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Galanthamine N-Oxide Sale

(Synonyms: 加兰他明 N-氧化物) 目录号 : GC64492

Galanthamine N-Oxide 是一种生物碱,分离于 Zephyranthes concolor 的球茎中。Galanthamine N-Oxide 抑制电鳗乙酰胆碱酯酶 (AChE),EC50 为 26.2 μM。Galanthamine N-Oxide 是TcAChE,hAChE 和 hBChE 酶活性位点中底物调节的显著抑制剂。

Galanthamine N-Oxide Chemical Structure

Cas No.:134332-50-6

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1 mg
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5 mg
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10 mg
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产品描述

Galanthamine N-Oxide is an alkaloid obtained from the bulbs of Zephyranthes concolor. Galanthamine N-Oxide inhibits electric eel acetylcholinesterase (AChE) with an EC50 of 26.2 μM. Galanthamine N-Oxide is a prominent inhibitor of substrate accommodation in the active site of the Torpedo californica AChE (TcAChE), hAChE and hBChE enzymes[1][2].

[1]. Reyes-Chilpa R, et al. Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor. Molecules. 2011 Nov 15;16(11):9520-33.

Chemical Properties

Cas No. 134332-50-6 SDF Download SDF
别名 加兰他明 N-氧化物
分子式 C17H21NO4 分子量 303.35
溶解度 DMSO : 6.25 mg/mL (20.60 mM; ultrasonic and warming and heat to 60°C) 储存条件 4°C, away from moisture and light
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1 mg 5 mg 10 mg
1 mM 3.2965 mL 16.4826 mL 32.9652 mL
5 mM 0.6593 mL 3.2965 mL 6.593 mL
10 mM 0.3297 mL 1.6483 mL 3.2965 mL
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Research Update

Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor

Molecules 2011 Nov 15;16(11):9520-33.PMID:22086403DOI:10.3390/molecules16119520.

The bulbs and aerial parts of Zephyranthes concolor (Lindl.) Benth. & Hook. f. (Amaryllidaceae), an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, Galanthamine N-Oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution (1)H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution (1)H- and (13)C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and Galanthamine N-Oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 × 10(-5) M, respectively), indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10(-3) M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic.

Alkaloids of Amaryllidaceae as Inhibitors of Cholinesterases (AChEs and BChEs): An Integrated Bioguided Study

Phytochem Anal 2018 Mar;29(2):217-227.PMID:29044771DOI:10.1002/pca.2736.

Introduction: Enzymatic inhibition of acetylcholinesterase (AChE) is an essential therapeutic target for the treatment of Alzheimer's disease (AD) and AChE inhibitors are the first-line drugs for it treatment. However, butyrylcholinesterase (BChE), contributes critically to cholinergic dysfunction associated with AD. Thus, the development of novel therapeutics may involve the inhibition of both cholinesterase enzymes. Objective: To evaluate, in an integrated bioguided study, cholinesterases alkaloidal inhibitors of Amaryllidaceae species. Methodology: The proposed method combines high-performance thin-layer chromatography (HPTLC) with data analysis by densitometry, enzymatic bioautography with different AChEs and BChEs, the detection of bioactive molecules through gas chromatography mass spectrometry (GC-MS) analysis of spots of interest, and theoretical in silico studies. Results: To evaluate the bioguided method, the AChE and BChE inhibitory activities of seven Amaryllidaceae plant extracts were evaluated. The alkaloid extracts of Eucharis bonplandii exhibited a high level of inhibitory activity (IC50 = 0.72 ± 0.05 μg/mL) against human recombinant AChE (hAChE). Regarding human serum BChE (hBChE), the bulb and leaf extracts of Crinum jagus had the highest activity (IC50 = 8.51 ± 0.56 μg/mL and 11.04 ± 1.21 μg/mL, respectively). In the HPTLC spots with high inhibitory activity, several alkaloids were detected using GC-MS, and some of these alkaloids were identified. Galanthamine, Galanthamine N-Oxide and powelline should be the most prominent inhibitors of substrate accommodation in the active site of the Torpedo californica AChE (TcAChE), hAChE and hBChE enzymes. Conclusions: These results are evidence of the chemical relevance of the Colombian's Amaryllidaceae species for the inhibition of cholinesterases and as potent sources for the palliative treatment of AD. Copyright © 2017 John Wiley & Sons, Ltd.