U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C28H34O15
Molecular Weight 610.5617
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HESPERIDIN

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@]([H])(OC[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(Oc3cc(c4C(=O)C[C@@]([H])(c5ccc(c(c5)O)OC)Oc4c3)O)O2)O)O)O)O1)O)O)O

InChI

InChIKey=QUQPHWDTPGMPEX-QJBIFVCTSA-N
InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1

HIDE SMILES / InChI

Molecular Formula C28H34O15
Molecular Weight 610.5617
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including: https://en.wikipedia.org/wiki/Hesperidin http://www.bimsifram.fr/hesperidin/indications_and_usage_of_hesperidin.htm

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees. Hesperidin was first isolated in 1828 by French chemist Lebreton from the white inner layer of citrus peels (mesocarp, albedo). As a flavanone found in citrus fruits (such as oranges, lemons or pummelo fruits), hesperidin is under laboratory research for possible biological properties. One area of research is focused on the possible chemopreventive effects of hesperidin, but there is no current proof that hesperidin has this role in human cancer mechanisms. Hesperidin was effective in an animal model of Alzheimer's, alleviating pathological changes induced by aluminum. Early research suggests that taking one tablet of a specific product (Daflon 500, Les Laboratoires Servier) containing hesperidin and diosmin by mouth for 45 days decreases blood sugar levels and improves blood sugarcontrol in women with type 2 diabetes. For Rheumatoid arthritis (RA): early research suggests that drinking a beverage containing alpha-glucosyl hesperidin for 12 weeks improves symptoms of RA. Orally, hesperidin can cause gastrointestinal side effects, including abdominal pain, diarrhea, and gastritis. Headache can also occur in some patients. The possible anti-inflammatory action of hesperidin is probably due to the possible anti-inflammatory action of its aglycone hesperetin. Hesperetin appears to interfere with the metabolism of arachidonic acid as well as with histamine release. Hesperetin appears to inhibit phospholipase A2, lipoxygenase and cyclo-oxygenase. There is evidence that hesperetin inhibits histamine release from mast cells, which would account for the possible anti-allergic activity of hesperidin. The possible hypolipidemic effect of hesperidin is probably due to hesperetin's possible action in lipid lowering. Hesperetin may reduce plasma cholesterol levels by inhibition of 3-hydroxy-3-methylglutaryl coenzyme A (HMG CoA) reductase, as well as acyl coenzyme A: cholesterol acytransferase (ACAT). Inhibition of these enzymes by hesperetin has been demonstrated in rats fed a high cholesterol diet. The mechanism of hesperidin's possible vasoprotective action is unclear. Animal studies have shown that hesperidin decreases microvascular permeability. Hesperidin, itself or via hesperetin, may protect endothelial cells from hypoxia by stimulating certain mitochondrial enzymes, such as succinate dehydrogenase. The mechanism of hesperidin's possible anticarcinogenic action is also unclear. One explanation may be the inhibition of polyamine synthesis. Inhibition of lipoxygenase and cyclo-oxygenase is another possibility.

CNS Activity

Curator's Comment:: Hesperidin (HESP), a flavanone glycoside, shows high antioxidant properties and posses ability to go through the blood–brain barrier. Therefore, it could be a potential drug molecule against aggregation based diseases such as Alzheimer’s, Parkinson’s, and systemic amyloidoses.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FRUIT ALLERGEN MIX

Approved Use

For the temporary relief of symptoms related to allergies to Vitamin C in foods and supplements, including fatigue, upper respiratory, gastrointestinal, musculoskeletal, and urinary symptoms.
Inactive ingredient
Volu-Firm Eye Renewal Cream

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases.
1990 Jul 5
Anti-AIDS agents, 10. Acacetin-7-O-beta-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids.
1994 Jan
Inhibition of HIV activation in latently infected cells by flavonoid compounds.
1996 Jan 1
Flavonoids and nitric oxide synthase.
2002 Dec
Effect of citrus flavonoids on lipid metabolism and glucose-regulating enzyme mRNA levels in type-2 diabetic mice.
2006
The immunomodulation of endotoxin-induced acute lung injury by hesperidin in vivo and in vitro.
2007 Apr 24
Hesperidin inhibited acetaldehyde-induced matrix metalloproteinase-9 gene expression in human hepatocellular carcinoma cells.
2009 Feb 10
Flavonoids inhibit high glucose-induced up-regulation of ICAM-1 via the p38 MAPK pathway in human vein endothelial cells.
2011 Dec 2
Investigation of the effects of some phenolic compounds on the activities of glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase from human erythrocytes.
2014 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: There is not enough evidence concerning doses of hesperidin used alone. Most studies describe the use of hesperidin in combination products that also contain other ingredients.
For arthritis: beverages containing 3 grams of a hesperidin derivative have been used every morning for 12 weeks. For blood vessel disorders (easily damaged capillary blood vessels): one tablet of Daflon ( 90% diosmin and 10% other flavonoids expressed as hesperidin.) has been used twice daily.
Route of Administration: Oral
In Vitro Use Guide
in vitro assay, a concentration of 200 μg/ml of hesperidin resulted in the mortality of 100% adult worms of Schistosoma (S.) mansoni within 72 h and a partial tegumental alteration in 10% of worms.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:27:36 UTC 2021
Edited
by admin
on Fri Jun 25 21:27:36 UTC 2021
Record UNII
E750O06Y6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HESPERIDIN
INCI   JAN   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
HESPERIDIN [INCI]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-
Common Name English
HESPERETIN 7-RUTINOSIDE
Common Name English
DIOSMIN [NDI]
Common Name English
HESPERIDIN [MART.]
Common Name English
HESPERIDIN [VANDF]
Common Name English
HESPERIDIN [JAN]
Common Name English
NDI 590 [FDMS]
Code English
DIOSVEIN
Brand Name English
HESPERIDOSIDE
Common Name English
NSC-44184
Code English
HESPERIDIN [MI]
Common Name English
CIRANTIN
Common Name English
HESPERETIN 7-RHAMNOGLUCOSIDE
Common Name English
5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-7-((6-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-4-CHROMANON
Common Name English
(2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Common Name English
HESPERIDIN [USP-RS]
Common Name English
HESPERIDIN [WHO-DD]
Common Name English
HESPERETIN-7-RUTINOSIDE
Common Name English
3',5'-DIHYDROXY-4'-METHOXY-7-RUTINOSYLOXYFLAVAN-4-ONE
Common Name English
Classification Tree Code System Code
DSLD 83 (Number of products:829)
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
NCI_THESAURUS C68461
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
Code System Code Type Description
CAS
520-26-3
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
EVMPD
SUB14093MIG
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
MESH
C506722
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
WIKIPEDIA
HESPERIDIN
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
DRUG BANK
DB04703
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
MERCK INDEX
M5976
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C68460
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
PUBCHEM
10621
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
MESH
D006569
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
RXCUI
5281
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY RxNorm
EPA CompTox
520-26-3
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
FDA UNII
E750O06Y6O
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL449317
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
USP_CATALOG
1304377
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
208-288-1
Created by admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
TRANSPORTER -> INHIBITOR
Related Record Type Details
PARENT -> IMPURITY
NMT 5%
USP
Related Record Type Details
ACTIVE MOIETY