Petunidin 3-O-glucoside
(Synonyms: 矮牵牛素葡萄糖苷) 目录号 : GC44606
An anthocyanin with antiproliferative properties
Cas No.:6988-81-4
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Petunidin 3-O-glucoside is an anthocyanin that has been found in red grapes and red wines with antiproliferative properties. It reduces DBTRG-05MG glioblastoma cell growth in a time- and concentration-dependent manner by increasing production of reactive oxygen species (ROS) and Bax protein levels and reducing Bcl-2 and caspase-3 activities. Petunidin 3-O-glucoside also reduces glucose uptake, lactic acid production, and NAD levels in DBTRG-05MG cells.
| Cas No. | 6988-81-4 | SDF | |
| 别名 | 矮牵牛素葡萄糖苷 | ||
| Canonical SMILES | OC1=CC(O)=C(C=C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)C(C3=CC(OC)=C(O)C(O)=C3)=[O+]4)C4=C1.[Cl-] | ||
| 分子式 | C22H23O12•Cl | 分子量 | 514.9 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:6): 0.14 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 1.9421 mL | 9.7106 mL | 19.4212 mL |
| 5 mM | 0.3884 mL | 1.9421 mL | 3.8842 mL |
| 10 mM | 0.1942 mL | 0.9711 mL | 1.9421 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。
The Luteolinidin and Petunidin 3- O-Glucoside: A Competitive Inhibitor of Tyrosinase
Molecules 2022 Sep 4;27(17):5703.PMID:36080469DOI:10.3390/molecules27175703.
The enzyme tyrosinase plays a key role in the early stages of melanin biosynthesis. This study evaluated the inhibitory activity of anthocyanidin (1) and anthocyanins (2-6) on the catalytic reaction. Of the six derivatives examined, 1-3 showed inhibitory activity with IC50 values of 3.7 ± 0.1, 10.3 ± 1.0, and 41.3 ± 3.2 μM, respectively. Based on enzyme kinetics, 1-3 were confirmed to be competitive inhibitors with Ki values of 2.8, 9.0, and 51.9 μM, respectively. Molecular docking analysis revealed the formation of a binary encounter complex between 1-3 and the tyrosinase catalytic site. Luteolinidin (1) and Petunidin 3-O-glucoside (2) may serve as tyrosinase inhibitors to block melanin production.
Metabolomic and transcriptomic analyses reveal the effects of self- and hetero-grafting on anthocyanin biosynthesis in grapevine
Hortic Res 2022 May 17;9:uhac103.PMID:35795384DOI:10.1093/hr/uhac103.
Grafting, which joins a scion from a cultivar with the stem of a rootstock from a grapevine wild relative, is commonly used in viticulture. Grafting has crucial effects on various phenotypes of the cultivar, including its phenology, biotic and abiotic resistance, berry metabolome, and coloration, but the underlying genetics and regulatory mechanisms are largely unexplored. In this study, we investigated the phenotypic, metabolomic, and transcriptomic profiles at three developmental stages (45, 75, and 105 days after flowering) of the Crimson Seedless cultivar (Vitis vinifera) grafted onto four rootstocks (three heterografts, CS/101-14, CS/SO4, and CS/110R and one self-graft, CS/CS) with own-rooted graft-free Crimson Seedless (CS) as the control. All the heterografts had a significant effect on berry reddening as early as ~45 days after flowering. The grafting of rootstocks promoted anthocyanin biosynthesis and accumulation in grape berries. The metabolomic features showed that cyanidin 3-O-glucoside, delphinidin 3-O-glucoside, malvidin 3-O-glucoside, peonidin 3-O-glucoside, and Petunidin 3-O-glucoside were the pigments responsible for the purplish-red peel color. Transcriptomic analyses revealed that anthocyanin biosynthesis-related genes, from upstream (phenylalanine ammonia-lyase) to downstream (anthocyanidin 3-O-glucosyltransferase and anthocyanidin synthase), were upregulated with the accumulation of anthocyanins in the heterografted plants. At the same time, all these genes were also highly expressed and more anthocyanin was accumulated in self-grafted CS/CS samples compared with own-rooted graft-free CS samples, suggesting that self-grafting may also have promoted berry reddening in grapevine. Our results reveal global transcriptomic and metabolomic features in berry color regulation under different grafting conditions that may be useful for improving berry quality in viticulture.
Myrcia eriopus DC. (Myrtaceae) fruits, a new endemic Brazilian source of bioactive anthocyanins
Nat Prod Res 2022 Jun;36(11):2853-2858.PMID:33949267DOI:10.1080/14786419.2021.1919106.
Myrcia eriopus DC. (Myrtaceae) is a native and endemic Brazilian species, and there is no information about its chemical composition. In our study, five different anthocyanins and two other phenolic compounds were described for the first time in M. eriopus fruits. Delphinidin 3-O-glucoside (1), cyanidin 3-O-glucoside (2), Petunidin 3-O-glucoside (3), peonidin 3-O-glucoside (4), malvidin 3-O-glucoside (5), gallic acid (6) and myricetin (7) were identified by offline system RP-HPLC-DAD/ESI-QTOF-MS and compared to the scientific literature. Furthermore, the lyophilized powder of M. eriopus fruits showed a high anthocyanin content (1878.14 mg cy-3-glu eqv/100 g f.w.), with greater levels of compounds 1 and 3, and an antioxidant potential in DPPH and ABTS assays (EC50 2419 μg/mL and 339 μmol Trolox/g f.w.), results superior to other non-conventional Brazilian fruits. This first report about the chemical composition of M. eriopus fruit reveals the potential of this fruit as a new source of bioactive anthocyanins.
Methylation level of potato gene OMT30376 regulates tuber anthocyanin transformations
Front Plant Sci 2022 Oct 7;13:1021617.PMID:36275587DOI:10.3389/fpls.2022.1021617.
After anthocyanin synthesis, a variety of anthocyanin compounds are produced through further methylation, glycosylation, and acylation. However, the effect of the potato methylase gene on anthocyanin biosynthesis has not been reported. Red and purple mutation types appear in tubers of the potato cultivar 'Purple Viking' with chimeric skin phenotypes. In this study, transcriptome and anthocyanin metabolome analyses were performed on skin of Purple Viking tubers and associated mutants. According to the metabolome analysis, the transformation of delphinidin into malvidin-3-O-glucoside and Petunidin 3-O-glucoside and that of cyanidin into rosinidin O-hexoside and peonidin-3-O-glucoside were hindered in red tubers. Expression of methyltransferase gene OMT30376 was significantly lower in red tubers than in purple ones, whereas the methylation level of OMT30376 was significantly higher in red tubers. In addition, red skin appeared in tubers from purple tuber plants treated with S-adenosylmethionine (SAM), indicating the difference between purple and red was caused by the methylation degree of the gene OMT30376. Thus, the results of the study suggest that the OMT30376 gene is involved in the transformation of anthocyanins in potato tubers. The results also provide an important reference to reveal the regulatory mechanisms of anthocyanin biosynthesis and transformation.
Integrative Analysis of Metabolomics and Transcriptomics Reveals Molecular Mechanisms of Anthocyanin Metabolism in the Zikui Tea Plant ( Camellia sinensis cv. Zikui)
Int J Mol Sci 2022 Apr 26;23(9):4780.PMID:35563169DOI:10.3390/ijms23094780.
In this study, we performed an association analysis of metabolomics and transcriptomics to reveal the anthocyanin biosynthesis mechanism in a new purple-leaf tea cultivar Zikui (Camellia sinensis cv. Zikui) (ZK). Three glycosylated anthocyanins were identified, including Petunidin 3-O-glucoside, cyanidin 3-O-galactoside, and cyanidin 3-O-glucoside, and their contents were the highest in ZK leaves at 15 days. This is the first report on Petunidin 3-O-glucoside in purple-leaf tea. Integrated analysis of the transcriptome and metabolome identified eleven dependent transcription factors, among which CsMYB90 had strong correlations with Petunidin 3-O-glucoside, cyanidin 3-O-galactoside, and cyanidin 3-O-glucoside (PCC > 0.8). Furthermore, we also identified key correlated structural genes, including two positively correlated F3’H (flavonoid-3′-hydroxylase) genes, two positively correlated ANS (anthocyanin synthase) genes, and three negatively correlated PPO (polyphenol oxidase) genes. Overexpression of CsMYB90 in tobacco resulted in dark-purple transgenic calluses. These results showed that the increased accumulation of three anthocyanins in ZK may promote purple-leaf coloration because of changes in the expression levels of genes, including CsMYB90, F3’Hs, ANSs, and PPOs. These findings reveal new insight into the molecular mechanism of anthocyanin biosynthesis in purple-leaf tea plants and provide a series of candidate genes for the breeding of anthocyanin-rich cultivars.