Table 3 in Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

Table 3 Biological activities of isolated Vinca minor alkaloids.
CompoundIC50 h AChE ± SEM (μM) aIC50 h BuChE ± SEM (μM) aIC50 POP ± SEM (μM) a% inhibition of GSK-3β SEM b ±logBB cPAMPA (P e; 10 6 cm s 1)dvincaminorine (1)> 100> 100429 ± 30–n.c.–vincaminoreine (2)> 1008.71 ± 0.49408 ± 60–0.262–eburnamonine (3)> 10093.49 ± 15.90n.d.–n.c.–minovine (4)> 10026.32 ± 2.52n.d.–n.c.–16-methoxyminovine (5)> 10025.01 ± 3.27n.t.–n.c.–vincatine (6)> 10043.47 ± 3.30n.d.–n.c.–minovincine (7)> 100> 100301 ± 15–n.c.–16-methoxyminovincine (8)> 100> 100n.d.–n.c.–vincaminorudeine (9)> 10084.91 ± 2.98n.d.–n.c.–demethoxyalstonamide (10)> 10056.38 ± 2.58n.d.–n.c.–vincorine (11)> 1009.75 ± 0.45n.t.–0.022–minovincinine (12)> 100> 100n.d.–n.c.–aspidospermidine (13)> 10033.60 ± 1.52n.d.–n.c.–19-oxoeburnamonine (14)> 100> 100n.t.–n.c.–akuammicine (15)> 10038.17 ± 0.84n.t.–n.c.–tubotaiwine (16)> 10011.70 ± 0.11n.d.–n.c.–raucubainine (17)> 10093.96 ± 6.80> 500–n.c.–aspidofractinine (18)> 100> 100n.d.–n.c.–2-ethyl-3[2-(3-ethylpiperidinyl)-ethyl]-1 H -> 1000.650 ± 0.01658 ± 431.43 ± 3.05¡0.16415.7 ± 1.3 (CNSþ)indole (19)dihydrovindolinine (20)> 100> 100n.d.–n.c.–strictamine (21)> 100> 100190 ± 11–n.c.–5-oxoaspidofractinine (22)> 100> 100n.t.–n.c.–raucubaine (23)> 100> 100n.t.–n.c.–galanthamine e1.72 ± 0.1242 ± 1––0.0475.1 (CNS) f +eserine e0.063 ± 0.0050.13 ± 0.01––0.177–berberine e0.72 ± 0.1131 ± 4142 ± 21–0.420–chlorothiazide e––––0.4181.1 ± 0.5 (CNS)
a Compound concentration required to decrease enzyme activity by 50%; the values are the mean SEM of three independent measurements, each performed in ± triplicate.
b Measured at a concentration of 100 μM.
c calculated at http://www.way2drug.com/geb.
d CNS(): high BBB permeation predicted with P (10 6 cm s 1)> 4.0, CNS(): low BBB permeation predicted with P (10 6 cm s 1) <2.0, CNS(): BBB permeation + e e ± uncertain with P (10 6 cm s 1) from 4.0 to 2.0.
e e Reference compound; f Taken from reference (Stavrakov et al., 2017); n.t. stands for not tested due to the isolation of low amount; n.d. stands for not measurable due to a problem with solubility; n.c. stands for not calculated.