Quercetin 3,7-dimethyl ether
目录号 : GC60315
Quercetin3,7-dimethylether可从CrotonschiedeanusSchlecht中分离得到，和NO/cGMP通路相关，可增加血管舒张活性。
Cas No.:2068-02-2
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
Quercetin 3,7-dimethyl ether， isolated from Croton schiedeanus Schlecht，has a NO/cGMP pathway-related profile, with increased vasorelaxant activity[1].
[1]. M F Guerrero, et al. Quercetin 3,7-dimethyl Ether: A Vasorelaxant Flavonoid Isolated From Croton Schiedeanus Schlecht. J Pharm Pharmacol. 2002 Oct;54(10):1373-8.
| Cas No. | 2068-02-2 | SDF | |
| Canonical SMILES | O=C1C(OC)=C(C2=CC=C(O)C(O)=C2)OC3=CC(OC)=CC(O)=C13 | ||
| 分子式 | C17H14O7 | 分子量 | 330.29 |
| 溶解度 | 储存条件 | ||
| 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 | 3.0276 mL | 15.1382 mL | 30.2764 mL |
| 5 mM | 0.6055 mL | 3.0276 mL | 6.0553 mL |
| 10 mM | 0.3028 mL | 1.5138 mL | 3.0276 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。
Quercetin 3,7-dimethyl ether: a vasorelaxant flavonoid isolated from Croton schiedeanus Schlecht
J Pharm Pharmacol 2002 Oct;54(10):1373-8.PMID:12396299DOI:10.1211/002235702760345455.
The vasorelaxant profile of Quercetin 3,7-dimethyl ether, a flavonoid isolated from Croton schiedeanus Schlecht (Euphorbiaceae), was assessed in aortic rings isolated from Wistar rats. To gain insight into its structure-activity relationship, we compared this substance with quercetin 3,4',7-trimethyl ether (ayanin), another flavonoid isolated from this plant, quercetin 3,3',4',7-tetramethyl ether, a flavonoid synthesized by us, and quercetin. In addition we examined the interaction of Quercetin 3,7-dimethyl ether with the nitric oxide (NO)/cyclic guanosine monophosphate (cGMP) pathway. According to their pEC50 values (concentration producing a 50% inhibition of the maximal contractile response) to phenylephrine-induced precontraction in rat isolated aorta, the potency order was Quercetin 3,7-dimethyl ether > quercetin > quercetin 3,4',7-trimethyl ether > quercetin 3,3',4',7-tetramethyl ether (4.70+/-0.18; 3.96+/-0.07; 3.64+/-0.02; 3.11+/-0.16). The relaxant effect of Quercetin 3,7-dimethyl ether was significantly decreased by the removal of endothelium as well as by methylene blue, an inhibitor of guanylyl cyclase, and by N(G)-nitro-L-arginine methyl ester hydrochloride (L-NAME), an NO-synthase inhibitor. Therefore, Quercetin 3,7-dimethyl ether has a NO/cGMP pathway-related profile, with increased vasorelaxant activity due to hydroxylation at positions 3 and 4 of the B ring. In addition, methylation at positions 3 and 7 with respect to quercetin of the C and A rings, respectively, seems to further enhance the vasorelaxant activity of Quercetin 3,7-dimethyl ether.
Toxic aromatic compounds from fruits of Narthecium ossifragum L
Phytochemistry 2016 Dec;132:76-85.PMID:27720435DOI:10.1016/j.phytochem.2016.09.010.
The intake of Narthecium ossifragum, commonly known as bog asphodel, has been associated with toxic effects observed in sheep for centuries. Although the plant has been studied for five centuries little is known about its chemical constituents. Six previously undescribed natural products, naringenin(3 → 6″)luteolin, naringenin(3 → 6″)chrysoeriol, liovil 4-O-β-glucopyranoside, 2,6-dimethoxy cinnamic acid, (E)-4-(3-hydroxy-2,2-dimethylchroman-6-yl)but-3-en-2-one and (E)-4-(4-(((E)-4-hydroxy-3-methylbut-2-en-1-yl)oxy)phenyl)but-3-en-2-one, have been identified from fruits of N. ossifragum for the first time. In addition, the rare natural product 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde and the five known compounds 4-hydroxycinnamic acid, quercetin 3,3'-dimethyl ether, Quercetin 3,7-dimethyl ether, chrysoeriol 7-O-β-glucopyranoside and the di-C-glycosylflavone isoschaftoside were all characterized for the first time from the fruits of N. ossifragum. The discovery of sufficient amounts of 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde in fresh plant material of N. ossifragum to allow complete structure elucidation by NMR and HRMS supports the possibility that fungi associated with N. ossifragum may be able to produce enough toxins to play a significant role in the pathogenicity of N. ossifragum. 4-Hydroxy-3-(3-methylbut-2-enyl)benzaldehyde showed mild toxicity towards normal rat kidney (NRK) and more profound activity towards MOLM13 acute myeloid leukemia cells (IC50 = 430 μM and 68 μM, respectively). Naringenin(3 → 6″)luteolin had IC50 of 230 μM towards NRK cells, and 115 μM towards MOLM13 cells. Microscopic evaluation suggests that these two compounds induce cell death by different mechanisms.
Non-targeted chromatographic analyses of cuticular wax flavonoids from Physalis alkekengi L
J Chromatogr A 2016 Mar 11;1437:95-106.PMID:26875116DOI:10.1016/j.chroma.2016.01.061.
Since Chinese lantern (Physalis alkekengi L.) represents a rich source of various bioactive secondary metabolites, there is an urge for its detailed characterization. Non-polar flavonoid aglycones represent one of the few bioactive species found in plant's cuticular waxes. The separation of flavonoids is already extensively covered in the literature, but methods dedicated to separation and identification of methylated flavonoids are rather scarce. In the present study a non-targeted approach for the separation, isolation and identification of methylated flavonoids present in P. alkekengi L. var. franchetii cuticular waxes was established. A rapid and simple separation on HPTLC silica gel was developed for preliminary screening of flavonoids. Fast HPLC-UV-MS(n) and HPLC-UV methods using a C6-Phenyl and a C18 stationary phase were also developed, respectively. In both cases, the right combination of temperature and tetrahydrofuran, as a mobile phase modifier, were shown to be crucial for a baseline separation of all studied compounds. By employing a semi-preparative analog of the C18 column, a simultaneous isolation of pure unknown analytes was achieved. Using these developed methods in combination with NMR, four 3-O-methylated flavonols were detected and identified in P. alkekengi L. var. franchetii cuticular waxes: myricetin 3,7,3'-trimethyl ether, Quercetin 3,7-dimethyl ether, myricetin 3,7,3',5'-tetramethyl ether and quercetin 3,7,3'-trimethyl ether. Moreover, the simple and fast isocratic HPLC-UV-MS(n) method (under 8min) should prove useful in quality control of P. alkekengi L. var. franchetii by enabling chromatographic fingerprinting of external methylated flavonols. Finally, a rationale for the mechanism of separation of these metabolites by HPLC is also given, which establishes a foundation for future development of chromatographic methods for methylated flavonols and related compounds.
Flavonol glycosides from Dasymaschalon sootepense
Phytochemistry 1998 Apr;47(7):1393-6.PMID:9611831DOI:10.1016/s0031-9422(97)00719-x.
Two novel flavonol glycosides have been isolated from a methanolic extract of Dasymaschalon sootepense leaves. They are the 3'-neohesperidoside and 3'(6G-alpha-rhamnosylneohesperidoside) of Quercetin 3,7-dimethyl ether.
Anti-Inflammatory and Skin-Moisturizing Effects of a Flavonoid Glycoside Extracted from the Aquatic Plant Nymphoides indica in Human Keratinocytes
Molecules 2018 Sep 13;23(9):2342.PMID:30216992DOI:10.3390/molecules23092342.
Nymphoides indica, an aquatic plant, is used as folk medicine in some countries. Our previous study demonstrated that the methanol extract of N. indica inhibited the activity of tyrosinases, tyrosine related protein (TRP)1 and TRP2, and microphthalmia-associated transcription factor, as well as the activity of protein kinase A, by effectively inhibiting cyclic adenosine monophosphate. Although the biological activities of N. indica extract have been reported, there are no reports on the skin bioactivity of the main compound(s) on human keratinocytes. This study investigated the anti-inflammatory and moisturizing effects of Quercetin 3,7-dimethyl ether 4'-glucoside (QDG) isolated from N. indica. In brief, ultraviolet B irradiated keratinocytes were pretreated with different concentrations of QDG, and the effects of QDG on various inflammatory markers were determined. QDG significantly inhibited inflammation-related cytokines and chemokines and enhanced the activation of skin barrier factors. Additionally, QDG also attenuated phosphorylation inhibition of the upstream cytokines and nuclear factor-κB expression. These results suggest that QDG isolated from N. indica may serve as a potential source of bioactive substances for chronic inflammatory skin diseases.