P8489
Protopine hydrochloride
≥98%, solid
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About This Item
Empirical Formula (Hill Notation):
C20H19NO5·HCl
CAS Number:
Molecular Weight:
389.83
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
EC Number:
228-196-5
MDL number:
InChI
1S/C20H19NO5.ClH/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17;/h2-3,7-8H,4-6,9-11H2,1H3;1H
InChI key
NWNVDSJZGYDVQW-UHFFFAOYSA-N
SMILES string
Cl.CN1CCc2cc3OCOc3cc2C(=O)Cc4ccc5OCOc5c4C1
assay
≥98%
form
solid
storage temp.
2-8°C
Quality Level
Related Categories
General description
Protopine is a celandine alkaloid and a bioactive compound associated with the plant families including fumariaceae, berberidaceae and papaveraceae. It is metabolized by demethylenation in the presence of the cytochrome enzymes cytochrome P450 family 2 subfamily d polypeptide 1 (CYP2D1) and cytochrome P450 family 2 subfamily c polypeptide 11 (CYP2C11).
Application
Protopine hydrochloride may be used in the calibration curve preparation for the quantification of alkaloids from Fumaria capreolata using liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-MS) and tandem mass spectrometry(MS/MS). It may also be used as an alkaloid in cytotoxicity and permeability studies carcinogenic cell lines.
Biochem/physiol Actions
Protopine hydrochloride is a Ca2+ channel blocker and antiplatelet agent.
Protopine possesses anti-parasitic, antimicrobial and anti-inflammatory property. It mediates mitotic arrest by favoring tubulin polymerization. Protopine elicits anti-invasive effects in breast cancer tumor progression.. It also provides protection against oxidative stress-induced cell death.
Disclaimer
Protect from light.
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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Yasuhiro Wada et al.
The Journal of organic chemistry, 72(19), 7301-7306 (2007-08-21)
For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno[2,1-a][3]benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group
Hongda Ma et al.
Journal of pharmaceutical and biomedical analysis, 49(2), 440-446 (2009-01-06)
A sensitive and specific liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) method has been developed and validated for the simultaneous quantification of tetrahydropalmatine, protopine and palmatine in rat plasma using phenacetin as the internal standard (IS). Two hundred microliters plasma samples were
Xiao Wang et al.
Journal of chromatography. A, 1115(1-2), 267-270 (2006-04-20)
pH-zone-refining counter-current chromatography was successfully applied to the separation of alkaloids from a crude extract of Corydalis decumbens (Thunb.) Pers. using a multilayer coil planet centrifuge (CPC). The experiment was performed with a two-phase solvent system composed of methyl tert-butyl
David K Liscombe et al.
The Journal of biological chemistry, 282(20), 14741-14751 (2007-03-29)
S-Adenosyl-l-methionine:tetrahydroprotoberberine cis-N-methyltransferase (EC 2.1.1.122) catalyzes the conversion of (S)-stylopine to the quaternary ammonium alkaloid, (S)-cis-N-methylstylopine, as a key step in the biosynthesis of protopine and benzophenanthridine alkaloids in plants. A full-length cDNA encoding a protein exhibiting 45 and 48% amino
Sonja Sturm et al.
Journal of chromatography. A, 1163(1-2), 138-144 (2007-07-14)
Identification of putative biomarker molecules within the genus Corydalis (Papaveraceae) was pursued by combining conventional off-line sample enrichment with high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance (HPLC-SPE-NMR) based structure elucidation. Off-line reversed phase solid phase extraction (SPE) was used to
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