Tellimagrandin II
(Synonyms: Eugeniin) 目录号 : GC64237
Tellimagrandin II (Eugeniin)，是 4C1-葡萄糖衍生的鞣花丹宁系列的第一个中间体，也抑制Staphylococcus aureus的耐药性。
Cas No.:81571-72-4
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
Tellimagrandin II (Eugeniin), the first intermediate in the 4C1-glucose derived series of ellagitannins, also inhibits antibiotic resistance of drug-resistant Staphylococcus aureus[1][2].
[1]. Ruth Niemetz, et al. Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves. Phytochemistry. 2003 Feb;62(3):301-6.
[2]. Yu-Wei Chang, et al. Tellimagrandin II, A Type of Plant Polyphenol Extracted from Trapa bispinosa Inhibits Antibiotic Resistance of Drug-Resistant Staphylococcus aureus. Int J Mol Sci. 2019 Nov 18;20(22):5790.
| Cas No. | 81571-72-4 | SDF | Download SDF |
| 别名 | Eugeniin | ||
| 分子式 | C41H30O26 | 分子量 | 938.66 |
| 溶解度 | DMSO : 100 mg/mL (106.53 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
| 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 | 1.0653 mL | 5.3267 mL | 10.6535 mL |
| 5 mM | 0.2131 mL | 1.0653 mL | 2.1307 mL |
| 10 mM | 0.1065 mL | 0.5327 mL | 1.0653 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。
Tellimagrandin II, A Type of Plant Polyphenol Extracted from Trapa bispinosa Inhibits Antibiotic Resistance of Drug-Resistant Staphylococcus aureus
Int J Mol Sci 2019 Nov 18;20(22):5790.PMID:31752109DOI:10.3390/ijms20225790.
The emergence of methicillin-resistant Staphylococcus aureus (MRSA) has become a critical global concern. Identifying new candidates of anti-S. aureus agents is urgently required because the therapeutic strategies for infected patients are limited currently. Therefore, the present study investigated whether Tellimagrandin II (TGII), a pure compound extracted from the shells of Trapa bispinosa, exhibits antibacterial effects against MRSA. We first showed that TGII exerted potent inhibitory activity against MRSA with a minimum inhibitory concentration of 128 μg/mL. The obtained fractional inhibitory concentration suggested that TGII could alone exert antistaphylococcal activity, and TGII combined with low doses of antibiotics displayed synergistic effects against MRSA. Moreover, we found that TGII exerted bactericidal activity by reducing the expression of mecA followed by the negative regulation of the penicillin-binding protein 2a (PBP2a) of MRSA. Transmission electron microscopy (TEM) images further confirmed that TGII destroyed the integrity of the cell wall of MRSA and caused the loss of cytoplasm content. In conclusion, we evidenced the antibacterial effects of TGII against MRSA, which enables the effective dose of current antibiotics to be reduced and the predicament of drug-resistant S. aureus isolates to be overcome.
Ellagitannin biosynthesis: laccase-catalyzed dimerization of Tellimagrandin II to cornusiin E in Tellima grandiflora
Phytochemistry 2003 Dec;64(7):1197-201.PMID:14599517DOI:10.1016/j.phytochem.2003.08.013.
An enzyme has been purified from leaves of the weed Tellima grandiflora (fringe cups, Saxifragaceae) that catalyzed the O2-dependent oxidation of the monomeric ellagitannin, Tellimagrandin II, to a dimeric derivative, cornusiin E. The apparently homogeneous enzyme preparation had a Mr of ca. 160,000 (with four subunits of Mr 40,000), a pH-optimum and an isoelectric point at pH 5.2, and was most stable at pH 4.3. Inhibition studies revealed that this new enzyme, for which the systematic name 'Tellimagrandin II: O2 oxidoreductase' is proposed, is a member of the laccase (EC 1.10.3.2) family of phenol oxidases. The properties of this enzyme differed from that of a related laccase that catalyzed the transition of 1,2,3,4,6-pentagalloylglucopyranose to Tellimagrandin II, the preceding step in the biosynthetic route to cornusin E.
Lipopolysaccharide-Induced Nitric Oxide and Prostaglandin E2 Production Is Inhibited by Tellimagrandin II in Mouse and Human Macrophages
Life (Basel) 2021 Apr 30;11(5):411.PMID:33946374DOI:10.3390/life11050411.
Sepsis develops from a serious microbial infection that causes the immune system to go into overdrive. The major microorganisms that induce sepsis are Gram-negative bacteria with lipopolysaccharide (LPS) in their cell walls. Nitric oxide (NO) and cyclooxygenase-2 (COX-2) are the key factors involved in the LPS-induced pro-inflammatory process. This study aimed to evaluate the effects of polyphenol Tellimagrandin II (TGII) on anti-inflammatory activity and its underlying basic mechanism in murine macrophage cell line RAW 264.7 and human monocyte-derived macrophages. Macrophages with more than 90% cell viability were found in the cytotoxicity assay under 50 μM TGII. Pre- or post-treatment with TGII significantly reduced LPS-induced inducible nitric oxide synthase (NOS2) protein and mRNA expression, reducing LPS-induced COX-2 protein. Downstream of NOS2 and COX-2, NO and prostaglandin E2 (PGE2) were significantly inhibited by TGII. Upstream of NOS2 and COX-2, phospho-p65, c-fos and phospho-c-jun were also reduced after pre-treatment with TGII. Mitogen-activated protein kinases (MAPKs) are also critical to nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) stimulation, and phospho-p38 expression was found to have been blocked by TGII. TGII efficiently reduces LPS-induced NO production and its upstream regulatory factors, suggesting that TGII may be a potential therapeutic agent for sepsis and other inflammatory diseases.
Oxidation of pentagalloylglucose to the ellagitannin, Tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves
Phytochemistry 2003 Feb;62(3):301-6.PMID:12620341DOI:10.1016/s0031-9422(02)00557-5.
A new enzyme has been isolated from leaves of the weed Tellima grandiflora (fringe cups, Saxifragaceae) that catalyzed the O(2)-dependent oxidation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose to Tellimagrandin II, the first intermediate in the (4)C(1)-glucose derived series of ellagitannins. CD-spectra revealed that the 4,6-O-HHDP-residue of the in vitro product had the (S)-stereoconfiguration characteristic of Tellimagrandin II from natural sources. The enzyme, for which a M(r) of ca. 60,000 was determined, was purified to apparent homogeneity. It had a pH-optimum at pH 5.0, an isoelectric point at pH 6.3 and was most stable at pH 4.2. Inhibition studies suggested that this new enzyme, for which the systematic name 'pentagalloylglucose: O(2) oxidoreductase' is proposed, belongs to the vast group of laccase-type phenol oxidases (EC 1.10.3.2).
Ellagitannin Chemistry. Syntheses of Tellimagrandin II and a Dehydrodigalloyl Ether-Containing Dimeric Gallotannin Analogue of Coriariin A
J Org Chem 1999 Jan 8;64(1):209-216.PMID:11674105DOI:10.1021/jo9816966.
The first chemical synthesis of the naturally occurring ellagitannin Tellimagrandin II is reported. Key steps of the synthesis include the atropselective oxidative coupling of suitably protected galloyl rings at the O(4) and O(6) positions of a glucopyranose core, and the stereoselective acylation of the derived anomeric alcohol with a galloyl chloride. In addition, the synthesis of a novel gallotannin-ellagitannin hybrid is described. This dimeric construct relied on a hetero Diels-Alder cycloaddition/reductive rearrangement sequence to deliver the intact skeleton from a monomeric pentagalloylglucose-based orthoquinone.