Chiral flavanones from Amygdalus lycioides Spach: structural elucidation and identification of TNFalpha inhibitors by bioactivity-guided fractionation.
Phytochemical investigation on the Amygdalus lycioides Spach branchelets resulted in the isolation of four chiral flavanones: (2R,3R)-Taxifolin, (2R,3R)-aromadendrin, (S)-5,7,3',5'-tetrahydroxyflavanone and (S)-naringenin. The flavanones were isolated by semi-preparative HPLC, their structures elucidated based on spectroscopic data and their absolute configuration assigned. As a part of our ethnobotanical-directed search for novel TNFα inhibitors, the bioassay-guided fractionation of the n-hexane-acetone (n-Hex-Ac, 1:1 v/v) Amygdalus lycioides Spach branchelets extract was performed. In this way, (S)-naringenin was identified as the constituent responsible for the TNFα blocking effect, being effective in vitro and in vivo after oral administration. This is the first investigation on bioactive secondary metabolites of Amygdalus lycioides Spach branchelets.
Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia 27100, Italy. raffaella.gaggeri@unipv.it
Raffaella
R
Gaggeri
Daniela
D
Rossi
Michael S
MS
Christodoulou
Daniele
D
Passarella
Flavio
F
Leoni
Ornella
O
Azzolina
Simona
S
Collina
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D044948:Flavonols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D051379:Mice; D027861:Prunus / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors*
D044948:Flavonols; D014409:Tumor Necrosis Factor-alpha