Myrtillin
(Synonyms: 氯化飞燕草素葡萄糖苷; Delphinidin 3-O-glucoside chloride; Delphinidin 3-O-β-glucoside chloride) 目录号 : GC44263
A natural anthocyanin
Cas No.:6906-38-3
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
| Cell experiment [1]: | |
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Cell lines |
MSCs |
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Preparation Method |
The cells cultured for 24 hours with 50 uM of Myrtillin and stimulated or not with 1.25 g/mL of LPS. |
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Reaction Conditions |
50 µM Myrtillin for 24 hours |
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Applications |
50 µM Myrtillin increased the percentage of cells in the S/G2/M cycle phase. Mesenchymal stem cells produce soluble factors. |
| Animal experiment [2]: | |
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Animal models |
Rabbit |
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Preparation Method |
A rabbit model of atherosclerosis (AS) was established by 12 weeks of a high-fat diet (HFD). The rabbits were divided into five groups: control, AS, simvastatin (4 mg/kg), and two Myrtillin groups (10 and 20 mg/kg). After treatment with Myrtillin or simvastatin by oral gavage for 12 weeks, the lipid profiles were measured. |
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Dosage form |
10 and 20 mg/kg Myrtillin for 12 weeks |
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Applications |
DP (20 mg/kg) decreased serum TG, TC, LDL-C, and HDL-C. Myrtillin (20 mg/kg) also reduced lipid levels in the liver and aorta. Myrtillin (20 mg/kg) down-regulated the mRNA levels of IL-6, VCAM-1, and NF-κB and up-regulated the mRNA levels of GSH-PX and SOD1. |
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References: [1]: Bruna Roberta Oliveira Neves, Sumara de Freitas, et,al. Delphinidin-3-O-glucoside in vitro suppresses NFκB and changes the secretome of mesenchymal stem cells affecting macrophage activation,Nutrition,2022,111853,ISSN 0899-9007, |
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Myrtillin (Delphinidin 3-o-glucoside) is a kind of anthocyanin monomer, which is mainly distributed in various plants and can be analyzed qualitatively and quantitatively by high performance liquid chromatography (HPLC) Mass spectrometry (Mass) and nuclear magnetic resonance (NMR)
Myrtillin at 50 uM does not affect cell viability, also showing that delphinidin in association with lipopolysaccharide was able to induce MSC proliferation. Additionally, delphinidin modulated the MSC immune response, showing increased levels of anti-inflammatory cytokines such as IL-10 and TGF-β as well as lower expression of NFκB[2]. Myrtillin showed potential for binding with and inhibiting immune checkpoints, PD-1 and PD-L1, which can activate immune response in the tumor microenvironment and induce cancer cell death[3].
Myrtillin (20 mg/kg) decreased serum TG, TC, LDL-C, and HDL-C. Myrtillin (20 mg/kg) also reduced lipid levels in the liver and aorta. Myrtillin (20 mg/kg) down-regulated the mRNA levels of IL-6, VCAM-1, and NF-κB and up-regulated the mRNA levels of GSH-PX and SOD1.DP alleviated the HFD-induced oxidative stress and inflammation in atherosclerosis rabbits[1].
References:
[1]: Sun B, Li F, et,al.Delphinidin-3-O-glucoside, an active compound of Hibiscus sabdariffa calyces, inhibits oxidative stress and inflammation in rabbits with atherosclerosis. Pharm Biol. 2022 Dec;60(1):247-254. doi: 10.1080/13880209.2021.2017469. PMID: 35130117; PMCID: PMC8823684.
[2]: Bruna Roberta Oliveira Neves, Sumara de Freitas, et,al. Delphinidin-3-O-glucoside in vitro suppresses NFκB and changes the secretome of mesenchymal stem cells affecting macrophage activation,Nutrition,2022,111853,ISSN 0899-9007,
[3]: Mazewski C, Kim MS,et,al. Anthocyanins, delphinidin-3-O-glucoside and cyanidin-3-O-glucoside, inhibit immune checkpoints in human colorectal cancer cells in vitro and in silico. Sci Rep. 2019 Aug 9;9(1):11560. doi: 10.1038/s41598-019-47903-0. PMID: 31399602; PMCID: PMC6689002.
桃金娘苷（Delphinidin 3-o-glucoside）是一种花青素单体，主要分布于各种植物中，可用高效液相色谱法（HPLC）质谱法（Mass）和核磁共振法进行定性和定量分析(NMR)
50 uM Myrtillin 不影响细胞活力，这也表明飞燕草素与脂多糖结合能够诱导 MSC 增殖。此外，飞燕草素调节 MSC 免疫反应，显示抗炎细胞因子水平升高，如 IL-10 和 TGF-β；以及 NFκB[2] 的较低表达。 Myrtillin 具有结合和抑制免疫检查点 PD-1 和 PD-L1 的潜力，可激活肿瘤微环境中的免疫反应并诱导癌细胞死亡[3]。
Myrtillin (20 mg/kg) 降低血清 TG、TC、LDL-C 和 HDL-C。 Myrtillin (20 mg/kg) 还可以降低肝脏和主动脉中的脂质水平。 Myrtillin (20 mg/kg) 下调 IL-6、VCAM-1 和 NF-κB 的 mRNA 水平并上调 GSH-PX 和 SOD1 的 mRNA 水平。DP 减轻了 HFD 诱导的氧化应激兔动脉粥样硬化和炎症[1]。
| Cas No. | 6906-38-3 | SDF | |
| 别名 | 氯化飞燕草素葡萄糖苷; Delphinidin 3-O-glucoside chloride; Delphinidin 3-O-β-glucoside 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(O)=C(O)C(O)=C4)=[O+]2.[Cl-] | ||
| 分子式 | C21H21O12•Cl | 分子量 | 500.8 |
| 溶解度 | DMF: 1.5 mg/ml,DMSO: 10 mg/ml,PBS (pH 7.2): 0.2 mg/ml | 储存条件 | Store at -20°C, sealed storage, away from moisture and 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 | 1.9968 mL | 9.984 mL | 19.9681 mL |
| 5 mM | 0.3994 mL | 1.9968 mL | 3.9936 mL |
| 10 mM | 0.1997 mL | 0.9984 mL | 1.9968 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。
Thermodynamic and kinetic properties of a new myrtillin-vescalagin hybrid pigment
J Agric Food Chem 2013 Nov 27;61(47):11569-78.PMID:24164407DOI:10.1021/jf403319u.
During red wine maturation in contact with oak wood, C-glucosidic ellagitannins can react with anthocyanins, leading to new pigments. In this work the thermodynamic and kinetic constants of the network pH-dependent equilibrium of a new Myrtillin (delphinidin 3-O-glucoside)-vescalagin hybrid pigment (1-deoxyvescalagin-(1β→8)-myrtillin) have been determined by UV-visible absorption and stopped-flow experiments and compared to those determined for Myrtillin. The vescalagin substitution at the C-8' center of Myrtillin entails important variations in the pigment behavior upon pH changes. The hybrid pigment showed lower pK'a and pKa values and a much higher value of Kt. As a consequence, at moderately acidic pH values (4 < pH < 6), the percentage of the hemiketal is much lower and the quinoidal base and the (E)-chalcone represent higher percentages relative to those for Myrtillin. Therefore, the hybrid pigment can provide in slightly acidic or neutral solutions an exceptionally different color compared to that of Myrtillin.
Hemisynthesis and structural and chromatic characterization of delphinidin 3-O-glucoside-vescalagin hybrid pigments
J Agric Food Chem 2013 Nov 27;61(47):11560-8.PMID:24215431DOI:10.1021/jf4033188.
During red wine maturation in the presence of oak wood, reactions involving anthocyanins and ellagitannins might affect wine organoleptic properties such as color and astringency. In this work, the condensation reaction between Myrtillin (delphinidin 3-O-glucoside) and vescalagin has been performed to determine the behavior of this anthocyanin in this kind of reaction and to assess the possible impact of such a reaction in wine color modulation. Two different hybrid pigments have been hemisynthetized and characterized by HPLC-DAD-MS and NMR spectroscopy. These pigments have been identified as 1-deoxyvescalagin-(1β→8)-myrtillin (major) and 1-deoxyvescalagin-(1β→6)-myrtillin (minor). The minor pigment could be formed both by the condensation reaction and by a regioisomerization process from the major pigment. Moreover, the chromatic properties of these pigments have been studied and compared to those of Myrtillin. The hybrid pigments showed an important bathochromic shift (ca. 20 nm) in the maximum absorbance wavelength and lower molar absorption coefficients.
Effect of polyphenols from coffee and grape on gene expression in myoblasts
Mech Ageing Dev 2018 Jun;172:115-122.PMID:29174054DOI:10.1016/j.mad.2017.11.015.
Coffee and grape contain various bioactive compounds like polyphenols that may exert beneficial effects, especially antioxidant activity, on human health upon consumption. However, the molecular mechanisms through which these effects are achieved are not fully elucidated. Thus, in the present study in order to investigate these mechanisms, a whole genome expression DNA microarray analysis was carried out in myoblasts treated with polyphenols of coffee and grape pomace at concentrations that improved the redox status. Grape was composed of catechin, epicatechin, cyanidin, malvidin, delphinidin, petunidin, Myrtillin, kuromanin, oenin, peonidin, quercetin, gallic acid and caftaric acid as LC-MS revealed, with a total polyphenolic content (TPC) of 648 mg of gallic acid equivalents/g of dry matter. Coffee had a TPC of 42.61 mg GAE/g coffee and was composed of 3-chlorogenic acid (16.61 mg/g), 4- and 5-chlorogenic acids (13.62 mg/g), as UHPLC-HRMS revealed. According to the results, grape polyphenols altered mainly the expression of cytoskeleton and differentiation-associated genes, while coffee compounds had a more profound effect, on the expression levels of many metabolic and antioxidant genes possibly through the nuclear factor (erythroid-derived 2) like-2 (Nrf2) pathway.
Interaction between gliadins and anthocyan derivatives
Food Chem 2011 Dec 1;129(3):1100-7.PMID:25212343DOI:10.1016/j.foodchem.2011.05.084.
The interaction of gliadins with some anthocyanins (e.g. Myrtillin, malvin, keracyanin, callistephin) and anthocyanidins (e.g. delphinidin, pelargonidin, cyanidin) has been analysed in aqueous solution at pH condition of the stomach, in which these compounds are initially metabolized. NMR, FT-IR and UV-Vis spectroscopic methods have been employed to determine the anthocyanin binding mode. The spectroscopic data seem to indicate that anthocyans are located along the polypeptide chains of gliadins in a generical molecular interaction between the two moieties. Our data do not exclude that hydrogen bonding interaction too is operating. Anthocyan-gliadins complexes are very soluble in acidic conditions. The results provide new insights into anthocyan-protein interaction and may have relevance to human health.
Circular dichroism of anthocyanidin 3-glucoside self-aggregates
Phytochemistry 2013 Apr;88:92-8.PMID:23337569DOI:10.1016/j.phytochem.2012.12.011.
Self-association constants for the flavylium cations of the six most common anthocyanidin 3-glucosides were determined by circular dichroism (CD) and UV-Vis spectroscopy. Along with previous (1)H NMR results, all measurements were consistent with a monomer-dimer model. The CD spectra of the anthocyanidin 3-glucosides were similar to the analogues 3,5-diglucosides. All dimers of the anthocyanidin 3-glucosides exhibited left-handed CD signals, with petunidin-3-glucoside and Myrtillin having the most intense signals. In addition, the magnitude of the molar ellipticity, [θ], was generally higher for the 3-glucosides than for the 3,5-diglucosides. For all six anthocyanins studied, the CD absorption spectra of their dimers showed evidence of the splitting of the monomer absorption into lower (J aggregates) and higher (H aggregates) energy bands. The angle and the distance between the dipolar moments of the two monomers comprising the dimer were obtained from the lower energy absorption band. While the angle was more or less similar in all six dimers, the separation distance between the monomer dipole moments differed dramatically. The intensity of the CD signal displayed a linear dependence with the inverse square of the dipole moment distances.