Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H19NO5 |
| Molecular Weight | 353.3686 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC2=C(C=C3OCOC3=C2)C(=O)CC4=C(C1)C5=C(OCO5)C=C4
InChI
InChIKey=GPTFURBXHJWNHR-UHFFFAOYSA-N
InChI=1S/C20H19NO5/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
| Molecular Formula | C20H19NO5 |
| Molecular Weight | 353.3686 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Protopine is the isoquinoline alkaloid found primarily in the plant families Berberidaceae, Ranunculaceae, Rutaceae, Fumariaceae. It has diverse biological activities, such as anti-thrombotic, anti-inflammatory, anti-parasitic activity, antimicrobial activity, as well as hepatoprotective effects in animal models. The biological activities of protopine are associated with its ability selectively inhibits K(ATP) channels by targeting on SUR1 subunit. In addition, was discovered that β2 -adrenoceptor (β2 -AR) is a target for antiasthma activities of protopine. On this target, binding of the drug occurs on the amino acid residual of Ser 169 through the formation of hydrogen bonds and receptor‐drug bumps.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [RP-HPLC method for determination of protopine in plasma and pharmacokinetics in rats]. | 2001 Oct |
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| Inhibition of mouse liver respiration by Chelidonium majus isoquinoline alkaloids. | 2003 Dec 15 |
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| Cytotoxic activity and quality control determinations on Chelidonium majus. | 2003 Feb |
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| In vitro anti-influenza virus activity of isoquinoline alkaloids from thalictrum species. | 2003 Feb |
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| Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana. | 2003 Feb |
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| Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum. | 2003 Jul |
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| Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. | 2003 Jun 5 |
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| In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis. | 2003 Mar |
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| Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells. | 2004 Dec 15 |
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| Cytochrome P450 isoenzymes involved in rat liver microsomal metabolism of californine and protopine. | 2004 Feb 6 |
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| How to treat tremor. | 2004 May |
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| Acetylcholinesterase inhibitors from the aerial parts of Corydalis speciosa. | 2004 Nov |
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| Protopine alkaloids in horse urine. | 2004 Nov 5 |
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| [Determination of protopine and isocorydine in root of Dactylicapnos scandens by HPLC]. | 2004 Oct |
|
| 1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae). | 2004 Oct |
|
| Effects of protopine on intracellular calcium and the PKC activity of rat aorta smooth muscle. | 2005 Apr 25 |
|
| [Studies on the alkaloids from the herb of Corydalis adunca]. | 2005 Feb |
|
| Effect of binary combination of some plant-derived molluscicides with MGK-264 or piperonyl butoxide on the reproduction of the snail Lymnaea acuminata. | 2005 Feb |
|
| Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro. | 2006 Mar |
|
| Protective effect of protopine on the focal cerebral ischaemic injury in rats. | 2007 Aug |
|
| Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding. | 2007 Jan |
|
| On the synthesis of protopine alkaloids. | 2007 Sep 14 |
|
| Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. | 2008 Jan 22 |
|
| Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine. | 2008 Jun |
|
| Protective effects of protopine on hydrogen peroxide-induced oxidative injury of PC12 cells via Ca(2+) antagonism and antioxidant mechanisms. | 2008 Sep 4 |
|
| Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts. | 2008 Sep-Oct |
|
| Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij. | 2009 |
|
| [Alkaloids from Dactylicapnos scandens Hutch]. | 2009 Aug |
|
| Simultaneous determination of tetrahydropalmatine, protopine, and palmatine in rat plasma by LC-ESI-MS and its application to a pharmacokinetic study. | 2009 Feb 20 |
|
| [Alkaloids from Macleaya cordata]. | 2009 Jul |
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| Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. | 2009 Mar 13 |
|
| Electron ionisation mass spectral study of 2-(2-carboxy-4, 5-dimethoxyphenyl)-6,7-dimethoxyisoquinolinium inner salt. | 2009 Nov |
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| Isoquinoline alkaloids from Macleaya cordata active against plant microbial pathogens. | 2009 Nov |
|
| Identification and characterization of a dual-acting antinematodal agent against the pinewood nematode, Bursaphelenchus xylophilus. | 2009 Nov 11 |
|
| Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. | 2010 Apr |
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| Antiplasmodial agents from the Bhutanese medicinal plant Corydalis calliantha. | 2010 Apr |
|
| In vivo anthelmintic activity of five alkaloids from Macleaya microcarpa (Maxim) Fedde against Dactylogyrus intermedius in Carassius auratus. | 2010 Aug 4 |
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| Phytochemical and antimicrobial characterization of Macleaya cordata herb. | 2010 Dec |
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| Optimization of microwave-assisted extraction of protopine and allocryptopine from stems of Macleaya cordata (Willd) R. Br. using response surface methodology. | 2010 Jul |
|
| A study on separation and extraction of four main alkaloids in Macleaya cordata (Willd) R. Br. with strip dispersion hybrid liquid membrane. | 2010 Jul |
|
| Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional liquid chromatography/tandem mass spectrometry. | 2010 Mar |
|
| BIAdb: a curated database of benzylisoquinoline alkaloids. | 2010 Mar 5 |
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| Validated liquid chromatography-tandem mass spectrometry method for quantitative determination of dauricine in human plasma and its application to pharmacokinetic study. | 2010 May 1 |
|
| Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). | 2010 Nov |
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| Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. | 2010 Nov 18 |
|
| [Determination of protopine in Corydalis racemose by HPLC]. | 2010 Sep |
|
| Extractions of isoquinoline alkaloids with butanol and octanol. | 2010 Sep |
|
| Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. | 2011 Jun 10 |
|
| Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia. | 2012 Aug 30 |
|
| A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. | 2013 Dec 12 |
Sample Use Guides
Protective action of protopine against experimental liver injury in mice: administration of two doses of protopine at 50 and 100 mg.kg-1 in an interval of 8 to 24 h before i.p. injection of CCl4, acetaminophen or thioacetamide.
Route of Administration:
Oral
The effects of protopine on human platelet aggregation and arachidonic acid (AA) metabolism via cyclooxygenase (COX) and lipoxygenase (LOP) enzymes were examined. Platelet aggregation induced by various platelet agonists (AA, ADP, collagen and PAF) was strongly inhibited by protopine in a concentration-related manner. The IC50 values (microM) of protopine (mean +/- SEM) against: AA; 12 +/- 2: ADP; 9 +/- 2: collagen; 16 +/- 2 and PAF; 11 +/- 1, were much less than those observed for aspirin.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 04:19:00 GMT 2023
by
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on
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| Record UNII |
UIW569HT35
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| Record Status |
Validated (UNII)
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