Compound page

.wrapper {display:none;}

You don't have javascript enabled. Please enable javascript and refresh the page !

C15H12O5
APtclcactv08032319312D 0   0.00000     0.00000
 
 32 33  0  0  0  0  0  0  0  0999 V2000
    3.4030   -2.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -2.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    3.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7331    2.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    3.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.2150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5380   -1.2150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321   -4.2150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991    4.2150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -1.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350   -1.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -2.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010    2.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7331    3.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030    0.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -0.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0010   -0.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -3.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5991    3.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690    0.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350    0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1350    1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6719    0.2850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660   -2.7150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6719   -2.7150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981    1.9050    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    0.9750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4641    3.4050    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2700    1.7850    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    4.2150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 22  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 22 23  1  0  0  0  0
 17 22  2  0  0  0  0
  1 12  2  0  0  0  0
 12 18  1  0  0  0  0
  2 13  1  0  0  0  0
 13 19  1  0  0  0  0
 23 24  2  0  0  0  0
  1 14  1  0  0  0  0
 15 24  1  0  0  0  0
 14 20  1  0  0  0  0
  3 15  2  0  0  0  0
  4 15  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5 16  2  0  0  0  0
 16 21  1  0  0  0  0
  2 14  2  0  0  0  0
  6 16  1  0  0  0  0
 23 25  1  0  0  0  0
  1 26  1  0  0  0  0
  7 18  1  0  0  0  0
  2 27  1  0  0  0  0
  8 19  1  0  0  0  0
 24 28  1  0  0  0  0
  9 20  1  0  0  0  0
  3 29  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  0  0  0  0
 10 21  1  0  0  0  0
M  END
$$$$

MOL SMILES InChIKey

Compound Description

A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' ,4, 4', and 6' respectively.

Identification

IUPAC Names

(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

Molecular Formula

C15H12O5

Mass

272.25278

Monoisotopic Mass

272.06847

Charge

InChI

InChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H/b6-3+

InChIKey

YQHMWTPYORBCMF-ZZXKWVIFSA-N

SMILES

Oc1ccc(cc1)\C=C\C(=O)c1c(O)cc(O)cc1O

Synonyms

2',4',6',4-tetrahydroxychalcone

2',4,4',6'-Tetrahydroxychalcone

2'4'6'4-Tetrahydroxychalcone

Chalconaringenin

Isosalipurpol

Naringenin chalcone

Species

Select Species

Select Pathways

Select Species

Select Pathways

Select Reaction

Select NMR spectra

Select MS spectra

Europe PubMed Central results

Anti-allergic activity of naringenin chalcone from a tomato skin extract.

Author: Yamamoto T, Yoshimura M, Yamaguchi F, Kouchi T, Tsuji R, Saito M, Obata A, Kikuchi M.

Abstract: The anti-allergic activity of a tomato extract was studied by using an in vitro histamine-release assay. The tomato skin extract exerted the strongest inhibition of histamine release. Chlorogenic acid, rutin and naringenin were identified in the 60% ethanol extract of tomato skin. However, the extract contained an unknown compound which strongly inhibited histamine release. This active compound in tomato skin was identified as naringenin chalcone (trans-2'4'6'4-tetrahydroxychalcone). Naringenin chalcone inhibited histamine release with an IC(50) value of 68 microg/ml. The anti-allergic activity of the tomato skin extract was next investigated by the in vivo mouse ear-swelling response. We found that naringenin chalcone showed the strongest inhibitory effect of the polyphenols of the tomato skin extract. These results indicate that a tomato skin extract could inhibit allergic reactions.

DOI: 10.1271/bbb.68.1706

Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages.

Author: Hirai S, Kim YI, Goto T, Kang MS, Yoshimura M, Obata A, Yu R, Kawada T.

Abstract: 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. 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. 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.

DOI: 10.1016/j.lfs.2007.09.001

Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells.

Author: Iwamura C, Shinoda K, Yoshimura M, Watanabe Y, Obata A, Nakayama T.

Abstract: <h4>Background</h4>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.<h4>Methods</h4>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.<h4>Results</h4>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.<h4>Conclusions</h4>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.

DOI: 10.2332/allergolint.09-oa-0118

Naringenin chalcone improves adipocyte functions by enhancing adiponectin production.

Author: Horiba T, Nishimura I, Nakai Y, Abe K, Sato R.

Abstract: Naringenin chalcone is a flavonoid contained in tomato peel. 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. 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.

DOI: 10.1016/j.mce.2010.03.020

Genetics of flavonoid, carotenoid, and chlorophyll pigments in melon fruit rinds.

Author: Tadmor Y, Burger J, Yaakov I, Feder A, Libhaber SE, Portnoy V, Meir A, Tzuri G, Sa'ar U, Rogachev I, Aharoni A, Abeliovich H, Schaffer AA, Lewinsohn E, Katzir N.

Abstract: External color has profound effects on acceptability of agricultural products by consumers. Carotenoids and chlorophylls are known to be the major pigments of melon (Cucumis melo L.) rinds. Flavonoids (especially chalcones and anthocyanins) are also prominent in other fruits but have not been reported to occur in melons fruit. We analyzed the pigments accumulating in rinds of different melon genotypes during fruit development. We found that melon rind color is based on different combinations of chlorophyll, carotenoids, and flavonoids according to the cultivar tested and their ratios changed during fruit maturation. Moreover, in "canary yellow" type melons, naringenin chalcone, a yellow flavonoid pigment previously unknown to occur in melons, has been identified as the major fruit colorant in mature rinds. Naringenin chalcone is also prominent in other melon types, occurring together with carotenoids (mainly β-carotene) and chlorophyll. Both chlorophyll and carotenoid pigments segregate jointly in an F(2) population originating from a cross between a yellow canary line and a line with green rind. In contrast, the content of naringenin chalcone segregates as a monogenic trait independently to carotenoids and chlorophyll. Transcription patterns of key structural phenylpropanoid and flavonoid biosynthetic pathway genes were monitored in attempts to explain naringenin chalcone accumulation in melon rinds. The transcript levels of CHI were low in both parental lines, but C4H, C4L, and CHS transcripts were upregulated in "Noy Amid", the parental line that accumulates naringenin chalcone. Our results indicate that naringenin chalcone accumulates independently from carotenoids and chlorophyll pigments in melon rinds and gives an insight into the molecular mechanism for the accumulation of naringenin chalcone in melon rinds.

DOI: 10.1021/jf1021797

Connect to another EMBL location

MTBLC15413: 2',4,4',6'-tetrahydroxychalcone