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Columbamine

$493

  • Brand : BIOFRON

  • Catalogue Number : BD-P0640

  • Specification : 98.0%(HPLC)

  • CAS number : 3621-36-1

  • Formula : C20H20NO4

  • Molecular Weight : 338.38

  • PUBCHEM ID : 72310

  • Volume : 20mg

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Catalogue Number

BD-P0640

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

338.38

Appearance

Orange crystalline

Botanical Source

Coptis chinensis Franch.; Stephania tetrandra S.Moore

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)O)OC

Synonyms

2-Hydroxy-3,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolinium/7,8,13,13a-Tetradehydro-2-hydroxy-3,9,10-trimethoxyberbinium/columbamine/jatrorrhizine/Dibenzo[a,g]quinolizinium, 5,6-dihydro-2-hydroxy-3,9,10-trimethoxy-/Dehydroisocorypalmine/2-Hydroxy-3,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium/3,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol

IUPAC Name

3,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol

Applications

Columbamine is a quaternary isoquinoline alkaloid isolated from Argemone mexicana.

Density

Solubility

DMSO : ≥ 23 mg/mL (67.97 mM);

Flash Point

Boiling Point

Melting Point

InChl

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

InChl Key

YYFOFDHQVIODOQ-UHFFFAOYSA-O

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:3621-36-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31400784

Abstract

Isoquinoline alkaloids possess broad pharmacological activities. In this study, the antifungal activity of twelve isoquinoline alkaloids, including berberine (1), jatrorrhizine (2), coptisine (3), corydaline (4), tetrahydroberberine (5), chelidonine (6), dihydrosanguinarine (7), chelerythrine (8), sanguinarine (9), palmatine (10), tetrahydropalmatine (11) and columbamine (12) were evaluated against eight plant pathogenic fungi in vitro. All the tested compounds showed varying degrees of inhibition against the eight tested plant fungi. Among them, sanguinarine exhibited high antifungal activity (EC50 ranging from 6.96-59.36 μg/mL). It displayed the best inhibitory activity against Magnaporthe oryzae (EC50 = 6.96 μg/mL), compared with azoxystrobin (EC50 = 12.04 μg/mL), and significantly suppressed spore germination of M. oryzae with the inhibition rate reaching 100% (50 μg/mL). The optical microscopy and scanning electron microscopy observations revealed that after treating M. oryzae mycelia with sanguinarine at 10 μg/mL, the mycelia appeared curved, collapsed and the cell membrane integrity was eventually damaged. Furthermore, the reactive oxygen species production, mitochondrial membrane potential and nuclear morphometry of mycelia had been changed, and the membrane function and cell proliferation of mycelia were destroyed. These results will enrich our insights into action mechanisms of antifungal activity of sanguinarine against M. oryzae.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Fungicidal activity; Isoquinoline alkaloids; Sanguinarine

Title

Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine.

Author

Zhao ZM1, Shang XF2, Lawoe RK1, Liu YQ3, Zhou R1, Sun Y1, Yan YF1, Li JC1, Yang GZ1, Yang CJ1.

Publish date

2019 Sep

PMID

30638299

Abstract

A new strategy by converging ultrafiltration high-performance liquid chromatography with ultraviolet and mass spectrometry and pH-zone-refining counter-current chromatography was developed for the rapid screening and separation of potential acetylcholinesterase inhibitors from the crude alkaloidals extract of Zanthoxylum nitidum. An optimized two-phase solvent system composed of chloroform/methanol/water (4:3:3, v/v) was used in this study. And, in the optimal solvent system, 45 mM hydrochloric acid was added to the aqueous stationary phase as the retainer, while 5 mM triethylamine was added to the organic mobile phase as the eluter. As a result, with the purity of over 95%, five alkaloids including jatrorrhizine (1, 340 mg), columbamine (2, 112 mg), skimmianine (3, 154 mg), palmatine (4, 226 mg), and epiberberine (5, 132 mg) were successfully purified in one step from 3.0 g crude alkaloidals extract. And their structures were identified by ultraviolet, mass spectrometry, 1 H and 13 C NMR spectroscopy. Notably, compounds 2, 4 and 5 were firstly reported in Z. nitidum. In addition, acetylcholinesterase inhibitory activities of compounds 1-5 were evaluated, and compounds 3, 4 and 5 exhibited stronger acetylcholinesterase inhibitory activity (IC50 values at 8.52 ± 0.64, 14.82 ± 1.21 and 3.12 ± 0.32 μg/mL, respectively) than berberine (IC50 value at 32.86 ± 2.14 μg/mL, positive control). The results indicated that the proposed method is an efficient technique to rapidly screen acetylcholinesterase inhibitors from complex samples, and could be served as a large-scale preparative technique for separating ionizable active compounds.

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS

Zanthoxylum nitidum; acetylcholinesterase inhibitors; counter-current chromatography; ultrafiltration

Title

Large-scale separation of acetylcholinesterase inhibitors from Zanthoxylum nitidum by pH-zone-refining counter-current chromatography target-guided by ultrafiltration high-performance liquid chromatography with ultraviolet and mass spectrometry screening.

Author

Liu M1, Liu Q1, Chen M1, Huang X1, Chen X1,2.

Publish date

2019 Mar

PMID

30582951

Abstract

Hepatocellular carcinoma (HCC) as primary liver cancer in adults is the most common cause led to internal cirrhosis responsible for patients’ death, which resulted in nearly a million deaths worldwide on both males and females in the developing and developed countries. Unfortunately, up to date, there are no highly effective treatment of medicine on HCC as lack of comprehensive cellular and molecular mechanism. According to the sources of human ancient history of medicine, traditional medicine could provide unique treatment to discontinue the challenging HCC. In this study, we inspected the effect of Columbamine (Col; C20H21NO5), an alkaloid isolated from calumba, on HCC utilizing three HCC cell-lines i.e. SMMC7721, HepG2 and Hep3B. Our data collected from these cell-lines exhibit strong Col suppression on the cell growth accompanying the dosage-dependent suppression, and we further confirmed the suppression on the tumor-growth in animal model. Rational of the Col suppression presents cellular mechanism by limiting the proliferation and colony formation of the cells marked with decreased expression of PCNA. Meanwhile decreases of migration indicated with increasing expression of E-cadherin and decreasing expression of N-cadherin, and of invasion labelled with decreasing expressions of MMP2 and MMP9, are accompanying the Col suppression along with the Col promoted apoptosis of the tumor cells. This programmed cell death marketed with cleaved Caspase 3 plus PAPR proteins, up-regulation of BAD and down-regulation of BCL2 is linked the Col suppression to unique calcium-related pathways. Our results unveiled that the Columbamine suppression on HCC based on the traditional medicine are clearly associated with PI3K/AKT, p38 and ERK1/2 MAPKs signaling pathways and guide further research orientation for developing the Col medicine against hepatocellular carcinoma.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Columbamine; Hepatocellular carcinoma (HCC); PI3K/AKT pathway; Traditional medicine; p38 and ERK1/2 MAPK pathway

Title

Columbamine suppresses hepatocellular carcinoma cells through down-regulation of PI3K/AKT, p38 and ERK1/2 MAPK signaling pathways.

Author

Lin Z1, Li S2, Guo P3, Wang L4, Zheng L1, Yan Z1, Chen X1, Cheng Z1, Yan H3, Zheng C3, Zhao C1.

Publish date

2019 Feb 1