Neohesperidin

Names

[ Name ]:
Neohesperidin

[Synonym ]:
HESPERETIN-7-NEOHESPERIDOSIDE
Hesperetin7-neohesperidoside
4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
(2S)-5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
hesperetin 7-O-neohesperoside
Neohesperidin
Neohesperdin
MFCD00017357
Hesperetin-7-O-neohesperidoside
EINECS 236-216-9
(S)-4'-Methoxy-3',5,7-trihydroxyflavanone-7-[2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside]
4H-1-Benzopyran-4-one, 2,3-dihydro-7-((2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
Hesperetin 7-O-neohesperidoside

Biological Activity

[Description]:

Neohesperidin is a flavonoid compound found in high amounts in Poncirus trifoliata with anti-oxidant and anti-inflammatory effects.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Natural Products >> Flavonoids

[In Vitro]

Neohesperidin induces cell apoptosis in human breast adenocarcinoma MDA-MB-231 cells. The IC50 values of neohesperidin at 24 and 48 h are 47.4±2.6 μM and 32.5±1.8 μM, respectively. The expressions of P53 and Bax in the neohesperidin-treated cells are significantly up-regulated, while that of Bcl-2 is down-regulated[1]. Neohesperidin exhibits antioxidant activity (IC50=22.31 μg/mL) in the DPPH radical-scavenging assay[2].

[In Vivo]

Neohesperidin (50 mg/kg) significantly inhibits 55.0% of HCl/ethanol-induced gastric lesions. In pylorus ligated rats, neohesperidin (50 mg/kg) significantly decreases the volume of gastric secretion and gastric acid output, and increases the pH[1]. Treatment of neohesperidin significantly decreases fasting glucose, serum glucose, and glycosylated serum protein (GSP) in mice. It significantly elevates oral glucose tolerance and insulin sensitivity and decreases insulin resistance in the diabetic mice. Neohesperidin significantly decreases serum triglycerides, total cholesterol, leptin level, and liver index in the mice[3].

[Animal admin]

Mice: All the mice are fasted 6 h before the test and then fed with water or neohesperidin by gavage. The mice are intraperitoneally injected with either 2 g/kg BW glucose or 1 IU/kg BW insulin for OGTT and ITT, respectively. Blood samples are collected from the tail vein for the measurement of basal blood glucose levels (0 min) before the injection of glucose or insulin. Additional blood glucose levels are measured at 30, 60, 90 and 120 min[3].

[References]

[1]. Lee JH, et al. Protective effects of neohesperidin and poncirin isolated from the fruits of Poncirus trifoliata on potential gastric disease. Phytother Res. 2009 Dec;23(12):1748-53.

[2]. Xu F, et al. Neohesperidin induces cellular apoptosis in human breast adenocarcinoma MDA-MB-231 cells via activating the Bcl-2/Bax-mediated signaling pathway. Nat Prod Commun. 2012 Nov;7(11):1475-8.

[3]. Jia S, et al. Hypoglycemic and hypolipidemic effects of neohesperidin derived from Citrus aurantium L. in diabetic KK-A(y) mice. Food Funct. 2015 Mar;6(3):878-86.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
933.7±65.0 °C at 760 mmHg

[ Melting Point ]:
239-243ºC

[ Molecular Formula ]:
C₂₈H₃₄O₁₅

[ Molecular Weight ]:
610.561

[ Flash Point ]:
306.7±27.8 °C

[ Exact Mass ]:
610.189758

[ PSA ]:
234.29000

[ LogP ]:
2.44

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

[ Index of Refraction ]:
1.695

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2981400

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 2,3-dihydro-7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)- beta-D- glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyp henyl)-, (S)-

CAS REGISTRY NUMBER :: 13241-33-3

BEILSTEIN REFERENCE NO. :: 0074945

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C28-H34-O15

MOLECULAR WEIGHT :: 610.62

Safety Information

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

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DJ2981400

Precursor & DownStream

Precursor

DownStream

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