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Rhoifolin

$216

  • Brand : BIOFRON

  • Catalogue Number : BD-D1347

  • Specification : 98%(HPLC)

  • CAS number : 17306-46-6

  • Formula : C27H30O14

  • Molecular Weight : 578.52

  • PUBCHEM ID : 5282150

  • Volume : 20mg

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Catalogue Number

BD-D1347

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8?

Molecular Weight

578.52

Appearance

Yellow crystalline powder

Botanical Source

Chorisia spp., Citrus aurantium (Seville orange), Rhus succedanea and many other plant spp.

Structure Type

Flavones/Flavanones

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

Synonyms

Apigenin-7-O-neohesperidoside/Apigenin-7-neohesperidoside/RHOIFOLOSIDE/7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-on 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-?-L-mannopyranosyl)-?-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-/7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one/Apigenin 7-O-neo-hesperidoside/5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside/4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-?-L-mannopyranosyl)-?-D-glucopyranosyl]-oxy]-5-hydroxy-2-(4-hydroxyphenyl)-/5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl-2-O-(6-deoxy-?-L-mannopyranosyl)-?-D-glucopyranoside/apigenin 7-O-neohesperidoside/Rhoifolin/Apigenin-7-rhamnoglucoside/5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-(6-deoxy-?-L-mannopyranosyl)-?-D-glucopyranoside/7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-?-L-mannopyranosyl)-?-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-

IUPAC Name

7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

Applications

Rhoifolin is a flavone glycoside isolated from Citrus grandis (L.) Osbeck leaves. Rhoifolin is beneficial for diabetic complications through enhanced adiponectin secretion, tyrosine phosphorylation of insulin receptor-? and glucose transporter 4 (GLUT 4) translocation[1]. Rhoifolin ameliorates titanium particle-stimulated osteolysis and attenuates osteoclastogenesis via RANKL-induced NF-?B and MAPK pathways[2].

Density

1.7±0.1 g/cm3

Solubility

Flash Point

305.4±27.8 °C

Boiling Point

916.5±65.0 °C at 760 mmHg

Melting Point

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#:17306-46-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30854667

Abstract

Prosthesis loosening is a highly troublesome clinical problem following total joint arthroplasty. Wear-particle-induced osteoclastogenesis has been shown to be the primary cause of periprosthetic osteolysis that eventually leads to aseptic prosthesis loosening. Therefore, inhibiting osteoclastogenesis is a promising strategy to control periprosthetic osteolysis. The possible mechanism of action of rhoifolin on osteoclastogenesis and titanium particle-induced calvarial osteolysis was examined in this study. The in vitro study showed that rhoifolin could strongly suppress the receptor activators of nuclear factor-?B (NF-?B) ligand-stimulated osteoclastogenesis, hydroxyapatite resorption, F-actin formation, and the gene expression of osteoclast-related genes. Western blot analysis illustrated that rhoifolin could attenuate the NF-?B and mitogen-activated protein kinase pathways, and the expression of transcriptional factors nuclear factor of activated T cells 1 (NFATc1) and c-Fos. Further studies indicated that rhoifolin inhibited p65 translocation to the nucleus and the activity of NFATc1 and NF-?B rhoifolin could decrease the number of tartrate-resistant acid phosphate-positive osteoclasts and titanium particle-induced C57 mouse calvarial bone loss in vivo. In conclusion, our results suggest that rhoifolin can ameliorate the osteoclasts-stimulated osteolysis, and may be a potential agent for the treatment of prosthesis loosening.

KEYWORDS

RANKL; osteoclast; rhoifolin; titanium particle

Title

Rhoifolin Ameliorates Titanium Particle-Stimulated Osteolysis and Attenuates Osteoclastogenesis via RANKL-induced NF-?B and MAPK Pathways

Author

Shijie Liao 1 2 , Fangmin Song 2 3 , Wenyu Feng 1 2 , Xiaofei Ding 1 2 , Jun Yao 1 2 , Huijie Song 4 , Yun Liu 1 , Shiting Ma 1 , Ziyi Wang 3 , Xixi Lin 2 , Jiake Xu 2 3 , Jinmin Zhao 1 2 , Qian Liu 1 2

Publish date

2019 Aug 17

PMID

8081478

Abstract

A method for determining flavonoids in human plasma is presented for application to pharmacokinetic studies of two flavonoids, rhoifolin and daidzin. Isocratic reversed-phase high-performance liquid chromatography (HPLC) was used with genistin as an internal standard and solid-phase extraction using a Sep-Pak C18 cartridge. The mobile phases were acetonitrile-0.1 M ammonium acetate solution (20:80, v/v) for rhoifolin and methanol-0.1 M ammonium acetate solution (33:67, v/v) for daidzin. The detection limits on-column were 2 ng for rhoifolin and 0.5 ng for daidzin.

KEYWORDS

RANKL; osteoclast; rhoifolin; titanium particle

Title

Determination of Rhoifolin and Daidzin in Human Plasma by High-Performance Liquid Chromatography

Author

K Ishii 1 , S Urano, T Furuta, Y Kasuya

Publish date

1994 May 13

PMID

20008903

Abstract

Citrus grandis (L.) Osbeck (red wendun) leaves have been used in traditional Chinese medicine to treat several illnesses including diabetes. However, there is no scientific evidence supporting these actions and its active compounds. Two flavone glycosides, rhoifolin and cosmosiin were isolated for the first time from red wendun leaves and, identified these leaves are rich source for rhoifolin (1.1%, w/w). In differentiated 3T3-L1 adipocytes, rhoifolin and cosmosiin showed dose-dependent response in concentration range of o.oo1-5 ?M and 1-20 ?M, respectively, in biological studies beneficial to diabetes. Particularly, rhoifolin and cosmosiin at 0.5 and 20 ?M, respectively showed nearly similar response to that 10 nM of insulin, on adiponectin secretion level. Furthermore, 5 ?M of rhoifolin and 20 ?M of cosmosiin showed equal potential with 10 nM of insulin to increase the phosphorylation of insulin receptor-?, in addition to their positive effect on GLUT4 translocation. These findings indicate that rhoifolin and cosmosiin from red wendun leaves may be beneficial for diabetic complications through their enhanced adiponectin secretion, tyrosine phosphorylation of insulin receptor-? and GLUT4 translocation.

Title

Insulin-Mimetic Action of Rhoifolin and Cosmosiin Isolated From Citrus Grandis (L.) Osbeck Leaves: Enhanced Adiponectin Secretion and Insulin Receptor Phosphorylation in 3T3-L1 Cells

Author

Yerra Koteswara Rao 1 , Meng-Jen Lee, Keru Chen, Yi-Ching Lee, Wen-Shi Wu, Yew-Min Tzeng

Publish date

2011