O. Separation-of-fr and . Meoh, 6 g) by MPLC (RP-C 18, 1% HCOOH))g ave twelve subfractions, Frs. 4.1 ? 4.12.Anal. HPLC (Waters SunFire C

1. Meoh, 1mlmin À 1 gradient elutionover 45 min;UV 254 nm, ELS)a nalyses showed that the isolated compounds are present in Frs8 mg)a nd 410 (150.0 mg). Fr.4.5 was subjectedtosemi-prep.HPLC (Waters SunFire RP-C 18 (19 Â 150 mm, 5 mm) 4.8 ml min À 1 gradient elution over 20 min;U V2 54 nm)t of urnish fours ubfractions, 1% HCOOH)55% MeOH/H 2 O(þ 0.1% HCOOH) to 68% MeOH/H 2 O(þ 0.1% HCOOH)

7. Meoh, 5mlmin À 1 isocraticelution over 15 min;UV254 nm)togive five subfractions

. Fr, 360 mg)was also subjected to prep.HPLC (Waters SunFire Prep RP-C 18 (19 Â 150 mm, 5 mm)

4. Meoh, 17 ml min À 1 gradient elution over 45 min;U V2 54 nm)t og ive 13 subfractions, Frs. 4.1' ? 4.13'.O ne of them afforded 1 (netamine O; 8.4 mg) Three others ubfractions were subjected to subsequent prep.H PLC (Waters SunFire Prep RP-C 18, 1% HCOOH) to 70% MeOH1% HCOOH), 17 ml min À 1 gradient elutionover 26 min;UV254 nm)togive pure compounds 2 (netamineP;3.9 mg), 4 (netamineR;1 .9 mg), and 5 (netamine S

R. Netamine, *. , *. , and 7. *. , -octahydro-7-propylcyclopenta[de]qui- nazolin-2-amine; 4) Pale yellow oil UV: 238 (0.63) IR:3300, 1650. 1 Hand 13 C-NMR:s ee Tables 2 and 3, 2008.

S. Netamine, *. , *. , and 7. *. , -octahydro-7-propylcyclopenta[de]qui- nazolin-2-amine; 5) Pale brown oil UV: 248 (0.30) IR:3300, 1650. 1 Hand 13 C-NMR:s ee Tables 2 and 3, 2008.

A. One-soln, reagent (Promega)a nd results are expressed as the percentage of inhibition of cellular proliferation of KB cells treated for 72 hw ith 1 ? 3 compared to cells treated with DMSO only (mean AE SE of triplicate).T he IC 50 determinationsw ere performed in duplicate experiments and are expressed as individual values, vitro Antiplasmodial Assays.P .falciparum strains wereutilized and details of the assay protocols have been previously reported [13]. Artemisinin( 98%; SigmaÀAldrich)a nd chloroquine ( > 98%; SigmaÀAldrich)w ere used as positive controls

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