Phytochem. 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 abs. 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 vol./vol.) Amygdalus lycioides Spach branchelets ext. 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.

Chiral flavanones from Amygdalus lycioides Spach : structural elucidation and identification of TNFalpha inhibitors by bioactivity-guided fractionation / R. Gaggeri, D. Rossi, M.S. Christodoulou, D. Passarella, F. Leoni, O. Azzolina, S. Collina. - In: MOLECULES. - ISSN 1420-3049. - 17:2(2012), pp. 1665-1674.

Chiral flavanones from Amygdalus lycioides Spach : structural elucidation and identification of TNFalpha inhibitors by bioactivity-guided fractionation

M.S. Christodoulou;D. Passarella;
2012

Abstract

Phytochem. 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 abs. 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 vol./vol.) Amygdalus lycioides Spach branchelets ext. 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.
amygdalus lycioides Spach; bioassay-guided fractionation; chiral flavanones; phytochemical fingerprint; structural elucidation; TNFα blockers
Settore CHIM/06 - Chimica Organica
2012
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/199112
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