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  • 2,3-脱氢水飞蓟宾

    2,3-Dehydrosilychristin

    2,3-脱氢水飞蓟宾
    产品编号 CFN95370
    CAS编号 57499-41-9
    分子式 = 分子量 C25H20O10 = 480.4
    产品纯度 >=98%
    物理属性 Powder
    化合物类型 Flavonoids
    植物来源 The herbs of Silybum marianum
    ChemFaces的产品在影响因子大于5的优秀和顶级科学期刊中被引用
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    产品名称 产品编号 CAS编号 包装 QQ客服
    2,3-脱氢水飞蓟宾 CFN95370 57499-41-9 1mg QQ客服:2056216494
    2,3-脱氢水飞蓟宾 CFN95370 57499-41-9 5mg QQ客服:2056216494
    2,3-脱氢水飞蓟宾 CFN95370 57499-41-9 10mg QQ客服:2056216494
    2,3-脱氢水飞蓟宾 CFN95370 57499-41-9 20mg QQ客服:2056216494
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    ChemFaces的产品在许多优秀和顶级科学期刊中被引用

    Cell. 2018 Jan 11;172(1-2):249-261.e12.
    doi: 10.1016/j.cell.2017.12.019.
    IF=36.216(2019)

    PMID: 29328914

    Cell Metab. 2020 Mar 3;31(3):534-548.e5.
    doi: 10.1016/j.cmet.2020.01.002.
    IF=22.415(2019)

    PMID: 32004475

    Mol Cell. 2017 Nov 16;68(4):673-685.e6.
    doi: 10.1016/j.molcel.2017.10.022.
    IF=14.548(2019)

    PMID: 29149595

    ACS Nano. 2018 Apr 24;12(4): 3385-3396.
    doi: 10.1021/acsnano.7b08969.
    IF=13.903(2019)

    PMID: 29553709

    Nature Plants. 2016 Dec 22;3: 16206.
    doi: 10.1038/nplants.2016.205.
    IF=13.297(2019)

    PMID: 28005066

    Sci Adv. 2018 Oct 24;4(10): eaat6994.
    doi: 10.1126/sciadv.aat6994.
    IF=12.804(2019)

    PMID: 30417089
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  • 国外学术期刊发表的引用ChemFaces产品的部分文献
  • Int J Mol Sci.2019, 20(8):E1855
  • Int J Mol Sci.2020, 21(24):9369.
  • Braz J Med Biol Res. 2016, 49(7)
  • Russian J Bioorganic Chemistry 2021, 47:1411-1417.
  • Biomed Pharmacother.2021, 137:111362.
  • Korean J Pain.2021, 34(4):405-416.
  • Nat Prod Sci.2018, 24(3):206
  • J Cell Physiol.2020, 10.1002
  • Front Microbiol.2019, 10:2806
  • Toxicol Appl Pharmacol.2021, 427:115668.
  • Antioxidants (Basel).2020, 9(2):E120
  • The Journal of Internal Korean Medicine2015, 36(4):486-497
  • J Nat Med.2020, 74(3):550-560.
  • Molecules.2019, 24(16):E2985
  • Metabolites.2020, 10(11):440.
  • Fitoterapia.2022, 157:105130.
  • J Agric Food Chem.2020, 68(51):15164-15175
  • Sci Rep. 2018, 10590
  • Molecules.2017, 22(11)
  • Antioxidants (Basel).2020, 9(2): E119
  • Naunyn Schmiedebergs Arch Pharmacol.2021, 394(1):107-115.
  • Institute of Food Science & Technology2021, 56(11).
  • Natural Product Communications2020, doi: 10.1177.
  • ...
  • 生物活性
    Description: 2,3-Dehydrosilychristin might have a biologically relevant inhibitory effect on ADH and glutamate dehydrogenase.2,3-Dehydrosilychristin is highly protective against copper-induced erythrocyte lysis .2,3-Dehydrosilychristin has antioxidant properties。
    In vitro:
    Nutrients . 2021 Nov 25;13(12):4238.
    Silymarin Dehydroflavonolignans Chelate Zinc and Partially Inhibit Alcohol Dehydrogenase[Pubmed: 34959790]
    Silymarin is known for its hepatoprotective effects. Although there is solid evidence for its protective effects against Amanita phalloides intoxication, only inconclusive data are available for alcoholic liver damage. Since silymarin flavonolignans have metal-chelating activity, we hypothesized that silymarin may influence alcoholic liver damage by inhibiting zinc-containing alcohol dehydrogenase (ADH). Therefore, we tested the zinc-chelating activity of pure silymarin flavonolignans and their effect on yeast and equine ADH. The most active compounds were also tested on bovine glutamate dehydrogenase, an enzyme blocked by zinc ions. Of the six flavonolignans tested, only 2,3-dehydroderivatives (2,3-dehydrosilybin and 2,3-dehydrosilychristin) significantly chelated zinc ions. Their effect on yeast ADH was modest but stronger than that of the clinically used ADH inhibitor fomepizole. In contrast, fomepizole strongly blocked mammalian (equine) ADH. 2,3-Dehydrosilybin at low micromolar concentrations also partially inhibited this enzyme. These results were confirmed by in silico docking of active dehydroflavonolignans with equine ADH. Glutamate dehydrogenase activity was decreased by zinc ions in a concentration-dependent manner, and this inhibition was abolished by a standard zinc chelating agent. In contrast, 2,3-dehydroflavonolignans blocked the enzyme both in the absence and presence of zinc ions. Therefore, 2,3-dehydrosilybin might have a biologically relevant inhibitory effect on ADH and glutamate dehydrogenase.
    Antioxidants (Basel) . 2021 Apr 27;10(5):679.
    Dehydroflavonolignans from Silymarin Potentiate Transition Metal Toxicity In Vitro but Are Protective for Isolated Erythrocytes Ex Vivo[Pubmed: 33925336]
    2,3-Dehydrosilybin (DHS) was previously shown to chelate and reduce both copper and iron ions. In this study, similar experiments with 2,3-dehydrosilychristin (DHSCH) showed that this congener of DHS also chelates and reduces both metals. Statistical analysis pointed to some differences between both compounds: in general, DHS appeared to be a more potent iron and copper chelator, and a copper reducing agent under acidic conditions, while DHSCH was a more potent copper reducing agent under neutral conditions. In the next step, both DHS and DHSCH were tested for metal-based Fenton chemistry in vitro using HPLC with coulometric detection. Neither of these compounds were able to block the iron-based Fenton reaction and, in addition, they mostly intensified hydroxyl radical production. In the copper-based Fenton reaction, the effect of DHSCH was again prooxidant or neutral, while the effect of DHS was profoundly condition-dependent. DHS was even able to attenuate the reaction under some conditions. Interestingly, both compounds were strongly protective against the copper-triggered lysis of red blood cells, with DHSCH being more potent. The results from this study indicated that, notwithstanding the prooxidative effects of both dehydroflavonolignans, their in vivo effect could be protective.
    J Nat Prod . 2016 Dec 23;79(12):3086-3092.
    Silychristin: Skeletal Alterations and Biological Activities[Pubmed: 28006905]
    Silychristin is the second most abundant flavonolignan (after silybin) present in the fruits of Silybum marianum. A group of compounds containing silychristin (3) and its derivatives such as 2,3-dehydrosilychristin (4), 2,3-dehydroanhydrosilychristin (5), anhydrosilychristin (6), silyhermin (7), and isosilychristin (8) were studied. Physicochemical data of these compounds acquired at high resolution were compared. The absolute configuration of silyhermin (7) was proposed to be identical to silychristin A (3a) in ring D (10R,11S). The preparation of 2,3-dehydrosilychristin (4) was optimized. The Folin-Ciocalteau reduction and DPPH and ABTS radical scavenging assays revealed silychristin and its analogues to be powerful antioxidants, which were found to be more potent than silybin and 2,3-dehydrosilybin. Compounds 4-6 exhibited inhibition of microsomal lipoperoxidation (IC50 4-6 μM). Moreover, compounds 4-8 were found to be almost noncytotoxic for 10 human cell lines of different histogenetic origins. On the basis of these results, compounds 3-6 are likely responsible for most of the antioxidant properties of silymarin attributed traditionally to silybin (silibinin).
    Biomed Pharmacother . 2021 Jun;138:111459.
    Interaction of silymarin components and their sulfate metabolites with human serum albumin and cytochrome P450 (2C9, 2C19, 2D6, and 3A4) enzymes[Pubmed: 33706132]
    Silymarin is a mixture of flavonolignans isolated from the fruit of milk thistle (Silybum marianum (L.) Gaertner). Milk thistle extract is the active ingredient of several medications and dietary supplements to treat liver injury/diseases. After the oral administration, flavonolignans are extensively biotransformed, resulting in the formation of sulfate and/or glucuronide metabolites. Previous studies demonstrated that silymarin components form stable complexes with serum albumin and can inhibit certain cytochrome P450 (CYP) enzymes. Nevertheless, in most of these investigations, silybin was tested; while no or only limited information is available regarding other silymarin components and metabolites. In this study, the interactions of five silymarin components (silybin A, silybin B, isosilybin A, silychristin, and 2,3-dehydrosilychristin) and their sulfate metabolites were examined with human serum albumin and CYP (2C9, 2C19, 2D6, and 3A4) enzymes. Our results demonstrate that each compound tested forms stable complexes with albumin, and certain silymarin components/metabolites can inhibit CYP enzymes. Most of the sulfate conjugates were less potent inhibitors of CYP enzymes, but 2,3-dehydrosilychristin-19-O-sulfate showed the strongest inhibitory effect on CYP3A4. Based on these observations, the simultaneous administration of high dose silymarin with medications should be carefully considered, because milk thistle flavonolignans and/or their sulfate metabolites may interfere with drug therapy.
    Nutrients . 2019 Sep 24;11(10):2286.
    The Effect of Silymarin Flavonolignans and Their Sulfated Conjugates on Platelet Aggregation and Blood Vessels Ex Vivo[Pubmed: 31554252]
    Silymarin is a traditional drug and food supplement employed for numerous liver disorders. The available studies indicate that its activities may be broader, in particular due to claimed benefits in some cardiovascular diseases, but the contributions of individual silymarin components are unclear. Therefore, we tested silymarin flavonolignans as pure diastereomers as well as their sulfated metabolites for potential vasorelaxant and antiplatelet effects in isolated rat aorta and in human blood, respectively. Eleven compounds from a panel of 17 tested exhibited a vasorelaxant effect, with half maximal effective concentrations (EC50) ranging from 20 to 100 μM, and some substances retained certain activity even in the range of hundreds of nM. Stereomers A were generally more potent as vasorelaxants than stereomers B. Interestingly, the most active compound was a metabolite-silychristin-19-O-sulfate. Although initial experiments showed that silybin, 2,3-dehydrosilybin, and 2,3-dehydrosilychristin were able to substantially block platelet aggregation, their effects were rapidly abolished with decreasing concentration, and were negligible at concentrations ≤100 μM. In conclusion, metabolites of silymarin flavonolignans seem to have biologically relevant vasodilatory properties, but the effect of silymarin components on platelets is low or negligible.
    Fitoterapia . 2017 Jun;119:115-120.
    Flavonolignan 2,3-dehydrosilydianin activates Nrf2 and upregulates NAD(P)H:quinone oxidoreductase 1 in Hepa1c1c7 cells[Pubmed: 28450126]
    Silybum marianum (milk thistle) is a medicinal plant used for the treatment of various liver disorders. This study examined whether the main flavonolignans from S. marianum (i.e. silybin, silychristin, silydianin) and their 2,3-dehydro derivatives (i.e. 2,3-dehydrosilybin, 2,3-dehydrosilychristin, 2,3-dehydrosilydianin) activate the Nrf2 pathway, which regulates the expression of genes encoding many cytoprotective enzymes, including NAD(P)H:quinone oxidoreductase 1 (NQO1). After 48h of exposure, 2,3-dehydrosilydianin at concentrations of 25μM and higher significantly elevated the activity of NQO1 in murine hepatoma Hepa1c1c7 cells. In contrast, other tested compounds at non-cytotoxic concentrations had a mild or negligible effect on the NQO1 activity. Using a luciferase reporter assay, 2,3-dehydrosilydianin was found to significantly activate transcription via the antioxidant response element in stably transfected human AREc32 reporter cells. Moreover, 2,3-dehydrosilydianin caused the accumulation of Nrf2 and significantly induced the expression of the Nqo1 gene at both the mRNA and protein levels in Hepa1c1c7 cells. We found that 2,3-dehydrosilydianin also increased to some extent the expression of other Nrf2 target genes, namely of the heme oxygenase-1 gene (Hmox1) and the glutamate-cysteine ligase modifier subunit gene (Gclm). We conclude that 2,3-dehydrosilydianin activates Nrf2 and induces Nrf2-mediated gene expression in Hepa1c1c7 cells.
    制备储备液(仅供参考)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.0816 mL 10.408 mL 20.816 mL 41.632 mL 52.04 mL
    5 mM 0.4163 mL 2.0816 mL 4.1632 mL 8.3264 mL 10.408 mL
    10 mM 0.2082 mL 1.0408 mL 2.0816 mL 4.1632 mL 5.204 mL
    50 mM 0.0416 mL 0.2082 mL 0.4163 mL 0.8326 mL 1.0408 mL
    100 mM 0.0208 mL 0.1041 mL 0.2082 mL 0.4163 mL 0.5204 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    部分图片展示
    产品名称 产品编号 CAS编号 分子式 = 分子量 位单 联系QQ
    水飞蓟亭B; Silychristin B CFN95160 879325-58-3 C25H22O10 = 482.4 5mg QQ客服:1457312923
    异水飞蓟亭; Isosilychristin CFN95369 77182-66-2 C25H22O10 = 482.4 5mg QQ客服:2159513211
    2,3-脱氢水飞蓟宾; 2,3-Dehydrosilychristin CFN95370 57499-41-9 C25H20O10 = 480.4 5mg QQ客服:1413575084
    异水飞蓟宾; Isosilybin CFN90260 72581-71-6 C25H22O10 = 482.44 20mg QQ客服:2056216494
    异水飞蓟宾A; Isosilybin A CFN91070 142796-21-2 C25H22O10 = 482.4 5mg QQ客服:215959384
    异水飞蓟宾B; Isosilybin B CFN91071 142796-22-3 C25H22O10 = 482.4 5mg QQ客服:2056216494
    水飞蓟宾; Silymarin CFN99542 22888-70-6 C25H22O10 = 482.46 20mg QQ客服:2159513211
    水飞蓟宾A; Silybin A CFN95149 22888-70-6 C25H22O10 = 482.4 20mg QQ客服:2159513211
    水飞蓟宾B; Silybin B CFN92916 142797-34-0 C25H22O10 = 482.44 10mg QQ客服:215959384
    2,3-脱氢水飞蓟宾A; 2,3-Dehydrosilybin A CFN70322 25166-14-7 C25H20O10 = 480.4 5mg QQ客服:2056216494

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