TABLE 1
IC50 values determined with 30-minute preincubation and inhibition characteristics for the alkaloids organized according to the isoquinoline alkaloid subgroups.
The methylenedioxyphenyl (MDP) moiety is shown in 1 (protopine) inside the circle.
| No. | Compound (Stereochemistry) | Structure | Shifted IC50a (95% CIb) (µM) | IC50-fold Shift or TDIc |
|---|---|---|---|---|
| Protopines |  | |||
| 1 | Protopine |  | 1.8 (1.1–2.8) | 1.5 |
| 2 | Hunnemannine |  | 79 (63–101) | N.D. |
| 3 | Cryptopine |  | 0.66 (0.53–0.82) | 4.9 |
| 4 | Allocryptopine |  | 76 (37–157) | 1.9 |
| 5 | Corycavidine (13S) |  | 15 (6.5–36) | 6.3 |
| 6 | Corycavamine (13R) |  | 0.19 (0.13–0.27) | 6.4 |
| 7 | Dihydrocryptopined(racemic) |  | 0.35 (0.23–0.53) | 3.5 |
| 8 | Dihydroprotopined(racemic) |  | 0.11 (0.078–0.16) | 2.7 |
| 9 | 2,3-Dimethoxy-7-methyl-9,10-dimethoxy-5,6,7,8,13,14-hexahydrodibenzo [d,h,] azecine |  | 23 (10–53) | >4.3 |
| Aporphines |  | |||
| 10 | Apomorphine (R) |  | 7.8 (4.7–13) | 2.3 |
| 11 | Bulbocapninemethyletherd (S) |  | 61 (48–77) | 1.5 |
| 12 | Bulbocapnine (S) |  | 8.4 (5.7–12) | 2.1 |
| 13 | Isocorydine (S) |  | 33 (20–54) | 1.9 |
| 14 | Corydine (S) |  | 91 (51–162) | TDI |
| 15 | Nantenine (S) |  | 3.5 (2.4–5.2) | N.D. |
| Spirobenzylisoquinolines |  | |||
| 16 | Parfumine (S) |  | 6.3 (3.7–11) | 2.4 |
| Phthalideisoquinolines |  | |||
| 17 | Capnoidine (1R, 9R) |  | 0.47 (0.37–0.60) | TDI |
| 18 | Bicuculline (1S, 9R) |  | 150 (91–246) | 9.5 |
| 19 | Noscapine (3S, 5R) |  | 0.20 (0.13–0.30) | 5.0 |
| Protoberberines |  | |||
| 20 | Canadined(racemic) |  | 0.29 (0.20–0.47) | 7.6 |
| 21 | Nandinine (racemic) |  | 0.37 (0.30–0.47) | 10.1 |
| 22 | Corydaline (13S, 13aR) |  | 3.1 (2.0–4.8) | TDI |
| 23 | Tetrahydropalmatine (13aR) |  | 7.0 (6.0–8.1) | 3.0 |
| 24 | Corypalmine (13aS) |  | 8.9 (0.1–18.5) | N.D. |
| 25 | Stylopined(racemic) |  | 0.13 (0.083–0.19) | 4.5 |
| 26 | Thalictricavine (13S, 13aR) |  | 2.4 (1.7–3.3) | 4.5 |
| 27 | Isocorybulbine (13S, 13aR) |  | 210 (141–324) | N.D. |
| 28 | Corybulbine (13S, 13aR) |  | 5.4 (3.6–8.1) | 3.4 |
| 29 | Scoulerine (13aS) |  | 22 (13–38) | 3.3 |
| 30 | Mecambridine (13aS) |  | 21 (15–31) | 4.7 |
| 31 | 2,3,10,11-Tetramethoxyberbinee(racemic) |  | 190 (141–258) | N.D. |
| 32 | 8-Ethyl-2,3,10,11-tetramethoxyberbinee (racemic) |   | 31 (23–43) | 4.8 |
| 33 | 8-Methyl-2,3,10,11-tetramethoxyberbinee (racemic) | 130 (97–176) | N.D. | |
| 34 | 8-Methyl-2,3,10,11-tetraethoxyberbinee (racemic) |  | 59 (39–87) | N.D. |
| 35 | 2,3-Dimethoxy-10,11-methylenedioxyberbinee (racemic) |  | 2.3 (1.7–3.1) | 3.8 |
| 36 | 2,3-Dimethoxy-9,10-methylenedioxyberbinee (racemic) |  | 5.0 (4.2–6.0) | 4.5 |
| 37 | 3,10,11-Trimethoxyberbinee (racemic) |  | 25 (11–58) | TDI |
| 38 | 3-Methoxyberbinee(racemic) |  | 2.4 (1.2–5.0) | TDI |
| 39 | 2,3-Dimethoxyberbinee(racemic) |  | 40 (28–56) | TDI |
| 40 | 3-Hydroxyberbinee(racemic) |  | 14 (10–18) | >7 |
| 41 | 2,3,9,10-Tetrahydroxyberbine(racemic) |  | 19 (12–30) | 1.5 |
| 42 | 3,10-Dimethoxy-11-hydroxyberbinee(racemic) |  | 11 (3.6–35) | >8.9 |
 | ||||
| 43 | Berberine hemisulfate | 150 (42–298) | 2.3 | |
| 44 | Palmatine |  | 120 (84–185) | 2.9 |
| Others | ||||
| 45 | Chelidonine (5bR, 6S, 12bS) |  | 1.4 (1.1–1.7) | 8.4 |
| 46 | Papaverine hydrochloride |  | 2.2 (1.6–3.2) | 1.6 |
| 47 | Sinomenine (9aR, 13aS, 14aS) |  | 55 (37–83) | 11.5 |
| 48 | Norlaudanosine hydrochloride (racemic) |  | 13 (11–15) | 3.3 |
| 49 | Pavine hydrochloride (racemic) |  | 82 (70–97) | 3.9 |