Xanthopurpurin
(Synonyms: 1,3-二羥蒽醌,Purpuroxanthin) 目录号 : GC61383Xanthopurpurin是从Rubiaakane根茎中分离的得到的一种蒽醌苷,主要对胶原诱导的血小板聚集有较强的抑制作用。
Cas No.:518-83-2
Sample solution is provided at 25 µL, 10mM.
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Xanthopurpurin, an anthraquinone glycoside, isolated from the roots of Rubia akane, shows mainly strong inhibition of collagen-induced platelet aggregation[1].
[1]. M I Chung, et al. Antiplatelet constituents of formosan Rubia akane. J Nat Prod. 1994 Feb;57(2):313-6.
Cas No. | 518-83-2 | SDF | |
别名 | 1,3-二羥蒽醌,Purpuroxanthin | ||
Canonical SMILES | O=C1C2=C(C=CC=C2)C(C3=CC(O)=CC(O)=C13)=O | ||
分子式 | C14H8O4 | 分子量 | 240.21 |
溶解度 | 储存条件 | Store at -20°C | |
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1 mg | 5 mg | 10 mg | |
1 mM | 4.163 mL | 20.8151 mL | 41.6302 mL |
5 mM | 0.8326 mL | 4.163 mL | 8.326 mL |
10 mM | 0.4163 mL | 2.0815 mL | 4.163 mL |
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Development of an ultra-performance liquid chromatography-electrospray ionization-Orbitrap mass spectrometry method for determination of Xanthopurpurin in rat plasma and its application to pharmacokinetic study
Biomed Chromatogr 2020 Jul;34(7):e4838.PMID:32246852DOI:10.1002/bmc.4838.
A rapid and sensitive method was developed and validated for the quantitative determination of Xanthopurpurin (XPP) in rat plasma using ultra-performance liquid chromatography-electrospray ionization-Orbitrap mass spectrometry. XPP inhibits IgE production and prevents peanut-induced anaphylaxis. The XPP and emodin (internal standard) were determined in negative ion mode with m/z 239.0350 → 211.0400 and 269.0455 → 241.0507, respectively. The separation process was achieved using an ACQUITY UPLC HSS T3 column with acetonitrile and 0.1% formic acid in water (85:15). The linear range was 0.5-100 ng/mL, and the correlation coefficient (r2 ) was > 0.993. The inter-day and intra-day precision was within an acceptable range of 15%. The extraction recovery and matrix effect were 78.9-87.2% and 94.3-98.5%, respectively. Under different conditions, the XPP was stable in the range of 5.6-10.6%. This method was successfully applied to study the pharmacokinetics of XPP with an oral dose of 10.0 mg/kg and intravenous dose of 2.0 mg/kg in rats. The absolute oral bioavailability of XPP was 4.6%.
Cytotoxic properties of the anthraquinone derivatives isolated from the roots of Rubia philippinensis
BMC Complement Altern Med 2018 Jul 3;18(1):200.PMID:29970094DOI:10.1186/s12906-018-2253-2.
Background: Cancer is one of the most frequently occurring diseases and is the second leading cause of death worldwide. In this study, anthraquinone derivatives (Compounds 1-5) were evaluated for their anti-cancer potential against various skin and breast cancer cell lines to assess whether these anthraquinone derivatives may serve as a lead for the augmentation of anti-cancer drug. Methods: Anthraquinone derivatives, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-(6'-O-acetyl)-α-rhamnosyl(1 → 2)-β-glucoside (Comp 1), 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone (Comp 2), and alizarin (Comp 3) were isolated from the dichloromethane fraction of the roots of Rubia philippinensis., whereas ethyl acetate fraction yielded Xanthopurpurin (Comp 4) and lucidin-ω-methyl ether (Comp 5). Structures of all the isolated compounds were determined by spectral data analysis. All isolated compounds (Comp 1-5) were assessed for cytotoxicity by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against four different cancer cell lines, i.e. human melanoma (SK-MEL-5), murine melanoma (B16F10), and human breast adenocarcinoma (MCF7 and MDA-MB-231). Results: Significant activity of the compounds 4 and 5 was observed against the breast cancer cell line MDA-MB-231 with IC50 values of 14.65 ± 1.45 and 13.03 ± 0.33 μM, respectively. Encouragingly, IC50 values of 67.89 ± 1.02 and 79.01 ± 0.03 μM against normal kidney epithelial cells (MDCK) were also obtained for compounds 4 and 5, respectively, which indicated very low toxicity and favorable selectivity indices for compounds 4 and 5 in the range of 1.85 to 3.95 and 2.11 to 6.06 against skin cancer cell lines (SK-MEL-5, and B16F10), and breast cancer cell lines (MCF7 and MDA-MB-231), respectively. Conclusion: Our results suggested that the compounds 4 (Xanthopurpurin) and 5 (lucidin-ω-methyl ether) showed high selective toxicity towards breast cancer cells at lower concentrations without showing toxicity towards normal cells, thus could be of potential as new lead molecules in cancer treatment.
Antiplatelet constituents of formosan Rubia akane
J Nat Prod 1994 Feb;57(2):313-6.PMID:8176404DOI:10.1021/np50104a020.
A known steroid, in addition to triterpenoids, anthraquinones, naphthalenes and a new anthraquinone glycoside, Xanthopurpurin 3-O-beta-D-glucoside, were isolated from the roots of Rubia akane grown in Taiwan. Mollugin, a naphthohydroquinone, showed strong inhibition of arachidonic acid (AA)-induced and collagen-induced platelet aggregation. In contrast, 2-methyl-1,3,6-trihydroxyl-9,10-anthraquinone, Xanthopurpurin 3-O-beta-D-glucoside, and Xanthopurpurin showed mainly strong inhibition of collagen-induced platelet aggregation.
[Changes of chemical constituents in Rubiae Radix et Rhizoma before and after carbonized by UPLC-Q-TOF-MS method]
Zhongguo Zhong Yao Za Zhi 2017 Mar;42(5):923-930.PMID:28994536DOI:10.19540/j.cnki.cjcmm.20170121.035.
In order to explore the effect on chemical constituents after carbonized, the changes of chemical constituents in raw and carbonized Rubiae Radix et Rhizoma were analyzed by UPLC-Q-TOF-MS. The research also used principal component analysis(PCA) and orthogonal partial least squares discriminant analysis(OPLS-DA) for data statistics to find out the main differences on components before and after carbonized. The accurate m/z values of Q-TOF-MS and Q-TOF-MS-MS fragments were applied to identify the structures. The results showed that 6 more discrepant constituents were existed between raw and carbonized Rubiae Radix et Rhizoma. Three constituents were selected as the main discrepant components according to the peak area (276 nm) and identified, as lucidin, Xanthopurpurin and 1,3,6-trihydroxy-2-methylanthraquinone. After carbonized, contents of Xanthopurpurin and 1,3,6-trihydroxy-2-methylanthraquinone were observably increasing, while lucidin was obviously decreasing. They could be used as the chemical markers for the differentiation between raw and carbonized Rubiae Radix et Rhizoma. The results of this experiment played an important role in the study of processing principle of carbonized Rubiae Radix et Rhizoma. It also provided important evidences for the interpretation of effective material based on carbonized Rubiae Radix et Rhizoma.
In vitro Antiviral Activity of Rubia cordifolia Aerial Part Extract against Rotavirus
Front Pharmacol 2016 Sep 13;7:308.PMID:27679574DOI:10.3389/fphar.2016.00308.
The root of Rubia cordifolia has been used traditionally as a hemostatic agent, while the aerial part of the plant consisting of leaf and stem is known to exhibit anti-diarrheal properties and has been widely used as a remedy in many parts of China. As rotavirus is one of the most commonly associated diarrhea-causing pathogen, this study aims to investigate the anti-rotaviral effect of R. cordifolia aerial part (RCAP). The cytotoxicity of RCAP toward MA-104 cells was evaluated using the WST-8 assay. Colloidal gold method and real time polymerase chain reaction (qPCR) assay were used to confirm the findings of the antiviral assay. Then, 4',6-diamidino-2-phenylindole (DAPI) staining method was subsequently used to investigate the mode of death among the cells. And the representative components of aqueous extract were isolated and identified. It was shown that both the viability of MA-104 cells and the viral load were reduced with increasing concentration of the extract. DAPI staining showed that virus-induced apoptosis was the cause of the low cell viability and viral load, an effect which was accelerated with incubation in the aqueous herbal extract. The major compounds postulated to exhibit this activity were isolated from the aqueous herbal extract and identified to be compounds Xanthopurpurin and Vanillic Acid. This study showed that RCAP extract effectively inhibited rotavirus multiplication by promoting virus-induced apoptosis in MA-104 cells.