner in RAW 264.7 cells. Luteolin 5-O-glucoside also suppresses the expression of iNOS and COX-2 in LPS-stimulated macrophages[1].
[1]. Anti-inflammatory activity of Korean thistle Cirsium maackii and its major flavonoid, luteolin 5-O-glucoside.Food Chem Toxicol. 2012 Jun;50(6):2171-9.
Cas No. | 20344-46-1 | SDF | |
别名 | 木犀草素-5-O-葡萄糖苷 | ||
Canonical SMILES | O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(O)=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=C13 | ||
分子式 | C21H20O11 | 分子量 | 448.38 |
溶解度 | 储存条件 | 4°C, protect from light | |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.2303 mL | 11.1513 mL | 22.3025 mL |
5 mM | 0.4461 mL | 2.2303 mL | 4.4605 mL |
10 mM | 0.223 mL | 1.1151 mL | 2.2303 mL |
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Anti-inflammatory activity of Korean thistle Cirsium maackii and its major flavonoid, Luteolin 5-O-glucoside
Food Chem Toxicol 2012 Jun;50(6):2171-9.PMID:22525859DOI:10.1016/j.fct.2012.04.011.
The anti-inflammatory activity of whole Cirsium maackii (family Compositae) plants and of its major flavonoid, Luteolin 5-O-glucoside, was evaluated for their ability to inhibit lipopolysaccharide (LPS)-induced nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) protein expression, and tert-butylhydroperoxide (t-BHP)-induced reactive oxygen species (ROS) generation in RAW 264.7 murine macrophage cells. The methanolic extract of C. maackii showed strong anti-inflammatory activity, and was thus fractionated with several solvents. The ethyl acetate-soluble fraction, exhibiting the highest anti-inflammatory activity potential, was further to yield a major flavonoid, Luteolin 5-O-glucoside. We found that Luteolin 5-O-glucoside, at a non-toxic concentration, inhibited LPS-induced NO production and t-BHP-induced ROS generation in a dose-dependent manner in RAW 264.7 cells. It also suppressed the expression of iNOS and COX-2 in LPS-stimulated macrophages. Furthermore, the efficacies of the methanolic extract of C. maackii in inhibiting both NO and ROS were attributed to its flavonoid content by HPLC analysis. These results indicated that C. maackii whole plants and its flavonoids inhibit the expression of iNOS and COX-2 in through the inhibition of ROS generation, and therefore can be considered as a useful therapeutic and preventive approach for the treatment of various inflammatory and oxidative stress-related diseases.
Quantitative flavonoid variation accompanied by change of flower colors in Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda
Nat Prod Commun 2015 Mar;10(3):413-6.PMID:25924517doi
The flavonoids in the flowers of Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda were isolated and identified. Quercetin and kaempferol 3-O-glucosides and 3-O-rutinosides were found in E. chrysantha, and quercetin 3-O-rutinoside, 3-O-glucoside and 3-O-pentosylrhamnosylglucoside, kaempferol 3-O-robinobioside, 3-O-rutinoside, 3-O-glucoside and 3-O-pentosylrhamnosylglucoside, and isorhamnetin 3-O-rutinoside were isolated from P. tobira. Ten flavonoids, quercetin 3-O-sophoroside, 3-O-rutinoside, 3-O-glucoside, kaempferol 3-O-sophoroside and 3-O-glucoside, Luteolin 5-O-glucoside, 7- O-glucoside and 7-O-hexoside, and apigenin 7-O-glucoside and 4'-O-hexoside were isolated from W floribunda. The major pigments of E. chrysantha were carotenoids. Their content decreased with the change in flower color to white from yellow via cream, and total flavonoid content also slightly decreased by ca. 0.8 in cream and ca. 0.9 fold in white flowers. In contrast with E. chrysantha, white flowers of P. tobira turn to cream and then yellow in which the major pigments are also carotenoids. In this species, both carotenoid and flavonoid contents are gradually increased from white to yellow flowers. Though the petal color of Wisteria floribunda is mauve, due to anthocyanin pigments, the yellow areas are due to carotenoids; these turn to white in the late flowering stage. However, their flavonoid contents were essentially the same among the yellow, cream and white spots of flags. Thus, it was shown by HPLC analysis of the flower flavonoids of E. chrysantha, P. tobira and W. floribunda, although the visible pigments such as carotenoids and anthocyanins are quantitatively varied, the quantitative variation in UV-absorbing substances, such as flavones and flavonols, differs with plant species.
Simultaneous determination of bioactive flavonoids in some selected Korean thistles by high-performance liquid chromatography
Arch Pharm Res 2011 Mar;34(3):455-61.PMID:21547678DOI:10.1007/s12272-011-0314-x.
In order to facilitate the quality control of some selected Korean thistles (Cirsii Herb), Cirsium japonicum var ussuriense, C. japonium var spinosissimum, C. setidens, C. pendulum, C. nipponicum, Carduus crispus, and Breea segetum, a simple, accurate and reliable high performance liguid chromatography method was developed for the simultaneous determination of the six flavonoids: Luteolin 5-O-glucoside (1), luteolin 7-O-glucoside (2), hispidulin 7-O-neohesperidoside (3), luteolin (4), pectolinarin (5), and apigenin (6), which were selected as the chemical markers of the thistles. Separation was achieved on an Agilent Eclipse XDB-C18 column with a gradient solvent system of 0.1% trifluoroacetic acid aqueous-methanol at a flow-rate of 1.0 mL/min and detected at 254 nm. All six calibration curves showed good linearity (R(2) > 0.991). The method was reproducible with intra- and inter-day variations of less than 6%. The recoveries were in the range of 90.01-100.05%. This analysis method was successfully utilized to quantify the six flavonoids in the 22 batches of the thistles. The results demonstrated that this method is simple, reliable and suitable for the quality control of this medicinal herb.
Protective effects of flavonoids isolated from Korean milk thistle Cirsium japonicum var. maackii (Maxim.) Matsum on tert-butyl hydroperoxide-induced hepatotoxicity in HepG2 cells
J Ethnopharmacol 2017 Sep 14;209:62-72.PMID:28735729DOI:10.1016/j.jep.2017.07.027.
Ethnopharmacological relevance: Milk thistle leaves and flowers have been traditionally used as herbal remedy to alleviate liver diseases for decades. Korean milk thistle, Cirsium japonicum var. maackii (Maxim.) Matsum has been employed in traditional folk medicine as diuretic, antiphlogistic, hemostatic, and detoxifying agents. Aim of the study: The aim of current investigation was to evaluate hepatoprotective properties of the MeOH extract of the roots, stems, leaves and flowers of Korean milk thistle as well as four isolated flavonoids, luteolin, Luteolin 5-O-glucoside, apigenin and apigenin 7-O-glucuronide during t-BHP-induced oxidative stress in HepG2 cells. Materials and methods: Hepatoprotective potential of the MeOH extracts and flavonoids derived from Korean milk thistle against t-BHP-induced oxidative stress in HepG2 cells were evaluated following MTT method. Incubating HepG2 cells with t-BHP markedly decreased the cell viability and increased the intracellular ROS generation accompanied by depleted GSH levels. Protein expression of heme oxygenase (HO-1) and nuclear factor-E2-related factor 2 (Nrf-2) was determined by Western blot. Results: Our findings revealed that pretreating HepG2 cells with MeOH extracts and bioactive flavonoids significantly attenuated the t-BHP-induced oxidative damage, followed by increased cell viability in a dose-dependent manner. The results illustrate that excess ROS generation was reduced and GSH levels increased dose-dependently when HepG2 cells were pretreated with four flavonoids. Moreover, Western blotting analysis demonstrated that protein expressions of Nrf-2 and HO-1 were also up-regulated by flavonoids treatment. Conclusions: These results clearly demonstrate that the MeOH extracts and flavonoids from Korean milk thistle protected HepG2 cells against oxidative damage triggered by t-BHP principally by modulating ROS generation and restoring depleted GSH levels in addition to the increased Nrf-2/HO-1 signaling cascade. These flavonoids are potential natural antioxidative biomarkers against oxidative stress-induced hepatotoxicity.