Delphinidin (chloride)
(Synonyms: 氯化花翠素) 目录号 : GC43406Natural vasorelaxant and inhibitor of EGFRs and HATs
Cas No.:528-53-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Delphinidin (chloride) is an anthocyanidin, a natural plant pigment which serves as the precursor of certain anthocyanins that provide the blue-red colors of flowers, fruits, and red wine.[1] Delphinidin induces the release of nitric oxide by vascular endothelium, causing vasorelaxation.[2] It also inhibits signaling through epithelial growth factor receptors, suppressing the expression of estrogen receptor α and inducing both apoptosis and autophagy at a dose of 1-40 μM.[3],[4] Delphinidin also inhibits the histone acetyltransferase activities of p300/CBP (IC50 = ~ 30 μM).[5]
Reference:
[1]. Holton, T.A., Brugliera, F., Lester, D.R., et al. Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 366, 276-279 (1993).
[2]. Andriambeloson, E., Magnier, C., Haan-Archipoff, G., et al. Natural dietary polyphenolic compounds cause endothelium-dependent vasorelaxation in rat thoracic aorta. Journal of Nutrition 128, 2324-2333 (1998).
[3]. Ozbay, T., and Nahta, R. Delphinidin inhibits HER2 and Erk1/2 signaling and suppresses growth of HER2-overexpressing and triple negative breast cancer cell lines. Breast Cancer 5, 143-154 (2011).
[4]. Aiyer, H.S., Warri, A.M., Woode, D.R., et al. Influence of berry polyphenols on receptor signaling and cell-death pathways: Implications for breast cancer prevention. Journal of Agricultural and Food Chemistry 1-16 (2012).
[5]. Seong, A.R., Yoo, J.Y., Choi, K.C., et al. Delphinidin, a specific inhibitor of histone acetyltransferase, suppresses inflammatory signaling via prevention of NF-κB acetylation in fibroblast-llike synoviocyte MH7A cells. Biochemical and Biophysical Research Communications 18(1), 581-586 (2011).
| Cas No. | 528-53-0 | SDF | |
| 别名 | 氯化花翠素 | ||
| 化学名 | 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium, chloride | ||
| Canonical SMILES | OC1=CC2=C(O)C=C(O)C=C2[O+]=C1C3=CC(O)=C(O)C(O)=C3.[Cl-] | ||
| 分子式 | C15H11ClO7 | 分子量 | 338.7 |
| 溶解度 | 30mg/mL in ethanol or DMSO or DMF | 储存条件 | -20°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 | 2.9525 mL | 14.7623 mL | 29.5247 mL |
| 5 mM | 0.5905 mL | 2.9525 mL | 5.9049 mL |
| 10 mM | 0.2952 mL | 1.4762 mL | 2.9525 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。
Delphinidin and Its Glycosides' War on Cancer: Preclinical Perspectives
Int J Mol Sci 2021 Oct 25;22(21):11500.PMID:34768930DOI:10.3390/ijms222111500.
Until now, several studies have looked at the issue of anthocyanin and cancer, namely the preventive and inhibitory effects of anthocyanins, as well as the underlying molecular processes. However, no targeted review is available regarding the anticarcinogenic effects of Delphinidin and its glycosides on various cancers and their plausible molecular mechanisms. Considerable evidence shows significant anticancer properties of delphinidin-rich preparations and Delphinidin alone both in vitro and in vivo. This review covers the in vitro and preclinical implications of delphinidin-mediated cell protection and cancer prevention; thus, we strongly recommend that delphinidin-rich preparations be further investigated as potential functional food, dietary antioxidant supplements, and natural health products targeting specific chronic diseases, including cancer. In addition to in vitro investigations, future research should focus on more animal and human studies to determine the true potential of Delphinidin.
Anthocyanins From Clitoria ternatea Flower: Biosynthesis, Extraction, Stability, Antioxidant Activity, and Applications
Front Plant Sci 2021 Dec 17;12:792303.PMID:34975979DOI:10.3389/fpls.2021.792303.
Clitoria ternatea plant is commonly grown as an ornamental plant and possesses great medicinal value. Its flower is edible and also known as blue pea or butterfly pea flower. The unique feature of anthocyanins present in blue pea flowers is the high abundance of polyacylated anthocyanins known as ternatins. Ternatins are polyacylated derivatives of Delphinidin 3,3',5'-triglucoside. This review covers the biosynthesis, extraction, stability, antioxidant activity, and applications of anthocyanins from Clitoria ternatea flower. Hot water extraction of dried or fresh petals of blue pea flower could be employed successfully to extract anthocyanins from blue pea flower for food application. Blue pea flower anthocyanins showed good thermal and storage stability, but less photostability. Blue pea flower anthocyanins also showed an intense blue colour in acidic pH between pH 3.2 to pH 5.2. Blue pea flower anthocyanin extracts demonstrate significant in vitro and cellular antioxidant activities. Blue pea flower anthocyanins could be used as a blue food colourant in acidic and neutral foods. The incorporation of blue pea flower anthocyanins in food increased the functional properties of food such as antioxidant and antimicrobial properties. Blue pea flower anthocyanins have also been used in intelligent packaging. A comparison of blue pea flower anthocyanins with two other natural blue colouring agents used in the food industry, spirulina or phycocyanin and genipin-derived pigments is also covered. Anthocyanins from blue pea flowers are promising natural blue food colouring agent.
Delphinidin chloride and Its Hydrolytic Metabolite Gallic Acid Promote Differentiation of Regulatory T cells and Have an Anti-inflammatory Effect on the Allograft Model
J Food Sci 2019 Apr;84(4):920-930.PMID:30977922DOI:10.1111/1750-3841.14490.
Regulatory T cells (Tregs) control the reactivity of other T cells to prevent excessive inflammatory responses. They also plays a role in preventing autoimmune diseases; but when they are overproduced, they decreased vital immunity, which can lead to invasion of external pathogens. Therefore, it is most important in preventing the development of immune diseases to maintain the homeostasis of these cells. Delphinidin chloride is an anthocyanidin and known to have anti-oxidant activities. However, its structure is very unstable and easily decomposed. One of these degradation products is gallic acid, which also has anti-oxidant effects. In this study, we examined the effect of these materials on Tregs in controlling immune response. It was found that these materials further promote differentiation into Tregs, and TGF-β and IL-2 related signals are involved in this process. Furthermore, it was verified that a variety of immunosuppressive proteins were secreted more, and the function of induced Tregs was also increased. Finally, in the allograft model, we could find a decrease in activated T cells when these materials were treated because they increased differentiation into Tregs. Therefore, these two materials are expected to become new candidates for the treatment of diseases caused by excessive activation of immune cells, such as autoimmune diseases. PRACTICAL APPLICATION: Delphinidin, a kind of anthocyanin rich in pigmented fruits, and its hydrolytic metabolite, gallic acid, are known to have antimicrobial and anti-oxidant properties. In this experiment, it was shown that Delphinidin and gallic acid had an effect of increasing the differentiation of regulatory T cells, and the effect of suppressing the function of memory T cells was also observed. Due to these functions, Delphinidin and gallic acid might have the potential to be used as immune suppressive agents in organ transplant and autoimmune disease patients or be a model for food development associated with the immune system.
The Multifunctional Benefits of Naturally Occurring Delphinidin and Its Glycosides
J Agric Food Chem 2019 Oct 16;67(41):11288-11306.PMID:31557009DOI:10.1021/acs.jafc.9b05079.
Delphinidin (Del) and its glycosides are water-soluble pigments, belonging to a subgroup of flavonoids. They are health-promoting candidates for pharmaceutical and nutraceutical uses, as indicated by exhibiting antioxidation, anti-inflammation, antimicroorganism, antidiabetes, antiobesity, cardiovascular protection, neuroprotection, and anticancer properties. Glycosylation modification of Del is associated with increased stability and reduced biological activity. Del and its glycosides can be the alternative inhibitors of CBRs, ERα/β, EGFR, BCRP, and SGLT-1, and virtual docking indicates that the sugar moiety may not effectively interact with the active sites of the targets. Structure-based characteristics confer the multifunctional properties of Del and its glycosides. Because of their health-promoting effects, Del and its glycosides are promising and have been developed as potential pharmaceuticals. However, more investigation on the underlying mechanisms of Del and its glycosides in mediating cellular processes with high specificity are still needed. The research progression of Del and its glycosides over the last 10 years is comprehensively reviewed in this article.
Antioxidant activity of Delphinidin and pelargonidin: Theory and practice
J Food Biochem 2022 Aug;46(8):e14192.PMID:35484873DOI:10.1111/jfbc.14192.
The quantum chemical density functional theory and in vitro chemical-based antioxidant assays were used to research the reaction mechanism of Delphinidin/pelargonidin with free radicals including superoxide anion radicals (O2 - ∙) and hydroperoxide radicals (OOH∙). The geometric configuration, bond dissociation energy, PCM (polarizable continuum model) solvent model reaction enthalpy changes were studied to explain the transition states, and the reaction enthalpy change value was calculated to determine the active site. From the results of spatial configuration, Delphinidin showed a stronger conjugation effect than that of pelargonidin. The dihedral angle between the three rings of Delphinidin was almost 180°, and the angle between the B and C rings was only -2.81868°. Both coplanar and antioxidant activity of Delphinidin was better than pelargonidin. The consequences of reaction enthalpy change in PCM were consistent with the bond dissociation energy. The phenolic hydroxyl bond dissociation energy of Delphinidin was slightly smaller than that of pelargonidin. Moreover, the C4' site of Delphinidin and the C3 site of pelargonidin were the active sites for scavenging free radicals. The free radical scavenging ability of Delphinidin was marginally higher than that of pelargonidin. On the other hand, in vitro antioxidant results proved the scavenging ability of Delphinidin and pelargonidin on superoxide anions, DPPH, and ABTS∙+ free radicals. It was shown that the chemical-based antioxidant activity was consistent with the theoretical calculation results, with Delphinidin showing greater antioxidant activity. These results could explain the antioxidant mechanism of Delphinidin/pelargonidin in scavenging free radicals from chemical reactions. PRACTICAL APPLICATIONS: This manuscript explained the antioxidant mechanism of Delphinidin/pelargonidin in scavenging free radicals through the analysis of the geometric configuration of Delphinidin/pelargonidin and the theoretical calculation of the reaction transition state. It could also speculate on the possible reaction sites, and provide a basis for judging how to efficiently select antioxidants with great antioxidant activity.