NCBI Taxonomy: 72187

Hylomecon japonica (ncbi_taxid: 72187)

found 30 associated metabolites at species taxonomy rank level.

Ancestor: Hylomecon

Child Taxonomies: none taxonomy data.

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 (353.1263)


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].

   

Sanguinarine

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium

[C20H14NO4]+ (332.0923)


Sanguinarine is a benzophenanthridine alkaloid, an alkaloid antibiotic and a botanical anti-fungal agent. Sanguinarine is a natural product found in Fumaria capreolata, Fumaria kralikii, and other organisms with data available. Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine. Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. (A3208, A3209, A3208, A3208, A3208). See also: Sanguinaria canadensis root (part of); Chelidonium majus flowering top (part of). Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule.[citation needed]; Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine Sanguinarine (13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium) is derived from the root of Sanguinaria canadensis and other poppy-fumaria species (for references, see Ref. 1). This benzophenanthridine alkaloid is a structural homologue of chelerythrine, which is a potent inhibitor of protein kinase C (2). Sanguinarine has been shown to display antitumor (3) and anti-inflammatory properties in animals (4) and to inhibit neutrophil function, including degranulation and phagocytosis in vitro(5). It is also a potent inhibitor of Na-K-dependent ATPase (6, 7, 8) and cholinesterase (9).

   

Norchelerythrine

17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaene

C20H15NO4 (333.1001)


Norchelerythrine is a benzophenanthridine alkaloid. Norchelerythrine is a natural product found in Zanthoxylum beecheyanum, Zanthoxylum scandens, and other organisms with data available. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D000970 - Antineoplastic Agents

   

Chelidonine

(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

C20H19NO5 (353.1263)


Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic. Chelidonine is a natural product found in Sarcocapnos baetica, Sarcocapnos saetabensis, and other organisms with data available. Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity. See also: Chelidonium majus flowering top (part of). CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2255 Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3]. Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3].

   

Chelerythrine

17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14(19),15,17,20-nonaen-21-ium

C21H18NO4+ (348.1236)


Chelerythrine is a benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae. It has a role as an EC 2.7.11.13 (protein kinase C) inhibitor, an antibacterial agent and an antineoplastic agent. It is a benzophenanthridine alkaloid and an organic cation. A benzophenanthridine alkaloid evaluated as a kinase-inhibitor. Chelerythrine is a natural product found in Zanthoxylum fagara, Zanthoxylum mayu, and other organisms with data available. Chelerythrine is a benzophenanthridine alkaloid extracted from the plant Greater celandine (Chelidonium majus). It is a potent, selective, and cell-permeable protein kinase C inhibitor. See also: Sanguinaria canadensis root (part of); Chelidonium majus flowering top (part of). A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D000970 - Antineoplastic Agents

   

Norsanguinarine

5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene

C19H11NO4 (317.0688)


Norsanguinarine is a member of phenanthridines. Norsanguinarine is a natural product found in Fumaria indica, Corydalis balansae, and other organisms with data available. Norsanguinarine is found in opium poppy. Norsanguinarine is an alkaloid from Papaver rhoeas (corn poppy D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids

   

norchelerythrine

norchelerythrine

C20H15NO4 (333.1001)


   

Chelidonin

Chelidonine

C20H19NO5 (353.1263)


Annotation level-1 http://casmi-contest.org/examples.shtml; CASMI2012 Example 1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.627 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.621 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2461; CONFIDENCE confident structure IPB_RECORD: 921; CONFIDENCE confident structure Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3]. Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3].

   

Protopine

Protopine

C20H19NO5 (353.1263)


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].

   

sanguinarine

sanguinarine

[C20H14NO4]+ (332.0923)


Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Benzylisoquinoline alkaloids D020011 - Protective Agents > D002316 - Cardiotonic Agents D000890 - Anti-Infective Agents D002317 - Cardiovascular Agents Annotation level-1 IPB_RECORD: 1581; CONFIDENCE confident structure

   

SANGUINARINE

NCGC00015959-03!SANGUINARINE

[C20H14NO4]+ (332.0923)


   
   

Chelerythrine

Chelerythrine

C21H18NO4 (348.1236)


   

Chelerythrine

Chelerythrine

[C21H18NO4]+ (348.1236)


Annotation level-1

   
   

toddaline

Chelerythrine

C21H18NO4+ (348.1236)


D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D000970 - Antineoplastic Agents

   

6900-99-8

(1,3)Benzodioxolo(5,6-c)phenanthridine, 1,2-dimethoxy-

C20H15NO4 (333.1001)


D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D000970 - Antineoplastic Agents

   

Pseudochelerythrine

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium

C20H14NO4+ (332.0923)


Sanguinarine is a benzophenanthridine alkaloid, an alkaloid antibiotic and a botanical anti-fungal agent. Sanguinarine is a natural product found in Fumaria capreolata, Fumaria kralikii, and other organisms with data available. Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine. Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. (A3208, A3209, A3208, A3208, A3208). See also: Sanguinaria canadensis root (part of); Chelidonium majus flowering top (part of). Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule.[citation needed]; Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine Sanguinarine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2447-54-3 (retrieved 2024-06-29) (CAS RN: 2447-54-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Chelerythrine

(1,3)Benzodioxolo(5,6-c)phenanthridine, 1,2-dimethoxy-

C20H15NO4 (333.1001)


Norchelerythrine is a benzophenanthridine alkaloid. Norchelerythrine is a natural product found in Zanthoxylum beecheyanum, Zanthoxylum scandens, and other organisms with data available. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D000970 - Antineoplastic Agents

   

[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]methanol

[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]methanol

C22H21NO5 (379.142)


   

(23s)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-ol

(23s)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-ol

C20H15NO5 (349.095)


   

(1r,3ar,5as,7s,9as,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3ar,5as,7s,9as,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O (412.3705)


   

[(23r)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-yl]methanol

[(23r)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-yl]methanol

C21H17NO5 (363.1107)


   

1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O (412.3705)


   

17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-ol

17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-ol

C21H19NO5 (365.1263)


   

(20s)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-ol

(20s)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-ol

C21H19NO5 (365.1263)


   

{24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-yl}methanol

{24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-yl}methanol

C21H17NO5 (363.1107)


   

{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}methanol

{17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl}methanol

C22H21NO5 (379.142)


   

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-ol

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14,16,21-octaen-23-ol

C20H15NO5 (349.095)


   

5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2(10),3,8,11,14(22),15,17(21),23-nonaene

5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2(10),3,8,11,14(22),15,17(21),23-nonaene

C19H11NO4 (317.0688)