Naringenin chalcone

Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14.

Naringenin chalcone improves adipocyte functions by enhancing adiponectin production.[Pubmed: 20363289]

Naringenin chalcone is a flavonoid contained in tomato peel.
METHODS AND RESULTS:
In this study, we investigated its effects on adipocyte functions related to metabolic processes, including adipocytokine production. Naringenin chalcone promoted the gene expression (8.0-fold, p<0.001) and protein secretion (2.2-fold, p<0.001) of adiponectin from 3T3-L1 adipocytes. Reporter gene assays revealed that naringenin enhanced the activity of peroxisome proliferator-activated receptor gamma. DNA microarray experiments and Gene Ontology analysis revealed that Naringenin chalcone also up-regulated the genes associated with mitochondrial energy metabolism, reflecting its insulin-sensitizing effects. Conversely, genes in categories such as those for cell adhesion were down-regulated. The expression of one adiponectin receptor, AdipoR2, was also increased (1.8-fold, p<0.01), suggesting that Naringenin chalcone could activate the adiponectin pathway through the elevation of both the ligand and its receptor.
CONCLUSIONS:
These results indicate that Naringenin chalcone is a potent tomato flavonoid that improves adipocyte metabolic functions and exerts insulin-sensitizing effects by activating an adiponectin-related pathway.

Life Sci. 2007 Sep 29;81(16):1272-9.

Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages.[Pubmed: 17915259]

Obese adipose tissue is characterized by an enhanced infiltration of macrophages. It is considered that the paracrine loop involving monocyte chemoattractant protein (MCP)-1 and tumor necrosis factor (TNF)-alpha between adipocytes and macrophages establishes a vicious cycle that augments the inflammatory changes and insulin resistance in obese adipose tissue. Polyphenols, which are widely distributed in fruit and vegetables, can act as antioxidants and some of them are also reported to have anti-inflammatory properties. Tomato is one of the most popular and extensively consumed vegetable crops worldwide, which also contains many flavonoids, mainly Naringenin chalcone.
METHODS AND RESULTS:
We investigated the effect of flavonoids, including Naringenin chalcone, on the production of proinflammatory mediators in lipopolysaccharide (LPS)-stimulated macrophages and in the interaction between adipocytes and macrophages. Naringenin chalcone inhibited the production of TNF-alpha, MCP-1, and nitric oxide (NO) by LPS-stimulated RAW 264 macrophages in a dose-dependent manner. Coculture of 3T3-L1 adipocytes and RAW 264 macrophages markedly enhanced the production of TNF-alpha, MCP-1, and NO compared with the control cultures; however, treatment with Naringenin chalcone dose-dependently inhibited the production of these proinflammatory mediators.
CONCLUSIONS:
These results indicate that Naringenin chalcone exhibits anti-inflammatory properties by inhibiting the production of proinflammatory cytokines in the interaction between adipocytes and macrophages. Naringenin chalcone may be useful for ameliorating the inflammatory changes in obese adipose tissue.

J Nat Prod . 2019 Feb 22;82(2):177-182.

In Vivo Anti-inflammatory and Antiallergic Activity of Pure Naringenin, Naringenin Chalcone, and Quercetin in Mice[Pubmed: 30688453]

Abstract Flavonoids, found in almost all fruits and vegetables, belong to a class of plant secondary metabolites with a polyphenolic structure and have properties with health-improving potential. However, few experimental studies on the effects of flavonoids have been carried out in vivo after external application and using pure compounds. Aiming to fill this gap, in this study we tested the topical anti-inflammatory and antiallergic activity of three flavonoids of high purity, naringenin, Naringenin chalcone, and quercetin, in mouse models. The topical anti-inflammatory effects were assessed against arachidonic acid- (AA) and tetradecanoylphorbol-13-acetate- (TPA) induced ear edema. The anti-inflammatory effect of naringenin against ear edema was noticeable at a 1% dose in the AA model and at half this dose in the TPA model. Quercetin (1.3%) did not exert any topical anti-inflammatory activity in the AA model, but its inhibitory effect in the TPA model was similar to that of naringenin (2%); in contrast, Naringenin chalcone was more active against the AA-induced than TPA-induced inflammation. The flavonoid effect on IgE-mediated passive cutaneous anaphylaxis was also studied in mice, both intravenously and topically. Naringenin, Naringenin chalcone, and quercetin all showed strong antiallergic activity after intravenous dosing (0.02%) and when applied topically (2%). The results of this study suggest that the flavonoids naringenin, Naringenin chalcone, and quercetin may be useful alternatives for the topical treatment of inflammatory and allergic skin disorders.

J Agric Food Chem. 2009 Jul 22;57(14):6432-7.

Identification and quantification of metabolites of orally administered naringenin chalcone in rats.[Pubmed: 19558184]

Naringenin chalcone is the main active component of tomato skin extract, which has an antiallergic activity.
METHODS AND RESULTS:
In this study, Naringenin chalcone was orally administered to rats, and the chemical structures and levels of the major metabolites in the plasma and urine of rats were determined. HPLC analysis indicated the presence of three major metabolites in the urine. LC-MS and NMR analyses tentatively identified these as Naringenin chalcone-2'-O-beta-D-glucuronide, naringenin-7-O-beta-D-glucuronide, and naringenin-4'-O-beta-D-glucuronide. Naringenin chalcone-2'-O-beta-D-glucuronide was the only metabolite detected in the plasma, and its peak plasma level was observed 1 h after Naringenin chalcone administration. Naringenin chalcone-2'-O-beta-D-glucuronide also inhibited histamine release from rat peritoneal mast cells stimulated with compound 48/80.
CONCLUSIONS:
This activity might contribute to the antiallergic activity of Naringenin chalcone in vivo. To the best of the authors' knowledge, this study is the first to report determination of Naringenin chalcone metabolites in rat plasma and urine.

Allergol Int. 2010 Mar;59(1):67-73.

Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells.[Pubmed: 20035147]

Some polyphenols possess anti-allergic activities. Naringenin chalcone is one of the polyphenols that is present in the skin of red tomatoes. In this study, we investigated the effect of Naringenin chalcone in allergic responses in vivo using an experimental mouse model system of allergic asthma.
METHODS AND RESULTS:
Allergic airway inflammation was induced in mice by sensitization and challenge with ovalbumin. Naringenin chalcone was orally administrated every day during the course of the experiment. Airway hyperreactivity, the eosinophilic infiltration in the bronchioalveolar lavage fluid and Th2 cytokine production from splenic CD4 T cells were assessed. Eosinophilic airway inflammation, airway hyperreactivity and Th2 cytokine production from CD4 T cells were significantly suppressed in mice that were treated with Naringenin chalcone. Hyperproduction of mucus was slightly reduced.
CONCLUSIONS:
The results of this study suggest that Naringenin chalcone suppresses asthmatic symptoms by inhibiting Th2 cytokine production from CD4 T cells. Thus, Naringenin chalcone may be a useful supplement for the suppression of allergic symptoms in humans.