Rhoifolin

Names

[ Name ]:
Rhoifolin

[Synonym ]:
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-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxyméthyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}tétrahydro-2H-pyran-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphényl)-4H-chromén-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-α-L-mannopyranosyl)-β-D-glucopyranosyl]-oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl-2-O-(6-deoxy-α-L-mannopyranosyl)-β-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-α-L-mannopyranosyl)-β-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-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-

Biological Activity

[Description]:

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-β and glucose transporter 4 (GLUT 4) translocation[1]. Rhoifolin ameliorates titanium particle-stimulated osteolysis and attenuates osteoclastogenesis via RANKL-induced NF-κB and MAPK pathways[2].

[Related Catalog]:

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Metabolic Disease

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> Insulin Receptor

[Target]

NF-κB

insulin receptor-β

MAPK

[References]

[1]. Rao YK, et al. 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. Evid Based Complement Alternat Med. 2011;2011:624375.

[2]. Liao S, et al. Rhoifolin ameliorates titanium particle-stimulated osteolysis and attenuates osteoclastogenesis via RANKL-induced NF-κB and MAPK pathways. J Cell Physiol. 2019 Aug;234(10):17600-17611.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
916.5±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₃₀O₁₄

[ Molecular Weight ]:
578.519

[ Flash Point ]:
305.4±27.8 °C

[ Exact Mass ]:
578.163574

[ PSA ]:
228.97000

[ LogP ]:
1.72

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.726

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Articles

Study on impurities in naringin extracted from Citrus grandis 'tomentosa'.

Zhong Yao Cai 35(1) , 56-61, (2012)

To investigate the impurities in naringin extracted from Citrus grandis 'Tomentosa'.High performance liquid chromatographies coupled with photodiode array and electrospray ionization mass spectrometry...

Determination of rhoifolin and daidzin in human plasma by high-performance liquid chromatography.

J. Chromatogr. B, Biomed. Appl. 655(2) , 300-4, (1994)

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 c...

[Studies on antibacterial constituents of Discocleidion rufescens (2)].

Zhongguo Zhong Yao Za Zhi 34 , 1377-1380, (2009)

To screen effective constituents of Discocleidion rufescens against bacteria.Compounds were isolated by bioassay-guided fractionation method with various chromatographic methods and their structures w...