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2007 Cassiarins A and B, Novel Antiplasmodial Alkaloids Aisla y Bioact
2007 Cassiarins A and B, Novel Antiplasmodial Alkaloids Aisla y Bioact
LETTERS
ABSTRACT
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Two novel alkaloids with an unprecedented tricyclic skeleton, cassiarins A (1) and B (2), have been isolated from the leaves of Cassia siamea,
and the structures were elucidated on the basis of spectroscopic data. Cassiarin A (1) showed a potent antiplasmodial activity.
Malaria caused by parasites of the genus Plasmodium is one were extracted with MeOH, and the extract was partitioned
of the leading infectious diseases in many tropical and some between EtOAc and 3% tartaric acid. The aqueous layer was
temperate regions.1 The emergence of widespread chloro- adjusted at pH 9 with saturated Na2CO3 and extracted with
quine-resistant and multiple-drug-resistant strains of malaria CHCl3. CHCl3-soluble alkaloidal materials were subjected
parasites leads to the need for the development of new to a silica gel column (CHCl3/MeOH, 1:0 f 0:1), in which
therapeutic agents against malaria.2 a fraction eluted with CHCl3/MeOH (4:1) was further
During our studies on new lead substances against malaria purified on a silica gel column with CHCl3/MeOH (9:1) to
from medicinal plants, cassiarins A (1) and B (2), novel afford cassiarins A (1, 0.0008% yield) and B (2, 0.0017%)
aromatic alkaloids with an unprecedented tricyclic skeleton together with anhydrobarakol (0.0002%)4 as reddish solids.
and potent antiplasmodial activity, have been isolated from The ESIMS of cassiarin A (1)5 showed a pseudomolecular
the leaves of Cassia siamea (Leguminosae), which have been ion peak at m/z 214 (M + H)+, and the molecular formula
widely used in traditional medicine, particularly for the C13H11NO2 was established by HRESIMS [m/z 214.0890,
treatment of periodic fever and malaria.3 This paper describes
the isolation and structural elucidation of 1 and 2. (1) Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Angew. Chem.
Int. Ed. 2003, 42, 5274-5293.
(2) Gelb, M. H.; Hol, W. G. Science 2002, 297, 343-344. De Smet, P.
A. G. N. Drugs 1997, 54, 801-840.
(3) (a) Mbatchi, S. F.; Mbatchi, B.; Banzouzi, J. T.; Bansimba, T.; Nsonde
Ntandou, G. F.; Ouamba, J. M.; Berry, A.; Benoit-Vical, F. J. Ethnophar-
macol. 2006, 104, 168-174. (b) Sanon, S.; Ollivier, E.; Azas, N.; Mahiou,
V.; Gasquet, M.; Ouattara, C. T.; Nebie, I.; Traore, A. S.; Esposito, F.;
Balansard, G.; Timon-David, P.; Fumoux, F. J. Ethnopharmacol. 2003, 86,
143-147.
(4) Bycroft, B. W.; Hassaniali-Walji, A.; Johnson, A. W.; King, T. J. J.
The leaves of C. siamea (300 g), which were collected at Chem. Soc. (C) 1970, 12, 1686-1689.
(5) Cassiarin A (1): reddish solid; IR (KBr) νmax 3420, 2940, 1660, 1620,
the Purwodadi Botanical Garden, Pasuruan, Indonesia (2005), 1395, 1370, and 1190 cm-1; UV (MeOH) λmax 215 nm ( 19 000), 230 (sh,
14 000), 253 ( 13 600), 315 (sh, 3600), 338 ( 5000), and 370 (sh,
† Hoshi University. 3200); 1H and 13C NMR data (Table 1); ESIMS m/z 214 (M + H)+;
‡ Airlangga University. HRESIMS m/z 214.0890 (M + H; calcd for C13H12NO2, 214.0868).