(-)-Isocorypalmine
(Synonyms: (-)-异延胡索单酚碱,Tetrahydrocolumbamine; (S)-Tetrahydrocolumbamine) 目录号 : GC34949
An isoquinoline alkaloid and metabolite of L-THP with diverse biological activities
Cas No.:483-34-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(–)-Isocorypalmine is an isoquinoline alkaloid and a metabolite of L-tetrahydropalmitine that has been found in Corydalis and has diverse biological activities.1,2,3,4,5 It binds to human dopamine D1-5 receptors with Ki values of 6.2, 41.8, 37.3, 77.4, and 9.5 nM, respectively.2 (–)-Isocorypalmine inhibits Epstein-Barr virus-early antigen (EBV-EA) activation induced by phorbol 12-myristate 13-acetate in Raji cells (IC50 = 300 mol ratio/32 pmol TPA), which is predictive for anti-tumor activity.3 It is cytotoxic to A549, SKOV3, SK-MEL-2, and HCT15 cancer cells (IC50s = 67.32, 47.37, 47.66, and 67.32 μM, respectively).4 (–)-Isocorypalmine is active against clinical strains of C. albicans, C. glabratas, C. krusei, C. parapsilosis, and C. neoformans (MICs = 40-320 μg/ml).5
1.Xiao, W., Zhuang, X., Shen, G., et al.Simultaneous quantification of ?-tetrahydropalmatine and its urine metabolites by ultra high performance liquid chromatography with tandem mass spectrometryJ. Sep. Sci.37(6)696-703(2014) 2.Lee, D.Y.W., Liu, J., Zhang, S., et al.Asymmetric total synthesis of tetrahydroprotoberberine derivatives andevaluation of their binding affinities at dopamine receptorsBioorg. Med. Chem. Lett.27(6)1437-1440(2017) 3.Ito, C., Itoigawa, M., Tokuda, H., et al.Chemopreventive activity of isoquinoline alkaloids from Corydalis plantsPlanta Med.67(5)473-475(2001) 4.Kim, K.H., Piao, C., J., Choi, S.U., et al.New cytotoxic tetrahydroprotoberberine-aporphine dimeric and aporphine alkaloids from Corydalis turtschaninoviiPlanta Med.76(15)1732-1738(2010) 5.Rao, G.-X., Zhang, S., Wang, H.-M., et al.Antifungal alkaloids from the fresh rattan stem of Fibraurea recisa PierreJ. Ethnopharmacol.123(1)1-5(2009)
| Cas No. | 483-34-1 | SDF | |
| 别名 | (-)-异延胡索单酚碱,Tetrahydrocolumbamine; (S)-Tetrahydrocolumbamine | ||
| Canonical SMILES | OC(C=C1[C@@]2([H])N3CC4=C(C=CC(OC)=C4OC)C2)=C(C=C1CC3)OC | ||
| 分子式 | C20H23NO4 | 分子量 | 341.4 |
| 溶解度 | Methanol: soluble | 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。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.9291 mL | 14.6456 mL | 29.2912 mL |
| 5 mM | 0.5858 mL | 2.9291 mL | 5.8582 mL |
| 10 mM | 0.2929 mL | 1.4646 mL | 2.9291 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
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，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
A divergent route to 9, 10-oxygenated tetrahydroprotoberberine and 8-oxoprotoberberine alkaloids: synthesis of (±)-Isocorypalmine and oxypalmatine
Tetrahedron 2015 Feb 25;71(8):1227-1231.PMID:25691805DOI:10.1016/j.tet.2015.01.004.
A new route which is germane to the synthesis of 9,10-oxygenated tetrahydroprotoberberines and 8-oxoprotoberberines is described. The route features the use of a diester (14) generated from reaction of dimethylmalonate with an aryl halide in the presence of n-butyllithium. The amide 17 prepared in subsequent steps is a versatile precursor for the synthesis of tetrahydroprotoberberine and 8-oxoprotoberberine scaffolds using standard high-yielding reactions. In this manner, (±)-Isocorypalmine and oxypalmatine have been synthesized in 23% and 22 % yields respectively.
New alkaloids from Corydalis species
Nat Prod Res 2009;23(3):250-5.PMID:19235025DOI:10.1080/14786410801996390.
A new alkaloid, chaerophylline (1), together with known alkaloids (-)-corypalmine, berberine chloride, (-)-Isocorypalmine, (-)-corydalmine and (+)-bicuculline have been isolated from the crude base fraction of Corydalis chaerophylla. The crude base fractions of Corydalis longipes gave a new alkaloid, longicine (4), together with known alkaloids (+/-)-alpha-hydrastine, (+/-)-beta-hydrastine, N-methylhydrasteine hydroxylactam, 1-methoxyberberine chloride and berberinium hydroxide. These alkaloids are reported for the first time from the above species and their structures were established by chemical and spectroscopic evidence.
A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi
Planta Med 2001 Jul;67(5):423-7.PMID:11488455DOI:10.1055/s-2001-15820.
A new tetrahydroprotoberberine N-oxide alkaloid, (-)-cis-isocorypalmine N-oxide (1), together with two known compounds, 6-methoxydihydrosanguinarine (2) and norjuziphine (3), were isolated in continuing studies of the entire Formosan Corydalis tashiroi plant. The structures of these three compounds were determined through spectral analyses. In addition, compounds 1, 2, 3 and the seven alkaloids previously reported: (-)-cis-corydalmine N-oxide, (-)-trans-corydalmine N-oxide, (-)-trans-isocorypalmine N-oxide, scoulerine, protopine, oxysanguinarine and corydalmine, were found to possess antiplatelet aggregation activity.
New tetrahydroprotoberberine N-oxide alkaloids and cytotoxic constituents of Corydalis tashiroi
Planta Med 1999 Oct;65(7):643-7.PMID:17260290DOI:10.1055/s-1999-14090.
Three new tetrahydroprotoberberine N-oxide alkaloids, (-)- cis-corydalmine N-oxide, (-)- trans-corydalmine N-oxide, and (-)- trans-isocorypalmine N-oxide, along with three known benzo[ C]phenanthridine alkaloids, norsanguinarine, dihydrosanguinarine, and oxysanguinarine, six known berberine alkaloids, (-)-tetrahydropalmatine, (-)-corydalmine, (-)-scoulerine, (-)-corynoxidine, (-)-epicorynoxidine, palmatine, and protopine, have been isolated from the herb Corydalis tashiroi. The structures of these compounds were elucidated by spectroscopic analysis. Three of the isolated compounds show significant cytotoxic activities (ED (50) values < 4 microg/ml) against P-388, KB16, A549, and HT-29 cell lines.
Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor
Molecules 2008 Sep 25;13(9):2303-12.PMID:18830156DOI:10.3390/molecules13092303.
Bioactivity-guided fractionation of Corydalis yanhusuo has resulted in the isolation of eight known isoquinoline alkaloids - tetrahydropalmatine, isocorypalmine, stylopine, corydaline, columbamine, coptisin, 13-methylpalmatine, and dehydrocorybulbine. The tertiary alkaloids were further analyzed by chiral HPLC to determine the ratios of d-and l-isomers. The isolated compounds were screened for their binding affinities at the dopamine D(1) receptor. Isocorypalmine had the highest affinity (K(i) = 83 nM). The structure-affinity relationships of these alkaloids are discussed.