Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H36O15 |
Molecular Weight | 624.5871 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(\C=C\C(=O)C2=C(OC)C=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O)C=C1O
InChI
InChIKey=FDHNLHLOJLLXDH-JIYHLSBYSA-N
InChI=1S/C29H36O15/c1-12-22(33)24(35)26(37)28(42-12)41-11-20-23(34)25(36)27(38)29(44-20)43-14-9-17(32)21(19(10-14)40-3)15(30)6-4-13-5-7-18(39-2)16(31)8-13/h4-10,12,20,22-29,31-38H,11H2,1-3H3/b6-4+/t12-,20+,22-,23+,24+,25-,26+,27+,28+,29+/m0/s1
DescriptionCurator'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
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
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | FRUIT ALLERGEN MIX Approved UseFor the temporary relief of symptoms related to allergies to Vitamin C in foods and supplements, including fatigue, upper respiratory, gastrointestinal, musculoskeletal, and urinary symptoms. |
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Inactive ingredient | Volu-Firm Eye Renewal Cream Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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Inhibition of HIV activation in latently infected cells by flavonoid compounds. | 1996 Jan 1 |
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Flavanone glycosides from Citrus junos and their anti-influenza virus activity. | 2001 Aug |
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Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression. | 2005 Sep-Oct |
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Effect of citrus flavonoids on lipid metabolism and glucose-regulating enzyme mRNA levels in type-2 diabetic mice. | 2006 |
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Antioxidant properties of hesperidin in nicotine-induced lung toxicity. | 2007 Oct |
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Effect of constituents from Fructus Aurantii Immaturus and Radix Paeoniae Alba on gastrointestinal movement. | 2009 Jan |
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The inhibitory effect of hesperidin on tumor cell invasiveness occurs via suppression of activator protein 1 and nuclear factor-kappaB in human hepatocellular carcinoma cells. | 2010 Apr 15 |
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Hesperidin alleviates acetaminophen induced toxicity in Wistar rats by abrogation of oxidative stress, apoptosis and inflammation. | 2012 Jan 25 |
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Hesperidin blunts streptozotocin-isoproternol induced myocardial toxicity in rats by altering of PPAR-γ receptor. | 2014 Aug 5 |
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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 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.akins.com/ns/DisplayMonograph.asp?storeID=a59a6b1c10e44c9e9420a7a75b27460a&DocID=hesperidin
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/23656891
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.
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C033022
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DTXSID90885262
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72086
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100000085802
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SUB14095MIG
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246-128-2
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6436550
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ACTIVE MOIETY
SUBSTANCE RECORD