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=CC3=C(OCO3)C=C2C(=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 |
|---|---|---|
| A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. | 2013-12-12 |
|
| Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia. | 2012-08-30 |
|
| Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. | 2011-06-10 |
|
| Phytochemical and antimicrobial characterization of Macleaya cordata herb. | 2010-12 |
|
| Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. | 2010-11-18 |
|
| Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). | 2010-11 |
|
| [Determination of protopine in Corydalis racemose by HPLC]. | 2010-09 |
|
| Extractions of isoquinoline alkaloids with butanol and octanol. | 2010-09 |
|
| In vivo anthelmintic activity of five alkaloids from Macleaya microcarpa (Maxim) Fedde against Dactylogyrus intermedius in Carassius auratus. | 2010-08-04 |
|
| Optimization of microwave-assisted extraction of protopine and allocryptopine from stems of Macleaya cordata (Willd) R. Br. using response surface methodology. | 2010-07 |
|
| A study on separation and extraction of four main alkaloids in Macleaya cordata (Willd) R. Br. with strip dispersion hybrid liquid membrane. | 2010-07 |
|
| Validated liquid chromatography-tandem mass spectrometry method for quantitative determination of dauricine in human plasma and its application to pharmacokinetic study. | 2010-05-01 |
|
| Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. | 2010-04 |
|
| Antiplasmodial agents from the Bhutanese medicinal plant Corydalis calliantha. | 2010-04 |
|
| BIAdb: a curated database of benzylisoquinoline alkaloids. | 2010-03-05 |
|
| Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional liquid chromatography/tandem mass spectrometry. | 2010-03 |
|
| Identification and characterization of a dual-acting antinematodal agent against the pinewood nematode, Bursaphelenchus xylophilus. | 2009-11-11 |
|
| Electron ionisation mass spectral study of 2-(2-carboxy-4, 5-dimethoxyphenyl)-6,7-dimethoxyisoquinolinium inner salt. | 2009-11 |
|
| Isoquinoline alkaloids from Macleaya cordata active against plant microbial pathogens. | 2009-11 |
|
| [Alkaloids from Dactylicapnos scandens Hutch]. | 2009-08 |
|
| [Alkaloids from Macleaya cordata]. | 2009-07 |
|
| Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. | 2009-03-13 |
|
| Simultaneous determination of tetrahydropalmatine, protopine, and palmatine in rat plasma by LC-ESI-MS and its application to a pharmacokinetic study. | 2009-02-20 |
|
| Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij. | 2009 |
|
| Protective effects of protopine on hydrogen peroxide-induced oxidative injury of PC12 cells via Ca(2+) antagonism and antioxidant mechanisms. | 2008-09-04 |
|
| Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine. | 2008-06 |
|
| Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts. | 2008-05-01 |
|
| Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. | 2008-01-22 |
|
| On the synthesis of protopine alkaloids. | 2007-09-14 |
|
| Conventional sample enrichment strategies combined with high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance analysis allows analyte identification from a single minuscule Corydalis solida plant tuber. | 2007-09-07 |
|
| Protective effect of protopine on the focal cerebral ischaemic injury in rats. | 2007-08 |
|
| Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. | 2007-05-18 |
|
| Antiviral and antimicrobial profiles of selected isoquinoline alkaloids from Fumaria and Corydalis species. | 2007-04-12 |
|
| Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. | 2007-04 |
|
| Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding. | 2007-01 |
|
| Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS. | 2006-12-06 |
|
| Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro. | 2006-10 |
|
| Protopine inhibits serotonin transporter and noradrenaline transporter and has the antidepressant-like effect in mice models. | 2006-06 |
|
| Large-scale separation of alkaloids from Corydalis decumbens by pH-zone-refining counter-current chromatography. | 2006-05-19 |
|
| 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. | 2006-03 |
|
| Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. | 2006-01-17 |
|
| Intestinal spasmolytic effects of STW 5 (Iberogast) and its components. | 2006 |
|
| Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. | 2005-10-15 |
|
| Regulation of glutamate level in rat brain through activation of glutamate dehydrogenase by Corydalis ternata. | 2005-08-31 |
|
| Theoretical and experimental NMR study of protopine hydrochloride isomers. | 2005-07 |
|
| Effects of protopine on intracellular calcium and the PKC activity of rat aorta smooth muscle. | 2005-04-25 |
|
| [Studies on the alkaloids from the herb of Corydalis adunca]. | 2005-02 |
|
| Effect of binary combination of some plant-derived molluscicides with MGK-264 or piperonyl butoxide on the reproduction of the snail Lymnaea acuminata. | 2005-02 |
|
| Acetylcholinesterase inhibitors from the aerial parts of Corydalis speciosa. | 2004-11 |
|
| [Determination of protopine and isocorydine in root of Dactylicapnos scandens by HPLC]. | 2004-10 |
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
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admin
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Edited
Mon Mar 31 21:21:48 GMT 2025
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| Record UNII |
UIW569HT35
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| Record Status |
Validated (UNII)
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300000032610
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SUBSTANCE->ACTIVE CONSTITUENT ALWAYS PRESENT |
