Histolocalization and physico-chemical characterization of dihydrochalcones: Insight into the role of apple major flavonoids

Gaucher, Matthieu; Bernonville, Thomas Dugé de; Lohou, David; Guyot, Sylvain; Guillemette, Thomas; Brisset, Marie-Noëlle; Dat, James F.

doi:10.1016/j.phytochem.2013.02.009

Cited by 46 publications

(39 citation statements)

References 68 publications

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“…Among the 137 chalcones studied, only four were active against the fungus (D7, D8, N5 and L21), representing 2.9% of the samples. This percentage seems to be in accordance with other researches, in which a percentage around or lower than 10% of active substances has been verified in the screening for compounds with potential biological activity (LOUZADA et al, 2009;CARVALHO et al, 2011;CHIARADIA et al, 2012;MARTINS et al, 2013;FERREIRA et al, 2014). This occurs due to the variation in the chemical structures of the compounds.…”

Section: Discussionsupporting

confidence: 92%

“…than those observed by Cotoras et al (2011) and Gaucher et al (2013), who reported only 30% and 50% inhibition of conidia germination of Botrytis cinerea and Venturia inaequalis, respectively. Apparently, this behaviour is mainly caused by the ketone group in the structures of chalcones (LÓPEZ et al, 2001), which can bind thiol groups in proteins, inhibiting fungal cell wall biosynthesis (BOWDEN; POZZO; DUAH, 1990).…”

Section: Discussioncontrasting

confidence: 60%

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Chalcones to control Alternaria alternata in murcott tangor fruits

Camargos¹,

Perina²,

Carvalho³

et al. 2016

Biosci. J.

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Alternaria brown spot (ABS), caused by the fungus Alternaria alternata pathotype tangerine, is one of the main phytosanitary problems for mandarin growers. About 15 applications per year of harmful fungicides are required for controlling ABS disease in citrus orchards. As chalcones seem to be less toxic to humans and environment than the commercial fungicides in use, this study initially aimed at synthesizing 137 chalcones through aldolic condensations between benzaldehydes and acetophenones. The resulting chalcones were screened for activity against A. alternata through a fungal growth assay that was carried out in 96-cell polypropylene plates, using the same concentration to all studied substances. The four active chalcones underwent conidia germination and mycelial growth, which confirmed the antifungal activity of the compounds. These chalcones were then poured onto Murcott tangor fruit that had been inoculated with conidia of the fungus. All four chalcones reduced the ABS progress to values significantly smaller (P≤0.05) than that observed for the control. Statistical calculations showed that the best results were afforded by two compounds, bearing a 2,4,5-trimethoxyphenyl group at position 3 of prop-2-enal and a 3-nitro-or 3-hydroxyphenyl group at position 1 of the aldehyde. Such compounds reduced the incidence of the disease in Murcott tangor fruit to values that did not differ statistically from those obtained with a commercial fungicide.

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Section: Discussionsupporting

confidence: 92%

Section: Discussioncontrasting

confidence: 60%

Chalcones to control Alternaria alternata in murcott tangor fruits

Camargos¹,

Perina²,

Carvalho³

et al. 2016

Biosci. J.

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“…1), a crystalline phenolic ketone and its most abundant glycosylated products, phloridzin (phloretin-2 0 -Oglucoside) and phloretin-2 0 -O-(2 0 -O-xylosyl) glycoside are simple dihydrochalcones. Several other derivatives such as 3-hydroxyphloretin, sieboldin (3-hydroxyphloretin-4 0 -O-glucoside), trilobatin (phloretin-4 0 -O-glucoside), phloretin-4 0 -O-galloyl glucoside, nothofagin (phloretin-3 0 -C-glucoside) and glycyphyllin (phloretin-2 0 -O-rhamnoside) have been isolated from natural sources (Gaucher et al 2013;Harborne 2013;Iwashina et al 2012). In phloretin, two aromatic phenol rings (ring A and B), hydroxyl groups and a carbonyl group are responsible for a wide spectrum of pharmacological effects.…”

Section: Chemistrymentioning

confidence: 99%

Health effects of phloretin: from chemistry to medicine

et al. 2017

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Dihydrochalcones are a class of secondary metabolites, whose demand in biological and pharmacological applications is rapidly growing. Phloretin is one of the best known and abundant dihydrochalcone characterized by the presence of 2,6-dihydroxyacetophenone pharmacophore. It is a versatile molecule with anticancer, antiosteoclastogenic, antifungal, antiviral, anti-inflammatory, antibacterial and estrogenic activities and able to increase the fluidity of biological membranes and penetration of administered drugs. In this review we have performed a critical evaluation of available literature as far as phloretin beneficial effects and activation/block of intracellular signal cascade are of concern. In addition, we supply useful information on its chemical properties, sources and bioavailability.

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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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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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Histolocalization and physico-chemical characterization of dihydrochalcones: Insight into the role of apple major flavonoids

Cited by 46 publications

References 68 publications

Chalcones to control Alternaria alternata in murcott tangor fruits

Chalcones to control Alternaria alternata in murcott tangor fruits

Health effects of phloretin: from chemistry to medicine

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

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