Robinetin
(Synonyms: 洋槐黄素,3,3',4',5',7-Pentahydroxyflavone) 目录号 : GC61576
A flavonol with diverse biological activities
Cas No.:490-31-3
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
Robinetin is a flavonol that has been found in R. pseudacacia and has diverse biological activities.1,2,3,4,5 It inhibits NADH oxidase with an IC50 value of 19 nmol/mg of protein in isolated beef heart mitochondria.2 Robinetin scavenges DPPH radicals in a cell-free assay and inhibits glutathione S-transferase (GST; IC50 = 1.39 ?M for the equine liver enzyme).3,4 It also inhibits multidrug resistance-associated protein 1 (MRP1) and MRP2 in MDCK-II cells (IC50s = 13.6 and 15 ?M, respectively, for the human proteins).5
1.Charlesworth, E.H., and Robinson, R.Anthoxanthins. Part XIII. Synthesis of a colouring matter of Robinia pseudacaciaJ. Chem. Soc.268-270(1933) 2.Hodnick, W.F., Duval, D.L., and Pardini, R.S.Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoidsBiochem. Pharmacol.47(3)573-580(1994) 3.Hyun, J., Woo, Y., Hwang, D.-S., et al.Relationships between structures of hydroxyflavones and their antioxidative effectsBioorg. Med. Chem. Lett.20(18)5510-5513(2010) 4.Bou?ová, I., Hájek, J., Dr?ata, J., et al.Naturally occurring flavonoids as inhibitors of purified cytosolic glutathione S-transferaseXenobiotica42(9)872-879(2012) 5.van Zanden, J.J., Wortelboer, H.M., Bijlsma, S., et al.Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2Biochem. Pharmacol.69(4)699-708(2005)
| Cas No. | 490-31-3 | SDF | |
| 别名 | 洋槐黄素,3,3',4',5',7-Pentahydroxyflavone | ||
| Canonical SMILES | O=C1C(O)=C(C2=CC(O)=C(O)C(O)=C2)OC3=CC(O)=CC=C13 | ||
| 分子式 | C15H10O7 | 分子量 | 302.24 |
| 溶解度 | DMSO: 120 mg/mL (397.04 mM) | 储存条件 | 4°C, protect from light, stored under nitrogen |
| 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 | 3.3086 mL | 16.5431 mL | 33.0863 mL |
| 5 mM | 0.6617 mL | 3.3086 mL | 6.6173 mL |
| 10 mM | 0.3309 mL | 1.6543 mL | 3.3086 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。
Antimicrobial activity of flavonoids
Int J Antimicrob Agents 2005 Nov;26(5):343-56.PMID:16323269DOI:10.1016/j.ijantimicag.2005.09.002.
Flavonoids are ubiquitous in photosynthesising cells and are commonly found in fruit, vegetables, nuts, seeds, stems, flowers, tea, wine, propolis and honey. For centuries, preparations containing these compounds as the principal physiologically active constituents have been used to treat human diseases. Increasingly, this class of natural products is becoming the subject of anti-infective research, and many groups have isolated and identified the structures of flavonoids possessing antifungal, antiviral and antibacterial activity. Moreover, several groups have demonstrated synergy between active flavonoids as well as between flavonoids and existing chemotherapeutics. Reports of activity in the field of antibacterial flavonoid research are widely conflicting, probably owing to inter- and intra-assay variation in susceptibility testing. However, several high-quality investigations have examined the relationship between flavonoid structure and antibacterial activity and these are in close agreement. In addition, numerous research groups have sought to elucidate the antibacterial mechanisms of action of selected flavonoids. The activity of quercetin, for example, has been at least partially attributed to inhibition of DNA gyrase. It has also been proposed that sophoraflavone G and (-)-epigallocatechin gallate inhibit cytoplasmic membrane function, and that licochalcones A and C inhibit energy metabolism. Other flavonoids whose mechanisms of action have been investigated include Robinetin, myricetin, apigenin, rutin, galangin, 2,4,2'-trihydroxy-5'-methylchalcone and lonchocarpol A. These compounds represent novel leads, and future studies may allow the development of a pharmacologically acceptable antimicrobial agent or class of agents.
Fisetin and Robinetin antiradical activity under solvent effect: density functional theory study
J Mol Model 2022 Aug 1;28(8):240.PMID:35913682DOI:10.1007/s00894-022-05223-7.
The structural and antioxidant activity of two flavonols, namely, Fisetin and Robinetin, have been investigated employing the density functional theory (DFT) using B3LYP functional and 6-311++G (d, p) basis set. The calculations were performed in the gas phase and under the solvent effect of water, dimethylsulfoxide (DMSO), methanol, and benzene. The Hydrogen-Atom Transfer (HAT), single Electron Transfer Followed by Proton Transfer (SET-PT), and sequential Proton Loss Electron Transfer (SPLET) mechanisms were investigated to rationalize the radical scavenging capacities and to identify the favored antioxidant mechanism. Hence, the bond dissociation enthalpies (BDE) ionization potential (IP), IE, proton dissociation enthalpy (PDE), proton affinity (PA), and electron Transfer enthalpy (ETE) related to each mechanism were reported and discussed in function of the solvent effect. For both flavonols, the results showed that 4'-OH hydroxyl is the preferred active site following the trend 4'-OH > 3'-OH > 3-OH > (5'-OH) > 7-OH. Besides, the HAT mechanism is energetically the most favored pathway. The energetically favored solvents follow the trends water > DMSO > benzene > methanol and benzene > DMSO > methanol > water, for Fisetin and Robinetin, respectively.
Effect of beta-cyclodextrin nanocavity confinement on the photophysics of Robinetin
J Photochem Photobiol B 2007 Dec 14;89(2-3):88-97.PMID:17951065DOI:10.1016/j.jphotobiol.2007.09.001.
We have studied the confinement of Robinetin, a therapeutically active plant flavonol, in cyclodextrin (CDx) nanocavities, using steady state and time resolved fluorescence spectroscopy. Enhanced tautomer emission (arising from excited state intramolecular proton transfer (ESIPT)) as well as dramatically blue shifted (approximately 10 nm in beta-CDx and approximately 33 nm in SHP beta-CDx) normal fluorescence observed upon addition of the beta-CDxs indicate that Robinetin readily enters the doughnut-shaped hydrophobic cavity of beta-CDx where the chromone moiety is well shielded from external hydrogen bonding perturbations. Detailed analyses of the fluorescence data (emission profile, anisotropy, decay times) indicate that Robinetin forms 1:1 inclusion complexes with both natural and chemically modified beta-cyclodextrins (beta-CDx and SHP beta-CDx) with affinity constant values K=195+/-17 M(-1) and 1055+/-48 M(-1) respectively, indicating the prospective utility of SHP beta-CDx in particular as an effective drug carrier. Unlike beta-CDxs, alpha-CDxs do not form inclusion complexes with Robinetin. To further characterize the Robinetin/beta-CDxs complexes, circular dichroism (CD) spectroscopic studies have been performed, which reveal that incorporation of Robinetin molecules in the chiral environment of the beta-CDxs strongly affects the electronic transitions of Robinetin leading to the occurrence of positive induced circular dichroism (ICD) bands in the near ultra-violet (UV) region. Molecular mechanics calculations show that the inclusion complex with the chromone ring inserted into the beta-CDx cavity is most favorable, in agreement with our spectroscopic data.
Binding of the bioflavonoid Robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation
J Photochem Photobiol B 2010 Jan 21;98(1):12-9.PMID:19914085DOI:10.1016/j.jphotobiol.2009.10.002.
Recent years have witnessed burgeoning interest in plant flavonoids as novel therapeutic drugs targeting cellular membranes and proteins. Motivated by this scenario, we explored the binding of Robinetin (3,7,3',4',5'-pentahydroxyflavone, a bioflavonoid with remarkable 'two color' intrinsic fluorescence properties), with egg yolk phosphatidylcholine (EYPC) liposomes and normal human hemoglobin (HbA), using steady state and time resolved fluorescence spectroscopy. Distinctive fluorescence signatures obtained for Robinetin indicate its partitioning (K(p)=8.65x10(4)) into the hydrophobic core of the membrane lipid bilayer. HbA-robinetin interaction was examined using both Robinetin fluorescence and flavonoid-induced quenching of the protein tryptophan fluorescence. Specific interaction with HbA was confirmed from three lines of evidence: (a) bimolecular quenching constant K(q)>>diffusion controlled limit; (b) closely matched values of Stern-Volmer quenching constant and binding constant; (c) tau(0)/tau=1 (where tau(0) and tau are the unquenched and quenched tryptophan fluorescence lifetimes, respectively). Absorption spectrophotometric assays reveal that Robinetin inhibits EYPC membrane lipid peroxidation and HbA glycosylation with high efficiency.
Anti-mutagenesis and anti-promotion by apigenin, Robinetin and indole-3-carbinol
Carcinogenesis 1986 Jun;7(6):959-63.PMID:3708757DOI:10.1093/carcin/7.6.959.
We assessed the anti-mutagenic and anti-promotion properties of two flavones, apigenin and Robinetin, and of indole-3-carbinol, because these compounds have been reported in vegetables, the consumption of which has been associated with reduced rates of cancer. However, the active components of these foods and their effects on carcinogenesis have not been established. Anti-mutagenicity was determined in the Salmonella typhimurium assay by measuring the effects of the test compounds on bacterial mutagenesis induced by methyl-nitrosourea (MNU), methyl-n-nitro-N-nitrosoguanidine (MNNG), benzo[a]pyrene (BaP) or 2-aminoanthracene (2-AA). Inclusion of apigenin resulted in a 62% and a 43% inhibition of mutagenicity with 13 nmol of 2-AA and 30 nmol BaP respectively. Robinetin caused an 87% inhibition of mutagenicity by 2-AA, but indole-3-carbinol had little or no effect on the mutagenicity of any of the compounds. None of the three compounds inhibited mutagenesis by MNU or MNNG and none were mutagenic or toxic when tested in the absence of mutagenic compounds at doses up to 20 micrograms/plate. Anti-promotion properties were assessed by measuring the effects of apigenin, Robinetin and indole-3-carbinol on induction of ornithine decarboxylase activity (ODC) in mouse epidermis by 17 nmol 12-O-tetradecanoyl phorbol-13-acetate (TPA). Pretreatment of the skin half an hour before TPA with apigenin, Robinetin, butylated hydroxyanisole, 13-cis-retinoic acid (all at 50 mumol) or di-fluoromethylornithine (1.6 mumol) inhibited ODC induction at 6 h after TPA by 67-80%. Pretreatment with 50 mumol indole-3-carbinol caused a 78% elevation in the TPA induction at this time. Dose response measurements were conducted with apigenin, indole-3-carbinol and Robinetin. Inhibition by 30-90% of TPA-induced ODC was observed at 6 h after TPA in mice pretreated with 12.5-100 mumol apigenin. Pretreatment with 37.5 or 50 mumol indole-3-carbinol or 0.5, 12.5 or 25 mumol Robinetin resulted in elevated induction of epidermal ODC by TPA at 6 h after TPA. However, treatment with 50 or 100 mumol Robinetin diminished ODC induction at 6 h after TPA. Treatment with 100 mumol apigenin or 50 or 100 mumol indole-3-carbinol in non-TPA-treated mouse skin caused elevations in epidermal ODC. In comparing the time course of ODC induction, indole-3-carbinol (50 mumol) pretreatment shifted the induction of epidermal ODC to earlier times, in addition to elevating ODC induction by TPA.(ABSTRACT TRUNCATED AT 400 WORDS)