NCBI Taxonomy: 141628

Vinca difformis (ncbi_taxid: 141628)

found 35 associated metabolites at species taxonomy rank level.

Ancestor: Vinca

Child Taxonomies: none taxonomy data.

Vincamine

Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

C21H26N2O3 (354.1943)


Vincamine is a vinca alkaloid, an alkaloid ester, an organic heteropentacyclic compound, a methyl ester and a hemiaminal. It has a role as an antihypertensive agent, a vasodilator agent and a metabolite. It is functionally related to an eburnamenine. Vincamine is a monoterpenoid indole alkaloid obtained from the leaves of *Vinca minor* with a vasodilatory property. Studies indicate that vincamine increases the regional cerebral blood flow. Vincamine is a natural product found in Vinca difformis, Vinca major, and other organisms with data available. A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders. Vincamine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1617-90-9 (retrieved 2024-07-01) (CAS RN: 1617-90-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Vincamine?is a monoterpenoid indole alkaloid extracted from the?Madagascar periwinkle. Vincamine?is a peripheral?vasodilator?and exerts a selective vasoregulator action on the brain microcapilar circulation[1]. Vincamine?is a?GPR40?agonist and acts as a β-cell protector by ameliorating β-cell dysfunction and promoting glucose-stimulated insulin secretion (GSIS).?Vincamine?improves glucose homeostasis?in vivo, and has the potential for the type 2 diabetes mellitus (T2DM) research[2]. Vincamine?is a monoterpenoid indole alkaloid extracted from the?Madagascar periwinkle. Vincamine?is a peripheral?vasodilator?and exerts a selective vasoregulator action on the brain microcapilar circulation[1]. Vincamine?is a?GPR40?agonist and acts as a β-cell protector by ameliorating β-cell dysfunction and promoting glucose-stimulated insulin secretion (GSIS).?Vincamine?improves glucose homeostasis?in vivo, and has the potential for the type 2 diabetes mellitus (T2DM) research[2].

   

Tombozine

(15α,19E)-Sarpagan-17-ol

C19H22N2O (294.1732)


   

Rhazin

methyl (1S,12S,13S,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraene-13-carboxylate

C21H24N2O3 (352.1787)


Akuammidine is a natural product found in Aspidosperma quebracho-blanco, Tabernaemontana citrifolia, and other organisms with data available.

   

Raupine

Sarpagan-10,17-diol

C19H22N2O2 (310.1681)


   

Velosimine

16-Episarpagan-17-al

C19H20N2O (292.1576)


An indole alkaloid that is sarpagan in which the methyl group attached to position 16 has been oxidised to the corresponding aldehyde.

   

Vincadifformine

6,7-Dihydrotabersonine

C21H26N2O2 (338.1994)


Origin: Plant; SubCategory_DNP: Monoterpenoid indole alkaloids, Aspidosperma alkaloids, Indole alkaloids

   

akuammigine

methyl (1R,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

C21H24N2O3 (352.1787)


A monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from Vinca sardoa and Uncaria rhynchophylla. D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

   

Vincadifformine

Vincadifformine

[C21H27N2O2]+ (339.2072)


Origin: Plant; SubCategory_DNP: Monoterpenoid indole alkaloids, Aspidosperma alkaloids, Indole alkaloids

   

Vincamin

Vincamine

C21H26N2O3 (354.1943)


C - Cardiovascular system > C04 - Peripheral vasodilators > C04A - Peripheral vasodilators D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D000970 - Antineoplastic Agents > D014748 - Vinca Alkaloids CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2327 Vincamine?is a monoterpenoid indole alkaloid extracted from the?Madagascar periwinkle. Vincamine?is a peripheral?vasodilator?and exerts a selective vasoregulator action on the brain microcapilar circulation[1]. Vincamine?is a?GPR40?agonist and acts as a β-cell protector by ameliorating β-cell dysfunction and promoting glucose-stimulated insulin secretion (GSIS).?Vincamine?improves glucose homeostasis?in vivo, and has the potential for the type 2 diabetes mellitus (T2DM) research[2]. Vincamine?is a monoterpenoid indole alkaloid extracted from the?Madagascar periwinkle. Vincamine?is a peripheral?vasodilator?and exerts a selective vasoregulator action on the brain microcapilar circulation[1]. Vincamine?is a?GPR40?agonist and acts as a β-cell protector by ameliorating β-cell dysfunction and promoting glucose-stimulated insulin secretion (GSIS).?Vincamine?improves glucose homeostasis?in vivo, and has the potential for the type 2 diabetes mellitus (T2DM) research[2].

   

methyl (1r,9s,10s,12r,13e)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

methyl (1r,9s,10s,12r,13e)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

C24H28N2O4 (408.2049)


   

methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

methyl (1r,13e,16s)-18-(acetyloxy)-13-ethylidene-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

C24H28N2O4 (408.2049)


   

15-ethyl-13-(hydroxymethyl)-17-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹¹,¹⁶]octadeca-2(10),4,6,8-tetraen-12-one

15-ethyl-13-(hydroxymethyl)-17-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹¹,¹⁶]octadeca-2(10),4,6,8-tetraen-12-one

C20H24N2O2 (324.1838)


   

methyl (1's,3r,4'as,5'as,10'as)-2-hydroxy-6,7-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

methyl (1's,3r,4'as,5'as,10'as)-2-hydroxy-6,7-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

C23H28N2O6 (428.1947)


   

methyl (1r,9s,10s,12s,13e)-13-ethylidene-18-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

methyl (1r,9s,10s,12s,13e)-13-ethylidene-18-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

C22H26N2O3 (366.1943)


   

[(1s,12s,13s,14r,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

[(1s,12s,13s,14r,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

C19H22N2O (294.1732)


   

methyl (1s,12s,14r,15e)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate

methyl (1s,12s,14r,15e)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate

C21H24N2O3 (352.1787)


   

methyl (1s,12s,13s)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate

methyl (1s,12s,13s)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carboxylate

C21H24N2O3 (352.1787)


   

(1r,12s)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-7-ol

(1r,12s)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-7-ol

C19H22N2O2 (310.1681)


   

(1r,11r,12z,17s)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carbaldehyde

(1r,11r,12z,17s)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carbaldehyde

C19H20N2O (292.1576)


   

(1r,9r,16r,21s)-2-methyl-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene

(1r,9r,16r,21s)-2-methyl-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene

C20H24N2 (292.1939)


   

methyl (1s,12r,19r)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate

methyl (1s,12r,19r)-12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,9-tetraene-10-carboxylate

C21H26N2O2 (338.1994)


   

(1s,12s)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

(1s,12s)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

C19H20N2O (292.1576)


   

methyl (1r,9r,16r,18r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

methyl (1r,9r,16r,18r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

C21H24N2O2 (336.1838)


   

methyl (1's,3r,4'as,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

methyl (1's,3r,4'as,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

C23H28N2O6 (428.1947)


   

(15s,16s,18r)-15-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0⁴,¹².0⁵,¹⁰.0¹⁶,¹⁸]icosa-4(12),5,7,9-tetraene

(15s,16s,18r)-15-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0⁴,¹².0⁵,¹⁰.0¹⁶,¹⁸]icosa-4(12),5,7,9-tetraene

C19H24N2O (296.1889)


   

methyl (1's,3r)-2-hydroxy-6,7-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

methyl (1's,3r)-2-hydroxy-6,7-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

C23H28N2O6 (428.1947)


   

(3e)-4-[(15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]but-3-en-2-one

(3e)-4-[(15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]but-3-en-2-one

C22H24N2O (332.1889)


   

methyl (1s,14s,15z,18s)-15-ethylidene-18-(hydroxymethyl)-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

methyl (1s,14s,15z,18s)-15-ethylidene-18-(hydroxymethyl)-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraene-18-carboxylate

C22H26N2O4 (382.1892)


   

methyl (1r,13z,16s)-13-ethylidene-18-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

methyl (1r,13z,16s)-13-ethylidene-18-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

C22H26N2O3 (366.1943)


   

methyl 2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

methyl 2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

C21H24N2O2 (336.1838)


   

(15r,16s,18r)-15-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0⁴,¹².0⁵,¹⁰.0¹⁶,¹⁸]icosa-4(12),5,7,9-tetraene

(15r,16s,18r)-15-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0⁴,¹².0⁵,¹⁰.0¹⁶,¹⁸]icosa-4(12),5,7,9-tetraene

C19H24N2O (296.1889)


   

normacusine b

normacusine b

C19H22N2O (294.1732)


   

methyl (1's,3s,4'as,5'ar,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

methyl (1's,3s,4'as,5'ar,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',4'a,5',5'a,7',8',10',10'a-octahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

C23H28N2O6 (428.1947)


   

(1s,12s,13r,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

(1s,12s,13r,14s,15e)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

C19H20N2O (292.1576)


   

(1s,12s,13r,14s)-15-ethylidene-7-hydroxy-13-(hydroxymethyl)-3,17λ⁵-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8,16-pentaen-17-ylium

(1s,12s,13r,14s)-15-ethylidene-7-hydroxy-13-(hydroxymethyl)-3,17λ⁵-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8,16-pentaen-17-ylium

[C19H21N2O2]+ (309.1603)