Nepitrin
(Synonyms: 假荆芥属苷,Nepetin-7-glucoside) 目录号 : GC38985A flavonoid glycoside with diverse biological activities
Cas No.:569-90-4
Sample solution is provided at 25 µL, 10mM.
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Nepitrin is a flavonoid glycoside that has been found in S. plebeia and has diverse biological activities.1,2,3 It protects lard from thermal oxidation when used at concentrations of 0.02 and 0.04%. Nepitrin inhibits carrageenin-induced edema and yeast-induced fever in rats.2 It decreases serum levels of triglycerides and LDL, as well as increases serum HDL levels, in a rat model of high-fat diet-induced atherosclerosis when administered at doses of 20 and 50 mg/kg.3
1.Weng, X.C., and Weng, W.Antioxidant activity of compounds isolated from Salvia plebiaFood Chem.71(4)489-493(2000) 2.Agarwal, O.P.The anti-inflammatory action of nepitrin, a flavonoidAgents Actions12(3)298-302(1982) 3.Devi, S., Rangra, N.K., Rawat, R., et al.Anti-atherogenic effect of Nepitrin-7-O-glucoside: A flavonoid isolated from Nepeta hindostana via acting on PPAR - α receptorSteroids165108770(2021)
Cas No. | 569-90-4 | SDF | |
别名 | 假荆芥属苷,Nepetin-7-glucoside | ||
Canonical SMILES | O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=C(OC)C(O)=C13 | ||
分子式 | C22H22O12 | 分子量 | 478.4 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.0903 mL | 10.4515 mL | 20.903 mL |
5 mM | 0.4181 mL | 2.0903 mL | 4.1806 mL |
10 mM | 0.209 mL | 1.0452 mL | 2.0903 mL |
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2.
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Anti-atherogenic effect of Nepitrin-7-O-glucoside: A flavonoid isolated from Nepeta hindostana via acting on PPAR - α receptor
Steroids 2021 Jan;165:108770.PMID:33227319DOI:10.1016/j.steroids.2020.108770.
Atherogenic dyslipidemia is a condition and responsible for the induction of major cardiovascular diseases. Traditionally, Nepeta hindostana a medicinal plant commonly used as cardioprotective in Indo-Pak regions has gained importance because of its therapeutic active flavonoid Nepitrin-7-O-glucoside. Flavonoid-glycosides are steroids having the ability to exert specific, decisive action on the cardiac muscle. In the present research work flavonoid, Nepitrin-7-O-glucoside was isolated from methanolic extract via chromatographic techniques. The structure was elucidated and confirmed by different spectral techniques like Mass and 1H NMR spectrometry. Various preclinical atherosclerosis parameters such as lipid levels, SGOT/SGPT, body weight, histology of aorta and heart were estimated and beneficial effect of Nepitrin in high-fat diet (HFD) induced atherosclerosis for six weeks were observed. Outcomes of the preclinical results showed and proved that Nepitrin significantly improved dyslipidemia at an effective dose of 50 mg/kg as compared with HFD control and Simvastatin. Molecular docking showed significant binding affinity towards the target PPAR-α receptor (PDB: 2P54). Further the docked ligands with PDB: 2P54 were exposed to molecular dynamics studies to confirm the dynamic behaviour of PPAR-α receptor. Outcomes of the results of the in-vivo study and molecular dynamics study were in correlation with each-others. Further, it can be concluded that Nepitrin has a potent antiatherogenic agent and act by reducing the lipid levels via acting on PPAR-α receptor and regenerating the damaged cells.
The anti-inflammatory action of Nepitrin, a flavonoid
Agents Actions 1982 Jul;12(3):298-302.PMID:6982607DOI:10.1007/BF01965393.
The anti-inflammatory efficacy of Nepitrin (5,3',4'-trihydroxy-6-methoxy flavone), a flavonoid, was investigated in both acute and chronic models of inflammation in rats. Nepitrin was found to possess significant anti-inflammatory activity in the exudative and proliferative phases of inflammation. This action of Nepitrin could be due to its anti-bradykinin and anti-angiotensin action. Nepitrin also possessed anti-pyretic and weak analgesic activity. The study reveals that Nepitrin may be useful as an anti-inflammatory and anti-arthritic agent.
Molecular docking and antiamnesic effects of Nepitrin isolated from Rosmarinus officinalis on scopolamine-induced memory impairment in mice
Biomed Pharmacother 2017 Dec;96:700-709.PMID:29040957DOI:10.1016/j.biopha.2017.09.121.
Rosmarinus officinalis has long been known as the herb of remembrance. The present study was undertaken to investigate the anti-amnesic effects of Nepitrin isolated from Rosmarinus officinalis using in-vivo models of Y-maze and novel object recognition test (NORT) along with in vitro antioxidant and acetylcholinesterase (AChE) and buterylcholinesterase (BuChE) inhibition potential. Nepitrin showed a concentration dependent inhibition of AChE and BuChE enzymes with IC50 values of 65 and 72μg/mL, respectively and antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2, 2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) with IC50 values 270 and 210μg/mL, respectively. In mice, Nepitrin reversed the amnesia induced by scopolamine as indicated by a dose-dependent increase in spontaneous alternation performance in the Y-maze task (p <0.05 versus scopolamine) and increase in the discrimination index in the novel object recognition test (NORT) comparable to the standard drug donepezil 2mg/kg. Molecular docking studies were performed and the GlideScore of Nepitrin was consistent with its experimental AChE inhibitory activities. Nepitrin occupied the same binding site forming similar interactions to those formed by donepezil in the crystal structure. Thus, Nepitrin could provide a lead for the development of therapeutic agent useful in cognition and memory disorders such as Alzheimer's disease.
[Structure elucidation of antioxidative polyphenols and their biological properties]
Yakugaku Zasshi 2014;134(9):957-64.PMID:25174366DOI:10.1248/yakushi.14-00170.
Tannins and related polyphenols have been reported to produce diverse biological effects that indicate their therapeutic potential, including antioxidative, antibacterial, and antiviral activities. In an exploratory study of natural antioxidants with biological effects, we investigated the tannin constituents of myrtaceous plants reported to be rich in polyphenols. We isolated 16 new compounds from five species of the Melaleuca, Eucalyptus, Syzygium, Pimenta, and Myrtus genera. Among the new polyphenols, nine were isolated from Melaleuca squarrosa and characterized as C-glucosidic ellagitannin monomers and oligomers. The structures of the other new polyphenols from myrtaceous plants and a novel compound obtained from the berries of Pyracantha coccinea (Rosaceae) were also elucidated based on spectroscopic and chemical evidence. The antioxidative activity of isolates in the present study was estimated by measuring 1,1-diphenyl-2-picrylhydrazyl radical (DPPH)-scavenging activity and in the oxygen radical absorbance capacity (ORAC) test. We found that oenothein B, a macrocyclic ellagitannin dimer, is widely distributed in the genus Eucalyptus and produces a significant immunomodulatory effect on human dendritic cells (DCs). In a survey of natural ligands that bind to the aryl hydrocarbon receptor (AhR), Nepitrin, a flavonoid glycoside, and other polyphenols were revealed to be promising therapeutic candidates.
Two matrix metalloproteinase inhibitors from scrophularia striata boiss
Iran J Pharm Res 2014 Winter;13(1):149-55.PMID:24734066doi
Many species belonging to the Scrophularia genus have been used since ancient times as folk remedies for many medical conditions such as scrofulas, scabies, tumors, eczema, psoriasis, inflammations. The aim of this study was to characterize the matrix metalloproteinases (MMPs) inhibitor compounds of the Scrophularia striata extract by bio-guide fractionation. The aerial parts of S. striata were collected and different extracts were sequentially prepared with increasingly polar solvents. The MMPs inhibitory activity of the crude extract and its fractions were evaluated by the Zymoanalysis method. The pure compounds were purified from the active fraction by chromatography methods. Chemical structures were deduced by nuclear magnetic resonance and mass spectrometry. Two active compounds (acteoside and Nepitrin) were identified by bio-guide fractionation. The inhibitory effects of Nepitrin and acteoside at 20 µg/mL were about 56 and 18 percent, respectivly. The inhibitory effects of acteoside at 80 µg/mL were increased to about 73 percent. In summary, the results suggest that Nepitrin effectively inhibited MMPs inhibitory activity at low concentrations, whereas acteoside showed inhibition at high concentrations.