NCBI Taxonomy: 379217

Cissampelos capensis (ncbi_taxid: 379217)

found 34 associated metabolites at species taxonomy rank level.

Ancestor: Cissampelos

Child Taxonomies: none taxonomy data.

Salutaridine

(1S,9R)-3-hydroxy-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaen-12-one

C19H21NO4 (327.1471)


Salutaridine is a morphinane alkaloid from the opium poppy, in which the 5,6,8,14-tetradehydromorphinan-7-one skeleton is substituted at position 4 by a hydroxyl group, positions 3 and 6 by methoxy groups and position N17 by a methyl group. An intermediate in the biosynthesis of narcotic analgesics such as morphine and codeine. It has a role as a metabolite and an anti-HBV agent. It is a conjugate base of a salutaridinium(1+). It derives from a hydride of a morphinan. Salutaridine is a natural product found in Sarcocapnos saetabensis, Platycapnos saxicola, and other organisms with data available. A morphinane alkaloid from the opium poppy, in which the 5,6,8,14-tetradehydromorphinan-7-one skeleton is substituted at position 4 by a hydroxyl group, positions 3 and 6 by methoxy groups and position N17 by a methyl group. An intermediate in the biosynthesis of narcotic analgesics such as morphine and codeine. D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids

   

Dicentrine

(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene

C20H21NO4 (339.1471)


Dicentrine is an aporphine alkaloid. Dicentrine is a natural product found in Cissampelos pareira, Stephania abyssinica, and other organisms with data available. Dicentrine is an anticancer compound isolated from Lindera, a species of flowering plants. Dicentrine is a natural product isolated from the plant Stephania epigaea Lo with antihypertensive effect. Dicentrine is an α1-adrenoceptor antagonist which has effective against human hyperplastic prostates[1].

   

(S)-Reticuline

7-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-1-((3-HYDROXY-4-METHOXYPHENYL)METHYL)-6-METHOXY-2-METHYL-, (1S)-

C19H23NO4 (329.1627)


(S)-Reticuline is an endogenous precursor of morphine (PMID: 15383669). (S)-Reticuline is a key intermediate in the synthesis of morphine, the major active metabolite of the opium poppy. "Endogenous morphine" has been long isolated and authenticated by mass spectrometry in trace amounts from animal- and human-specific tissue or fluids (PMID: 15874902). Human neuroblastoma cells (SH-SY5Y) were shown capable of synthesizing morphine as well. (S)-Reticuline undergoes a change of configuration at C-1 during its transformation into salutaridinol and thebaine. From thebaine, there is a bifurcate pathway leading to morphine proceeding via codeine or oripavine, in both plants and mammals (PMID 15937106). (S)-reticuline is the (S)-enantiomer of reticuline. It has a role as an EC 2.1.1.116 [3-hydroxy-N-methyl-(S)-coclaurine 4-O-methyltransferase] inhibitor. It is a conjugate base of a (S)-reticulinium(1+). It is an enantiomer of a (R)-reticuline. Reticuline is a natural product found in Fumaria capreolata, Berberis integerrima, and other organisms with data available. See also: Peumus boldus leaf (part of). Alkaloid from Papaver somniferum (opium poppy) and Annona reticulata (custard apple) The (S)-enantiomer of reticuline.

   

bulbocapnine

d-Bulbocapnine

C19H19NO4 (325.1314)


An aporphine alkaloid that has been isolated from Corydalis and exhibits inhibitory activity against enzymes such as tyrosine 3-monooxygenase and diamine oxidase.

   

Suavedol

Spiro[2,5-cyclohexadiene-1,7(1H)-cyclopent[ij]isoquinolin]-4-one,2,3,8,8a-tetrahydro-6-hydroxy-5-methoxy-1-methyl-

C18H19NO3 (297.1365)


C78276 - Agent Affecting Digestive System or Metabolism > C29701 - Anti-ulcer Agent

   

(R)-Pronuciferine

10,11-dimethoxy-5-methyl-5-azaspiro[cyclohexane-1,2-tricyclo[6.3.1.0⁴,¹²]dodecane]-1(12),2,5,8,10-pentaen-4-one

C19H21NO3 (311.1521)


Alkaloid from Nelumbo nucifera (East India lotus). (R)-Pronuciferine is found in many foods, some of which are poppy, coffee and coffee products, sacred lotus, and cherimoya. (R)-Pronuciferine is found in cherimoya. (R)-Pronuciferine is an alkaloid from Nelumbo nucifera (East India lotus

   

Cycleanine

Cycleanine

C38H42N2O6 (622.3043)


Cycleanine is a potent vascular selective Calcium antagonist. Cycleanine has analgesic, muscle relaxant and anti-inflammatory activities. Cycleanine has potential for anti-ovarian cancer acting through the apoptosis pathway[1][2]. Cycleanine is a potent vascular selective Calcium antagonist. Cycleanine has analgesic, muscle relaxant and anti-inflammatory activities. Cycleanine has potential for anti-ovarian cancer acting through the apoptosis pathway[1][2].

   

(S)-Neolitsine

13-methyl-5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

C19H17NO4 (323.1158)


(S)-Neolitsine is found in herbs and spices. (S)-Neolitsine is an alkaloid from the leaves of Laurus nobilis (bay laurel).

   

Bulbocapnine

17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-18-ol

C19H19NO4 (325.1314)


   

Glaucine

4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

C21H25NO4 (355.1783)


Glaucine is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Glaucine is practically insoluble (in water) and a very strong basic compound (based on its pKa). Glaucine can be found in barley and custard apple, which makes glaucine a potential biomarker for the consumption of these food products. Glaucine has bronchodilator and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker, and is used medically as an antitussive in some countries. Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images, and has been detected as a novel psychoactive drug . Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 μM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3]. Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 μM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3]. Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 μM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3].

   

Glaziovine

11-hydroxy-10-methoxy-5-methyl-5-azaspiro[cyclohexane-1,2-tricyclo[6.3.1.0⁴,¹²]dodecane]-1(11),2,5,8(12),9-pentaen-4-one

C18H19NO3 (297.1365)


C78276 - Agent Affecting Digestive System or Metabolism > C29701 - Anti-ulcer Agent

   

Insularine

O-Methylinsulanoline

C38H40N2O6 (620.2886)


   

Glaziovine

L-(-)-N-Methylcrotsparine

C18H19NO3 (297.1365)


   
   

salutaridine

salutaridine

C19H21NO4 (327.1471)


Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Morphine alkaloids

   

Neolitsine

13-methyl-5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0^{2,10}.0^{4,8}.0^{16,23}.0^{18,22}]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

C19H17NO4 (323.1158)


   

(+)-Pronuciferine

(+)-Pronuciferine

C19H21NO3 (311.1521)


An isoquinoline alkaloid isolated from Berberis coletioides.

   

(4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

(4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

C18H19NO3 (297.1365)


   

(12r)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaene

(12r)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaene

C20H21NO4 (339.1471)


   

3-hydroxy-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10,13-pentaen-12-one

3-hydroxy-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6,10,13-pentaen-12-one

C19H21NO4 (327.1471)


   

11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

C18H19NO3 (297.1365)


   

(12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaen-18-ol

(12s)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaen-18-ol

C19H19NO4 (325.1314)


   

16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaene

16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaene

C20H21NO4 (339.1471)


   

(1r,16r)-10,26-dimethoxy-15,31-dimethyl-7,24,34-trioxa-15,31-diazaoctacyclo[19.10.3.2³,⁶.1⁸,¹².1¹⁸,²².0²⁵,³³.0²⁸,³².0¹⁶,³⁶]octatriaconta-3,5,8,10,12(36),18,20,22(35),25(33),26,28(32),37-dodecaen-9-ol

(1r,16r)-10,26-dimethoxy-15,31-dimethyl-7,24,34-trioxa-15,31-diazaoctacyclo[19.10.3.2³,⁶.1⁸,¹².1¹⁸,²².0²⁵,³³.0²⁸,³².0¹⁶,³⁶]octatriaconta-3,5,8,10,12(36),18,20,22(35),25(33),26,28(32),37-dodecaen-9-ol

C37H38N2O6 (606.273)


   

(1r,16r)-10,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-9-ol

(1r,16r)-10,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-9-ol

C37H40N2O6 (608.2886)


   

4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.2¹³,¹⁶.1³,⁷.1¹⁸,²².0¹¹,³⁶.0²⁶,³³]hexatriaconta-1(30),3,5,7(36),13,15,18,20,22(33),28,31,34-dodecaene

4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.2¹³,¹⁶.1³,⁷.1¹⁸,²².0¹¹,³⁶.0²⁶,³³]hexatriaconta-1(30),3,5,7(36),13,15,18,20,22(33),28,31,34-dodecaene

C38H42N2O6 (622.3043)


   

10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

C19H21NO3 (311.1521)


   

9,10,26-trimethoxy-15,31-dimethyl-7,24,34-trioxa-15,31-diazaoctacyclo[19.10.3.2³,⁶.1⁸,¹².1¹⁸,²².0²⁵,³³.0²⁸,³².0¹⁶,³⁶]octatriaconta-3,5,8,10,12(36),18,20,22(35),25(33),26,28(32),37-dodecaene

9,10,26-trimethoxy-15,31-dimethyl-7,24,34-trioxa-15,31-diazaoctacyclo[19.10.3.2³,⁶.1⁸,¹².1¹⁸,²².0²⁵,³³.0²⁸,³².0¹⁶,³⁶]octatriaconta-3,5,8,10,12(36),18,20,22(35),25(33),26,28(32),37-dodecaene

C38H40N2O6 (620.2886)


   

(4's)-11'-hydroxy-10'-methoxy-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

(4's)-11'-hydroxy-10'-methoxy-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

C17H17NO3 (283.1208)


   

(12r)-17-methoxy-11,18-dimethyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene

(12r)-17-methoxy-11,18-dimethyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaene

C20H21NO3 (323.1521)


   

(12s)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaene

(12s)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14(19),15,17-hexaene

C20H21NO4 (339.1471)


   

(1r,17r)-27,38-dimethoxy-16,32-dimethyl-9,25,35,39-tetraoxa-16,32-diazanonacyclo[20.10.3.2¹⁰,¹³.1³,⁷.1⁶,¹¹.1¹⁹,²³.0¹²,¹⁷.0²⁶,³⁴.0²⁹,³³]tetraconta-3,5,7(40),10,12,19,21,23(36),26(34),27,29(33),37-dodecaene

(1r,17r)-27,38-dimethoxy-16,32-dimethyl-9,25,35,39-tetraoxa-16,32-diazanonacyclo[20.10.3.2¹⁰,¹³.1³,⁷.1⁶,¹¹.1¹⁹,²³.0¹²,¹⁷.0²⁶,³⁴.0²⁹,³³]tetraconta-3,5,7(40),10,12,19,21,23(36),26(34),27,29(33),37-dodecaene

C38H38N2O6 (618.273)


   

(9s)-4,15,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaen-5-ol

(9s)-4,15,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaen-5-ol

C20H23NO4 (341.1627)


   

(9r)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

(9r)-4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene

C21H25NO4 (355.1783)