cis-Resveratrol
(Synonyms: 顺式白藜芦醇) 目录号 : GC41462A phenolic antioxidant present in red wine
Cas No.:61434-67-1
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
Resveratrol is a potent phenolic antioxidant found in grapes, red wine, and various berries that also has antiproliferative and anti-inflammatory activity. cis-Resveratrol is the double bond isomer of trans-resveratrol, the more often studied and naturally abundant of the two resveratrol isomers. cis-Resveratrol exhibits antioxidant activity in the µM range similar to that observed with trans-resveratrol. It blocks production of reactive oxygen species (ROS) by inhibition of NAD(P)H oxidase and also inhibits production of nitric oxide. At a concentration of 100 µM, cis-resveratrol significantly inhibits the expression of genes related to the Rel/NF-κB/IκB family, adhesion molecules, and acute-phase proteins in LPS and INF-γ-stimulated murine peritoneal macrophages. cis-Resveratrol inhibits uptake of noradrenaline and 5-HT by synaptosomes from rat brain with IC50 values of 79 and 51 µM, respectively. It also inhibits human monoamine oxidase-A (MOA-A) and MOA-B with IC50 values of 25 and 61 µM, respectively, which is similar to, but slightly less effective than, values obtained with trans-resveratrol.
Reference:
[1]. Rotondo, S., Rajtar, G., Manarini, S., et al. Effect of trans-resveratrol, a natural polyphenolic compound, on human polymorphonuclear leukocyte function. British Journal of Pharmacology 123, 1691-1699 (1998).
[2]. Orallo, F. Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Current Medicinal Chemistry 13, 87-98 (2006).
[3]. Leiro, J., Arranz, J.A., Fraiz, N., et al. Effect of cis-resveratrol on genes involved in nuclear factor kappa B signaling. International Immunopharmacology 5, 393-406 (2005).
[4]. Yáñez, M., Fraiz, N., Cano, E., et al. Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochemical and Biophysical Research Communications 344, 688-695 (2006).
| Cas No. | 61434-67-1 | SDF | |
| 别名 | 顺式白藜芦醇 | ||
| 化学名 | 5[(1Z)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol | ||
| Canonical SMILES | OC1=CC(/C=C\C2=CC=C(O)C=C2)=CC(O)=C1 | ||
| 分子式 | C14H12O3 | 分子量 | 228.2 |
| 溶解度 | 50mg/mL in DMSO, or in DMF | 储存条件 | Store at -80°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 | 4.3821 mL | 21.9106 mL | 43.8212 mL |
| 5 mM | 0.8764 mL | 4.3821 mL | 8.7642 mL |
| 10 mM | 0.4382 mL | 2.1911 mL | 4.3821 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。
Cis- and trans-resveratrol have opposite effects on histone serine-ADP-ribosylation and tyrosine induced neurodegeneration
Nat Commun 2022 Jun 10;13(1):3244.PMID:35688816DOI:10.1038/s41467-022-30785-8.
Serum tyrosine levels increase during aging, neurocognitive, metabolic, and cardiovascular disorders. However, calorie restriction (CR) and sleep lower serum tyrosine levels. We previously showed that tyrosine inhibits tyrosyl-tRNA synthetase (TyrRS)-mediated activation of poly-ADP-ribose polymerase 1 (PARP1). Here, we show that histone serine-ADP-ribosylation is decreased in Alzheimer's Disease (AD) brains, and increased tyrosine levels deplete TyrRS and cause neuronal DNA damage. However, dopamine and brain-derived neurotrophic factor (BDNF) increase TyrRS and histone serine-ADP-ribosylation. Furthermore, cis-Resveratrol (cis-RSV) that binds to TyrRS mimicking a 'tyrosine-free' conformation increases TyrRS, facilitates histone serine-ADP-ribosylation-dependent DNA repair, and provides neuroprotection in a TyrRS-dependent manner. Conversely, trans-RSV that binds to TyrRS mimicking a 'tyrosine-like' conformation decreases TyrRS, inhibits serine-ADP-ribosylation-dependent DNA repair, and induces neurodegeneration in rat cortical neurons. Our findings suggest that age-associated increase in serum tyrosine levels may effect neurocognitive and metabolic disorders and offer a plausible explanation for divergent results obtained in clinical trials using resveratrol.
Metabolism of cis- and trans-Resveratrol and Dihydroresveratrol in an Intestinal Epithelial Model
Nutrients 2020 Feb 25;12(3):595.PMID:32106482DOI:10.3390/nu12030595.
Trans-resveratrol, a well-known plant phenolic compound, has been intensively investigated due to its association with the so-called French paradox. However, despite its high pharmacological potential, trans-resveratrol has shown relatively low bioavailability. Trans-resveratrol is intensively metabolized in the intestine and liver, yielding metabolites that may be responsible for its high bioactivity. The aim of this study was to investigate and compare the metabolism of trans-resveratrol (tRes), cis-Resveratrol (cRes) and dihydroresveratrol (dhRes) in an in vitro epithelial model using Caco-2 cell lines. Obtained metabolites of tRes, cRes and dhRes were analyzed by LC/MS Q-TOF, and significant differences in the metabolism of each compound were observed. The majority of tRes was transported unchanged through the Caco-2 cells, while cRes was mostly metabolized. The main metabolite of both cis- and trans-resveratrol observed as a result of colon microbial metabolism, dhRes, was metabolized almost completely, with only traces of the unchanged molecule being found. A sulphate conjugate was identified as the main metabolite of tRes in our model, while a glucuronide conjugate was the major metabolite of cRes and dhRes. Since metabolism of simple phenolics and polyphenols plays a crucial role in their bioavailability, detailed knowledge of their transformation is of high scientific value.
Effects of trans- versus cis-Resveratrol on adrenergic contractions of the rat tail artery and role of endothelium
Physiol Rep 2021 Jan;8(24):e14666.PMID:33369273DOI:10.14814/phy2.14666.
The health benefits of the natural polyphenol trans-resveratrol may play an important role in preventing a variety of diseases. Resveratrol has been shown to reduce blood pressure and improve metabolic diseases such as type 2 diabetes mellitus and obesity. Our previous studies examined the role of K+ channels in the vasorelaxation responses to trans-resveratrol in the rat tail artery. During these studies, we uncovered a novel transient contraction prior to the sustained relaxation effect of trans-resveratrol. Thus, the purpose of this study was to determine the role of the endothelium in these vascular contraction and relaxation responses to trans-resveratrol. We additionally sought to determine if the cis-isomer of resveratrol exerts any of the same vascular effects as the trans-isomer. The vascular responses to trans-resveratrol were examined in rat tail arteries with intact or denuded endothelium over a 2-hr period. Additionally, the vascular responses to trans- and cis-Resveratrol were compared in rat tail arteries with intact endothelium. Both the transient contractile response and the persistent relaxation response to trans-resveratrol were similar in the arterial rings with intact or denuded endothelium. There was a significant correlation between the initial contraction-enhancing action of trans-resveratrol and the magnitude of the sustained relaxation for vessels with both intact and denuded endothelium. Moreover, we demonstrated that cis-Resveratrol produced a significantly greater relaxation response as compared to trans-resveratrol without the initial contractile response. These data demonstrate the role of the vascular smooth muscle in the vascular responses to resveratrol and the potential clinical benefits of the cis-isomer of resveratrol as compared to the trans-isomer.
A comparison of β-casein complexes and micelles as vehicles for trans-/cis-Resveratrol
Food Chem 2020 Nov 15;330:127209.PMID:32535314DOI:10.1016/j.foodchem.2020.127209.
Bovine β-casein is an amphiphilic protein that exists as a monomer and self-organizes into micelles in aqueous solution. The protein has been used as natural vehicles for bioactives. Trans-resveratrol has received significant attention due to its vast health benefits and conversion to cis-isomer during processing and storage. However, cis-isomer has not yet gained as much attention as that of trans-isomer. In this study, the interaction of β-casein with trans- and cis-Resveratrol was characterized. Trans-resveratrol exhibited a higher affinity for β-casein than cis-isomer, and β-casein could bind two isomers simultaneously to form protein-diligand complexes. Both trans- and cis-isomers could be encapsulated into β-casein micelles with encapsulation efficiencies of ~69% and ~57%, respectively. The β-casein micelles could delay photo-isomerization of trans-isomer to cis-isomer, while β-casein-ligand complex showed a better protective effect for both isomers during storage than β-casein micelles. These results might be useful for the development of protein-based carriers for the polyphenols.
cis-Resveratrol produces anti-inflammatory effects by inhibiting canonical and non-canonical inflammasomes in macrophages
Innate Immun 2014 Oct;20(7):735-50.PMID:24149798DOI:10.1177/1753425913507096.
Resveratrol, a natural phenolic compound found in red grapes and wine, exists as cis and trans isomers. Recent studies have shown that trans-resveratrol possesses anti-inflammatory, anti-oxidant, anti-carcinogenic, anti-tumor and immunomodulatory properties. However, it remains unclear whether cis-Resveratrol may exhibit similar activities. The objective of the present study was to examine the effects of cis- and trans-resveratrol on the production of pro-inflammatory cytokines and mediators in human macrophages. We examined the possibility that cis- and trans-resveratrol may affect cytokine secretion by modulating inflammasomes, intracellular multi-protein complexes, the assembly of which leads to caspase-1 activation and secretion of active IL-1β by macrophages. Our results show that pre-treatment of macrophages with cis-Resveratrol not only reduces pro-IL-1β production and IL-1β secretion, but also suppresses ATP-induced transcription and activation of caspase-1 and caspase-4. Notably, cis-Resveratrol inhibits the expression of the purinergic receptor, P2X(7)R, and the endoplasmic reticulum stress marker, Glc-regulated protein 78, but also reduces reactive oxygen species production. Moreover, cis-Resveratrol attenuates cyclooxygenase-2 expression and prostaglandin E2 production. cis-Resveratrol also decreases the phosphorylation of p38 MAPK and expression of the c-Jun protein. These results indicate that cis-Resveratrol produces anti-inflammatory effects by inhibiting both the canonical and non-canonical inflammasomes, and associated pathways in human macrophages.