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MedKoo Cat#: 112071 | Name: Columbamine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Columbamine is an alkaloid that inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC50 = 30.6 µM). It also decreases glucose consumption of, and triglyceride levels in, HepG2 cells.

Chemical Structure

Columbamine
CAS#3621-36-1

Theoretical Analysis

MedKoo Cat#: 112071

Name: Columbamine

CAS#: 3621-36-1

Chemical Formula: C20H20NO4

Exact Mass: 338.1387

Molecular Weight: 338.38

Elemental Analysis: C, 70.99; H, 5.96; N, 4.14; O, 18.91

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Columbamine; Columbamin; Dehydroisocorypalmine
IUPAC/Chemical Name
2-hydroxy-3,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium
InChi Key
YYFOFDHQVIODOQ-UHFFFAOYSA-O
InChi Code
InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1
SMILES Code
OC1=C(C=C2CC[N+]3=C(C2=C1)C=C4C=CC(OC)=C(OC)C4=C3)OC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 338.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Columbamine-Mediated PTEN/AKT Signal Pathway Regulates the Progression of Glioma [Retraction]. Cancer Manag Res. 2021 Jul 19;13:5761. doi: 10.2147/CMAR.S329186. PMID: 34321923; PMCID: PMC8302809. 2: Niu HT, Liu Y, Wang YZ, Tian Y, Yang M, Jiang HS. Columbamine-Mediated PTEN/AKT Signal Pathway Regulates the Progression of Glioma. Cancer Manag Res. 2021 Jan 19;13:489-497. doi: 10.2147/CMAR.S286866. Retraction in: Cancer Manag Res. 2021 Jul 19;13:5761. PMID: 33500662; PMCID: PMC7826076. 3: Wang K, Feng X, Chai L, Cao S, Qiu F. The metabolism of berberine and its contribution to the pharmacological effects. Drug Metab Rev. 2017 May;49(2):139-157. doi: 10.1080/03602532.2017.1306544. Epub 2017 Apr 3. PMID: 28290706. 4: Yang T, Wei L, Ma X, Ke H. Columbamine suppresses proliferation and invasion of melanoma cell A375 via HSP90-mediated STAT3 activation. J Recept Signal Transduct Res. 2021 Feb;41(1):99-104. doi: 10.1080/10799893.2020.1794003. Epub 2020 Jul 16. PMID: 32669028. 5: Lei C, Yao Y, Shen B, Liu J, Pan Q, Liu N, Li L, Huang J, Long Z, Shao L. Columbamine suppresses the proliferation and malignization of colon cancer cells via abolishing Wnt/β-catenin signaling pathway. Cancer Manag Res. 2019 Sep 23;11:8635-8645. doi: 10.2147/CMAR.S209861. PMID: 31572013; PMCID: PMC6764743. 6: Tu TQ, Do PT, Van Nguyen D, Pham NTT, Nguyen TT, Chu MH. The columbamine O-methyltransferase gene (CoOMT) is capable of increasing alkaloid content in transgenic tobacco plants. Mol Biol Rep. 2022 Apr;49(4):2667-2675. doi: 10.1007/s11033-021-07074-6. Epub 2022 Jan 21. PMID: 35059967. 7: Cava MP, Reed TA. A synthesis of columbamine from berberine. J Org Chem. 1967 May;32(5):1640-1. doi: 10.1021/jo01280a087. PMID: 6041436. 8: He L, Zhong Z, Chen M, Liang Q, Wang Y, Tan W. Current Advances in Coptidis Rhizoma for Gastrointestinal and Other Cancers. Front Pharmacol. 2022 Jan 3;12:775084. doi: 10.3389/fphar.2021.775084. Erratum in: Front Pharmacol. 2022 May 26;13:931882. PMID: 35046810; PMCID: PMC8762280. 9: Lin Z, Li S, Guo P, Wang L, Zheng L, Yan Z, Chen X, Cheng Z, Yan H, Zheng C, Zhao C. Columbamine suppresses hepatocellular carcinoma cells through down- regulation of PI3K/AKT, p38 and ERK1/2 MAPK signaling pathways. Life Sci. 2019 Feb 1;218:197-204. doi: 10.1016/j.lfs.2018.12.038. Epub 2018 Dec 21. PMID: 30582951. 10: Bao M, Cao Z, Yu D, Fu S, Zhang G, Yang P, Pan Y, Yang B, Han H, Zhou Q. Columbamine suppresses the proliferation and neovascularization of metastatic osteosarcoma U2OS cells with low cytotoxicity. Toxicol Lett. 2012 Dec 17;215(3):174-80. doi: 10.1016/j.toxlet.2012.10.015. Epub 2012 Nov 2. PMID: 23124089. 11: Tao C, Hu SQ, Chen J, Chen YJ, Sun KH, Cui GZ, Ma M, Wu ZZ. Highly efficient synthesis and monoamine oxidase B inhibitory profile of demethyleneberberine, columbamine and palmatine. Neurochem Int. 2020 Oct;139:104807. doi: 10.1016/j.neuint.2020.104807. Epub 2020 Jul 22. PMID: 32711021. 12: Morishige T, Dubouzet E, Choi KB, Yazaki K, Sato F. Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells. Eur J Biochem. 2002 Nov;269(22):5659-67. doi: 10.1046/j.1432-1033.2002.03275.x. PMID: 12423366. 13: Wang Y, Han Y, Chai F, Xiang H, Huang T, Kou S, Han B, Gong X, Ye X. The antihypercholesterolemic effect of columbamine from Rhizoma Coptidis in HFHC- diet induced hamsters through HNF-4α/FTF-mediated CYP7A1 activation. Fitoterapia. 2016 Dec;115:111-121. doi: 10.1016/j.fitote.2016.09.019. Epub 2016 Oct 3. PMID: 27713083. 14: Rueffer M, Amann M, Zenk MH. S-Adenosyl-L-methionine: Columbamine-O-methyl transferase, a compartmentalized enzyme in protoberberine biosynthesis. Plant Cell Rep. 1986 Jun;5(3):182-5. doi: 10.1007/BF00269113. PMID: 24248127. 15: Virtanen P, Lassila V, Njimi T, Mengata DE. Natural protoberberine alkaloids from Enantia chlorantha, palmatine, columbamine and jatrorrhizine for thioacetamide-traumatized rat liver. Acta Anat (Basel). 1988;131(2):166-70. doi: 10.1159/000146507. PMID: 3369286. 16: Wang J, Jiang Y, Wang B, Zhang N. A review on analytical methods for natural berberine alkaloids. J Sep Sci. 2019 May;42(9):1794-1815. doi: 10.1002/jssc.201800952. Epub 2019 Apr 14. PMID: 30793835. 17: Liu X, Li W, Zhang H, Wang X, Huang Y, Li Y, Pan G. Biodistribution and pharmacokinetic profile of berberine and its metabolites in hepatocytes. Phytomedicine. 2022 Sep;104:154288. doi: 10.1016/j.phymed.2022.154288. Epub 2022 Jun 19. PMID: 35785560. 18: Wang AQ, Yuan QJ, Guo N, Yang B, Sun Y. [Research progress on medicinal resources of Coptis and its isoquinoline alkaloids]. Zhongguo Zhong Yao Za Zhi. 2021 Jul;46(14):3504-3513. Chinese. doi: 10.19540/j.cnki.cjcmm.20210430.103. PMID: 34402272. 19: Domagalina E, Smajkiewicz A. Izolowanie magnofloryny i kolumbaminy z Berberis vulgaris [Isolation of magnophlorine and columbamine from Berberis vulgaris]. Acta Pol Pharm. 1971;28(1):81-7. Polish. PMID: 5577816. 20: Nijland MM, van Laer AM, Uffelie OF. Voorkomen van jatrorrizine en columbamine in Enantia polycarpa (DC.) Engler en Diels. Papierchromatografische scheiding van palmatine en berberine [The occurrence of jatrorrhizine and columbamine in Enantia polycarpa (DC.) Engler and Diels. Paperchromatographic separation of palmatine and berberine]. Pharm Weekbl. 1966 May 6;101(18):405-7. Dutch. PMID: 5934972.

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