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N-Nornuciferine Sale

(Synonyms: N-去甲荷叶碱) 目录号 : GC36754

An alkaloid with cholinesterase inhibitory activity

N-Nornuciferine Chemical Structure

Cas No.:4846-19-9

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实验参考方法

Kinase experiment:

For the determination of the inhibition constant Ki values, various final concentrations of the specific substrate dextromethorphan for CYP2D6 in the range of 1 to 10 mM and different concentrations of the N-Nornuciferine in the range of 0 to 25 mM are used. After preincubation for 10 min, the reactions are initiated by the addition of NADPH. Each incubation test is performed in triplicate. Thirty minutes after the incubation is initiated, the reaction is stopped by the addition of 100 mL of ice-cold acetonitrile containing 1 mg/mL propranolol (IS). The incubation mixtures are then centrifuged at 15,000g for 10 min at 4 °C. Ten-microliter aliquots of the supernatants are injected into an LC-MS/MS system[1].

References:

[1]. Ye LH, et al. Identification and characterization of potent CYP2D6 inhibitors in lotus leaves. J Ethnopharmacol. 2014 Apr 11;153(1):190-6.

产品描述

N-Nornuciferine is an alkaloid that has been found in A. grandifolia and has cholinesterase inhibitory activity.1 It is an inhibitor of butyrylcholinesterase (BChE; IC50 = 5.6 ?M for the mouse enzyme).

1.Cometa, M.F., Fortuna, S., Palazzino, G., et al.New cholinesterase inhibiting bisbenzylisoquinoline alkaloids from Abuta grandifoliaFitoterapia83(3)476-480(2012)

Chemical Properties

Cas No. 4846-19-9 SDF
别名 N-去甲荷叶碱
Canonical SMILES COC1=C(OC)C2=C3C(CCN[C@]3([H])CC4=CC=CC=C24)=C1
分子式 C18H19NO2 分子量 281.35
溶解度 Soluble in DMSO 储存条件 Store at -20°C,protect from light
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Research Update

Pharmacokinetics of Nuciferine and N-Nornuciferine, Two Major Alkaloids From Nelumbo nucifera Leaves, in Rat Plasma and the Brain

Front Pharmacol 2018 Aug 29;9:902.PMID:30210336DOI:10.3389/fphar.2018.00902.

The leaf of the lotus (Nelumbo nucifera) is a natural plant resource used as both food and herbal medicine (He-Ye) in China. Alkaloids are considered the major bioactive compound of the herb and exhibit various biological activities, including anti-hyperlipidemia, anti-obesity, anti-inflammatory, and anti-hyperuricemic effects. Nuciferine (NF) and N-nuciferine (N-NF) are two major alkaloids found in the herb. In the present work, the plasma and brain pharmacokinetics of the two compounds were investigated after oral and intravenous (i.v.) administration of a lotus leaf alkaloid fraction to SD rats via ultra-performance liquid chromatography coupled with photodiode array detection and brain microdialysis. After oral administration (50 mg/kg), the two compounds NF and N-NF were rapidly absorbed into the blood and reached a mean maximum concentration (Cmax) of 1.71 μg/mL at 0.9 h and 0.57 μg/mL at 1.65 h, respectively. After i.v. administration (10 mg/kg), NF and N-NF were found to have a relatively wide volume of distribution (Vd, λz, 9.48 and 15.17 L/kg, respectively) and slow elimination half-life (t1/2, λz, 2.09 and 3.84 h, respectively). The oral bioavailability of NF and N-NF was estimated as 58.13% and 79.91%, respectively. After i.v. dosing (20 mg/kg), the two compounds rapidly crossed the blood-brain barrier and reached their Cmax (in unbound form): 0.32 and 0.16 μg/mL at 0.89 and 1.22 h, respectively. Both alkaloids had widespread distribution in the brain, with Vd, λz/F-values of 19.78 L/kg and 16.17 L/kg, respectively. The mean t1/2, λz values of NF and N-NF in the brain were 1.24 and 1.39 h, respectively. These results can help us to better understand the characteristics and neuro-pharmacological effects of the lotus alkaloid fraction.

Application of ionic liquids based microwave-assisted extraction of three alkaloids N-Nornuciferine, O-nornuciferine, and nuciferine from lotus leaf

Talanta 2010 Jan 15;80(3):1292-7.PMID:20006090DOI:10.1016/j.talanta.2009.09.027.

The application of ionic liquids based microwave-assisted extraction (ILMAE) was successfully developed for extracting three alkaloids N-Nornuciferine, O-nornuciferine, and nuciferine from lotus leaf. Seven kinds of 1-alkyl-3-methylimidazolium with different cations and anions were investigated in this work and 1.0M 1-hexyl-3-methylimidazolium bromide ([C(6)MIM]Br) solution was selected as solvent. In addition, the microwave parameters including irradiation power, extraction time and solid-liquid ratio were optimized. Compared with the regular MAE and conventional heat-reflux extraction (HRE), the proposed approach exhibited higher efficiency (0.9-43.7% enhanced) and shorter extraction time (from 2h to 2min), which indicated ILMAE was an efficient, rapid and simple sample preparation technique. Moreover, the proposed method was validated by the linearity, reproducibility, and recovery experiments. Good linearity was observed with the regression coefficients (r(2)) between 0.9998 and 0.9999. The recoveries of all methods were in the range of 94.6% and 105.5% with RSD lower than 6.6%, which indicated that the proposed method was credible.

Mechanisms Underlying the Action of Ziziphi Spinosae Semen in the Treatment of Insomnia: A Study Involving Network Pharmacology and Experimental Validation

Front Pharmacol 2021 Dec 24;12:752211.PMID:35002696DOI:10.3389/fphar.2021.752211.

Purpose: This study aimed to investigate the potential mechanisms and related bioactive components of ZSS for the treatment of insomnia. Method: The insomnia model of rat induced by PCPA was established. After oral administration of ZSS extract, the general morphological observation, pentobarbital sodium-induced sleep test and histopathological evaluation were carried out. Network pharmacology, assisted by UHPLC-Q-Exactive-MS/MS analysis, was developed to identify the targets of ZSS in the treatment of insomnia, as well as the corresponding signaling pathways. In addition, we validated the identified targets and pathways by RT-qPCR and immunohistochemical analysis. Results: The pentobarbital sodium-induced sleep test, determination of 5-HT and GABA levles in hypothalamic tissues and HE staining showed that ZSS extract was an effective treatment for insomnia. Network pharmacology analysis identified a total of 19 candidate bioactive ingredients in ZSS extract, along with 433 potentially related targets. Next, we performed protein-protein interaction (PPI), MCODE clustering analysis, GO functional enrichment analysis, KEGG pathway enrichment analysis, and ingredient-target-pathway (I-T-P) sub-networks analysis. These methods allowed us to investigate the synergistic therapeutic effects of crucial pathways, including the serotonergic and GABAergic synapse pathways. Our analyses revealed that palmitic acid, coclaurine, jujuboside A, N-Nornuciferine, caaverine, magnoflorine, jujuboside B, and betulinic acid, all played key roles in the regulation of these crucial pathways. Finally, we used the PCPA-induced insomnia in rats to validate the data generated by network pharmacology; these in vivo experiments clearly showed that pathways associated with the serotonergic and GABAergic system were activated in the rats model. Furthermore, ZSS treatment significantly suppressed high levels of HTR1A, GABRA1, and GABRG2 expression in the hypothalamus and reduced the expression levels of HTR2A. Conclusion: Based on the combination of comprehensive network pharmacology and in vivo experiments, we successfully identified the potential pharmacological mechanisms underlying the action of ZSS in the treatment of insomnia. The results provide a theoretical basis for further development and utilization of ZSS, and also provide support for the development of innovative drugs for the treatment of insomnia.

Evaluation of green and efficient deep eutectic solvents as media for extracting alkaloids from lotus leaf

Biomed Chromatogr 2022 Mar;36(3):e5293.PMID:34873711DOI:10.1002/bmc.5293.

Deep eutectic solvents (DESs) were applied as eco-friendly solvents in this study for the extraction of alkaloids from lotus leaf, including O-nornuciferine, N-Nornuciferine, nuciferine and roemerine. A series of hydrophilic and hydrophobic DESs with different hydrogen bond donors and a acceptors were synthesized and screened for a suitable DESs for extraction of alkaloids from lotus leaf. The study results showed that the hydrophilic DES with choline chloride and propanediol had the highest extraction yield. The main factors affecting the extraction efficiency-choline chloride-propanediol ratio, water content in deep eutectic solvents, solid-liquid ratio and extraction time-were investigated via a single-factor experiment. The optimized extraction conditions were 30% of water in choline chloride-propanediol (1:4) for heated extraction for 30 min and solid-liquid ratio 1:100 g/ml. Under optimum conditions, the extraction yields of O-nornuciferine, N-Nornuciferine, nuciferine and roemerine were 0.069, 0.152, 0.334 and 0.041 g/100 g respectively, which were higher than those of methanol in acidified aqueous solution. This study suggests considerable potential for DESs as promising materials for the green and efficient extraction solvents for bioactive alkaloids from natural sources.

Discovery of eight alkaloids with D1 and D2 antagonist activity in leaves of Nelumbo nucifera Gaertn. Using FLIPR assays

J Ethnopharmacol 2021 Oct 5;278:114335.PMID:34139281DOI:10.1016/j.jep.2021.114335.

Ethnopharmacological relevance: Dopamine receptors are long-standing primary targets in the treatment of mental diseases and there is growing evidence that suggests relationships between obesity and the dopamine system, especially dopamine D1 and D2 receptors. Leaves of Nelumbo nucifera Gaertn. (lotus leaves) have been medically used for helping long-term maintenance of weight loss. Whether and how components of lotus leaves function through the dopamine receptors remains unclear. Aim of the study: This work aimed to discover dopamine receptor-active alkaloids isolated from the lotus leaves, to evaluate their potencies and to analyze their structure activity relationship. Materials and methods: Dried lotus leaves were prepared and total extract was divided into alkaloids and flavones. Eight alkaloids were separated and characterized by a combination of high-performance liquid chromatography, quadrupole time-of-flight mass spectrometry and nuclear magnetic resonance, and assayed by a fluorometric imaging plate reader platform. Human embryonic kidney 239 cell lines expressing dopamine D1, D2 and serotonin 2A (5-HT2A) receptors, respectively, were cultured and used in the assay. Results: Alkaloids in the lotus leaves were the bioactive phytochemicals and inhibited dopamine from accessing the D1 and D2 receptors. All eight compounds functioned as D1-receptor antagonists and except N-Nornuciferine, seven alkaloids functioned as D2-receptor antagonists. (S)-coclaurine and (R)-coclaurine are optical isomers and antagonized both D1 and D2 with equivalent potencies, suggesting that the optical rotation of the methylene linker in the monobenzyl isoquinoline backbone did not influence their activity. Among the eight alkaloids, O-nornuciferine was the potent antagonist to both receptors (the lowest IC50 values, D1: 2.09 ± 0.65 μM and D2: 1.14 ± 0.10 μM) while N-Nornuciferine was found to be the least potent as it moderately antagonized D1 and was inactive on D2. O-nornuciferine was also a 5-HT2A antagonist (IC50~20 μM) while N-Nornuciferine had no activity. These hinted the importance of a methyl group attached to the nitrogen atom in the aporphine backbone. Armepavine showed a nearly 10-fold selectivity to D2. Conclusions: In this work, eight alkaloids were isolated from the leaves of Nelumbo nucifera Gaertn. and assayed on the D1 and D2 receptors. They were D1/D2 antagonists with IC50 values in the mid- to low-micromolar range and O-nornuciferine was the most potent alkaloid among the eight. This family of alkaloids was biochemically evaluated on the dopamine receptors by the same platform for the first time.