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

Gaggeri, Raffaella; Rossi, Daniela; Christodoulou, Michael S.; Passarella, Daniele; Leoni, Flavio; Azzolina, Ornella; Collina, Simona

doi:10.3390/molecules17021665

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

Raffaella Gaggeri

^1,†,

Daniela Rossi

^1,†,

Michael S. Christodoulou

²,

²,

³,

¹ and

^1,4,*

Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia 27100, Italy

Department of Organic and Industrial Chemistry, University of Milan, via Venezian 21, Milano 20133, Italy

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

Author to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

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

Received: 30 December 2011 / Revised: 31 January 2012 / Accepted: 1 February 2012 / Published: 8 February 2012

(This article belongs to the Section Natural Products Chemistry)

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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. View Full-Text

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. https://doi.org/10.3390/molecules17021665

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. https://doi.org/10.3390/molecules17021665

Chicago/Turabian Style

Gaggeri, Raffaella, Daniela Rossi, Michael S. Christodoulou, Daniele Passarella, Flavio Leoni, Ornella Azzolina, and Simona Collina. 2012. "Chiral Flavanones from Amygdalus lycioides Spach: Structural Elucidation and Identification of TNFalpha Inhibitors by Bioactivity-guided Fractionation" Molecules 17, no. 2: 1665-1674. https://doi.org/10.3390/molecules17021665

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

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