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Chelidonine

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-C1006

  • Specification : 98%

  • CAS number : 476-32-4

  • Formula : C20H19NO5

  • Molecular Weight : 353.37

  • PUBCHEM ID : 197810

  • Volume : 20mg

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Catalogue Number

BF-C1006

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

353.37

Appearance

Off-White crystalline powder

Botanical Source

Chelidonium majus

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6

Synonyms

(5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]dioxolo[4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol/Chelidonine/Khelidonin/(5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol/[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-/Chelidonin/(5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol/[5bR-(5ba,6b,12b4a)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-di oxolo[4,5-i]phenanthridin-6-ol/Diphylline/Helidonine/Stylophorin

IUPAC Name

(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

260.7±30.1 °C

Boiling Point

507.4±50.0 °C at 760 mmHg

Melting Point

135-140ºC

InChl

InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1

InChl Key

GHKISGDRQRSCII-ZOCIIQOWSA-N

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#:476-32-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

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

31382302

Abstract

Pyrrolizidine alkaloids are secondary plant constituents that became a subject of public concern because of their hepatotoxic, pneumotoxic, genotoxic, and cytotoxic effects. Due to disregardful harvesting and/or contamination with pyrrolizidine alkaloid-containing plants, there is a high risk of ingesting these substances with plant extracts or natural products. The limit for the daily intake was set to 0.007 µg/kg body weight. If contained in an extract, cleanup methods may help to minimize the pyrrolizidine alkaloid concentration. For this purpose, a material for depleting pyrrolizidine alkaloids in herbal preparations was developed based on the approach of molecular imprinting using monocrotaline. Molecular imprinted polymers are substances with specific binding characteristics, depending on the template used for imprinting. By means of group imprinting, only one molecule is used for creating selective cavities for many molecular pyrrolizidine alkaloid variations. Design of Experiment was used for the development using a 25 screening plan resulting in 64 polymers (32 MIPs/32 NIPs). Rebinding trials revealed that the developed material can compete with common cation exchangers and is more suitable for depleting pyrrolizidine alkaloids than C18- material. Matrix trials using an extract from Chelidonium majus show that there is sufficient binding capacity for pyrrolizidine alkaloids (80%), but the material is lacking in selectivity towards pyrrolizidine alkaloids in the presence of other alkaloids with similar functional groups such as berberine, chelidonine, and coptisine. Beyond this interaction, the selectivity could be proven for other structurally different compounds on the example of chelidonic acid.

Georg Thieme Verlag KG Stuttgart · New York.

Title

Development of a Selective Adsorbing Material for Binding of Pyrrolizidine Alkaloids in Herbal Extracts, Based on Molecular Group Imprinting.

Author

Kopp T1,2, Abdel-Tawab M1, Khoeiklang M1, Mizaikoff B2.

Publish date

2019 Sep

PMID

31261913

Abstract

A novel strategy was developed to identify hepatotoxic compounds in traditional Chinese medicines (TCMs). It is based on the exposure of HL-7702 cells to a TCM extract, followed by the identification and further determination of potential hepatotoxic compounds accumulated in the cells by liquid chromatography-tandem mass spectrometry (LC-MS/MS). As a case study, potential hepatotoxic components in Chelidonium majus L. were screened out. Five alkaloids (sanguinarine, coptisine, chelerythrine, protopine, and chelidonine) were identified by LC-MS/MS within 10 min, and their intracellular concentrations were first simultaneously measured by LC-MS/MS with a run time of 4 min. A cell viability assay was performed to assess the cytotoxicity of each alkaloid. With their higher intracellular concentrations, sanguinarine, coptisine, and chelerythrine were identified as the main hepatotoxic constituents in Ch. majus. The study provides a powerful tool for the fast prediction of cytotoxic components in complex natural mixtures on a high-throughput basis.

KEYWORDS

Chelidonium majus L.; LC-MS/MS; alkaloids; cytotoxicity; hepatotoxicity; intracellular accumulation

Title

Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC-MS/MS.

Author

Wu C1, Wang X1, Xu M2, Liu Y1, Di X3.

Publish date

2019 Jun 29


Description :

Chelidonine is an isoquinoline alkaloid isolated from Chelidonium majus L., causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, with anticancer and antiviral activity[1].