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Eriocitrin

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-E3011

  • Specification : 95%

  • CAS number : 13463-28-0

  • Formula : C27H32O15

  • Molecular Weight : 596.53

  • PUBCHEM ID : 83489

  • Volume : 100mg

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Catalogue Number

BF-E3011

Analysis Method

HPLC,NMR,MS

Specification

95%

Storage

2-8°C

Molecular Weight

596.53

Appearance

Light yellow powder

Botanical Source

Citrus aurantium,Arachniodes exilis,Citrus changshan-huyou,Citrus limon

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

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

Synonyms

6-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranoside de 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-chromen-7-yle/2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-chromen-7-yl-6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside/Eriodictyol-7-rutinoside/2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside/Eriodictyol 7-O-rutinoside/4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-/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-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-on/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-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-one/2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside/(S)-7-((6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-4H-benzopyran-4-one/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-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-one/(S)-7-((6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-4H-benzopyran-4-one/Eriocitrin

IUPAC 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

Density

1.7±0.1 g/cm3

Solubility

Methanol

Flash Point

317.0±27.8 °C

Boiling Point

956.9±65.0 °C at 760 mmHg

Melting Point

161-190ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:13463-28-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

32191577

Abstract

Eriocitrin (EC) is an abundant flavonoid in lemons, which is known as a strong antioxidant agent. This study investigated the biological and molecular mechanisms underlying the anti-obesity effect of EC in high-fat diet (HFD)-fed obese mice. C57BL/6N mice were fed an HFD (40 kcal% fat) with or without 0.005% (w/w) EC for 16 weeks. Dietary EC improved adiposity by increasing adipocyte fatty acid (FA) oxidation, energy expenditure, and mRNA expression of thermogenesis-related genes in brown adipose tissue (BAT) and skeletal muscle, whereas it also decreased lipogenesis-related gene expression in white adipose tissue. In addition to adiposity, EC prevented hepatic steatosis by diminishing lipogenesis while enhancing FA oxidation in the liver and fecal lipid excretion, which was linked to attenuation of hyperlipidemia. Moreover, EC improved insulin sensitivity by decreasing hepatic gluconeogenesis and proinflammatory responses. These findings indicate that EC may protect against diet-induced adiposity and related metabolic disorders by controlling thermogenesis of BAT and skeletal muscle, FA oxidation, lipogenesis, fecal lipid excretion, glucose utilization, and gluconeogenesis.

KEYWORDS

NAFLD; adiposity; energy expenditure; eriocitrin; fatty acid oxidation; insulin resistance.

Title

Eriocitrin Improves Adiposity and Related Metabolic Disorders in High-Fat Diet-Induced Obese Mice

Author

Eun-Young Kwon 1 2 , Myung-Sook Choi 1 2

Publish date

2020 Mar

PMID

24424211

Abstract

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.

Title

Eriocitrin Ameliorates Diet-Induced Hepatic Steatosis With Activation of Mitochondrial Biogenesis

Author

Masanori Hiramitsu 1 , Yasuhito Shimada 2 , Junya Kuroyanagi 3 , Takashi Inoue 4 , Takao Katagiri 4 , Liqing Zang 5 , Yuhei Nishimura 6 , Norihiro Nishimura 5 , Toshio Tanaka 6

Publish date

2014 Jan 15

PMID

27766389

Abstract

Hepatocellular carcinoma is a lethal cancer with high recurrence ratio and lacks effective therapeutics. In the past few years, it has been reported that increased intake of vegetables and fruits could reduce the cancer incidence, which suggests dietary agents might possess anticancer effects. Eriocitrin is a flavonoid isolated from lemon, which is known as a strong antioxidant agent. We here for the first time demonstrated that 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. Furthermore, we found that eriocitrin could trigger apoptosis by activating mitochondria-involved intrinsic signaling pathway. Thus, eriocitrin might be regarded as a potential chemopreventive natural product to inhibit the early malignant transformation of hepatocellular carcinoma.

KEYWORDS

Apoptosis; Cell cycle arrest; Eriocitrin; Hepatocellular carcinoma.

Title

Eriocitrin From Lemon Suppresses the Proliferation of Human Hepatocellular Carcinoma Cells Through Inducing Apoptosis and Arresting Cell Cycle

Author

Ziyou Wang 1 2 , Hua Zhang 1 2 , Jiahui Zhou 1 2 , Xiangning Zhang 1 2 , Liyong Chen 1 2 , Kangxing Chen 1 2 , Zunnan Huang 3 4

Publish date

2016 Dec


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[1].