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

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

1,†email, 1,†email, 2email, 2email, 3email, 1email and 1,4,* email
Received: 30 December 2011; in revised form: 31 January 2012 / Accepted: 1 February 2012 / Published: 8 February 2012
(This article belongs to the Section Metabolites)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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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.

AMA Style

Gaggeri R, Rossi D, Christodoulou MS, 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(2):1665-1674.

Chicago/Turabian Style

Gaggeri, Raffaella; Rossi, Daniela; Christodoulou, Michael S.; Passarella, Daniele; Leoni, Flavio; Azzolina, Ornella; Collina, Simona. 2012. "Chiral Flavanones from Amygdalus lycioides Spach: Structural Elucidation and Identification of TNFalpha Inhibitors by Bioactivity-guided Fractionation." Molecules 17, no. 2: 1665-1674.


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