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.
Family Species Extract Solvent Compound IC50 (μM) (strain)
Annonaceae Friesodielsia discolor EtOAc 3'-formyl-2',4'-dihydroxy-6'-methoxychalcone (5) 9.2 (K1)
8-formyl-7-hydroxy-5-methoxyflavanone (6) 9.3 (K1)
tectochrysin (7) 7.8 (K1)
Mitrephora diversifolia CH2Cl2/MeOH 5-hydroxy-6-methoxyonychine (8) 9.9 (3D7); 11.4 (Dd2)
Miliusa cuneata Acetone miliusacunines A (9) 19.3 (TM4)
miliusacunines B (10) 10.8 (K1)
Araceae Rhaphidophora decursiva MeOH polysyphorin (1) 1.7 (D6); 1.5 (W2)
rhaphidecurperoxin (2) 1.8 (D6); 1.4 (W2)
rhaphidecursinol A (11) 7.2 (D6); 4.2 (W2)
rhaphidecursinol B (12) 12.9 (D6); 11.2 (W2)
grandisin (13) 3.5 (D6); 3.4 (W2)
epigrandisin (14) >23 (D6); 7.7 (W2)
decursivine (15) 11.2 (D6); 12.6 (W2)
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)
luteolin 7-O-glucoside (18) 61.1 (D10); 62.5 (W2)
Carpesium divaricatum MeOH 2-isopropenyl-6-acetyl-8-methoxy-1,3-benzodioxin-4-one (19) 2.3 (D10)
Microglossa pyrifolia Petroleum ether-EtOAc (1:1, v/v) E-phytol (20) 8.5 (PoW); 11.5 (Dd2)
6E-geranylgeraniol-19-oic acid (21) 12.9 (PoW); 15.6 (Dd2)
Echinops hoehnelii CH2Cl2 5-(penta-1,3-diynyl)-2-(3,4-dihydroxybut-1-ynyl)-thiophene (22) 50.2% (100 mg/kg)
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)
((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)
23-O-(trans)-feruloyl-23-hydroxybetulin (26) 0.5–3.0 (HB3)
((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)
tormentic acid (33) 19.0–25.2 (W2)
Chloranthaceae Chloranthus. fortunei EtOH fortunilide A (34) 0.005 (Dd2)
fortunilide B (35) 0.02 (Dd2)
fortunilide C (36) 0.2 (Dd2)
fortunilide D (37) 0.03 (Dd2)
fortunilide E (38) 0.04 (Dd2)
fortunilide F (39) 5.3 (Dd2)
fortunilide G (40) 0.05 (Dd2)
fortunilide H (41) 0.2 (Dd2)
fortunilide I (42) 0.09 (Dd2)
fortunilide J (43) 9.9 (Dd2)
fortunilide K (44) 4.7 (Dd2)
fortunilide L (45) 0.1 (Dd2)
sarglabolide I (46) 4.6 (Dd2)
sarglabolide J (47) 0.007 (Dd2)
shizukaol K (48) 0.9 (Dd2)
shizukaol I (49) 0.1 (Dd2)
shizukaol C (50) 0.02 (Dd2)
schizukaol M (51) 0.10 (Dd2)
chlorahololide D (53) 0.01 (Dd2)
C. multisachys - chloramultilide B (65) 7.1 (Dd2)
C. serratus and C. spicatus - chlorajaponilide C (52) 0.001 (Dd2)
shizukaol N (54) 0.1 (Dd2)
shizukaol E (58) 1.8 (Dd2)
shizukaol D (59) 0.6 (Dd2)
shizukaol F (60) 0.01 (Dd2)
shizukaol G (61) 0.01 (Dd2)
shizukaol B (62) 0.03 (Dd2)
spicachlorantin D (63) 0.5 (Dd2)
shizukaol A (64) 1.5 (Dd2)
Sarcandra glabra - sarcandrolide B (55) 0.27 (Dd2)
sarcandrolide A (56) 0.3 (Dd2)
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)
10-hydroxy-13-methoxy-9-methyl-15-oxo-20-norkaur-16-en-18-oic acid γ-lactone (37) 1.9 (FCR-3)
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)
mckeanianones B (70) 6.7 (TM4)
mckeanianones C (71) 6.0 (TM4)
bannaxanthones I (72) 8.5 (TM4)
bannaxanthones E (73) 8.3 (TM4)
Connaraceae Rourea minor (Gaertn.) Aubl. CHCl3 rourinoside (74) 3.7 (D6); 2.1 (W2)
rouremin (75) 5.1 (D6); 4.5 (W2)
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)
3-epideoxyflindissol (78) 128.0 (D10)
3β-O-cis-coumaroyl betulinic acid (79) 10.4 (D10)
3β-O-trans-coumaroyl betulinic acid (80) 15.3 (D10)
Cucurbitaceae Cogniauxia podolaenaBaill. CH2Cl2 cucurbitacin B (81) 2.9 (FcM29 strain)
cucurbitacin D (82) 7.8 (FcM29 strain)
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
(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
Strophioblachia fimbricalyx MeOH 9-O-demethyltrigonostemone (87) 8.7 (K1)
3,6,9-trimethoxyphenanthropolone (88) 9.9 (K1)
Fabaceae Cajanus cajan L. - cajachalcone (89) 7.4 (K1)
Piptadenia pervillei EtOAc (+)-catechin 5-gallate (70) 1.2 (FcB1)
(+)-catechin 3-gallate (91) 1.0 (FcB1)
Prosopis glandulosa var. glandulosa EtOH prosopilosidine (92) 0.1 (D6); 0.3 (W2)
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)
Psorospermum glaberrimum Hexane 3-geranyloxyemodin anthrone (99) 1.7 (W2)
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)
Phlomis brunneogaleata MeOH luteolin 7-O-β-d-glucopyranoside (102) 5.4 (K1)
chrysoeriol 7-O-β-d-glucopyranoside (103) 12.7 (K1)
Salvia radula MeOH:CHCl3 = 1:1 betulafolientriol oxide (104) 10.4 (FCR-3)
salvigenin (105) 75.0 (FCR-3)
Loganiaceae Strychnos icaja EtOAc-EtOH-NH4OH (96:3:1) 15-hydroxyvomicine (106) 101.0 (W2)
N-methyl-sec-iso-pseudostrychnine (107) 110.6 (W2)
Lythraceae Ammannia multiflora, A. baccifera MeOH 4-hydroxy-α-tetralone (108) 194.0 (NF-54)
tetralone-4-O-β-d-glucopyranoside (109) 124.0 (NF-54)
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)
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)
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)
F. septica MeOH dehydrotylophorine (115) 0.4 (3D7)
dehydroantofine (116) 0.03 (3D7)
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)
(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)
P. tricuspe Petroleum ether dictyochromenol (121) 9.6 (FcB1)
3-farnesyl-p-hydroxy benzoic acid (122) 29.8 (FcB1)
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)
(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)
3α,23-dihydroxyurs-12-en-28-oic acid (130) 9.7 (D6); 12.7 (W2)
oleanolic acid (131) 4.6 (D6); 5.1 (W2)
Rutaceae Citropsis articulata MeOH 5-hydroxynoracronycine (132) 2.8 (FcB1)
1,5-dihydroxy-2,3-dimethoxy-10-methyl-9-acridone (133) 10.0 (FcB1)
Zanthoxylum chiloperone var. angustifolium Engl. CH2Cl2 trans-avicennol (134) 7.8 (K1); 1.5 (F32); 3.5 (PFB); 6.4 (FcB1)
canthin-6-one (135) 24.1 (K1); 9.1 (F32); 14.6 (PFB); 18.2 (FcB1)
5-methoxycanthin-6-one (136) 20.4 (K1); 41.6 (F32)
Simaroubaceae Eurycoma longifolia CH2Cl2 eurycomanone (137) 0.06 (D6); 0.04 (W2)
pasakbumin B (138) 0.08 (D6); 0.05 (W2)
Picrolemma sprucei Hexane/H2O neosergeolide (139) 0.002 (K1)
Apocynaceae Aspidosperma vargasii EtOH ellipticine (140) 0.07 (K1)
A. desmanthum EtOH aspidocarpine (141) 0.02 (K1)
Piperaceae Pothomorphe peltata CHCl3/EtOH 4-nerolidylcatechol (142) 0.7 (K1)
Theaceae Camellia sinensis mefloquine (143)
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)
grewin (146) 11.2 (D6); 5.5 (W2)
nitidanin (147) 21.2 (D6); 18.4 (W2)
2α,3β-dihydroxyolean-12-en-28-oic acid (148) 21.1 (D6); 8.6 (W2)
2,6-dimethoxy-1-acetonylquinol (149) 42.2 (D6); 23.0 (W2)
Verbenaceae Lippia javanica EtOAc (aerial parts) lippialactone (150) 23.8 (D10)
a IC50: Concentration that resulted in 50% death of Plasmodium falciparum. b ED50: Concentration that resulted in 50% cell death.
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