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Antiplasmodial activities of compounds isolated from terrestrial plants |
Pan WH, Xu XY, Shi N, Tsang SW, Zhang HJ. Antimalarial Activity of Plant Metabolites. Int J Mol Sci. 2018 19(5). PMID: 29734792. |
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Family |
Species |
Extract Solvent |
Compound |
IC50 (μM) (strain) |
Annonaceae |
Friesodielsia discolor |
EtOAc |
3'-formyl-2',4'-dihydroxy-6'-methoxychalcone (5) |
9.2 (K1) |
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8-formyl-7-hydroxy-5-methoxyflavanone (6) |
9.3 (K1) |
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tectochrysin (7) |
7.8 (K1) |
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Mitrephora diversifolia |
CH2Cl2/MeOH |
5-hydroxy-6-methoxyonychine (8) |
9.9 (3D7); 11.4 (Dd2) |
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Miliusa cuneata |
Acetone |
miliusacunines A (9) |
19.3 (TM4) |
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miliusacunines B (10) |
10.8 (K1) |
Araceae |
Rhaphidophora decursiva |
MeOH |
polysyphorin (1) |
1.7 (D6); 1.5 (W2) |
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rhaphidecurperoxin (2) |
1.8 (D6); 1.4 (W2) |
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rhaphidecursinol A (11) |
7.2 (D6); 4.2 (W2) |
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rhaphidecursinol B (12) |
12.9 (D6); 11.2 (W2) |
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grandisin (13) |
3.5 (D6); 3.4 (W2) |
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epigrandisin (14) |
>23 (D6); 7.7 (W2) |
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decursivine (15) |
11.2 (D6); 12.6 (W2) |
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Roridin E (3) |
0.0004 (D6); 0.001 (W2) |
Asclepiadaceae |
Gongronema napalense |
EtOH |
gongroneside A (16) |
1.6 (D6); 1.4 (W2) |
Asteraceae |
Achillea millefolium |
MeOH |
apigenin 7-O-glucoside (17) |
25.3 (D10); 15.3 (W2) |
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luteolin 7-O-glucoside (18) |
61.1 (D10); 62.5 (W2) |
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Carpesium divaricatum |
MeOH |
2-isopropenyl-6-acetyl-8-methoxy-1,3-benzodioxin-4-one (19) |
2.3 (D10) |
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Microglossa pyrifolia |
Petroleum ether-EtOAc (1:1, v/v) |
E-phytol (20) |
8.5 (PoW); 11.5 (Dd2) |
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6E-geranylgeraniol-19-oic acid (21) |
12.9 (PoW); 15.6 (Dd2) |
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Echinops hoehnelii |
CH2Cl2 |
5-(penta-1,3-diynyl)-2-(3,4-dihydroxybut-1-ynyl)-thiophene (22) |
50.2% (100 mg/kg) |
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5-(penta-1,3-diynyl)-2-(3-chloro-4-acetoxy-but-1-yn)-thiophene (23) |
32.7% (100 mg/kg) |
Buxaceae |
Buxus semperviren |
MeOH |
((1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-3a-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-8-yl)methyl (E)-3-(4-hydroxyphenyl)acrylate (24) |
0.5–3.0 (HB3) |
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((1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-3a-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-8-yl)methyl (E)-3-(4-hydroxyphenyl)acrylate (25) |
0.5–3.0 (HB3) |
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23-O-(trans)-feruloyl-23-hydroxybetulin (26) |
0.5–3.0 (HB3) |
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((1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-3a-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-8-yl)methyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate(27–31) |
0.5–3.0 (HB3) |
Cecropiaceae |
Cecropia pachystachya |
EtOH |
β-sitosterol (32) |
>120 (W2) |
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tormentic acid (33) |
19.0–25.2 (W2) |
Chloranthaceae |
Chloranthus. fortunei |
EtOH |
fortunilide A (34) |
0.005 (Dd2) |
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fortunilide B (35) |
0.02 (Dd2) |
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fortunilide C (36) |
0.2 (Dd2) |
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fortunilide D (37) |
0.03 (Dd2) |
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fortunilide E (38) |
0.04 (Dd2) |
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fortunilide F (39) |
5.3 (Dd2) |
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fortunilide G (40) |
0.05 (Dd2) |
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fortunilide H (41) |
0.2 (Dd2) |
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fortunilide I (42) |
0.09 (Dd2) |
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fortunilide J (43) |
9.9 (Dd2) |
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fortunilide K (44) |
4.7 (Dd2) |
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fortunilide L (45) |
0.1 (Dd2) |
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sarglabolide I (46) |
4.6 (Dd2) |
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sarglabolide J (47) |
0.007 (Dd2) |
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shizukaol K (48) |
0.9 (Dd2) |
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shizukaol I (49) |
0.1 (Dd2) |
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shizukaol C (50) |
0.02 (Dd2) |
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schizukaol M (51) |
0.10 (Dd2) |
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chlorahololide D (53) |
0.01 (Dd2) |
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C. multisachys |
- |
chloramultilide B (65) |
7.1 (Dd2) |
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C. serratus and C. spicatus |
- |
chlorajaponilide C (52) |
0.001 (Dd2) |
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shizukaol N (54) |
0.1 (Dd2) |
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shizukaol E (58) |
1.8 (Dd2) |
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shizukaol D (59) |
0.6 (Dd2) |
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shizukaol F (60) |
0.01 (Dd2) |
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shizukaol G (61) |
0.01 (Dd2) |
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shizukaol B (62) |
0.03 (Dd2) |
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spicachlorantin D (63) |
0.5 (Dd2) |
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shizukaol A (64) |
1.5 (Dd2) |
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Sarcandra glabra |
- |
sarcandrolide B (55) |
0.27 (Dd2) |
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sarcandrolide A (56) |
0.3 (Dd2) |
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sarcandrolide J (57) |
11.4 (Dd2) |
Chrysobalanceae |
Parinari capensis |
Petroleum ether and CH2Cl2 |
10,13-dihydroxy-9-methyl-15-oxo-20-norkaur-16-en-18-oic acid γ-lactone (66) |
1.7 (FCR-3) |
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10-hydroxy-13-methoxy-9-methyl-15-oxo-20-norkaur-16-en-18-oic acid γ-lactone (37) |
1.9 (FCR-3) |
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10-hydroxy-9-methyl-15-oxo-20-norkaur-16-en-18-oic acid γ-lactone (68) |
5.0 (FCR-3) |
Clusiaceae |
Garcinia mckeaniana |
Acetone |
mckeanianones A (69) |
6.2 (TM4) |
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mckeanianones B (70) |
6.7 (TM4) |
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mckeanianones C (71) |
6.0 (TM4) |
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bannaxanthones I (72) |
8.5 (TM4) |
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bannaxanthones E (73) |
8.3 (TM4) |
Connaraceae |
Rourea minor (Gaertn.) Aubl. |
CHCl3 |
rourinoside (74) |
3.7 (D6); 2.1 (W2) |
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rouremin (75) |
5.1 (D6); 4.5 (W2) |
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1-(26-hydroxyhexacosanoyl)-glycerol (76) |
9.5 (D6); 12.7 (W2) |
Cornaceae |
Cornus florida L. |
EtOH |
ergosta-4,6,8,22-tetraene-3-one (77) |
61.0 (D10) |
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3-epideoxyflindissol (78) |
128.0 (D10) |
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3β-O-cis-coumaroyl betulinic acid (79) |
10.4 (D10) |
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3β-O-trans-coumaroyl betulinic acid (80) |
15.3 (D10) |
Cucurbitaceae |
Cogniauxia podolaenaBaill. |
CH2Cl2 |
cucurbitacin B (81) |
2.9 (FcM29 strain) |
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cucurbitacin D (82) |
7.8 (FcM29 strain) |
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20-epibryonolic acid (83) |
4.4 (FcM29 strain) |
Ebenaceae |
Diospyros quaesita Thw. |
CHCl3 |
betulinic acid 3-caffeate (84) |
1.4 (D6); 1.0 (W2) |
Euphorbiaceae |
Jatropha isabelli |
- |
O-((5E,7S,8Z,10R,12S,12aS)-4,4,8,10,14-pentamethyl-13-oxo-3,4,7,9a,10,11,12,12a-octahydro-2,12-(epiethan[2]yl[1]ylidene)cyclopenta[b][1]oxacycloundecin-7-yl) 1H-imidazole-1-carbothioate 85 |
– |
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(5Z,8Z,10R,12S,12aS)-4,4,8,10,14-pentamethyl-5-(4-(trifluoromethyl)phenyl)-3,4,10,11,12,12a-hexahydro-2,12-(epiethan[2]yl[1]ylidene)cyclopenta[b][1]oxacycloundecine-7,13(9aH)-dione 86 |
– |
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Strophioblachia fimbricalyx |
MeOH |
9-O-demethyltrigonostemone (87) |
8.7 (K1) |
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3,6,9-trimethoxyphenanthropolone (88) |
9.9 (K1) |
Fabaceae |
Cajanus cajan L. |
- |
cajachalcone (89) |
7.4 (K1) |
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Piptadenia pervillei |
EtOAc |
(+)-catechin 5-gallate (70) |
1.2 (FcB1) |
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(+)-catechin 3-gallate (91) |
1.0 (FcB1) |
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Prosopis glandulosa var. glandulosa |
EtOH |
prosopilosidine (92) |
0.1 (D6); 0.3 (W2) |
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isoprosopilosidine (93) |
0.1 (D6); 0.3 (W2) |
Fagaceae |
Quercus laceyi |
MeOH |
kaempferol 3-O-glucosides (94–97) |
0.6–2.1 (HB3) |
Hypericaceae |
Vismia orientalis |
- |
vismione D (98) |
2.4 (K1) |
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Psorospermum glaberrimum |
Hexane |
3-geranyloxyemodin anthrone (99) |
1.7 (W2) |
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acetylvismione D (100) |
0.1 (W2) |
Lamiaceae |
Ocimum sanctum |
EtOAc |
(3S,5aR,13bS,14aR)-3-(2-hydroxyethyl)-10-methoxy-2,3,5a,6-tetrahydro-1H,14H-benzo[b]cyclopropa[1,7a]pyrrolizino[2,1-h][1,6]naphthyridin-7(5H)-one 101 |
0.1 (3D7) |
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Phlomis brunneogaleata |
MeOH |
luteolin 7-O-β-d-glucopyranoside (102) |
5.4 (K1) |
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chrysoeriol 7-O-β-d-glucopyranoside (103) |
12.7 (K1) |
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Salvia radula |
MeOH:CHCl3 = 1:1 |
betulafolientriol oxide (104) |
10.4 (FCR-3) |
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salvigenin (105) |
75.0 (FCR-3) |
Loganiaceae |
Strychnos icaja |
EtOAc-EtOH-NH4OH (96:3:1) |
15-hydroxyvomicine (106) |
101.0 (W2) |
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N-methyl-sec-iso-pseudostrychnine (107) |
110.6 (W2) |
Lythraceae |
Ammannia multiflora, A. baccifera |
MeOH |
4-hydroxy-α-tetralone (108) |
194.0 (NF-54) |
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tetralone-4-O-β-d-glucopyranoside (109) |
124.0 (NF-54) |
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ammaniol (110) |
88.3 (NF-54) |
Malvaceae |
Thespesia danis. |
Acetone–water (7:3) |
(R)-(−)-gossypol (111) |
4.5 (3D7) |
Monimiaceae |
Doryphora sassafras |
CH2Cl2/MeOH |
1-(4-hydroxybenzyl)-6,7-methylenedioxy-2-methylisoquinolinium trifluoroacetate (112) |
3.0 (3D7); 4.4 (Dd2) |
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Glossocalyx brevipes Benth. |
CHCl3/MeOH (1/1) |
methyl 2-(1′β-geranyl-5′β-hydroxy-2′-oxocyclohex-3′-enyl) acetate (113) |
2.2 (D6); 6.6 (W2) |
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2-(1′β-geranyl-5′β-hydroxy-2′-oxocyclohex-3′-enyl) acetic acid (114) |
4.8 (D6); 8.3 (W2) |
Moraceae |
Ficus fistulosa |
- |
verrucarin L acetate (4) |
0.001 (D6); 0.001 (W2) |
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F. septica |
MeOH |
dehydrotylophorine (115) |
0.4 (3D7) |
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dehydroantofine (116) |
0.03 (3D7) |
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3,6,7-trimethoxy-12,13-dihydro-11H-dibenzo[f,h]pyrrolo[1,2-b]isoquinolin-10-ium; tylophoridicine D (117) |
0.06 (3D7) |
Myristicaceae |
Knema glauca |
EtOAc |
malabaricone A (118) |
8.5 (K1) |
Piperaceae |
Piper sarmentosum |
Hexane-MeOH |
sarmentine (119) |
85.5 (K1) |
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(2E,4E,6E)-7-(benzo[d][1,3]dioxol-5-yl)-1-(pyrrolidin-1-yl)hepta-2,4,6-trien-1-one; 1-piperettyl pyrrolidine (120) |
21.9 (K1) |
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P. tricuspe |
Petroleum ether |
dictyochromenol (121) |
9.6 (FcB1) |
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3-farnesyl-p-hydroxy benzoic acid (122) |
29.8 (FcB1) |
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2′E,6′E 2-farnesyl hydroquinone (123) |
1.4 (FcB1) |
Platanaceae |
Platanus occidentalis |
MeOH |
kaempferol 3-O-rhamnosides (124–127) |
0.5–1.8 (HB3) |
Rubiaceae |
Nauclea orientalis |
MeOH |
naucleaorine (128) |
6.9 (D6); 8.0 (W2) |
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(1S,2R,4S)-4-methoxy-2-((((2R,3S,4S,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)methyl)-1-vinyl-2,3,4,7,8,13-hexahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinolin-5(1H)-one; epimethoxynaucleaorine (129) |
12.4 (D6); 13.2 (W2) |
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3α,23-dihydroxyurs-12-en-28-oic acid (130) |
9.7 (D6); 12.7 (W2) |
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oleanolic acid (131) |
4.6 (D6); 5.1 (W2) |
Rutaceae |
Citropsis articulata |
MeOH |
5-hydroxynoracronycine (132) |
2.8 (FcB1) |
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1,5-dihydroxy-2,3-dimethoxy-10-methyl-9-acridone (133) |
10.0 (FcB1) |
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Zanthoxylum chiloperone var. angustifolium Engl. |
CH2Cl2 |
trans-avicennol (134) |
7.8 (K1); 1.5 (F32); 3.5 (PFB); 6.4 (FcB1) |
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canthin-6-one (135) |
24.1 (K1); 9.1 (F32); 14.6 (PFB); 18.2 (FcB1) |
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5-methoxycanthin-6-one (136) |
20.4 (K1); 41.6 (F32) |
Simaroubaceae |
Eurycoma longifolia |
CH2Cl2 |
eurycomanone (137) |
0.06 (D6); 0.04 (W2) |
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pasakbumin B (138) |
0.08 (D6); 0.05 (W2) |
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Picrolemma sprucei |
Hexane/H2O |
neosergeolide (139) |
0.002 (K1) |
Apocynaceae |
Aspidosperma vargasii |
EtOH |
ellipticine (140) |
0.07 (K1) |
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A. desmanthum |
EtOH |
aspidocarpine (141) |
0.02 (K1) |
Piperaceae |
Pothomorphe peltata |
CHCl3/EtOH |
4-nerolidylcatechol (142) |
0.7 (K1) |
Theaceae |
Camellia sinensis |
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mefloquine (143) |
– |
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gallocatecin (144) |
– |
Tiliaceae |
Grewia bilamellata |
MeOH |
(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bS)-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethylicosahydro-1H-cyclopenta[a]chrysen-9-ol; 3α,20-lupandiol (145) |
19.8 (D6); 19.1 (W2) |
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grewin (146) |
11.2 (D6); 5.5 (W2) |
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nitidanin (147) |
21.2 (D6); 18.4 (W2) |
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2α,3β-dihydroxyolean-12-en-28-oic acid (148) |
21.1 (D6); 8.6 (W2) |
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2,6-dimethoxy-1-acetonylquinol (149) |
42.2 (D6); 23.0 (W2) |
Verbenaceae |
Lippia javanica |
EtOAc (aerial parts) |
lippialactone (150) |
23.8 (D10) |
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a IC50: Concentration that resulted in 50% death of Plasmodium falciparum. b ED50: Concentration that resulted in 50% cell death. |
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