Astringin
(Synonyms: 白皮杉醇葡萄糖苷; trans-Astringin) 目录号 : GC35416
A phenolic stilbene glucoside with antioxidant and antineoplastic activities
Cas No.:29884-49-9
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
Astringin is a phenolic stilbene glucoside that has been found in V. vinifera and has antioxidant and antineoplastic activities.1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals (IC50 = 30.2 μM) in a cell-free assay and inhibits cupric ion-induced lipid peroxidation of human LDL (IC50 = 3 μM).1 Astringin (10 ?g/ml) inhibits development of preneoplastic lesions induced by 7,12-dimethylbenz(a)anthracene (DMBA) in mouse mammary gland organ cultures by 68.8%.2
1.Tegeo, P.W., Fauconneau, B., Deffieux, G., et al.Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell culturesJ. Nat. Prod.61(5)655-657(1998) 2.Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al.Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell culturesNutr. Cancer40(2)173-179(2001)
| Cas No. | 29884-49-9 | SDF | |
| 别名 | 白皮杉醇葡萄糖苷; trans-Astringin | ||
| Canonical SMILES | OC1=C(O)C=CC(/C=C/C2=CC(O)=CC(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)=C2)=C1 | ||
| 分子式 | C20H22O9 | 分子量 | 406.38 |
| 溶解度 | DMSO: 150 mg/mL (369.11 mM) | 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 | 2.4608 mL | 12.3038 mL | 24.6075 mL |
| 5 mM | 0.4922 mL | 2.4608 mL | 4.9215 mL |
| 10 mM | 0.2461 mL | 1.2304 mL | 2.4608 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。
Comparison of Ferroptosis-Inhibitory Mechanisms between Ferrostatin-1 and Dietary Stilbenes (Piceatannol and Astringin)
Molecules 2021 Feb 19;26(4):1092.PMID:33669598DOI:10.3390/molecules26041092.
Synthetic arylamines and dietary phytophenolics could inhibit ferroptosis, a recently discovered regulated cell death process. However, no study indicates whether their inhibitory mechanisms are inherently different. Herein, the ferroptosis-inhibitory mechanisms of selected ferrostatin-1 (Fer-1) and two dietary stilbenes (piceatannol and Astringin) were compared. Cellular assays suggested that the ferroptosis-inhibitory and electron-transfer potential levels decreased as follows: Fer-1 >> piceatannol > Astringin; however, the hydrogen-donating potential had an order different from that observed by the antioxidant experiments and quantum chemistry calculations. Quantum calculations suggested that Fer-1 has a much lower ionization potential than the two stilbenes, and the aromatic N-atoms were surrounded by the largest electron clouds. By comparison, the C4'O-H groups in the two stilbenes exhibited the lowest bond disassociation enthalpies. Finally, the three were found to produce corresponding dimer peaks through ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry analysis. In conclusion, Fer-1 mainly depends on the electron transfer of aromatic N-atoms to construct a redox recycle. However, piceatannol and Astringin preferentially donate hydrogen atoms at the 4'-OH position to mediate the conventional antioxidant mechanism that inhibits ferroptosis, and to ultimately form dimers. These results suggest that dietary phytophenols may be safer ferroptosis inhibitors for balancing normal and ferroptotic cells than arylamines with high electron-transfer potential.
Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of Astringin, a piceatannol glucoside, by P450 BM3
Enzyme Microb Technol 2017 Feb;97:34-42.PMID:28010771DOI:10.1016/j.enzmictec.2016.11.003.
Enzymatic conversion of natural glycosides to their corresponding hydroxylated products using cytochromes P450 has significant advantages over synthetic chemistry and even enzyme-catalyzed glycosylation of chemicals. At present, the basic strategy for making glycosides of stilbenoid compounds is to use the glycosylation activity of enzymes, such as glycosyltransferases. Here, an efficient synthesis of a valuable (E)-astringin, a piceatannol glucoside, was developed using CYP102A1 via the highly regioselective C-3' hydroxylation of polydatin, a resveratrol glucoside. (E)-astringin is a high added value compound found in plants and wine. Benzylic hydroxylation of polydatin provides an attractive route to (E)-astringin, a catechol product. Thus far, chemical and enzymatic methods of producing (E)-astringin have not been developed. In the present study, a set of CYP102A1 mutants from Bacillus megaterium was found to catalyze regioselective hydroxylation of polydatin at the C-3' position to generate an (E)-astringin, a piceatannol glucoside.
Biosynthesis of the major tetrahydroxystilbenes in spruce, Astringin and isorhapontin, proceeds via resveratrol and is enhanced by fungal infection
Plant Physiol 2011 Oct;157(2):876-90.PMID:21865488DOI:10.1104/pp.111.181420.
Stilbenes are dibenzyl polyphenolic compounds produced in several unrelated plant families that appear to protect against various biotic and abiotic stresses. Stilbene biosynthesis has been well described in economically important plants, such as grape (Vitis vinifera), peanut (Arachis hypogaea), and pine (Pinus species). However, very little is known about the biosynthesis and ecological role of stilbenes in spruce (Picea), an important gymnosperm tree genus in temperate and boreal forests. To investigate the biosynthesis of stilbenes in spruce, we identified two similar stilbene synthase (STS) genes in Norway spruce (Picea abies), PaSTS1 and PaSTS2, which had orthologs with high sequence identity in sitka (Picea sitchensis) and white (Picea glauca) spruce. Despite the conservation of STS sequences in these three spruce species, they differed substantially from angiosperm STSs. Several types of in vitro and in vivo assays revealed that the P. abies STSs catalyze the condensation of p-coumaroyl-coenzyme A and three molecules of malonyl-coenzyme A to yield the trihydroxystilbene resveratrol but do not directly form the dominant spruce stilbenes, which are tetrahydroxylated. However, in transgenic Norway spruce overexpressing PaSTS1, significantly higher amounts of the tetrahydroxystilbene glycosides, Astringin and isorhapontin, were produced. This result suggests that the first step of stilbene biosynthesis in spruce is the formation of resveratrol, which is further modified by hydroxylation, O-methylation, and O-glucosylation to yield Astringin and isorhapontin. Inoculating spruce with fungal mycelium increased STS transcript abundance and tetrahydroxystilbene glycoside production. Extracts from STS-overexpressing lines significantly inhibited fungal growth in vitro compared with extracts from control lines, suggesting that spruce stilbenes have a role in antifungal defense.
Role of viticultural factors on stilbene concentrations of grapes and wine
Drugs Exp Clin Res 2003;29(5-6):181-7.PMID:15134373doi
Stilbenes are phenolics that can be found in different grapevine organs, such as berries, leaves, canes and roots. Stilbenes act as antifungal compounds since they are synthesized by the plant in response to pathogen attack. Other abiotic elicitors, such as ultraviolet rays and heavy metals, can trigger stilbene production. Many stilbenic compounds have been detected in grapes and wine (resveratrol, piceid, viniferins, Astringin, etc.). The latest stilbene to be analyzed is piceatannol (or astringinin). Stilbene synthesis in grapes depends on different viticultural factors such as the grape variety, the environment and cultural practices. Concerning grape variety, red berry-grapes have higher stilbene levels than white berry-grapes. With regard to climate, preliminary results suggest a positive correlation between vineyard elevation and stilbene grape concentrations. Quality-oriented cultural practices produce grapes with high levels of stilbenes.
Natural stilbenes effects in animal models of Alzheimer's disease
Neural Regen Res 2020 May;15(5):843-849.PMID:31719245DOI:10.4103/1673-5374.268970.
Alzheimer's disease is one of the most frequent neurodegenerative diseases. This pathology is characterized by protein aggregates, mainly constituted by amyloid peptide and tau, leading to neuronal death and cognitive impairments. Drugs currently proposed to treat this pathology do not prevent neurodegenerative processes and are mainly symptomatic therapies. However, stilbenes presenting multiple pharmacological effects could be good potential therapeutic candidates. The aim of this review is to gather the more significant papers among the broad literature on this topic, concerning the beneficial effects of stilbenes (resveratrol derivatives) in animal models of Alzheimer's disease. Indeed, numerous studies focus on cellular models, but an in vivo approach remains of primary importance since in animals (mice or rats, generally), bioavailability and metabolism are taken into account, which is not the case in in vitro studies. Furthermore, examination of memory ability is feasible in animal models, which strengthens the relevance of a compound with a view to future therapy in humans. This paper is addressed to any researcher who needs to study untested natural stilbenes or who wants to experiment the most effective natural stilbenes in largest animals or in humans. This review shows that resveratrol, the reference polyphenol, is largely studied and seems to have interesting properties on amyloid plaques, and cognitive impairment. However, some resveratrol derivatives such as gnetin C, trans-piceid, or Astringin have never been tested on animals. Furthermore, pterostilbene is of particular interest, by its improvement of cognitive disorders and its neuroprotective role. It could be relevant to evaluate this molecule in clinical trials.