Syncarpamide, a new antiplasmodial (+)-norepinephrine derivative from Zanthoxylum syncarpum.
A new (+)-norepinephrine derivative, syncarpamide (1), along with a known coumarin, (+)-S-marmesin (2), and one known alkaloid, decarine (3), have been isolated from the stem of Zanthoxylum syncarpum. The structure of compound 1 was elucidated on the basis of 1D and 2D NMR, MS, IR, optical rotation, and CD analyses. Its absolute stereochemistry was elucidated by synthesis of its enantiomer and subsequent comparison of CD data. Characterizations of compounds 2 and 3 were based on spectral analysis and comparison with reported data. Compounds 1 and 3 showed antiplasmodial activity, with IC(50) values of 2.04 and 1.44 microM against Plasmodium falciparum D(6) clone and 3.06 and 0.88 microM against P. falciparum W(2) clone, respectively. Compound 3 showed cytotoxicity at 56.42 microM, whereas compound 1 was not cytotoxic at 10.42 microM. Compound 1 was tested for hypotensive activity, but no activity was observed. Compound 2 showed no antiplasmodial or antimicrobial activities.
Ross
Samir A
SA
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677-1848, USA. sross@olemiss.edu
Sultana
Gazi N N
GN
Burandt
Charles L
CL
ElSohly
Mahmoud A
MA
Marais
Jannie P J
JP
Ferreira
Daneel
D
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002942:Circular Dichroism; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009638:Norepinephrine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D021261:Parasitic Sensitivity Tests; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D053284:Polyunsaturated Alkamides; D013237:Stereoisomerism; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014687:Venezuela; D032106:Zanthoxylum / Q000737:chemistry*
D000962:Antimalarials; D003374:Coumarins; D053284:Polyunsaturated Alkamides; D014344:Trypanocidal Agents; C483277:syncarpamide; C001684:marmesin; D009638:Norepinephrine