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Molecules 2012, 17(2), 1665-1674; doi:10.3390/molecules17021665

Chiral Flavanones from Amygdalus lycioides Spach: Structural Elucidation and Identification of TNFalpha Inhibitors by Bioactivity-guided Fractionation

1
Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia 27100, Italy
2
Department of Organic and Industrial Chemistry, University of Milan, via Venezian 21, Milano 20133, Italy
3
Italfarmaco Research Center,Viale dei Lavoratori 54, Cinisello Balsamo (MI) 20092, Italy
4
Center for Studies and Researches in Ethnopharmacy (C.I.St.R.E.), University of Pavia, via Taramelli 12, Pavia 27100, Italy
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 30 December 2011 / Revised: 31 January 2012 / Accepted: 1 February 2012 / Published: 8 February 2012
(This article belongs to the Section Natural Products)
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Abstract

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.
Keywords: Amygdalus lycioides Spach; bioassay-guided fractionation; chiral flavanones; structural elucidation; phytochemical fingerprint; TNFα blockers Amygdalus lycioides Spach; bioassay-guided fractionation; chiral flavanones; structural elucidation; phytochemical fingerprint; TNFα blockers
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Gaggeri, R.; Rossi, D.; Christodoulou, M.S.; Passarella, D.; Leoni, F.; Azzolina, O.; Collina, S. Chiral Flavanones from Amygdalus lycioides Spach: Structural Elucidation and Identification of TNFalpha Inhibitors by Bioactivity-guided Fractionation. Molecules 2012, 17, 1665-1674.

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