Oenin
(Synonyms: 氯化锦葵色素-3-Β-葡糖苷,Malvidin-3-O-glucoside chloride; Oenin chloride) 目录号 : GC44494
A natural anthocyanin
Cas No.:7228-78-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oenin is a natural anthocyanin found in plants. It is the 3-glucoside of malvidin, an O-methylated anthocyanidin. Oenin has neuroprotective effects, reducing amyloid β-induced cytotoxicity and diminishing reactive oxygen species production in Neuro-2A cells when applied at 50 µM. Oenin, at 30 µM, also stimulates autophagy in human osteosarcoma U2OS cells.
| Cas No. | 7228-78-6 | SDF | |
| 别名 | 氯化锦葵色素-3-Β-葡糖苷,Malvidin-3-O-glucoside chloride; Oenin chloride | ||
| Canonical SMILES | OC(C=C1O)=CC2=C1C=C(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)C(C4=CC(OC)=C(O)C(OC)=C4)=[O+]2.[Cl-] | ||
| 分子式 | C23H25O12•Cl | 分子量 | 528.9 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 2 mg/ml,PBS (pH 7.2): 0.5 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 | 1.8907 mL | 9.4536 mL | 18.9072 mL |
| 5 mM | 0.3781 mL | 1.8907 mL | 3.7814 mL |
| 10 mM | 0.1891 mL | 0.9454 mL | 1.8907 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。
Oenin/Syringic Acid Copigmentation: Insights From a Theoretical Study
Front Chem 2019 Aug 19;7:579.PMID:31482087DOI:10.3389/fchem.2019.00579.
On the basis of the dispersion-corrected density functional theory, a computational model is proposed to describe the Oenin/syringic acid copigmentation and to explore the non-covalent interaction between the anthocyanin and the copigment in the framework of implicit solvent approach. The predicted binding free energy and visible spectrum shift of this copigmentation complex are in accordance with the experimental observations. The used model provides a good structural description of Oenin/syringic acid complex and suggests that the intermolecular hydrogen bonding, in which the hydroxyl-rich sugar moiety in Oenin plays a key role, may be the determinant for the formation and nature of the copigmentation complex.
Oenin and Quercetin Copigmentation: Highlights From Density Functional Theory
Front Chem 2018 Jun 28;6:245.PMID:30003074DOI:10.3389/fchem.2018.00245.
Making use of anthocyanin copigmentation, it is possible to effectively improve color quality and stability of red wines and other foods. This can be done by selecting strong copigments, but a 1-fold experimental screening usually entails a high cost and a low efficiency. The aim of this work is to show how a theoretical model based on density functional theory can be useful for an accurate and rapid prediction of copigmentation ability of a copigment. The present study, concerning the copigmentation between Oenin and quercetin under the framework of implicit solvent, indicates that, in these conditions, the intermolecular hydrogen bonds play an important role in the system stabilization. The dispersion interaction slightly affects the structure, energies and UV-Vis spectral properties of the copigmentation complex.
Copigmentation evidence of Oenin with phenolic compounds: A comparative study of spectrographic, thermodynamic and theoretical data
Food Chem 2020 May 30;313:126163.PMID:31945702DOI:10.1016/j.foodchem.2020.126163.
The copigmentation effects of polyphenol with different structures vary greatly. Therefore, the aim of this study is to investigate possible interactions in red wine model solutions between Oenin and three phenolic compounds: danshensu, caffeic acid and rosmarinic acid. Our results show that the copigmentation of rosmarinic acid is the strongest among the compounds tested. The colourimetric parameters indicate that colour intensity becomes enhanced with increasing concentration of these copigments, leading to darker and more vivid bluish colours. Thermodynamic and quantum chemical investigations are performed to interpret the absorption properties in the visible range. Fluorescence spectroscopy confirms the interaction between caffeic acid and Oenin, while FTIR spectroscopic results further suggest a role for hydrogen bonds in the overall process. To our knowledge, this is the first experimentally corroborated direct evidence of hydrogen bonds in copigmentation.
Structural features of copigmentation of Oenin with different polyphenol copigments
J Agric Food Chem 2013 Jul 17;61(28):6942-8.PMID:23829187DOI:10.1021/jf401174b.
The copigmentation binding constants (K) for the interaction of different copigments with Oenin (major red wine anthocyanin) were determined. All tests were performed in a 12% ethanol citrate buffer solution (0.2 M) at pH 3.5, with an ionic strength adjusted to 0.5 M by the addition of sodium chloride. Over the past years, several copigmentation studies were made and many copigments were tested, but none of them included prodelphinidin B3 or a dimeric-type adduct like oenin-(O)-catechin, probably due to the difficulty in obtaining them. The data yielded from this study allowed concluding that (a) the presence of a pyrogallol group in the B ring of the flavan-3-ol structure slightly increases the copimentation potential and (b) within all copigments tested oenin-(O)-catechin was revealed to be the best. According to computational studies performed on epicatechin/Oenin, epigallocatechin/Oenin, procyanidin B3/Oenin, and oenin-(O)-catechin/Oenin complexes, the ΔGbinding energy of the oenin-(O)-catechin/Oenin complex is the most negative compared to the other copigmentation complexes, hence being more stable and thermodynamically favored. All structural data show that oenin-(O)-catechin and epigallocatechin are closer to the pigment molecule, which is in accordance with these two copigments having the highest experimental copigmentation binding constants for Oenin.
The Anthocyanins, Oenin and Callistephin, Protect RPE Cells Against Oxidative Stress
Photochem Photobiol 2017 Mar;93(2):590-599.PMID:27935050DOI:10.1111/php.12683.
The retinal pigment epithelium (RPE) is a highly metabolic layer of postmitotic cells lining Bruch's membrane in the retina. While these cells contain endogenous photosensitizers that mediate blue light-induced damage, it has also been shown that blue light exposure damages mitochondrial DNA in RPE cells resulting in mitochondrial dysfunction and unregulated generation of reactive oxygen species (ROS). As RPE cells are postmitotic, it is imperative to decrease oxidative stress to these cells and preserve function. Dietary plant-derived antioxidants such as anthocyanins offer a simple and accessible solution for decreasing oxidative stress. The anthocyanins malvidin-3-O-glucoside (Oenin) and pelargonidin-3-O-glucoside (callistephin) were tested for their ability and efficacy in decreasing ROS generation and preserving mitochondrial redox activity in blue light-irradiated ARPE-19 cells. A significant decrease in intracellular ROS with concurrent increase in mitochondrial redox activity was observed for tested concentrations of Oenin, while callistephin was beneficial to stressed cells at higher concentrations. These findings suggest anthocyanins are effective antioxidants in blue light-stressed RPE cells in vitro. Additionally, oxidation products of these anthocyanins were examined using LC/MS and findings suggest the possibility of multiple oxidation sites for these compounds.