Eriocitrin

CAS# 13463-28-0

Eriocitrin

2D Structure

Catalog No. BCN1208----Order now to get a substantial discount!

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Eriocitrin

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Chemical Properties of Eriocitrin

Cas No. 13463-28-0 SDF Download SDF
PubChem ID 83489 Appearance White powder
Formula C27H32O15 M.Wt 596.53
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Eriodictioside; Eriodictyol 7-O-rutinoside; 3',4',5,7-Tetrahydroxyflavanone 7-rutinoside
Solubility DMSO : 125 mg/mL (209.55 mM; Need ultrasonic)
Chemical Name (2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O
Standard InChIKey OMQADRGFMLGFJF-MNPJBKLOSA-N
Standard InChI InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Eriocitrin

1 Mentha sp. 2 Thymus sp.

Biological Activity of Eriocitrin

DescriptionEriocitrin is powerful antioxidative flavonoid, it can prevent oxidative damages caused by acute exercise-induced oxidative stress, it also has lipid-lowering effect in rats on a high-fat and high-cholesterol diet. Eriocitrin is a potent inhibitor of human carbonic anhydrase VA isozyme.
TargetsLDL | ATP synthase
In vitro

Lipid-Lowering Effect of Eriocitrin, the Main Flavonoid in Lemon Fruit, in Rats on a High-Fat and High-Cholesterol Diet[Reference: WebLink]

J. Food Sci., 2006, 71(71):S633–S7.

Eriocitrin (eriodictyol 7-O-β-rutinoside) is the main flavonoid in lemon fruit.
METHODS AND RESULTS:
In this study, Eriocitrin was investigated for its lowering effect on serum and hepatic lipids in high-fat and high-cholesterol fed rats. Rats in the control group (N = 6) were fed a 20% lard and 1% cholesterol diet for 21 d, and rats in the 0.35% Eriocitrin group (N = 6) and 0.70% Eriocitrin group (N = 6) were fed a diet supplemented with Eriocitrin 0.35% and 0.70%, respectively. The content of hepatic total cholesterol and triglyceride in the Eriocitrin group was no different from that of the control group. The total cholesterol, VLDL+LDL, triglyceride, and phospholipid in the serum of the 0.35% Eriocitrin group showed significantly lower concentrations than the control group (P < 0.05), although there was no difference in the HDL concentrations among the groups. The lowering effect of Eriocitrin for serum total cholesterol was thought to be caused by a decrease in VLDL+LDL.
CONCLUSIONS:
The 0.35% Eriocitrin group was shown to have a significant increase in excretion of fecal bile acid (P < 0.05) and a tendency for enhanced hepatic m-RNA levels of LDL receptor in comparison with the control group.

In vivo

Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis.[Pubmed: 24424211]

Sci Rep. 2014 Jan 15;4:3708.

Lemon (Citrus limon) contains various bioactive flavonoids, and prevents obesity and obesity-associated metabolic diseases. We focused on Eriocitrin (eriodictyol 7-rutinoside), a powerful antioxidative flavonoid in lemon with lipid-lowering effects in a rat model of high-fat diet.
METHODS AND RESULTS:
To investigate the mechanism of action of Eriocitrin, we conducted feeding experiments on zebrafish with diet-induced obesity. Oral administration of Eriocitrin (32 mg/kg/day for 28 days) improved dyslipidaemia and decreased lipid droplets in the liver. DNA microarray analysis revealed that Eriocitrin increased mRNA of mitochondrial biogenesis genes, such as mitochondria transcription factor, nuclear respiratory factor 1, cytochrome c oxidase subunit 4, and ATP synthase. In HepG2 cells, Eriocitrin also induced the corresponding orthologues, and reduced lipid accumulation under conditions of lipid loading. Eriocitrin increased mitochondrial size and mtDNA content, which resulted in ATP production in HepG2 cells and zebrafish.
CONCLUSIONS:
In summary, dietary Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis.

Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats.[Pubmed: 10956094]

J Agric Food Chem. 2000 Aug;48(8):3217-24.

Eriocitrin, a flavonoid glycoside present in lemon fruit, is metabolized in vivo to a series of eriodictyol, methylated eriodictyol, 3,4-dihydroxyhydrocinnamic acid, and their conjugates.
METHODS AND RESULTS:
Plasma antioxidant activity increased following oral administration of aqueous Eriocitrin solutions to rats. Eriocitrin metabolites were found in plasma and renal excreted urine through HPLC and LC-MS analyses. Eriocitrin was not detected in plasma and urine, but eriodictyol, homoeriodictyol, and hesperetin in their conjugated forms were detected in plasma of 4.0 h following administration of Eriocitrin. In urine for 24 h, both nonconjugates and conjugates of these metabolites were detected. 3,4-Dihydroxyhydrocinnamic acid, which is metabolized from eriodictyol by intestinal bacteria, was detected in slight amounts with each form in 4.0-h plasma and 24-h urine. Eriocitrin was suggested to be metabolized by intestinal bacteria, and then eriodictyol and 3,4-dihydroxyhydrocinnamic of its metabolite were absorbed.
CONCLUSIONS:
Following administration of Eriocitrin, plasma exhibited an elevated resistance effect to lipid peroxidation. Eriocitrin metabolites functioning as antioxidant agents are discussed.

Protocol of Eriocitrin

Kinase Assay

Eriocitrin and Apigenin as New Carbonic Anhydrase VA Inhibitors from a Virtual Screening of Calabrian Natural Products.[Pubmed: 25590364]

Planta Med. 2015 Apr;81(6):533-40.


METHODS AND RESULTS:
In this work, we performed a structure-based virtual screening against five carbonic anhydrase isoforms using, as a ligand library, natural components of Citrus bergamia (Bergamot) and Allium cepa var. Tropea (red onion) sources, which are some typical Calabrian products. The most relevant Bergamot and red onion components, identified as potentially new hits by means of the computational work, were submitted to in vitro tests in order to confirm the ability to exert the predicted biological activity.
CONCLUSIONS:
Apigenin and Eriocitrin were identified as new potent inhibitors of human carbonic anhydrase VA isozyme.

Animal Research

Lemon flavonoid, eriocitrin, suppresses exercise-induced oxidative damage in rat liver.[Pubmed: 12551749]

Life Sci. 2003 Feb 21;72(14):1609-16.


METHODS AND RESULTS:
To examine the preventive effect of the lemon flavonoid, Eriocitrin (eriodictyol 7-O-rutinoside), on oxidative stress during acute exercise in vivo, levels of N( epsilon )- (hexanoyl)lysine, HEL; o,o-dityrosine, DT; and nitrotyrosine, NT, as oxidative stress markers, were determined by ELISA in livers of trained rats in addition to thiobarbituric acid-reactive substance (TBARS). Eriocitrin administration prior to exercise significantly suppressed the increases in TBARS caused by lipid peroxidation during acute exercise. The contents of HEL, DT, and NT in rat liver increased dramatically by exercise without Eriocitrin administration. However, these increases were significantly suppressed by Eriocitrin administration before exercise. Moreover, in this study, to clarify whether Eriocitrin influences glutathione metabolite system that is considered to be important for a defense against the damage by oxidative stress, the levels of glutathione in rat liver were determined during exercise. The level of reduced glutathione after exercise was maintained by administration of Eriocitrin. The increase in the concentration of oxidized glutathione caused by exercise was significantly suppressed by Eriocitrin. This result suggested that Eriocitrin might play an important role in the control of the change in glutathione redox status in rat liver during exercise.
CONCLUSIONS:
These findings showed that Eriocitrin was effective in the prevention of oxidative damages caused by acute exercise-induced oxidative stress.

Eriocitrin Dilution Calculator

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Preparing Stock Solutions of Eriocitrin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6764 mL 8.3818 mL 16.7636 mL 33.5272 mL 41.909 mL
5 mM 0.3353 mL 1.6764 mL 3.3527 mL 6.7054 mL 8.3818 mL
10 mM 0.1676 mL 0.8382 mL 1.6764 mL 3.3527 mL 4.1909 mL
50 mM 0.0335 mL 0.1676 mL 0.3353 mL 0.6705 mL 0.8382 mL
100 mM 0.0168 mL 0.0838 mL 0.1676 mL 0.3353 mL 0.4191 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Eriocitrin

Lemon flavonoid, eriocitrin, suppresses exercise-induced oxidative damage in rat liver.[Pubmed:12551749]

Life Sci. 2003 Feb 21;72(14):1609-16.

To examine the preventive effect of the lemon flavonoid, Eriocitrin (eriodictyol 7-O-rutinoside), on oxidative stress during acute exercise in vivo, levels of N( epsilon )- (hexanoyl)lysine, HEL; o,o-dityrosine, DT; and nitrotyrosine, NT, as oxidative stress markers, were determined by ELISA in livers of trained rats in addition to thiobarbituric acid-reactive substance (TBARS). Eriocitrin administration prior to exercise significantly suppressed the increases in TBARS caused by lipid peroxidation during acute exercise. The contents of HEL, DT, and NT in rat liver increased dramatically by exercise without Eriocitrin administration. However, these increases were significantly suppressed by Eriocitrin administration before exercise. Moreover, in this study, to clarify whether Eriocitrin influences glutathione metabolite system that is considered to be important for a defense against the damage by oxidative stress, the levels of glutathione in rat liver were determined during exercise. The level of reduced glutathione after exercise was maintained by administration of Eriocitrin. The increase in the concentration of oxidized glutathione caused by exercise was significantly suppressed by Eriocitrin. This result suggested that Eriocitrin might play an important role in the control of the change in glutathione redox status in rat liver during exercise. These findings showed that Eriocitrin was effective in the prevention of oxidative damages caused by acute exercise-induced oxidative stress.

Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis.[Pubmed:24424211]

Sci Rep. 2014 Jan 15;4:3708.

Lemon (Citrus limon) contains various bioactive flavonoids, and prevents obesity and obesity-associated metabolic diseases. We focused on Eriocitrin (eriodictyol 7-rutinoside), a powerful antioxidative flavonoid in lemon with lipid-lowering effects in a rat model of high-fat diet. To investigate the mechanism of action of Eriocitrin, we conducted feeding experiments on zebrafish with diet-induced obesity. Oral administration of Eriocitrin (32 mg/kg/day for 28 days) improved dyslipidaemia and decreased lipid droplets in the liver. DNA microarray analysis revealed that Eriocitrin increased mRNA of mitochondrial biogenesis genes, such as mitochondria transcription factor, nuclear respiratory factor 1, cytochrome c oxidase subunit 4, and ATP synthase. In HepG2 cells, Eriocitrin also induced the corresponding orthologues, and reduced lipid accumulation under conditions of lipid loading. Eriocitrin increased mitochondrial size and mtDNA content, which resulted in ATP production in HepG2 cells and zebrafish. In summary, dietary Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis.

Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats.[Pubmed:10956094]

J Agric Food Chem. 2000 Aug;48(8):3217-24.

Eriocitrin, a flavonoid glycoside present in lemon fruit, is metabolized in vivo to a series of eriodictyol, methylated eriodictyol, 3,4-dihydroxyhydrocinnamic acid, and their conjugates. Plasma antioxidant activity increased following oral administration of aqueous Eriocitrin solutions to rats. Eriocitrin metabolites were found in plasma and renal excreted urine through HPLC and LC-MS analyses. Eriocitrin was not detected in plasma and urine, but eriodictyol, homoeriodictyol, and hesperetin in their conjugated forms were detected in plasma of 4.0 h following administration of Eriocitrin. In urine for 24 h, both nonconjugates and conjugates of these metabolites were detected. 3,4-Dihydroxyhydrocinnamic acid, which is metabolized from eriodictyol by intestinal bacteria, was detected in slight amounts with each form in 4.0-h plasma and 24-h urine. Eriocitrin was suggested to be metabolized by intestinal bacteria, and then eriodictyol and 3,4-dihydroxyhydrocinnamic of its metabolite were absorbed. Following administration of Eriocitrin, plasma exhibited an elevated resistance effect to lipid peroxidation. Eriocitrin metabolites functioning as antioxidant agents are discussed.

Description

Eriocitrin is a flavonoid isolated from lemon, which is a strong antioxidant agent. Eriocitrin could inhibit the proliferation of hepatocellular carcinoma cell lines by arresting cell cycle in S phase through up-regulation of p53, cyclin A, cyclin D3 and CDK6. Eriocitrin triggers apoptosis by activating mitochondria-involved intrinsic signaling pathway.

Keywords:

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