Anti-allergic Activity of Naringenin Chalcone from a Tomato Skin Extract

CitationIn vitro structure-toxicity relationship of chalcones in human hepatic stellate cells 2015 Toxicology This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. In vitro AbstractXanthohumol (XN), the major prenylated chalcone from hops (Humulus lupulus L.), has received much attention within the last years, due to its multiple pharmacological activities including anti-proliferative, anti-inflammatory, antioxidant, pro-apoptotic, anti-bacterial and anti-adhesive effects. However, there exists a huge number of metabolites and structurallyrelated chalcones, which can be expected, or are already known, to exhibit various effects on cells. We have therefore analyzed the effects of XN and 18 other chalcones in a panel, consisting of multiple cell-based assays. Readouts of these assays addressed distinct aspects of cell-toxicity, like proliferation, mitochondrial health, cell cycle and other cellular features. Besides known active structural elements of chalcones, like the Michael system, we have identified several moieties that seem to have an impact on specific effects and toxicity in human liver cells in vitro. Based on these observations, we present a structure-toxicity model, which will be crucial to understand the molecular mechanisms of wanted effects and unwanted side-effects of chalcones.

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“…tomatoes (Yamamoto et al, 2004), citruses (Iwase et al, 2001), apples (Gaucher et al, 2013)) or herbal drugs (e.g.…”

Section: Introductionmentioning

confidence: 99%

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

et al. 2015

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“…More particularly, naringenin chalcone and rutin, the most abundant flavonoids in tomato fruit, have shown important beneficial properties to human health. The first metabolite was proven to show antiallergic activity (6), whereas the second one has long been studied for human healthprotecting properties (7). Due to these beneficial effects, in recent years there has been an increasing interest in developing fruits and vegetables with a high content of such compounds.…”

Section: Introductionmentioning

confidence: 99%

Flavonoid Profiling and Biosynthetic Gene Expression in Flesh and Peel of Two Tomato Genotypes Grown under UV-B-Depleted Conditions during Ripening

Giuntini

Lazzeri

Calvenzani

et al. 2008

J. Agric. Food Chem.

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The effect of shielding solar ultraviolet B radiation on the accumulation of some flavonoids and their precursor hydroxycinnamic acids in tomato (Solanum lycopersicum) was evaluated by liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). In particular, flesh and peel of two tomato hybrids, DRW 5981 and Esperanza, were separately analyzed. The hybrids have been chosen for their different responses to the light, since it was previously reported that they show different pigmentation and opposite behavior under UV-B in terms of carotenoids and ascorbic acid content at different ripening stages. To determine the effect of UV-B radiation during tomato ripening, we also measured the expression of some flavonoid biosynthetic genes by realtime reverse transcription-polymerase chain reaction (RT-PCR) analysis. The results allowed us to conclude that UV-B radiation deeply and differentially affects the content of the considered flavonoids and hydroxycinnamic acids as well as the expression of some of their biosynthetic genes in both flesh and peel during the ripening process. On the other hand, the collected data clearly showed that this influence varies between different genotypes. We conclude that the use of specific plastic covers able to eliminate UV-B radiation may be an environmentally friendly approach to modulate the expression of structural genes and, in turn, to enhance healthy antioxidant compounds in fruits of specific tomato cultivars.

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“…Acid catalyzed synthesis is also well established using p-toluene sulfonic acid under focused microwave irradiation [8], thionyl chloride [9], dry hydrochloric acid and borontri uoride-etherate [10]. Some chalcones are known for their biological activities as they exhibit cytotoxic [11], antibacterial [12], antifungal [13], antimalarial and antitubercular [14], anti-in ammatory [15], antimalarial [16], antiviral [17], tyrosinase inhibitor [18], antiallergenic [19], antioxidant [20] and antihyperglycemic [21] activities. The asymmetric unit cell of the titled compound contains one independent molecule.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C₁₉H₁₈O₄

El-Sayed

Almaneai

Ghabbour

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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Anti-allergic Activity of Naringenin Chalcone from a Tomato Skin Extract

Cited by 149 publications

References 24 publications

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

Flavonoid Profiling and Biosynthetic Gene Expression in Flesh and Peel of Two Tomato Genotypes Grown under UV-B-Depleted Conditions during Ripening

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C₁₉H₁₈O₄

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Anti-allergic Activity of Naringenin Chalcone from a Tomato Skin Extract

Cited by 149 publications

References 24 publications

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

Flavonoid Profiling and Biosynthetic Gene Expression in Flesh and Peel of Two Tomato Genotypes Grown under UV-B-Depleted Conditions during Ripening

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H18O4

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Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C₁₉H₁₈O₄