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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
Structure of HESPERETIN

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

HIDE SMILES / InChI

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
34.6 µM [IC50]
2.7 µM [IC50]
3.3 nM [Ki]
102.1 nM [Ki]
454.1 nM [Ki]
511.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
150 mg of hesperetin as a single dose.
Route of Administration: Oral
In Vitro Use Guide
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.