Antiplasmodial activity of aporphine alkaloids and sesquiterpene lactones from Liriodendron tulipifera L.
OBJECTIVE
The objective of this study was to isolate and characterize the active constituents of the traditionally used antimalarial plant Liriodendron tulipifera by antiplasmodial-assay guided fractionation.


METHODS
Bark and leaves were extracted with solvents of increasing polarity. Fractions were generated using flash chromatography, counter current chromatography and preparative HPLC and subjected to in vitro antiplasmodial and cytotoxicity assays. Active fractions were subjected to further fractionation until pure compounds were isolated, for which the IC(50) values were calculated.


CONCLUSIONS
Six known aporphine alkaloids, asimilobine (1), norushinsunine (2), norglaucine (3), liriodenine (4), anonaine (5) and oxoglaucine (6) were found to be responsible for the antiplasmodial activity of the bark. Leaves yielded two known sesquiterpene lactones, peroxyferolide (7) and lipiferolide (8) with antiplasmodial activity. The antiplasmodial activity of (2) (IC(50)=29.6 μg/mL), (3) (IC(50)=22.0 μg/mL), (6) (IC(50)=9.1 μg/mL), (7) (IC(50)=6.2 μg/mL) and (8) (IC(50)=1.8 μg/mL) are reported for the first time.


CONCLUSIONS
This work supports the historical use of Liriodendron tulipifera as an antimalarial remedy of the United States and characterizes its antiplasmodial constituents.
Graziose
Rocky
R
Biotech Center, Rutgers, The State University of New Jersey, Cook College, New Brunswick, NJ 08901, USA.
Rathinasabapathy
Thirumurugan
T
Lategan
Carmen
C
Poulev
Alexander
A
Smith
Peter J
PJ
Grace
Mary
M
Lila
Mary Ann
MA
Raskin
Ilya
I
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001060:Aporphines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D031567:Liriodendron / Q000737:chemistry*; D008288:Malaria / Q000188:drug therapy*; D008517:Phytotherapy; D024301:Plant Bark; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018515:Plant Leaves; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014481:United States
D000470:Alkaloids; D000962:Antimalarials; D001060:Aporphines; D007783:Lactones; D010936:Plant Extracts; D012717:Sesquiterpenes; C081279:aporphine
J Nat Prod. 2009 Aug;72(8):1516-9
19639965
J Pharm Pharmacol. 2009 Nov;61(11):1401-33
19903367
Mil Med. 2007 Jun;172(6):650-5
17615851
J Immunol Methods. 1983 Dec 16;65(1-2):55-63
6606682
J Org Chem. 1970 Jun;35(6):1928-36
5446985
Planta Med. 2000 Jun;66(5):478-80
10909274
J Nat Prod. 1993 Sep;56(9):1468-78
8254346
Lancet Infect Dis. 2004 Jun;4(6):327-36
15172341
Expert Rev Anti Infect Ther. 2009 Oct;7(8):999-1013
19803708
J Nat Prod. 1994 Jan;57(1):68-73
8158166
J Pharm Sci. 1969 Jul;58(7):877-80
5810209
Curr Drug Discov Technol. 2010 Mar;7(1):2-12
20156139
J Hist Med Allied Sci. 1976 Jul;31(3):343-67
780420
Science. 1976 Aug 20;193(4254):673-5
781840
Int J Parasitol. 2008 Jan;38(1):33-41
17720165
Bioorg Med Chem. 2009 May 1;17(9):3229-56
19299148