Eupatorin
(Synonyms: 半齿泽兰素) 目录号 : GC36017
A flavonoid with diverse biological activities
Cas No.:855-96-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Eupatorin is a flavonoid that has been found in L. camara and has diverse biological activities.1,2,3,4 It inhibits the growth of HeLa, MK-1, and B16/F10 tumor cells (GI50s = 15, 58, and 44 ?M, respectively).1 Eupatorin is active against T. cruzi epimastigotes and trypomastigotes (IC50s = 0.2 and 61.8 ?g/ml, respectively) without inducing cytotoxicity in Vero cells (IC50 = >500 ?g/ml).2 It induces vasorelaxation in isolated rat thoracic aortic rings precontracted with phenylephrine (pD2 = 6.66).3 Eupatorin (10 and 100 ?M) reduces nuclear translocation of NF-κB and STAT1α in J774 murine macrophages and reduces paw edema in a mouse model of carrageenan-induced paw inflammation when administered at a dose of 50 mg/kg.4
1.Nagao, T., Abe, F., Kinjo, J., et al.Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationshipBiol. Pharm. Bull.25(7)875-879(2002) 2.Beer, M.F., Frank, F.M., Germán Elso, O., et al.Trypanocidal and leishmanicidal activities of flavonoids isolated from Stevia satureiifolia var. satureiifoliaPharm. Biol.54(10)2188-2195(2016) 3.Yam, M.F., Tan, C.S., Ahmad, M., et al.Mechanism of vasorelaxation induced by eupatorin in the rats aortic ringEur. J. Pharmacol.78927-36(2016) 4.Laavola, M., Nieminen, R., Yam, M.F., et al.Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activationPlanta Med.78(8)779-786(2012)
| Cas No. | 855-96-9 | SDF | |
| 别名 | 半齿泽兰素 | ||
| Canonical SMILES | O=C1C=C(C2=CC=C(OC)C(O)=C2)OC3=CC(OC)=C(OC)C(O)=C13 | ||
| 分子式 | C18H16O7 | 分子量 | 344.32 |
| 溶解度 | DMF: 10 mg/ml,DMSO: 10 mg/ml,DMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml | 储存条件 | Store at -20°C |
| 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 | 2.9043 mL | 14.5214 mL | 29.0428 mL |
| 5 mM | 0.5809 mL | 2.9043 mL | 5.8086 mL |
| 10 mM | 0.2904 mL | 1.4521 mL | 2.9043 mL |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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。
Cytotoxicity of Eupatorin in MCF-7 and MDA-MB-231 human breast cancer cells via cell cycle arrest, anti-angiogenesis and induction of apoptosis
Sci Rep 2019 Feb 6;9(1):1514.PMID:30728391DOI:10.1038/s41598-018-37796-w.
Eupatorin has been reported with in vitro cytotoxic effect on several human cancer cells. However, reports on the mode of action and detail mechanism of Eupatorin in vitro in breast cancer disease are limited. Hence, Eupatorin's effect on the human breast carcinoma cell line MCF-7 and MDA-MB-231 was investigated. MTT assay showed that Eupatorin had cytotoxic effects on MCF-7 and MDA-MB-231 cells but was non-toxic to the normal cells of MCF-10a in a time-dose dependent manner. At 24 h, the Eupatorin showed mild cytotoxicity on both MCF-7 and MDA-MB-231 cells with IC50 values higher than 20 μg/mL. After 48 h, Eupatorin at 5 μg/mL inhibited the proliferation of MCF-7 and MDA-MB-231 cells by 50% while the IC50 of MCF-10a was significantly (p < 0.05) high with 30 μg/mL. The concentration of Eupatorin at 5 μg/mL induced apoptosis mainly through intrinsic pathway by facilitating higher fold of caspase 9 compared to caspase 8 at 48 h. The cell cycle profile also showed that Eupatorin (5 μg/mL) exerted anti-proliferation activity with the cell cycle arrest of MCF-7 and MDA-MB-231 cells at sub Gθ/G1 in a time-dependent manner. In addition, wound healing assay showed an incomplete wound closure of scratched MDA-MB-231 cells, and more than 60% of the MDA-MB-231 cells were prevented to migrate and invade the membrane in the Boyden chamber after 24 h. Eupatorin also inhibited angiogenic sprouting of new blood vessels in ex vivo mouse aorta ring assay. In gene expression assay, Eupatorin up-regulated pro-apoptotic genes such as Bak1, HIF1A, Bax, Bad, cytochrome c and SMAC/Diablo and blocked the Phospho-Akt pathway. In conclusion, Eupatorin is a potent candidate to induce apoptosis and concurrently inhibit the invasion, migration and angiogenesis of MDA-MB-231 and MCF-7 cells through inhibition of Phospho-Akt pathway and cell cycle blockade.
Eupatorin and Salviandulin-A, with Antimicrobial and Anti-Inflammatory Effects from Salvia lavanduloides Kunth Leaves
Plants (Basel) 2022 Jun 30;11(13):1739.PMID:35807691DOI:10.3390/plants11131739.
This study describes the antimicrobial and anti-inflammatory effects from extracts obtained from the leaves of Salvia lavanduloides. The plant material was macerated with three solvents of ascending polarity (n-hexane (Sl-Hex), ethyl acetate (Sl-AcOEt), and dichloromethane (Sl-D)). The extracts, fractions (SlD-2 and SlD-3), and isolated compounds (15,16-epoxy-10-β-hydroxy-neo-cleroda-3,7,13(16),14-tetraene-17,12R:18,19-diolide (1), salviandulin A (2), and Eupatorin (3)) were evaluated as antimicrobials against Gram-negative, Gram-positive bacteria and the fungus Candida albicans (Ca) using the minimum inhibitory concentration (MIC) and the anti-inflammatory activity induced by 13-acetate of 12-O-tetradecanoylforbol (TPA). Sl-D and Sl-AcOEt extracts, SlD-2 and SlD-3 fractions showed the highest antimicrobial activity. The isolated compounds showed good activity against Pseudomonas aeruginosa with a MIC < 2 μg/mL, while the anti-inflammatory activity, the Sl-Hex, Sl-D extracts, and SlD-3 fraction presented an inhibition of 62, 45 and 61%, respectively, while (2) 70% and (3) 72%.
Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model
Integr Cancer Ther 2020 Jan-Dec;19:1534735420935625.PMID:32830560DOI:10.1177/1534735420935625.
Eupatorin is a polymethoxy flavone extracted from Orthosiphon stamineus and was reported to exhibit cytotoxic effects on several cancer cell lines. However, its effect as an anti-breast cancer agent in vivo has yet to be determined. This study aims to elucidate the potential of Eupatorin as an anti-breast cancer agent in vivo using 4T1 challenged BALB/c mice model. In this article, BALB/c mice (20-22 g) challenged with 4T1 cells were treated with 5 mg/kg or 20 mg/kg Eupatorin, while the untreated and healthy mice were fed with olive oil (vehicle) via oral gavage. After 28 days of experiment, the mice were sacrificed and blood was collected for serum cytokine assay, while tumors were harvested to extract RNA and protein for gene expression assay and hematoxylin-eosin staining. Organs such as spleen and lung were harvested for immune suppression and clonogenic assay, respectively. Eupatorin (20 mg/kg) was effective in delaying the tumor development and reducing metastasis to the lung compared with the untreated mice. Eupatorin (20 mg/kg) also enhanced the immunity as the population of NK1.1+ and CD8+ in the splenocytes and the serum interferon-γ were increased. Concurrently, Eupatorin treatment also has downregulated the expression of pro-inflammatory and metastatic related genes (IL-1β. MMP9, TNF-α, and NF-κB). Thus, this study demonstrated that Eupatorin at the highest dosage of 20 mg/kg body weight was effective in delaying the 4T1-induced breast tumor growth in the animal model.
Identification of Metabolites of Eupatorin in Vivo and in Vitro Based on UHPLC-Q-TOF-MS/MS
Molecules 2019 Jul 23;24(14):2658.PMID:31340434DOI:10.3390/molecules24142658.
Eupatorin is the major bioactive component of Java tea (Orthosiphon stamineus), exhibiting strong anticancer and anti-inflammatory activities. However, no research on the metabolism of Eupatorin has been reported to date. In the present study, ultra-high-performance liquid chromatography coupled with hybrid triple quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF-MS) combined with an efficient online data acquisition and a multiple data processing method were developed for metabolite identification in vivo (rat plasma, bile, urine and feces) and in vitro (rat liver microsomes and intestinal flora). A total of 51 metabolites in vivo, 60 metabolites in vitro were structurally characterized. The loss of CH2, CH2O, O, CO, oxidation, methylation, glucuronidation, sulfate conjugation, N-acetylation, hydrogenation, ketone formation, glycine conjugation, glutamine conjugation and glucose conjugation were the main metabolic pathways of Eupatorin. This was the first identification of metabolites of Eupatorin in vivo and in vitro and it will provide reference and valuable evidence for further development of new pharmaceuticals and pharmacological mechanisms.
Flavonoids Eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation
Planta Med 2012 May;78(8):779-86.PMID:22516932DOI:10.1055/s-0031-1298458.
Cytokines and other inflammatory mediators, such as prostaglandin E₂ (PGE₂) and nitric oxide (NO) produced by cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS), respectively, activate and drive inflammation and therefore serve as targets for anti-inflammatory drug development. Orthosiphon stamineus is an indigenous medicinal plant of Southeast Asia that has been traditionally used in the treatment of rheumatoid arthritis, gout, and other inflammatory disorders. The present study investigated the anti-inflammatory properties of Orthosiphon stamineus leaf chloroform extract (CE), its flavonoid-containing CE fraction 2 (CF2), and the flavonoids Eupatorin, eupatorin-5-methyl ether (TMF), and sinensetin, identified from the CF2. It was found that CE (20 and 50 µg/mL) and CF2 (20 and 50 µg/mL) inhibited iNOS expression and NO production, as well as PGE₂ production. Eupatorin and sinensetin inhibited iNOS and COX-2 expression and the production of NO (IC₅₀ 5.2 µM and 9.2 µM for Eupatorin and sinensetin, respectively) and PGE₂ (IC₅₀ 5.0 µM and 2.7 µM for Eupatorin and sinensetin, respectively) in a dose-dependent manner. The extracts and the compounds also inhibited tumor necrosis factor α (TNF-α) production (IC₅₀ 5.0 µM and 2.7 µM for Eupatorin and sinensetin, respectively). Eupatorin and sinensetin inhibited lipopolysaccharide (LPS)-induced activation of transcription factor signal transducers and activators of transcription 1α (STAT1α). Furthermore, Eupatorin (50 mg/kg i. p.) and sinensetin (50 mg/kg i. p.) inhibited carrageenan-induced paw inflammation in mice. The results suggest that CE and CF2, as well as the known constituents of CF2, i.e., Eupatorin and sinensetin, have meaningful anti-inflammatory properties which may be utilized in the development of novel anti-inflammatory treatments.