3-O-Methylellagic acid
(Synonyms: 3-甲基鞣花酸) 目录号 : GC61812
3-O-Methylellagicacid是一种天然产物，从Myrciariacauliflora中分离得到，具有抗炎活性。3-O-Methylellagicacid对葡萄糖转运有抑制作用。3-O-Methylellagicacid具有抗菌活性，对葡萄球菌ATCC25923菌株作用的MIC值为32μg/mL。
Cas No.:51768-38-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-O-Methylellagic acid is a nature product that can be isolated from Myrciaria cauliflora, with anti-inflammatory activity. 3-O-Methylellagic acid shows an inhibitory effect on glucose transport assay. 3-O-Methylellagic acid has antibacterial activity, with a MIC of 32 μg/mL for Staph. Aureus ATCC 25923[1][2][3].
[1]. Da-Ke Zhao, et al. Jaboticabin and Related Polyphenols from Jaboticaba ( Myrciaria cauliflora) with Anti-inflammatory Activity for Chronic Obstructive Pulmonary Disease. J Agric Food Chem. 2019 Feb 6;67(5):1513-1520. [2]. Active compounds from Lagerstroemia speciosa, insulin-like glucose uptake-stimulatory/inhibitory and adipocyte differentiation-inhibitory activities in 3T3-L1 cells. J Agric Food Chem. 2008 Dec 24;56(24):11668-74. [3]. Sgariglia, M. A.,et al. Isolation of antibacterial components from infusion of Caesalpinia paraguariensis bark. A bio-guided phytochemical study. Food Chemistry, 2011. 126(2), 395-404.
| Cas No. | 51768-38-8 | SDF | |
| 别名 | 3-甲基鞣花酸 | ||
| Canonical SMILES | O=C1C2=CC(O)=C(OC)C(O3)=C2C4=C(C3=O)C=C(O)C(O)=C4O1 | ||
| 分子式 | C15H8O8 | 分子量 | 316.22 |
| 溶解度 | 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 | 3.1624 mL | 15.8118 mL | 31.6236 mL |
| 5 mM | 0.6325 mL | 3.1624 mL | 6.3247 mL |
| 10 mM | 0.3162 mL | 1.5812 mL | 3.1624 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
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。
ent-Eudesmane sesquiterpenoids, galloyl esters of the oak lactone precursor, and a 3-O-Methylellagic acid glycoside from the wood of Platycarya strobilacea
Phytochemistry 2011 Jun;72(8):796-803.PMID:21440271DOI:10.1016/j.phytochem.2011.02.020.
ent-Eudesmane sesquiterpenoids, 8,11-dihydroxy-2,4-cycloeudesmane, 11-hydroxy-2,4-cycloeudesman-8-one and 2,4-cyclo-7(11)-eudesmen-8-one, were isolated from the wood of Platycarya strobilacea, which has been used as an aromatic tree since at least the 18th century. On charring the wood, 2,4-cyclo-7(11)-eudesmen-8-one was detected in the smoke. In the charred wood, the concentrations of ellagitannins, such as galloyl pedunculagin, dramatically decreased, whereas concentrations of pentagalloyl glucose, and other gallotannins were relatively stable. In addition, two other compounds, the 6'-O-m- and p-digalloyl oak lactone precursor and the 3-O-Methylellagic acid 4'-O-(4″-O-galloyl)-xylopyranoside, were isolated from the charred wood along with m- and p-digallic acid.
Ellagitannins and simple phenolics from the halophytic plant Tamarix nilotica
Nat Prod Res 2022 Jan;36(1):177-185.PMID:32496129DOI:10.1080/14786419.2020.1774757.
Three new [nilotinins M8‒M10 (1‒3)] and two known [tamarixinin A (4) and gemin D (5)] ellagitannins and seven simple phenolics [gallic acid (6), methyl gallate (7), 3,4-di-O-methylgallic acid (8), ellagic acid (9), 3-O-Methylellagic acid (10), methyl ferulate 3-O-sulphate (11), and 7,4'-di-O-methylkaempferol (12)] were isolated from the halophytic plant Tamarix nilotica (Ehrenb.) Bunge (Tamaricaceae). Their structures were determined based on intensive spectroscopic studies and comparisons with reported data. Compounds 4, and 6-8 were evaluated for their cytotoxicity against lung adenocarcinoma cell line (A549) and anti-leishmanial activity against Leishmania major. Compounds 4, 6 and 7 showed promising cytotoxic properties against A549 (IC50 29 ± 2.3, 10.5 ± 0.7, and 20.7 ± 1.9 μg/mL), while compounds 4 and 7 showed higher growth-inhibitory effects against L. major promastigotes (IC50 40.5 ± 2.7 and 38.4 ± 2.5 μg/mL), as compared with the standards doxorubicin (IC50 0.42 µg/mL) and miltefosine (IC50 9.43 μg/mL), respectively.
Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark
J Ethnopharmacol 2013 May 2;147(1):63-73.PMID:23415707DOI:10.1016/j.jep.2012.12.030.
Ethnopharmacological relevance: Caesalpinia paraguariensis (D. Parodi) Burkart stem bark infusion (CPBI) is traditionally used in Argentina because their "vulnerary" properties. Aim of the study: CPBI was studied throughout bio-guided purification procedures conducted by in vitro biological assays in order to isolate the main bioactive compounds. Material and methods: Anti-inflammatory activity was assessed by enzyme inhibition assays of Hyaluronidase (Hyal) and inducible Nitric Oxide Synthase (iNOS). The antioxidant properties were evaluated by DPPH free radical scavenging assay, lipid peroxidation inhibition assay on erythrocyte membranes, and a cell-based assay that included the fluorescent probe (DCFH-DA) for indicating reactive oxygen species (ROS) generation. Bioactive compounds were purified by chromatographic methods and their structures elucidated using spectroscopic methods (ESI-MS and 1D/2D-(1)H/(13)C-NMR). Results: Four main bioactive compounds were isolated from CPBI: ellagic acid (1), 3-O-Methylellagic acid (2), 3,3'-di-O-methylellagic acid (3) and 3,3'-di-O-methylellagic-4-β-D-xylopyranoside (4). These were bioactive at concentrations in which are present in CPBI, being compounds 2 and 3 the best enzyme inhibitors of Hyal and iNOS, reaching the 90% inhibitory concentration (IC90) values ranging from 2.8 to 16.4 μM, that are better than that of the positive controls, aspirin (IC90: no reached) and aminoguanidine (IC90: 20.2 μM) respectively. Compounds 2 and 3 were also better scavengers for lipoperoxides than butylated hydroxytoluene (BHT), reaching the 90% effective concentration (EC90) at 1.2-4.5 μg/ml, and for DPPH radical (2.5-7.3 μg/ml); moreover compounds were able to exert its scavenging action on intracellular ROS. Structural features relevant to the biological activities are discussed. Conclusions: This work provides scientific validity to the popular usage of CPBI.
Ellagic acid rhamnosides from the stem bark of Eucalyptus globulus
Phytochemistry 2001 Jun;57(4):587-91.PMID:11394863DOI:10.1016/s0031-9422(01)00146-7.
Four ellagic acid rhamnosides were isolated from the stem bark of Eucalyptus globulus. Their structures have been established on the basis of the analysis of their 1H NMR, 13C NMR, HMBC, IR and MS spectral data. The HMBC data of these compounds were most useful for their structure determinations, with these bring determined to be 3-O-Methylellagic acid 3'-O-alpha-rhamnopyranoside, 3-O-Methylellagic acid 3'-O-alpha-3''-O-acetylrhamnopyranoside, 3-O-Methylellagic acid 3'-O-alpha-2''-O-acetylrhamnopyranoside, 3-O-Methylellagic acid 3'-O-alpha-4''-O-acetylrhamnopyranoside, respectively. Their antioxidant activities were evaluated by measuring the inhibition of lipid peroxidation using rat liver microsomes, with IC50 values of 10.0-14.0 microg/ml.
Compounds from Terminalia mantaly L. (Combretaceae) Stem Bark Exhibit Potent Inhibition against Some Pathogenic Yeasts and Enzymes of Metabolic Significance
Medicines (Basel) 2017 Jan 24;4(1):6.PMID:28930221DOI:10.3390/medicines4010006.
Background: Pathogenic yeasts resistance to current drugs emphasizes the need for new, safe, and cost-effective drugs. Also, new inhibitors are needed to control the effects of enzymes that are implicated in metabolic dysfunctions such as cancer, obesity, and epilepsy. Methods: The anti-yeast extract from Terminalia mantaly (Combretaceae) was fractionated and the structures of the isolated compounds established by means of spectroscopic analysis and comparison with literature data. Activity was assessed against Candida albicans, C. parapsilosis and C. krusei using the microdilution method, and against four enzymes of metabolic significance: glucose-6-phosphate dehydrogenase, human erythrocyte carbonic anhydrase I and II, and glutathione S-transferase. Results: Seven compounds, 3,3'-di-O-methylellagic acid 4'-O-α-rhamnopyranoside; 3-O-Methylellagic acid; arjungenin or 2,3,19,23-tetrahydroxyolean-12-en-28-oïc acid; arjunglucoside or 2,3,19,23-tetrahydroxyolean-12-en-28-oïc acid glucopyranoside; 2α,3α,24-trihydroxyolean-11,13(18)-dien-28-oïc acid; stigmasterol; and stigmasterol 3-O-β-d-glucopyranoside were isolated from the extract. Among those, 3,3'-di-O-methylellagic acid 4'-O-α-rhamnopyranoside, 3-O-Methylellagic acid, and arjunglucoside showed anti-yeast activity comparable to that of reference fluconazole with minimal inhibitory concentrations (MIC) below 32 µg/mL. Besides, Arjunglucoside potently inhibited the tested enzymes with 50% inhibitory concentrations (IC50) below 4 µM and inhibitory constant (Ki) <3 µM. Conclusions: The results achieved indicate that further SAR studies will likely identify potent hit derivatives that should subsequently enter the drug development pipeline.