(-)-nucipherine
Nuciferine
CAS: 475-83-2
Molecular Formula: C19H21NO2
(-)-nucipherine - Names and Identifiers
| Name | Nuciferine |
| Synonyms | 6a Nuciferin Nuciferine (-)-nucipherine (r)-1,2-dimethoxyaporphine Lotus Leaf Extract Nuciferin satis indigotica fort Extract 1,2-dimethoxy-6a-beta-aporphin 1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline (6aR)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 4H-Dibenzo[de,g]quinoline,5,6,6a,7-tetrahydro-1,2-diMethoxy-6-Methyl-, (6aR)- Nuciferine 1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline |
| CAS | 475-83-2 |
| InChI | InChI=1/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3 |
(-)-nucipherine - Physico-chemical Properties
| Molecular Formula | C19H21NO2 |
| Molar Mass | 295.38 |
| Density | 1.1156 (rough estimate) |
| Melting Point | 165.5°C |
| Boling Point | 437.06°C (rough estimate) |
| Specific Rotation(α) | (c, 1 in EtOH)-164 |
| Flash Point | 151.9°C |
| Solubility | Easily soluble in low-polarity organic solvents such as benzene, ether, chloroform, haloalkanes, etc., and have better solubility in hydrophilic organic solvents such as acetone and ethanol, but less soluble or almost insoluble in water |
| Vapor Presure | 1.27E-07mmHg at 25°C |
| Appearance | White powder |
| Color | white to beige |
| pKa | 7.87±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5000 (estimate) |
| MDL | MFCD01664592 |
| Physical and Chemical Properties | Soluble in benzene, ether, chloroform, halogenated alkanes and other organic solvents with low polarity, in acetone, ethanol and other hydrophilic organic solvents also have better solubility, the solubility in water is small or almost insoluble from the dried leaves of the Lotus |
| In vitro study | Nuciferine is a partial agonist at DD 2 receptor with an activity (E max =67% of dopamine) similar to aripiprazole (E max =50% of dopamine). In line with its partial agonist activity, Nuciferine inhibited dopamine-induced activation of G i with a potency similar to clozapine (Nuciferine K B =62 nM; Clozapine K B =20 nM) as determined via Schild regression analysis. The natural product Nuciferine acts as an effective inhibitor of adult worm motility. Nuciferine is effective at inhibiting both basal and 5-HT evoked motility of adult schistosomes. Nuciferine inhibits Sm.5HTR L and schistosomule with 0.24±0.04 and 0.62±0.22 μM, respectively. |
| In vivo study | In rodent models relevant to antipsychotic drug action, Nuciferine blocks head-twitch responses and discriminative stimulus effects of a 5-HT 2A agonist, substituted for clozapine discriminative stimulus, enhanced amphetamine induced locomotor activity, inhibited phencyclidine (PCP)-induced locomotor activity, and rescued PCP-induced disruption of prepulse inhibition without induction of catalepsy. In the presence of 1 or 3 mg/kg Nuciferine, cumulative PCP doses produce similar substitution to PCP alone. In the clozapine-trained animals, a dose-dependent substitution for 1.25 mg/kg clozapine is seen at 10 mg/kg Nuciferine (80.63% drug lever responding), with an ED 50 value of 5.42 mg/kg (95% CI 3.09-9.48 mg/kg) while the lower doses tested (0.1 mg/kg-3 mg/kg) fails to produce substitution for clozapine’s discriminative cue. In addition to a high percentage of responding on the clozapine-appropriate lever, 10 mg/kg Nuciferine also produces significant rate suppression as compared to vehicle control points (p<0.001). |
(-)-nucipherine - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 1544PSN1 6.1 / PGIII |
| HS Code | 29389090 |
| Toxicity | LD50 orl-rat: 280 mg/kg AIPTAK 197,261,72 |
(-)-nucipherine - Reference
| Reference Show more | 1. Meng Jie Liu Suzhen Zhou Bin Cui Xiaodi Chen Zhenhua. Simultaneous determination of nuciferine, Rutin and quercetin in lotus leaf by HPLC [J]. Chinese patent medicine 2016 38(01):111-114. 2. Li Mengjie, Liu Suzhen, Zhou Bin, et al. Simultaneous determination of three effective components in lotus leaf granules by RP-HPLC method [J]. China Pharmacy 2016(18th issue):2532-2534. 3. Wu Peng, Li Huifen, Zhang Xuelan, Cui Weiliang, Wang Junxiu. Study on the transformation mechanism of main chemical components in lotus leaves by fried charcoal [J]. Chinese patent medicines, 2015,37(08):1767-1770. 4. Hou Chengbo, Dong Yue Liu, Yin Xiu-Wen, etc. Study on intestinal permeability of multiple components of lotus leaf [J]. Chinese Journal of Traditional Chinese Medicine, 2016, 41(07):1183-1187. 5. Fan Li. Study on antibacterial effect of nuciferine in Penicillium medium [J]. Biochemical Engineering, 2018, 4(06):99-101. 6. Yin Xiuwen, Hou Chengbo, Chen Jiangpeng, etc. In vivo one-way intestinal perfusion model was used to study the intestinal permeability of lotus leaf multi-component whole body [J]. Chinese Journal of Traditional Chinese Medicine, 2017, 42(008):1525-1531. 7. Chen Qiang, Zhang Hua, sha mei, Liu Yongjing. Simultaneous determination of four alkaloids in lotus leaf by one-Test multi-evaluation method [J]. Fujian Journal of Traditional Chinese Medicine, 2020,51(06):29-32. 8. Zheng Yanyan, Li Li, Yuan Xiaoqing, Kong Fang, Liu Yanjuan. Optimization of enzymatic-assisted ultrasonic extraction of total alkaloids from Lotus leaves by response surface methodology [J]. Journal of Anhui Agricultural Sciences, 2020,48(21):183-187. 9. Fugang Wang, Juan Cao, Xueqin Hou, Zhiyong Li & Xiaolan Qu (2018) Pharmacokinetics, tissue distribution, bioavailability, and excretion of nuciferine, an alkaloid from lotus, in rats by LC/MS/MS, Drug Development and Industrial Pharmacy, 44:9, 1557-1562, D 10. Chen, X., Zheng, X., Zhang M. et al. Nuciferine alleviates LPS-induced mastitis in mice via suppressing the TLR4-NF-κB signaling pathway. Inflamm. Res. 67, 903-911 (2018). https://doi.org/10.1007/s00011-018-1183-2 11. Zhang, Lei, et al. "Direct coupling of thin-layer chromatography-bioautography with electrostatic field induced spray ionization-mass spectrometry for separation and identification of lipase inhibitors in lotus leaves." Analytica chimica acta 967 (2017): 5 12. Zhang, Lei, et al. "Direct coupling of thin-layer chromatography-bioautography with electrostatic field induced spray ionization-mass spectrometry for separation and identification of lipase inhibitors in lotus leaves." Analytica chimica acta 967 (2017): 5 13. [IF=6.558] Lei Zhang et al."Direct coupling of thin-layer chromatography-bioautography with electrostatic field induced spray ionization-mass spectrometry for separation and identification of lipase inhibitors in lotus leaves."Anal Chim Acta. 2017 May;967:52 14. [IF=5.279] Xianbao Deng et al."Analysis of Isoquinoline Alkaloid Composition and Wound-Induced Variation in Nelumbo Using HPLC-MS/MS."J Agr Food Chem. 2016;64(5):1130-1136 15. [IF=3.512] Thitirat Meelaph et al."Coregulation of Biosynthetic Genes and Transcription Factors for Aporphine-Type Alkaloid Production in Wounded Lotus Provides Insight into the Biosynthetic Pathway of Nuciferine."Acs Omega. 2018;3(8):8794-8802 16. [IF=3.225] Fugang Wang et al."Pharmacokinetics, tissue distribution, bioavailability, and excretion of nuciferine, an alkaloid from lotus, in rats by LC/MS/MS."Drug Dev Ind Pharm. 2018;44(9):1557-1562 17. [IF=3.174] Chen Xingxing et al."Nuciferine alleviates LPS-induced mastitis in mice via suppressing the TLR4-NF-κB signaling pathway."Inflamm Res. 2018 Dec;67(11):903-911 18. [IF=3] Zhang Pengyu et al."Discovery of novel antagonists on β2-adrenoceptor from natural products using a label-free cell phenotypic assay."N-S Arch Pharmacol. 2018 Dec;391(12):1411-1420 19. [IF=5.396] Zhen Shi et al."Nuciferine improves high-fat diet-induced obesity via reducing intestinal permeability by increasing autophagy and remodeling the gut microbiota."Food Funct. 2021 Jul;12(13):5850-5861 20. [IF=4.451] Haiyan Wen et al."Nuciferine attenuates the progression of osteoarthritis by targeting PI3K/Akt/NF-κB signaling pathway."J Funct Foods. 2021 Nov;86:104682 21. [IF=3.935] Peiliang Zhang et al."TLC-electrostatic field induced spray ionization-MS analysis of diverse structural skeletons and its coupling with TLC bioautography for characterization of lipase inhibitory components in American ginseng."J Pharmaceut Biomed. 2019 22. [IF=3.373] Na Zhang et al."TLC-MS identification of alkaloids in Leonuri Herba and Leonuri Fructus aided by a newly developed universal derivatisation reagent optimised by the response surface method."Phytochem Analysis. 2021 May;32(3):242-251 23. [IF=7.514] YueTong Yu et al."Identification and Quantification of Oligomeric Proanthocyanidins, Alkaloids, and Flavonoids in Lotus Seeds: A Potentially Rich Source of Bioactive Compounds."Food Chem. 2022 Jan;:132124 24. [IF=1.902] Yongjing Liu et al."Evaluation of Green and Efficient deep eutectic solvents as media for extracting Alkaloids from Lotus Leaf."Biomedical Chromatography. 2021 Dec 06 25. [IF=11.413] Xiliang Du et al."Nuciferine protects against high-fat diet-induced hepatic steatosis and insulin resistance via activating TFEB-mediated autophagy-lysosomal pathway."Acta Pharm Sin B. 2021 Dec;: 26. [IF=3.394] Chang Chen et al."Protective Effects Nuciferine in Middle Cerebral Artery Occlusion Rats Based on Transcriptomics."Brain Sciences. 2022 May;12(5):572 27. [IF=7.491] Yeqing Ruan et al."Processing tactics for low-cost production of pure nuciferine from lotus leaf."ULTRASONICS SONOCHEMISTRY. 2022 May;86:106026 |
(-)-nucipherine - Introduction
Pharmacological effects: It has the effect of reducing weight and lipid.
Last Update：2022-10-16 17:25:21
(-)-nucipherine - Reference Information
| Plant source: | Lotus leaf |
| alkaloid | nuciferine is an aporphine alkaloid extracted from the dried leaves of the Nymphaeaceae plant lotus. It is the main lipid-lowering active ingredient in lotus leaves. It is extracted from dried and crushed lotus leaves by a series of methods such as cellulase pretreatment, dilute hydrochloric acid extraction, ultrasonic-assisted extraction, and chloroform extraction. Traditional Chinese medicine believes that the lotus leaf is bitter and astringent in nature, flat, and belongs to the liver, spleen, stomach, and heart meridian. It has the effects of clearing heat and dampness, raising hair and clearing yang, cooling blood and stopping bleeding. The main chemical components of lotus leaves are nuciferine, citric acid, oxalic acid, etc. The main weight loss effect is nuciferine. Pharmacological studies have shown that lotus leaves have diuresis and laxative, intestinal toxicity, lipid-lowering and oil-removing, heat-clearing and antipyretic, etc. It can significantly reduce the content of triglyceride and cholesterol in serum, and has the health effect of regulating blood lipids. The use of lotus leaves to lose weight does not require deliberate dieting and has no side effects on the human body. |
| Biological activity | Nuciferine is a 5-HT2A,5-HT2C and 5-HT2B antagonist, IC50 is 478 nM,131 nM and 1 μM respectively; It is also an inverse agonist of 5-HT7, IC50 is 150 nM. |
| use | for content determination/identification/pharmacological experiments and other pharmacological effects: it has the effect of reducing weight and lipid. Clear heat and relieve heat, raise the hair and clear yang, cool the blood and stop bleeding. |
Last Update：2024-04-09 15:16:50
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