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

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.

Anti-neuroinflammatory and NQO1 inducing activity of natural phytochemicals from Coreopsis tinctoria

“…However, three singlets shown in the 1 H NMR spectra of 15 and 16 proved the substitution at C-3′ and C-5′. The 1 H NMR and 13 C NMR data of 13-16 were compared with those reported and then assigned in Table 3 (Foo, 1987;Gaggeri et al, 2012;Wang, Yang, Guo, & Liu, 2009;Zhao et al, 2013).…”

An overview of developing TNF-α targeted therapy for the treatment of psoriasis

“…Historically, Amygdalus lyioides has been used as an antiinflammatory and antimicrobial remedy in Iran [109]. Narigenin is a recently isolated secondary metabolite that shows promising anti-TNF-a effects in preclinical studies [109][110][111]. In one study, this compound was found to have increased anti-TNF-a activity when loaded into sericin microparticles (derived from the silk protein sericin) for topical application when compared with naringenin alone [111].…”

“…This compound is also found in very small quantities in oranges, apples and tomatoes [110]. Historically, Amygdalus lyioides has been used as an antiinflammatory and antimicrobial remedy in Iran [109]. Narigenin is a recently isolated secondary metabolite that shows promising anti-TNF-a effects in preclinical studies [109][110][111].…”

“…Naringenin is a flavanone isolated from Amygdalus lyioides Spach branchlets [109]. This compound is also found in very small quantities in oranges, apples and tomatoes [110].…”

Copper-induced changes in nutrient uptake, enzymatic and non-enzymatic antioxidant systems in horehound ( Marrubium vulgare L.)

“…Extract preparation.-Basing on our experience [Martino et al (2008), Gaggeri et al (2012), Rossi et al (2017)], extracts have been prepared applying a Miscrowave Assisetd extraction procedure. Powdered leaves (1 g) were homogenized with 80 % methanol (20 mL) and extract-ed in a multimode microwave apparatus using a closed-vessel system (MARSX press, CEM Corporation, Matthews, NC, USA) under the following conditions: temperature 60 °C, power 100 w, pressure 120 psi, run time 10 min.…”