Caffeic acid esters and lignans from Piper sanguineispicum.
Three new caffeic acid esters (1-3), four new lignans (4-7), and the known compounds (7'S)-parabenzlactone (8), dihydrocubebin (9), and justiflorinol (10) have been isolated from leaves of Piper sanguineispicum. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRCIMS, CD experiments, and chemical methods. Compounds 1-10 were assessed for their antileishmanial potential against axenic amastigote forms of Leishmania amazonensis. Caffeic acid esters 1 and 3 exhibited the best antileishmanial activity (IC(50) 2.0 and 1.8 μM, respectively) with moderate cytotoxicity on murine macrophages.
Université de Toulouse, UPS, UMR 152 (Laboratoire de Pharmacochimie des Substances Naturelles et Pharmacophores Redox), F-31062 Toulouse Cedex 9, France.
Billy Joel
BJ
Cabanillas
Anne-Cécile
AC
Le Lamer
Denis
D
Castillo
Jorge
J
Arevalo
Rosario
R
Rojas
Guillaume
G
Odonne
Geneviève
G
Bourdy
Béatrice
B
Moukarzel
Michel
M
Sauvain
Nicolas
N
Fabre
D000818:Animals; D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002522:Chlorocebus aethiops; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004148:Dioxolanes / Q000737:chemistry / Q000302:isolation & purification; D004354:Drug Screening Assays, Antitumor; D004952:Esters; D005260:Female; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects*; D051379:Mice; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D031701:Piper / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D014709:Vero Cells
C554319:(S)-1'-methylbutyl caffeate; C554320:(S)-1'-methylhexyl caffeate; C554321:(S)-1'-methyloctyl caffeate; D002109:Caffeic Acids; D003603:Cytotoxins; D004148:Dioxolanes; D004952:Esters; D017705:Lignans; C501782:justiflorinol; C011228:dihydrocubebin