Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H14O6 |
Molecular Weight | 302.2788 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(O)C=C(C=C1)[C@@H]2CC(=O)C3=C(O2)C=C(O)C=C3O
InChI
InChIKey=AIONOLUJZLIMTK-AWEZNQCLSA-N
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26188593Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20696580 | https://www.ncbi.nlm.nih.gov/pubmed/26498393 |
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26188593
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20696580 | https://www.ncbi.nlm.nih.gov/pubmed/26498393 |
Hesperetin is a cholesterol-lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions. In vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity, as well as activity again. Hesperetin reduces or inhibits the activity of acyl-coenzyme A: cholesterol acyltransferase genes (ACAT1 and ACAT2) and it reduces microsomal triglyceride transfer protein (MTP) activity. Hesperetin also seems to upregulate the LDL receptor. This leads to the reduced assembly and secretion of apoB-containing lipoproteins and enhanced reuptake of those lipoproteins, thereby lowering cholesterol levels. Hesperetin's 7-O-glycoside, hesperidin, is a naturally occurring flavanon-glycoside, the main flavonoid in lemons and sweet oranges.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
34.6 µM [IC50] | ||
Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
2.7 µM [IC50] | ||
Target ID: CHEMBL2326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26498393 |
3.3 nM [Ki] | ||
Target ID: CHEMBL3729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26498393 |
102.1 nM [Ki] | ||
Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26498393 |
454.1 nM [Ki] | ||
Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 |
511.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Effect of hesperetin, a citrus flavonoid, on the liver triacylglycerol content and phosphatidate phosphohydrolase activity in orotic acid-fed rats. | 2001 |
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Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. | 2001 Dec |
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In vitro biological activity of prenylflavanones. | 2001 Jan-Feb |
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Specific flavonoids induced nod gene expression and pre-activated nod genes of Rhizobium leguminosarum increased pea (Pisum sativum L.) and lentil (Lens culinaris L.) nodulation in controlled growth chamber environments. | 2001 Jul |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Secretion of hepatocyte apoB is inhibited by the flavonoids, naringenin and hesperetin, via reduced activity and expression of ACAT2 and MTP. | 2001 May |
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Antimicrobial activity of prenylflavanones. | 2001 Nov-Dec |
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Effect of exogenous flavonoids on nodulation of pea (Pisum sativum L.). | 2002 Aug |
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In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. | 2002 May |
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Plasma concentrations of the flavonoids hesperetin, naringenin and quercetin in human subjects following their habitual diets, and diets high or low in fruit and vegetables. | 2002 Sep |
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Interaction between flavonoids and the blood-brain barrier: in vitro studies. | 2003 Apr |
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Separation of some chiral flavanones by micellar electrokinetic chromatography. | 2003 Aug |
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Hypocholesterolemic activity of hesperetin derivatives. | 2003 Aug 18 |
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Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2003 Dec |
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Anti-Sindbis activity of flavanones hesperetin and naringenin. | 2003 Jan |
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Kinetic and stoichiometric assessment of the antioxidant activity of flavonoids by electron spin resonance spectroscopy. | 2003 Mar 12 |
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Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. | 2003 May |
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Hesperetin glucuronide, a photoprotective agent arising from flavonoid metabolism in human skin fibroblasts. | 2003 Sep |
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Reports: plasma and dietary phytoestrogens and risk of premalignant lesions of the cervix. | 2004 |
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Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity. | 2004 |
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Effects of some natural flavonoids on retinal function recovery after ischemic insult in the rat. | 2004 Apr |
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Improvement in solubility and dissolution rate of flavonoids by complexation with beta-cyclodextrin. | 2004 Apr 16 |
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Antiallergic activity of hesperidin is activated by intestinal microflora. | 2004 Aug |
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The flavones luteolin and apigenin inhibit in vitro antigen-specific proliferation and interferon-gamma production by murine and human autoimmune T cells. | 2004 Aug 15 |
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Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice. | 2004 Jan 28 |
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Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport. | 2004 Jul |
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Evaluation of hesperetin 7-O-lauryl ether as lipid-lowering agent in high-cholesterol-fed rats. | 2004 Jul 1 |
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Determination of hesperetin, cinnamic acid and nicotinic acid in propolis with micellar electrokinetic capillary chromatography. | 2004 Jun |
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Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma. | 2004 Mar 5 |
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Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. | 2004 Oct 20 |
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Anti-inflammatory effect of heme oxygenase 1: glycosylation and nitric oxide inhibition in macrophages. | 2005 Feb |
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Oral flavonoids delay recovery from experimental autoimmune encephalomyelitis in SJL mice. | 2005 Jul 15 |
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Impact of high pressure and pulsed electric fields on bioactive compounds and antioxidant activity of orange juice in comparison with traditional thermal processing. | 2005 Jun 1 |
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High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones. | 2005 May 27 |
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Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. | 2005 Oct |
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Interactive effects of polyphenols, tocopherol and ascorbic acid on the Cu2+-mediated oxidative modification of human low density lipoproteins. | 2005 Oct |
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Capillary electrochromatography of biologically relevant flavonoids. | 2006 Feb |
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Different anticonvulsive effects of hesperidin and its aglycone hesperetin on electrical activity in the rat hippocampus in-vitro. | 2006 Mar |
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The bioavailability of polyphenols is highly governed by the capacity of the intestine and of the liver to secrete conjugated metabolites. | 2006 Mar |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22307524
150 mg of hesperetin as a single dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22307524
Effectiveness of a plasma hesperetin metabolite on the release of nitric oxide (NO) and the activity of nicotinamide adenine dinucleotide phosphate-oxidase (NADPH oxidase) in endothelial cells was examined. Hesperetin or Hp7GA were dissolved in methanol and diluted with the medium. The final methanol concentration of the cell culture had no effect on the cell viability. Cells were placed in a dish (diameter, 15.5 mm) in an atmosphere of 5% CO2 /95% air at 37 C. Then the medium was replaced with fresh medium containing the test compounds. After treatment with test compounds (1, 5, 10, 25, and 50 mM) for 24 h, NO released from HUVECs was measured using 4-amino-5-methylamino-2,7-difluorofluorescein (DAF-FM) as a fluorescence probe.
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DB01094
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DTXSID4022319
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Q9Q3D557F1
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2002
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Q9Q3D557F1
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HESPERETIN
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208-290-2
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1314255
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28230
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C68461
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520-33-2
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72281
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m5975
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SUBSTANCE RECORD