NCBI Taxonomy: 99321

Argemone munita (ncbi_taxid: 99321)

found 29 associated metabolites at species taxonomy rank level.

Ancestor: Argemone

Child Taxonomies: Argemone munita subsp. robusta, Argemone munita subsp. argentea, Argemone munita subsp. rotundata

Protopine

15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one

C20H19NO5 (353.12631640000006)


Protopine is a dibenzazecine alkaloid isolated from Fumaria vaillantii. It has a role as a plant metabolite. Protopine is a natural product found in Corydalis heterocarpa var. japonica, Fumaria capreolata, and other organisms with data available. Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic. See also: Sanguinaria canadensis root (part of); Chelidonium majus flowering top (part of). Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic [HMDB] Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic. Protopine is an alkaloid occurring in opium poppy,[2] Corydalis tubers[3] and other plants of the family papaveraceae, like Fumaria officinalis.[4] Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic transformations: 1) berberine bridge enzyme to (S)-Scoulerine; 2) (S)-cheilanthifoline synthase/CYP719A25 to (S)-Cheilanthifoline; 3) (S)-stylopine synthase/CYP719A20 to (S)-Stylopine; 4) (S)-tetrahydroprotoberberine N-methyltransferase to (S)-cis-N-Methylstylopine; and ultimately, 5) N-methylstylopine hydroxylase to protopine.[5] It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an analgesic.[6][7] Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2]. Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].

   

alpha-Allocryptopine

7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4(9),5,7,14,16(20)-hexaen-2-one

C21H23NO5 (369.1576148)


Alpha-allocryptopine, also known as alpha-fagarine or beta-homochelidonine, is a member of the class of compounds known as protopine alkaloids. Protopine alkaloids are alkaloids with a structure based on a tricyclic protopine formed by oxidative ring fission of protoberberine N-metho salts. Alpha-allocryptopine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Alpha-allocryptopine can be found in barley, which makes alpha-allocryptopine a potential biomarker for the consumption of this food product. Allocryptopine is a dibenzazecine alkaloid, an organic heterotetracyclic compound, a tertiary amino compound, a cyclic ketone, a cyclic acetal and an aromatic ether. Allocryptopine is a natural product found in Zanthoxylum beecheyanum, Berberis integerrima, and other organisms with data available. See also: Sanguinaria canadensis root (part of). KEIO_ID A137; [MS2] KO008812 KEIO_ID A137; [MS3] KO008813 KEIO_ID A137 Allocryptopine, a derivative of tetrahydropalmatine, is extracted from Macleaya cordata (Thunb.) Pers. Papaveraceae. Allocryptopine has antiarrhythmic effects and potently blocks human ether-a-go-go related gene (hERG) current[1][2]. Allocryptopine, a derivative of tetrahydropalmatine, is extracted from Macleaya cordata (Thunb.) Pers. Papaveraceae. Allocryptopine has antiarrhythmic effects and potently blocks human ether-a-go-go related gene (hERG) current[1][2].

   

Allocryptopine

7,8-DIMETHOXY-11-METHYL-17,19-DIOXA-11-AZATETRACYCLO[12.7.0.0?,?.0(1)?,(2)?]HENICOSA-1(14),4(9),5,7,15,20-HEXAEN-2-ONE

C21H23NO5 (369.15761480000003)


Allocryptopine is a dibenzazecine alkaloid, an organic heterotetracyclic compound, a tertiary amino compound, a cyclic ketone, a cyclic acetal and an aromatic ether. Allocryptopine is a natural product found in Zanthoxylum beecheyanum, Berberis integerrima, and other organisms with data available. See also: Sanguinaria canadensis root (part of). IPB_RECORD: 788; CONFIDENCE confident structure Allocryptopine, a derivative of tetrahydropalmatine, is extracted from Macleaya cordata (Thunb.) Pers. Papaveraceae. Allocryptopine has antiarrhythmic effects and potently blocks human ether-a-go-go related gene (hERG) current[1][2]. Allocryptopine, a derivative of tetrahydropalmatine, is extracted from Macleaya cordata (Thunb.) Pers. Papaveraceae. Allocryptopine has antiarrhythmic effects and potently blocks human ether-a-go-go related gene (hERG) current[1][2].

   

Protopine

Protopine

C20H19NO5 (353.12631640000006)


Annotation level-1 D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists relative retention time with respect to 9-anthracene Carboxylic Acid is 0.601 D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002491 - Central Nervous System Agents > D000700 - Analgesics relative retention time with respect to 9-anthracene Carboxylic Acid is 0.596 IPB_RECORD: 1441; CONFIDENCE confident structure Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2]. Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].

   

Fagarine I

Allocryptopine

C21H23NO5 (369.15761480000003)


Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Morphine alkaloids, Cryptopine alkaloids Allocryptopine, a derivative of tetrahydropalmatine, is extracted from Macleaya cordata (Thunb.) Pers. Papaveraceae. Allocryptopine has antiarrhythmic effects and potently blocks human ether-a-go-go related gene (hERG) current[1][2]. Allocryptopine, a derivative of tetrahydropalmatine, is extracted from Macleaya cordata (Thunb.) Pers. Papaveraceae. Allocryptopine has antiarrhythmic effects and potently blocks human ether-a-go-go related gene (hERG) current[1][2].

   

(1s,9s)-5,12-dimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14-hexaene-4,13-diol

(1s,9s)-5,12-dimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14-hexaene-4,13-diol

C19H21NO4 (327.14705060000006)


   

7,8,16,17-tetramethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]octadeca-1(14),4,6,8,15,17-hexaen-2-one

7,8,16,17-tetramethoxy-11-methyl-11-azatricyclo[12.4.0.0⁴,⁹]octadeca-1(14),4,6,8,15,17-hexaen-2-one

C22H27NO5 (385.18891320000006)


   

(1s,9s)-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4,6,10(15),11,13-hexaene-3,12-diol

(1s,9s)-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4,6,10(15),11,13-hexaene-3,12-diol

C19H21NO4 (327.14705060000006)


   

(1s,9s)-5,12,13-trimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14-hexaen-4-ol

(1s,9s)-5,12,13-trimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14-hexaen-4-ol

C20H23NO4 (341.16269980000004)


   

(1s,9s)-4,12,13-trimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14-hexaen-5-ol

(1s,9s)-4,12,13-trimethoxy-17-methyl-17-azatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14-hexaen-5-ol

C20H23NO4 (341.16269980000004)