N1,N5,N10-Tris(4-hydroxycinnamoyl)spermidines from Microdesmis keayana roots.
Three new N1,N5,N10-tris(4-hydroxycinnamoyl)spermidines were isolated from a methanolic root extract of Microdesmis keayana. They were identified as N5,N10-di(p-coumaroyl)-N1-feruloylspermidine,N5-(p-coumaroyl)-N1,N10-diferuloylspermidine, and N1,N5,N10-triferuloylspermidine, and were named keayanidines A, B, and C (1-3), respectively. Their structures were established by spectral techniques(electrospray mass spectrometry, one- and two-dimensional NMR). A 4',4'',4'''-trimethylated derivative was prepared by methylation of keayanidine C, and the same compound was synthesized fromspermidine and 3,4-dimethoxycinnamic acid to confirm the spectral attributions of the NMR data of the natural compounds. Radical-scavenging properties of all compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical spectrophotometric assay.
Zamble
Alexis
A
Laboratoire de Pharmacognosie, E.A. 1043, Faculté de Pharmacie, Université de Lille 2, B.P. 83, F-59006 Lille Cedex.
Sahpaz
Sevser
S
Hennebelle
Thierry
T
Carato
Pascal
P
Bailleul
François
F
D003373:Coumaric Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal; D021241:Spectrometry, Mass, Electrospray Ionization; D013095:Spermidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*
D003373:Coumaric Acids; D010936:Plant Extracts; D013095:Spermidine; D000432:Methanol