Fagraldehyde, a secoiridoid isolated from Fagraea fragrans.
A secoiridoid aglycone with an atypical skeleton, named fagraldehyde (1), together with several known secoiridoids (gentiopicroside (2), sweroside (3), and swertiamarin (4)) were isolated from the bark and leaves of Fagraea fragrans collected in Cambodia. The conformations of 1 were evaluated on the basis of molecular modeling and NOESY correlations. A hypothetical biogenesis of fagraldehyde was proposed to explain the unusual skeleton. Compound 1 was weakly active in vitro against Plasmodium falciparum.
Jonville
Marie-Caroline
MC
Laboratoire de Pharmacognosie, Drug Research Center (CIRM), Université de Liège, CHU-B36, 1 AVenue de l'Hôpital, B-4000 Liège, Belgium. MC.Jonville@ulg.ac.be
Capel
Marie
M
Frédérich
Michel
M
Angenot
Luc
L
Dive
Georges
G
Faure
Robert
R
Azas
Nadine
N
Ollivier
Evelyne
E
D000818:Animals; D002160:Cambodia; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification; D057888:Iridoid Glucosides; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007770:L-Lactate Dehydrogenase / Q000032:analysis; D024301:Plant Bark / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal; D010963:Plasmodium falciparum / Q000187:drug effects*; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification
D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; D011753:Pyrones; C534646:fagraldehyde; C012997:gentiopicroside; C013270:swertiamarin; D007770:L-Lactate Dehydrogenase; C049412:sweroside