NCBI Taxonomy: 1961247

Cyclea atjehensis (ncbi_taxid: 1961247)

found 21 associated metabolites at species taxonomy rank level.

Ancestor: Cyclea

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 (353.12631640000006)


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].

   

Argemonine

N-Methylpavine

C21H25NO4 (355.178349)


   

Laurotetanine

4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol

C19H21NO4 (327.14705060000006)


Laurotetanine is found in cherimoya. Laurotetanine is an alkaloid from the leaves of Peumus boldus (boldo Alkaloid from the leaves of Peumus boldus (boldo). Laurotetanine is found in cherimoya.

   

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].

   
   

(-)-Argemonine

(-)-Argemonine

C21H25NO4 (355.178349)


The (-)-(S,S)-enantiomer of argemonine.

   

(12s)-18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(19),2,4(8),9,16(20),17-hexaene-13-carbaldehyde

(12s)-18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(19),2,4(8),9,16(20),17-hexaene-13-carbaldehyde

C20H19NO5 (353.12631640000006)


   

25,35-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9,11,18,20,22(33),24(32),25,27,29,34,36-tetradecaene-10,21-diol

25,35-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9,11,18,20,22(33),24(32),25,27,29,34,36-tetradecaene-10,21-diol

C36H34N2O6 (590.2416744)


   

25,35-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(30),3,5,9,11,18,20,22(33),24,26,28,31,34,36-tetradecaen-21-ol

25,35-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(30),3,5,9,11,18,20,22(33),24,26,28,31,34,36-tetradecaen-21-ol

C36H34N2O5 (574.2467594)


   

21,25,35-trimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9(35),10,12(34),18,20,22(33),24(32),25,27,29,36-tetradecaen-10-ol

21,25,35-trimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9(35),10,12(34),18,20,22(33),24(32),25,27,29,36-tetradecaen-10-ol

C37H36N2O6 (604.2573236000001)


   

1-[(1r,19r)-24-hydroxy-28-methoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

1-[(1r,19r)-24-hydroxy-28-methoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

C37H36N2O7 (620.2522386)


   

1-[(1s,19s)-24,28-dimethoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

1-[(1s,19s)-24,28-dimethoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

C38H38N2O7 (634.2678877999999)


   

18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(19),2,4(8),9,16(20),17-hexaene

18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(19),2,4(8),9,16(20),17-hexaene

C19H19NO4 (325.1314014)


   

1-[(1r,19s)-24-hydroxy-28-methoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

1-[(1r,19s)-24-hydroxy-28-methoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

C37H36N2O7 (620.2522386)


   

4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaen-5-ol

4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaen-5-ol

C19H21NO4 (327.14705060000006)


   

(16s)-21,25,35-trimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9(35),10,12(34),18,20,22(33),24(32),25,27,29,36-tetradecaen-10-ol

(16s)-21,25,35-trimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9(35),10,12(34),18,20,22(33),24(32),25,27,29,36-tetradecaen-10-ol

C37H36N2O6 (604.2573236000001)


   

(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)


   

(16s)-25,35-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9,11,18,20,22(33),24(32),25,27,29,34,36-tetradecaene-10,21-diol

(16s)-25,35-dimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.2⁹,¹².1¹⁸,²².0¹¹,¹⁶.0²⁷,³¹]heptatriaconta-1(31),3,5,9,11,18,20,22(33),24(32),25,27,29,34,36-tetradecaene-10,21-diol

C36H34N2O6 (590.2416744)


   

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

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)


   

(12s)-18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(19),2,4(8),9,16(20),17-hexaene

(12s)-18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(19),2,4(8),9,16(20),17-hexaene

C19H19NO4 (325.1314014)


   

1-[(1r,19s)-24,28-dimethoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

1-[(1r,19s)-24,28-dimethoxy-18-methyl-7,10,12,26-tetraoxa-18,33-diazaoctacyclo[25.6.2.2³,⁶.1⁸,¹⁵.1²¹,²⁵.0⁹,¹³.0³⁰,³⁴.0¹⁹,³⁷]nonatriaconta-3,5,8,13,15(37),21,23,25(36),27(35),28,30(34),38-dodecaen-33-yl]ethanone

C38H38N2O7 (634.2678877999999)