Dihydroresveratrol
(Synonyms: 二氢白藜芦醇) 目录号 : GC38098
A bibenzyl with diverse biological activities
Cas No.:58436-28-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dihydroresveratrol is a polyketide synthase-derived bibenzyl that has been found in C. sativa and has diverse biological activities.1,2,3,4 It is also an active metabolite of resveratrol that is formed by gut microbiota.5 Dihydroresveratrol inhibits DNA polymerase α but not DNA polymerase δ (Kis =29.3 and >100 ?M, respectively) and the formation of thiobarbituric acid reactive substances (TBARS) in rat liver microsomes (EC50 = 1.57 ?M).2 It stimulates the proliferation of hormone-sensitive MCF-7 breast cancer cells but not hormone-resistant MDA-MB-231 and BT474 breast cancer cells when used at concentrations ranging from 0.01 pM to 100 nM.3 Dihydroresveratrol decreases interalveolar septal thickness and alveolar hemorrhage in a rat model of lung injury induced by cerulein- and LPS-stimulated pancreatitis when administered at a dose of 50 mg/kg.4
1.Boddington, K.F., Soubeyrand, E., Van Gelder, K., et al.Bibenzyl synthesis in Cannabis sativa L.Plant J.109(3)693-707(2022) 2.Stivala, L.A., Savio, M., Carafoli, F., et al.Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrolJ. Biol. Chem.276(25)22586-22594(2001) 3.Gakh, A.A., Anisimova, N.Y., Kiselevsky, M.V., et al.Dihydro-resveratrol—A potent dietary polyphenolBioorg. Med. Chem. Lett.20(20)6149-6151(2010) 4.Lin, Z.-S., Ku, C.F., Guan, Y.-F., et al.Dihydro-resveratrol ameliorates lung injury in rats with cerulein-induced acute pancreatitisPhytother. Res.30(4)663-670(2016) 5.Bode, L.M., Bunzel, B., Huch, M., et al.In vivo and in vitro metabolism of trans-resveratrol by human gut microbiotaAm. J. Clin. Nutr.97(2)295-309(2013)
| Cas No. | 58436-28-5 | SDF | |
| 别名 | 二氢白藜芦醇 | ||
| Canonical SMILES | OC1=CC(CCC2=CC=C(O)C=C2)=CC(O)=C1 | ||
| 分子式 | C14H14O3 | 分子量 | 230.26 |
| 溶解度 | DMF: >100 mg/ml,DMSO: >50 mg/ml,Ethanol: >50 mg/ml,PBS (pH 7.2): <100 µ g/ml | 储存条件 | 4°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 | 4.3429 mL | 21.7146 mL | 43.4292 mL |
| 5 mM | 0.8686 mL | 4.3429 mL | 8.6858 mL |
| 10 mM | 0.4343 mL | 2.1715 mL | 4.3429 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。
Dihydroresveratrol Type Dihydrostilbenoids: Chemical Diversity, Chemosystematics, and Bioactivity
Curr Med Chem 2018;25(10):1194-1240.PMID:28875843DOI:10.2174/0929867324666170830112343.
Background: Dihydrostilbenoids, a diverse class of natural products differing from stilbenoids by the missing double bond in the ethylene chain linking the aromatic moieties, have been reported from fungi, mosses, ferns, and flowering plants. Objective: Occurrence, structure, and bioactivity of naturally occurring Dihydroresveratrol type dihydrostilbenoids are discussed in this review. Method: A Reaxys database search for Dihydroresveratrol derivatives with possible substitutions on all atoms, but excluding non-natural products and compounds featuring additional rings involving the ethyl connecting chain, was performed. Results: Structures include simple Dihydroresveratrol derivatives, compounds substituted with complex side chains composed of acyl moieties and sugars, and compounds containing polycyclic cores attached to dihydrostilbenoid units. Dihydrostilbenoids have a wide spectrum of bioactivities ranging from expectable antioxidant and anti-inflammatory activities to interesting neuroprotective and anticancer activity. The anticancer activity in particular is very pronounced for some plant-derived dihydrostilbenoids and makes them interesting lead compounds for drug development. Apart from some reports on Dihydroresveratrol derivatives as phytoalexins against plant-pathogenic fungi, only very limited information is available on the ecological role of these compounds for the organisms producing them. Conclusion: Dihydrostilbenoids are a class of natural products possessing significant biological activities; their scattered but not ubiquitous occurrence throughout the kingdoms of plants and fungi is not easily explained. We are convinced that future studies will identify new sources of dihydrostilbenoids, and we hope that the present review will inspire such studies and will help in directing such efforts to suitable source organisms and towards promising bioactivities.
Bioavailability of resveratrol
Ann N Y Acad Sci 2011 Jan;1215:9-15.PMID:21261636DOI:10.1111/j.1749-6632.2010.05842.x.
This paper reviews our current understanding of the absorption, bioavailability, and metabolism of resveratrol, with an emphasis on humans. The oral absorption of resveratrol in humans is about 75% and is thought to occur mainly by transepithelial diffusion. Extensive metabolism in the intestine and liver results in an oral bioavailability considerably less than 1%. Dose escalation and repeated dose administration of resveratrol does not appear to alter this significantly. Metabolic studies, both in plasma and in urine, have revealed major metabolites to be glucuronides and sulfates of resveratrol. However, reduced Dihydroresveratrol conjugates, in addition to highly polar unknown products, may account for as much as 50% of an oral resveratrol dose. Although major sites of metabolism include the intestine and liver (as expected), colonic bacterial metabolism may be more important than previously thought. Deconjugation enzymes such as β-glucuronidase and sulfatase, as well as specific tissue accumulation of resveratrol, may enhance resveratrol efficacy at target sites. Resveratrol analogs, such as methylated derivatives with improved bioavailability, may be important in future research.
Dihydroresveratrol cellobioside and xylobioside as effective melanogenesis activators
Carbohydr Res 2016 Dec 21;436:45-49.PMID:27863303DOI:10.1016/j.carres.2016.11.004.
Dihydroresveratrol cellobioside and xylobioside, whose structures were designed based on that of the naturally occurring melanogenesis-controlling agent Dihydroresveratrol glucoside, were synthesized via Schmidt glycosylation as the key step. Both analogues stimulated melanogenesis with efficacies comparable to that of 8-methoxypsoralen, a well-known melanogenesis activator. This suggests that diglycosyl modification of the 4'-OH on the Dihydroresveratrol skeleton leads to the activation of melanogenesis, both with and without hydroxymethyl groups in the sugar moieties.
Resveratrol, lunularin and Dihydroresveratrol do not act as caloric restriction mimetics when administered intraperitoneally in mice
Sci Rep 2019 Mar 14;9(1):4445.PMID:30872769DOI:10.1038/s41598-019-41050-2.
Resveratrol as well as caloric restriction were shown to extend lifespan in some model organisms and may possibly delay onset of ageing-related diseases in humans. Yet, resveratrol supplementation does not always extend lifespan of animal models or improve health status of humans. Because of interindividual differences in human microbiota, resveratrol metabolite production in the gut differs. While some individuals produce lunularin and Dihydroresveratrol in their gut, others produce Dihydroresveratrol only. Therefore, we addressed the question whether these metabolites differ in their biological impact on ageing and intraperitoneally injected 13-month-old C57BL/6JRj mice on an ad-libitum (AL) HFD with resveratrol, Dihydroresveratrol or lunularin (24 mg/kg bodyweight; 3 times/week). Compared to mice injected with vehicle (AL-control), resveratrol and Dihydroresveratrol did not change bodyweight and had no impact on insulin or glucose levels while lunularin slightly reduced feed intake and bodyweight gain. CR-mice showed lowered cholesterol, insulin and leptin levels, elevated adiponectin and phosphorylated AMPK levels in liver as well as increased transcription of Pck1 and Pgc1α when compared to the AL-control. In contrast, injections with the test substances did not change these parameters. We therefore conclude that in our model, resveratrol, lunularin and Dihydroresveratrol did not act as CR mimetics.
Determination of Dihydroresveratrol in rat plasma by HPLC
J Agric Food Chem 2010 Jun 23;58(12):7472-5.PMID:20509689DOI:10.1021/jf100836j.
Dihydroresveratrol is a metabolite of trans-resveratrol formed in the intestine by the hydrogenation of the double bond by microflora. The aim of the present study was to validate a method to measure Dihydroresveratrol in rat plasma and then to quantify its plasmatic concentration after the oral administration of 60 mg/kg to Sprague-Dawley rats. Dihydroresveratrol was extracted from acidified plasma with a C18 cartridge, eluted with methanol, and concentrated prior to HPLC analysis with diode-array detection (HPLC-DAD) at 276 nm. The method was validated by spiking blank plasma samples with pure Dihydroresveratrol, obtaining a linear correlation and good interday and intraday precisions, expressed as coefficient of variation (<7%). The average recovery was 96.7% and the limit of detection was 275 nM. The oral administration of Dihydroresveratrol to rats and its subsequent detection, along with Dihydroresveratrol glucuronide and sulfate, provides evidence of its absorption and metabolism.