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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.
30854667
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.
RANKL; osteoclast; rhoifolin; titanium particle
Rhoifolin Ameliorates Titanium Particle-Stimulated Osteolysis and Attenuates Osteoclastogenesis via RANKL-induced NF-?B and MAPK Pathways
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
2019 Aug 17
8081478
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.
RANKL; osteoclast; rhoifolin; titanium particle
Determination of Rhoifolin and Daidzin in Human Plasma by High-Performance Liquid Chromatography
K Ishii 1 , S Urano, T Furuta, Y Kasuya
1994 May 13
20008903
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.
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
Yerra Koteswara Rao 1 , Meng-Jen Lee, Keru Chen, Yi-Ching Lee, Wen-Shi Wu, Yew-Min Tzeng
2011
