Isolation of secondary metabolites from Hortia oreadica (Rutaceae) leaves through high-speed counter-current chromatography.
High-speed counter-current chromatography (HSCCC) with a two-phase solvent system (hexane-ethanol-acetonitrile-water 10:8:1:1, v/v) was applied to examine the leaves of Hortia oreadica, which afforded the known limonoid guyanin (1), the alkaloids rutaecarpin (2) and dictamnine (6), the dihydrocinnamic acid derivatives methyl 5,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoate (3), 5,8-dimethoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid (4), together with the new E-3,4-dimethoxy-alpha(3-hydroxy-4-carbomethoxyphenyl)cinnamic acid (5). The recovery of compounds 1-6 was determined by comparison with LC-atmospheric pressure chemical ionization MS/MS data: 66.2%, 93.1%, 102.5%, 101.2%, 99.0% and 84.9%, respectively. Compound 3 showed IC(50) of 23.6microM against Plasmodium falciparum and 15.6microM against Trypanosoma brucei rhodesienses and was not toxic to KB cells (IC(50)>100microM).
Severino
Vanessa Gisele Pasqualotto
VG
Universidade Federal de São Carlos, Departamento de Química, SP, Brazil.
Cazal
Cristiane de Melo
Cde M
Forim
Moacir Rossi
MR
da Silva
Maria Fátima das Graças Fernandes
MF
Rodrigues-Filho
Edson
E
Fernandes
João Batista
JB
Vieira
Paulo Cezar
PC
D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002934:Cinnamates / Q000302:isolation & purification / Q000494:pharmacology; D003377:Countercurrent Distribution / Q000379:methods*; D006801:Humans; D026121:Indole Alkaloids / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D036701:Limonins / Q000302:isolation & purification / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D011799:Quinazolines / Q000302:isolation & purification / Q000494:pharmacology; D011804:Quinolines / Q000302:isolation & purification / Q000494:pharmacology; D027821:Rutaceae / Q000737:chemistry* / Q000378:metabolism; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects; D052999:Quinazolinones
D002934:Cinnamates; D026121:Indole Alkaloids; D036701:Limonins; D010936:Plant Extracts; D011799:Quinazolines; D011804:Quinolines; C029010:cinnamic acid; C028632:rutecarpine; D052999:Quinazolinones; C026398:dictamnine