Colchicoside
(Synonyms: 秋水仙碱苷) 目录号 : GC47118
A glycoside form of 3-demethylcolchicine
Cas No.:477-29-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Colchicoside is a glycoside form of 3-demethylcolchicine that has been found in G. superba.1 Unlike cholchicine and 3-demethylcolchicine, colchicoside does not displace [3H]-colchicine from rat brain tubulin in vitro when used at a concentration of 25 μM.2 Colchicoside (1 and 10 μM) increases levels of the cytochrome P450 (CYP) isoforms CYP2C9 and CYP2E1 in primary human hepatocytes.3
1.Capistrano, I.R., Vangestel, C., Vanpachtenbeke, H., et al.Coadministration of a Gloriosa superba extract improves the in vivo antitumoural activity of gemcitabine in a murine pancreatic tumour modePhytomedicine23(12)1434-1440(2016) 2.Sugio, K., Maruyama, M., Tsurufuji, S., et al.Separation of tubulin-binding and anti-inflammatory activity in colchicine analogs and congenersLife Sci.40(1)35-39(1987) 3.DvorÁk, Z., UlrichovÁ, J., ModrianskÝ, M., et al.Effect of colchicine and its derivatives on the expression of selected isoforms of cytochrome P450 in primary cultures of human hepatocytesActa Univ. Palacki. Olomuc. Fac. Med.14347-50(2000)
| Cas No. | 477-29-2 | SDF | |
| 别名 | 秋水仙碱苷 | ||
| Canonical SMILES | O[C@H]([C@H]1O)[C@H](O)[C@@H](CO)O[C@H]1OC2=CC3=C(C(C([C@@H](NC(C)=O)CC3)=C4)=CC=C(OC)C4=O)C(OC)=C2OC | ||
| 分子式 | C27H33NO11 | 分子量 | 547.6 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,PBS (pH 7.2): 10 mg/ml | 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 | 1.8262 mL | 9.1308 mL | 18.2615 mL |
| 5 mM | 0.3652 mL | 1.8262 mL | 3.6523 mL |
| 10 mM | 0.1826 mL | 0.9131 mL | 1.8262 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。
Comparison of Seeds of Colchicum speciosum and Gloriosa superba in respect to Colchicine and Colchicoside Contents by RP-LC
Nat Prod Commun 2016 Mar;11(3):397-400.PMID:27169190doi
In this study, colchicine (CLN) and Colchicoside (CLS) contents of the methanolic extracts of the seeds of Colchicum speciosum Steven that were collected from Uzungöl, Trabzon and also the seeds belonging to two different samples of Gloriosa superba Linn. imported from India were compared by using RP-LC (Reversed Phase High Pressure Liquid Chromatography). This proposed method is advantageous in terms of sample preparation and selective separation of the compounds. Also the method was successfully validated in accordance with the International Conference on Harmonization (ICH) guideline acceptance criteria for system suitability, linearity and range, precision, specificity and accuracy. As a conclusion of this analysis, the Colchicoside and colchicine contents of G. superba (GSI), G. superba (GSII) and C. speciosum (CS) were found to be 312.9 mg/100 g and 333.1 mg/100 g; 434.0 mg/100 g and 471.1 mg/100 g, and 51.9 mg/100 g and 75.9 mg/100 g, respectively.
Thiocolchicoside exhibits anticancer effects through downregulation of NF-κB pathway and its regulated gene products linked to inflammation and cancer
Cancer Prev Res (Phila) 2010 Nov;3(11):1462-72.PMID:20978115DOI:10.1158/1940-6207.CAPR-10-0037.
The discovery of new uses for older, clinically approved drugs is one way to expedite drug development for cancer. Thiocolchicoside, a semisynthetic Colchicoside from the plant Gloriosa superba, is a muscle relaxant and used to treat rheumatologic and orthopedic disorders because of its analgesic and anti-inflammatory mechanisms. Given that activation of the transcription factor NF-κB plays a major role in inflammation and tumorigenesis, we postulated that thiocolchicoside would inhibit NF-κB and exhibit anticancer effects through the modulation of NF-κB-regulated proteins. We show that thiocolchicoside inhibited proliferation of leukemia, myeloma, squamous cell carcinoma, breast, colon, and kidney cancer cells. Formation of tumor colonies was also suppressed by thiocolchicoside. The Colchicoside induced apoptosis, as indicated by caspase-3 and poly(ADP-ribose) polymerase cleavage, and suppressed the expression of cell survival [e.g., Bcl-2, X-linked inhibitor of apoptosis (XIAP), MCL-1, bcl-xL, cIAP-1, cIAP-2, and cFLIP] proteins. Cell proliferation biomarkers such as c-MYC and phosphorylation of phosphoinositide 3-kinase and glycogen synthase kinase 3β were also blocked by thiocolchicoside. Because most cell survival and proliferation gene products are regulated by NF-κB, we studied the effect of thiocolchicoside on this transcription factor and found that thiocolchicoside inhibited NF-κB activation, degradation of inhibitory κBα (IκBα), IκBα ubiquitination, and phosphorylation, abolished the activation of IκBα kinase, and suppressed p65 nuclear translocation. This effect of thiocolchicoside on the NF-κB pathway led to inhibition of NF-κB reporter activity and cyclooxygenase-2 promoter activity. Our results indicate that thiocolchicoside exhibits anticancer activity through inhibition of NF-κB and NF-κB-regulated gene products, which provides novel insight into a half-century old drug.
Enzymatic modification of natural compounds with pharmacological properties
Ann N Y Acad Sci 1998 Dec 13;864:70-80.PMID:9928082DOI:10.1111/j.1749-6632.1998.tb10289.x.
Glycosides of various classes of natural products are widely distributed in nature, where they are often present esterified with aliphatic and aromatic acids at specific OH's of their sugar moieties. Many of these compounds are pharmacologically important molecules or possess other interesting properties. For instance, ginsenosides (e.g., 3) are therapeutic dammarane-type oligoglycosides isolated from the water-soluble portion of the dried roots and leaves of Panax ginseng C.A. Meyer (Aralianceae), a plant widely used in traditional Chinese medicine. In recent years, we have exploited the regioselectivity of lipases and proteases in organic solvents for the synthesis of specific esters of ginsenosides as well as the selectivity of the beta-1,4-galactosyltransferase from bovine colostrum to obtain new glycosyl derivatives of these compounds. The application of these two enzymatic methodologies has also been exemplified with other natural compounds with pharmacological properties: digitonin (5), Colchicoside (6), and flavonoid glycosides.