Peonidin 3-O-glucoside (chloride)
(Synonyms: 氯化葡萄糖苷芍药素) 目录号 : GC45777
An anthocyanin with diverse biological activities
Cas No.:6906-39-4
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
Peonidin 3-O-glucoside is a metabolite of cyanidin 3-glucoside and an anthocyanin that has been found in red wine extracts and has diverse biological activities, including antioxidant, anti-inflammatory, antiproliferative, and anti-metastatic properties.1,2,3,4,5 Peonidin 3-O-glucoside scavenges 2,2-diphenyl 1-picylhydrazyl and ABTS radicals in cell-free assays (EC50s = 757 and 98 μM, respectively).2 It inhibits IL-1β-induced phosphorylation of IKKα, IκBα, and ERK in human articular chondrocytes when used at a concentration of 2.5 μM.3 Peonidin 3-O-glucoside inhibits the growth of Hs578T human breast cancer cells in vitro in a concentration-dependent manner and decreases pulmonary metastasis in a mouse model of Lewis lung carcinoma when administered at a dose of 20 mg/kg.4,5
|1. Vanzo, A., Vrhovsek, U., Tramer, F., et al. Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver. J. Nat. Prod. 74(5), 1049-1054 (2011).|2. Li, Y., Li, L., Cui, Y., et al. Separation and purification of polyphenols from red wine extracts using high speed counter current chromatography. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1054, 105-113 (2017).|3. Wongwichai, T., Teeyakasem, P., Pruksakorn, D., et al. Anthocyanins and metabolites from purple rice inhibit IL-1β-induced matrix metalloproteinases expression in human articular chondrocytes through the NF-κB and ERK/MAPK pathway. Biomed. Pharmacother. 112:108610, (2019).|4. Chen, P.-N., Chu, S.-C., Chiou, H.-L., et al. Cyanidin 3-glucoside and peonidin 3-glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo. Nutr. Cancer 53(2), 232-243 (2005).|5. Ho, M.-L., Chen, P.-N., Chu, S.-C., et al. Peonidin 3-glucoside inhibits lung cancer metastasis by downregulation of proteinases activities and MAPK pathway. Nutr. Cancer 62(4), 505-516 (2010).
| Cas No. | 6906-39-4 | SDF | |
| 别名 | 氯化葡萄糖苷芍药素 | ||
| Canonical SMILES | OC1=CC(O)=C(C=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C3=CC(OC)=C(O)C=C3)=[O+]4)C4=C1.[Cl-] | ||
| 分子式 | C22H23O11.Cl | 分子量 | 498.9 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at 2-8°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 | 2.0044 mL | 10.022 mL | 20.0441 mL |
| 5 mM | 0.4009 mL | 2.0044 mL | 4.0088 mL |
| 10 mM | 0.2004 mL | 1.0022 mL | 2.0044 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。
Integrated metabolome and transcriptome analysis of the anthocyanin biosynthetic pathway in relation to color mutation in miniature roses
BMC Plant Biol 2021 Jun 4;21(1):257.PMID:34088264DOI:10.1186/s12870-021-03063-w.
Background: Roses are famous ornamental plants worldwide. Floral coloration is one of the most prominent traits in roses and is mainly regulated through the anthocyanin biosynthetic pathway. In this study, we investigated the key genes and metabolites of the anthocyanin biosynthetic pathway involved in color mutation in miniature roses. A comparative metabolome and transcriptome analysis was carried out on the Neptune King rose and its color mutant, Queen rose, at the blooming stage. Neptune King rose has light pink colored petals while Queen rose has deep pink colored petals. Result: A total of 190 flavonoid-related metabolites and 38,551 unique genes were identified. The contents of 45 flavonoid-related metabolites, and the expression of 15 genes participating in the flavonoid pathway, varied significantly between the two cultivars. Seven anthocyanins (cyanidin 3-O-glucosyl-malonylglucoside, cyanidin O-syringic acid, cyanidin 3-O-rutinoside, cyanidin 3-O-galactoside, cyanidin 3-O-glucoside, Peonidin 3-O-glucoside chloride, and pelargonidin 3-O-glucoside) were found to be the major metabolites, with higher abundance in the Queen rose. Thirteen anthocyanin biosynthetic related genes showed an upregulation trend in the mutant flower, which may favor the higher levels of anthocyanins in the mutant. Besides, eight TRANSPARENT TESTA 12 genes were found upregulated in Queen rose, probably contributing to a high vacuolar sequestration of anthocyanins. Thirty transcription factors, including two MYB and one bHLH, were differentially expressed between the two cultivars. Conclusions: This study provides important insights into major genes and metabolites of the anthocyanin biosynthetic pathway modulating flower coloration in miniature rose. The results will be conducive for manipulating the anthocyanin pathways in order to engineer novel miniature rose cultivars with specific colors.
Metabolite identification in fresh wheat grains of different colors and the influence of heat processing on metabolites via targeted and non-targeted metabolomics
Food Res Int 2022 Oct;160:111728.PMID:36076417DOI:10.1016/j.foodres.2022.111728.
Phenolic antioxidants are phytochemical components in wheat grains that provide a variety of potential health benefits. The metabolites and antioxidant activity of fresh, mature, and heat-treated, wheat grains with black, blue, purple, and white grain coats were identified by targeted and non-targeted metabolomics. The total phenolic (TPC) and flavonoid contents (TFC) and antioxidant activity (AOA) increased with the darkening of grain color, the general trend being black > purple > blue > white. Purple and black wheat are rich in rutin (3916 µg/kg and 3066 µg/kg, respectively) and peonidin-3-O-glucoside chloride (2595 µg/kg and 1740 µg/kg, respectively), while blue wheat is rich in luteolin (2076 µg/kg). In most cases, TPC, TFC, and AOA had the greatest values in fresh grains and the lowest values in mature grains. Using non-targeted metabolomics, a total of 866 metabolites were identified in the tested fresh wheat grains, 106 flavonoids and 39 phenolic acids. In total, the relative abundance of flavonoids in purple and black wheat was higher than in blue wheat, indicating a higher nutritional value of fresh black and purple grains. After heat processing, the content of most metabolites decreased in heat-treated purple grain, whereas heat treatment significantly increased the content of peonidin-3-O-glucoside chloride (2.27-fold) and cynaroside (12.01-fold). This study clarifies that seed coat color and processing treatments impact the metabolite contents and antioxidant activity of wheat grains, providing valuable information for improving the nutritional quality of food during processing.
Flavonoids Accumulation in Fruit Peel and Expression Profiling of Related Genes in Purple ( Passiflora edulis f. edulis) and Yellow ( Passiflora edulis f. flavicarpa) Passion Fruits
Plants (Basel) 2021 Oct 20;10(11):2240.PMID:34834602DOI:10.3390/plants10112240.
Flavonoids play a key role as a secondary antioxidant defense system against different biotic and abiotic stresses, and also act as coloring compounds in various fruiting plants. In this study, fruit samples of purple (Passiflora edulis f. edulis) and yellow (Passiflora edulis f. flavicarpa) passion fruit were collected at five developmental stages (i.e., fruitlet, green, veraison, maturation, and ripening stage) from an orchard located at Nanping, Fujian, China. The contents of flavonoid, anthocyanin, proanthocyanin, and their metabolites were determined using ultra-performance liquid chromatography-mass spectrometry (UPLC-MS), activities of key enzymes involved in flavonoid metabolism were measured, and expression profiling of related genes was done using quantitative real-time PCR (qRT-PCR). The results revealed that total flavonoids, anthocyanins, and procyanidins were found to be increased in the fruit peel of both cultivars with fruit maturity. Total flavonoids, anthocyanins, procyanidins, flavonoid metabolites (i.e., rutin, luteolin, and quercetin), and anthocyanin metabolites (i.e., cyanidin-3-O-glucoside chloride, peonidin-3-O-glucoside, and pelargonidin-3-O-glucoside) were found abundant in the peel of purple passion fruit, as compared to yellow passion fruit. Principle component analysis showed that the enzymes, i.e., C4H, 4CL, UFGT, and GST were maybe involved in the regulation of flavonoids metabolism in the peel of passion fruit cultivars. Meanwhile, PePAL4, Pe4CL2,3, PeCHS2, and PeGST7 may play an important role in flavonoid metabolism in fruit peel of the passion fruit. This study provides new insights for future elucidation of key mechanisms regulating flavonoids biosynthesis in passion fruit.
Encapsulation of stevia rebaudiana Bertoni aqueous crude extracts by ionic gelation - Effects of alginate blends and gelling solutions on the polyphenolic profile
Food Chem 2019 Mar 1;275:123-134.PMID:30724178DOI:10.1016/j.foodchem.2018.09.086.
We formulated and characterised two alginate blends for the encapsulation of stevia extract (SE) via ionic gelation through an extrusion technique. Calcium chloride in SE and calcium chloride solutions were assessed as crosslinkers to overcome phenolic losses by diffusion and increase encapsulation efficiency (EE). Regardless of the blend, all stevia-loaded beads exhibited high EE (62.7-101.0%). The size of the beads decreased as EE increased. Fourier transform infrared analysis showed increased hydrogen bonding between SE and alginates, confirming the successful incorporation of SE within the matrix. Untargeted metabolomics profiling identified 479 free and encapsulated polyphenolic compounds. Flavonoids (catechin and luteolin equivalents) were predominant in SE whereas tyrosols and 5-pentadecylresorcinol equivalents were predominant in all bead formulations. Three-common discriminant compounds were exclusive to each blend and were inversely affected by the crosslinking conditions. Both alginate blends have been shown to be feasible as carrier systems of stevia extracts independent of crosslinking conditions.
Integrative Transcriptomic and Metabolomic Analysis Reveals the Molecular Mechanism of Red Maple ( Acer rubrum L.) Leaf Coloring
Metabolites 2023 Mar 23;13(4):464.PMID:37110123DOI:10.3390/metabo13040464.
This study employed a combination of ultraviolet spectrophotometry, LC-ESI-MS/MS system, and RNA-sequencing technology; the extracts and isolation of total RNA from the red and yellow leaf strains of red maple (Acer rubrum L.) at different developmental stages were subjected to an intercomparison of the dynamic content of chlorophyll and total anthocyanin, flavonoid metabolite fingerprinting, and gene expression. The metabonomic results indicated that one hundred and ninety-two flavonoids were identified, which could be classified into eight categories in the red maple leaves. Among them, 39% and 19% were flavones and flavonols, respectively. The metabolomic analysis identified 23, 32, 24, 24, 38, and 41 DAMs in the AR1018r vs. AR1031r comparison, the AR1018r vs. AR1119r comparison, the AR1031r vs. AR1119r comparison, the AR1018y vs. AR1031y comparison, the AR1018y vs. AR1119y comparison, and the AR1031y vs. AR1119y comparison, respectively. In total, 6003 and 8888 DEGs were identified in AR1018r vs. AR1031r comparison and in the AR1018y vs. AR1031y comparison, respectively. The GO and KEGG analyses showed that the DEGs were mainly involved in plant hormone signal transduction, flavonoid biosynthesis, and other metabolite metabolic processes. The comprehensive analysis revealed that caffeoyl-CoA 3-O-methyltransferase (Cluster-28704.45358 and Cluster-28704.50421) was up-regulated in the red strain but down-regulated in the yellow strain, while Peonidin 3-O-glucoside chloride and Pelargonidin 3-O-beta-D-glucoside were up-regulated in both the red and yellow strains. By successfully integrating the analyses on the behavior of pigment accumulation, dynamics of flavonoids, and differentially expressed genes with omics tools, the regulation mechanisms underlying leaf coloring in red maple at the transcriptomic and metabolomic levels were demonstrated, and the results provide valuable information for further research on gene function in red maple.