Atherosperminine
(Synonyms: 芒籽宁,Atherospermine) 目录号 : GC60604
Atherosperminine(Atherospermine)是一种天然的生物碱。Atherosperminine在体外表现出抗疟原虫活性，其IC50值为5.80μM。Atherosperminine是一种良好的还原剂，具有螯合金属的能力，具有促氧化活性。Atherosperminine对气管有非特异性的弛缓作用。
Cas No.:5531-98-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
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- SDS (Safety Data Sheet)
- Datasheet
Atherosperminine（Atherospermine）is a nature occurring alkaloid, has antiplasmodial activities in vitro, with an IC50 of 5.80 μM. Atherosperminine is good reductants with the ability to chelate metals and presented pro-oxidant activity. Atherosperminine exerts a non-specific relaxant effect on the trachealis[1].
[1]. Ayu Afiqah Nasrullah, et al. Antiplasmodial Alkaloids from the Bark of Cryptocarya nigra (Lauraceae). Molecules. 2013 Jul; 18(7): 8009-8017. [2]. C H Lin, et al. The relaxant actions on guinea-pig trachealis of atherosperminine isolated from Fissistigma. Eur J Pharmacol. 1993 Jun 11;237(1):109-16.
| Cas No. | 5531-98-6 | SDF | |
| 别名 | 芒籽宁,Atherospermine | ||
| Canonical SMILES | CN(C)CCC1=C2C=CC3=CC=CC=C3C2=C(OC)C(OC)=C1 | ||
| 分子式 | C20H23NO2 | 分子量 | 309.4 |
| 溶解度 | 储存条件 | Store at -20°C | |
| 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。 |
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| 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。 | ||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.2321 mL | 16.1603 mL | 32.3206 mL |
| 5 mM | 0.6464 mL | 3.2321 mL | 6.4641 mL |
| 10 mM | 0.3232 mL | 1.616 mL | 3.2321 mL |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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，
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2.
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The relaxant actions on guinea-pig trachealis of Atherosperminine isolated from Fissistigma glaucescens
Eur J Pharmacol 1993 Jun 11;237(1):109-16.PMID:8395388DOI:10.1016/0014-2999(93)90099-4.
The pharmacological activity of Atherosperminine, isolated from Fissistigma glaucescens, was determined in isolated guinea-pig trachealis. Atherosperminine (25-100 microM) and theophylline (10-1000 microM) both inhibited the contractile response caused by carbachol, prostaglandin F2 alpha (PGF2 alpha), U46619 (thromboxane A2 analogue), leukotriene C4 (LTC4) and Ca2+ (in the presence of 120 mM KCl) in a concentration-dependent manner. The inhibition was characterized by a rightwards shift of the concentration-response curves with suppression of the maximal contraction. Propranolol (1 microM), glibenclamide (10 microM) and removal of tracheal epithelium did not modify the relaxant action of Atherosperminine. Atherosperminine (25 and 50 microM) caused a 2.4- and 5.0-fold, respectively, potentiation of the action of forskolin to cause tracheal relaxation but did not potentiate the action of sodium nitroprusside or cromakalim. Atherosperminine (50 microM) potentiated the action of forskolin to increase tissue cAMP content and, in higher concentrations (100 and 250 microM), itself increased tissue cAMP but not cGMP content. Atherosperminine markedly inhibited cAMP phosphodiesterase but not cGMP phosphodiesterase in homogenates of guinea-pig trachealis. It is concluded that Atherosperminine exerts a non-specific relaxant effect on the trachealis. Its major mechanism of action appears to be inhibition of cAMP phosphodiesterase, perhaps with a minor effect on cGMP phosphodiesterase at higher concentrations.
Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product Atherosperminine
Psychopharmacology (Berl) 1978 Sep 15;59(1):29-33.PMID:100809DOI:10.1007/BF00428026.
(--)-Nuciferine and its Hofmann degradation product Atherosperminine showed divergent psychopharmacological effects. Because nuciferine has been reported to be a neuroleptic and Atherosperminine has some chemical resemblance to dopamine, they were investigated for their dopamine-receptor activities. Nuciferine had a pharmacologic profile of action associated with dopamine-receptor blockade; i.e., it induced catalepsy, inhibited spontaneous motor activity, conditioned avoidance response, amphetamine toxicity and stereotypy. On the other hand, Atherosperminine produced effects associated with dopamine receptor stimulation, i.e., stereotypy, increase in spontaneous motor activity and amphetamine toxicity, reversal of haloperidol-induced catalepsy and inhibition of conditioned avoidance response, inhibition of morphine analgesia, and potentiation of the anticonvulsant action of diphenylhydantoin. The results are discussed on the basis of the chemical configuration of the two compounds.
Antiplasmodial alkaloids from the bark of Cryptocarya nigra (Lauraceae)
Molecules 2013 Jul 8;18(7):8009-17.PMID:23884132DOI:10.3390/molecules18078009.
A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 μg/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), Atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D- and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), Atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC50 values of 5.40, 5.80 and 0.75 μM, respectively. In addition, (+)-N-methylisocolaurine (1) and Atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC50 values of 50.08 ug/mL and 42.87 ug/mL, respectively.
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae)
Bioorg Med Chem 2016 Sep 15;24(18):4464-4469.PMID:27492195DOI:10.1016/j.bmc.2016.07.043.
Alzheimer's disease is the most common form of dementia among older adults. Acetylcholinesterase and butyrylcholinesterase are two enzymes involved in the breaking down of the neurotransmitter acetylcholine. Inhibitors for these enzymes have potential to prolong the availability of acetylcholine. Hence, the search for such inhibitors especially from natural products is needed in developing potential drugs for Alzheimer's disease. The present study investigates the cholinesterase inhibitory activity of compounds isolated from three Cryptocarya species towards acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Nine alkaloids were isolated; (+)-nornantenine 1, (-)-desmethylsecoantofine 2, (+)-oridine 3, (+)-laurotetanine 4 from the leaves of Cryptocarya densiflora BI., Atherosperminine 5, (+)-N-methylisococlaurine 6, (+)-N-methyllaurotetanine 7 from the bark of Cryptocarya infectoria Miq., 2-methoxyatherosperminine 8 and (+)-reticuline 9 from the bark of Cryptocarya griffithiana Wight. In general, most of the alkaloids showed higher inhibition towards BChE as compared to AChE. The phenanthrene type alkaloid; 2-methoxyatherosperminine 8, exhibited the most potent inhibition against BChE with IC50 value of 3.95μM. Analysis of the Lineweaver-Burk (LB) plot of BChE activity over a range of substrate concentration suggested that 2-methoxyatherosperminine 8 exhibited mixed-mode inhibition with an inhibition constant (Ki) of 6.72μM. Molecular docking studies revealed that 2-methoxyatherosperminine 8 docked well at the choline binding site and catalytic triad of hBChE (butyrylcholinesterase from Homo sapiens); hydrogen bonding with Tyr 128 and His 438 residues respectively.
Armepavine oxalate induces cell death on CCRF-CEM leukemia cell line through an apoptotic pathway
Life Sci 2004 Jun 18;75(5):549-57.PMID:15158365DOI:10.1016/j.lfs.2003.12.017.
Drug-induced cell death can occur as a result of DNA damage, which in turn may lead to the reduction of bcl-2 expression and activation of caspase-3 expression. In the present study, we investigated the effect of armepavines and Atherosperminine on the cell survival rate and expression of bcl-2 and caspase-3 in CCRF-CEM cells. Our data have revealed that armepavine oxalate reduced the survival rate of CCRF-CEM cells in a dose- and time-dependent manner by MTT assay. However, no significant effects of armepavine MeI and Atherosperminine N-oxide on the survival rate of the CCRF-CEM cell were observed. Armepavine oxalate-induced cell death was considered to be apoptotic on the basis of observed formation of the DNA ladder and the typical apoptotic morphological change by Hoechst 33258 staining. The expression of bcl-2 protein in CCRF-CEM cells treated with 30 microM armepavine oxalate was significantly decreased in western blotting analysis. In contrast, the expression of active caspase-3 in the cells was increased by armepavine oxalate in a dose-dependent manner. These findings indicate the involvement of bcl-2 and caspase-3 in the apoptotic process of CCRF-CEM cells induced by armepavine oxalate. The increased expression of active caspase-3 as well as decreased expression of bcl-2 support the assumption the armepavine oxalate-treated cells may be capable to complete the entire apoptotic process ending in cell fragmentation.