Table 1.
Plumeran indole alkaloids isolated from Aspidosperma.
| Alkaloid | Species [2] | Data |
|---|---|---|
| (−)-Vincadifformine (1) | A. macrocarpon, A. pyrifolium | 1H-NMR [29], 13C-NMR [30] |
| Fendlispermine (2) | A. fendleri | * |
| Spegazzinine (3) | A. chakensis | 1H-NMR [31] |
| Spegazzinidine (4) | A. chakensis | 1H-NMR [31] |
| 1,2-Dehydroaspidospermidine (5) | A. neblinae, A. quebracho-blanco | 1H-NMR, 13C-NMR [32] |
| 1,2-Dehydro- N-deacetyl-aspidospermin (6) | A. neblinae | IR, UV, MS [33] |
| (+)-Pyrifolidine (7) | A. cylindrocarpon, A. neblinae, A. pyrifolium, A. refractum, A. quebracho-blanco | 1H-NMR, 13C-NMR [32] |
| (+)-Aspidospermine (8) | A. album, A. australe, A. exalatum, A. peroba, A. polyneuron, A. pyricollum, A. pyrifolium, A. quebracho-blanco, A. quirandy, A. sessiflorum, A. rhombeosignatum | 1H-NMR, 13C-NMR [34,35] |
| 15-Methoxyaspidospermine (9) | A. pyrifolium | 1H-NMR, 13C-NMR [32] |
| Aspidospermidine (10) | A. neblinae, A. quebracho-blanco, A. pyrifolium, A. rhombeosignatum | GC/MS [36,37] |
| Deacetylaspidospermine (11) | A. neblinae, A. polyneuron, A. pyrifolium, A. quebracho-blanco | 1H-NMR [38] |
| (+)- O-Demethylaspidospermine (12) | A. discolor, A. eburneum, A. excelsum, A. neblinae, A. pyricollum | 1H-NMR [39] |
| N-Methyl-deacetylaspidospermine (13) | A. quebracho-blanco | MS [40] |
| Demethoxyaspidospermine (14) | A. discolor, A. macgravianum, A. neblinae, A. pyrifolium | 1H-NMR [39] |
| Aspidosine (15) | A. quebracho-blanco | IR, MS [41] |
| 10-Methoxy-aspidospermidine (16) | A. pyrifolium | 1H-NMR, 13C-NMR [42] |
| Demethoxypalosine (17) | A. discolor, A. exalatum, A. limae, A. rhombeosignatum | MS [39] |
| Palosine (18) | A. polyneuron, A. pyrifolium | 1H-NMR, 13C-NMR [42] |
| O-Demethylpalosine (19) | A. exalatum, A. limae, A. pyrifolium | 1H-NMR [43] |
| Aspidocarpine (20) | A. album, A. formosanum, A. limae, A. marcgravianum,A.megalocarpon | 1H-NMR, 13C-NMR [44] |
| O-Demethylaspidocarpine (21) | A. album, A. cuspa, A. melanocalyx | 1H-NMR [45] |
| Deacetylpyrifolidine (22) | A. neblinae, A. quebracho-blanco | GC/MS [46] |
| 15-Methoxypyrifolidine (23) | A. pyrifolium | 1H-NMR, 13C-NMR [32] |
| Aspidolimine (24) | A. limae, A. obscurinervium | 1H-NMR [47] |
| N-Propionyl-16,17-dihydroxyaspidospermidine (25) | A. melanocalyx | GC/MS [48] |
| N-formyl-aspidospermidine (26) | A. pyrifolium | ** [49] |
| N-Methylaspidospermidine (27) | A. quebracho-blanco | 1H-NMR, 13C-NMR [50] |
| Limaspermine (28) | A. limae | 1H-NMR [51] |
| 11-Methoxylimaspermine (29) | A. album | 1H-NMR [52] |
| Limaspermidine (30) | A. rhombeosignatum | MS [53] |
| Limapodine (31) | A. album, A. limae, A. marcgravianum | 1H-NMR [52] |
| 11-Methoxylimapodine (32) | A. limae | 1H-NMR [52] |
| Cylindrocarpinol (33) | A. cylindrocarpon | IR, MS [54] |
| N-Formylcilindrocarpinol (34) | A. cylindrocarpon | 1H-NMR [55] |
| N-Acetylcylindrocarpinol (35) | A. cylindrocarpon | 1H-NMR [25] |
| Cylindrocarine (36) | A. cylindrocarpon | 1H-NMR[23,25], 13C-NMR [23] |
| 19-Hidroxycylindrocarine (37) | A. cylindrocarpon | 1H-NMR [54] |
| Cylindrocarpidine (38) | A. cylindrocarpon | 1H-NMR [25], 13C-NMR [32] |
| Cylindrocarpine (39) | A. cylindrocarpon | 1H-NMR [56] |
| N-Methyl-cylindrocarine (40) | A. cylindrocarpon | 1H-NMR [55] |
| N-Formyl-cylindrocarine (41) | A. cylindrocarpon | 1H-NMR, 13C-NMR [23] |
| N-Benzoylcylindrocarine (42) | A. cylindrocarpon | 1H-NMR [55] |
| 12-Demethoxy- N-acetylcylindrocarine (43) | A. cylindrocarpon | 1H-NMR, 13C-NMR [23] |
| N-Dihydrocinamoil-19-hydroxy-cylindrocarine (44) | A. cylindrocarpon | 1H-NMR [55] |
| N-Formyl-19-hydroxycylindrocarine (45) | A. cylindrocarpon | 1H-NMR [23] |
| N-Cinnamoyl-19-hidroxycylindrocarine (46) | A. cylindrocarpon | 1H-NMR [23] |
* Data not found; ** The alkaloid was identified by comparison, after the acetylation of aspidospermidine.