Neosperidin dihydrochalcone

Names

[ CAS No. ]:
20702-77-6

[ Name ]:
Neosperidin dihydrochalcone

[Synonym ]:
Neosperidin Dihydro halcone
NEOHESPERIDINE DC
Neohesperidine hydrate
3,5-Dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
neohesperidine dihydrochalcone
Neohesperidin Dihydrochalcone Hydrate
EINECS 243-978-6
1-[4-[[2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-1-propanone
Neohesperidin dc
Dihydrohesperetin-7-O-neohesperidoside
E-959
UNII-3X476D83QV
MFCD03840557
Neohesperidin dihydrochalcone
1-Propanone, 1-[4-[[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)-
NEOHESPERIDIN DIHYDROCHALONE
Nhdc
Neohesperidin DHC
Neosperidin dihydrochalcone
FEMA 3811

Biological Activity

[Description]:

Neohesperidin dihydrochalcone is a synthetic glycoside chalcone, is added to various foods and beverages as a low caloric artificial sweetener.

[Related Catalog]:

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> ROS

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[In Vitro]

Neohesperidin dihydrochalcone shows remarkable radical scavenging activity against stable radical and reactive oxygen species (ROS) in concentration dependent manner. Especially, neohesperidin dihydrochalcone is the most potent inhibitor of H2O2 and HOCl. Neohesperidin dihydrochalcone shows HOCl scavenging activity of 93.5% and H2O2 scavenging property of 73.5%. Neohesperidin dihydrochalcone shows extensive inhibitory effect especially on non-radical ROS H2O2 and HOCl with IC50 values of 205.1, 25.5 μM[1]. Neohesperidin dihydrochalcone is found to be an activator of porcine pancreatic alpha-amylase (PPA) with an IC50 of 389 μM[2].

[In Vivo]

Neohesperidin dihydrochalcone administration results in significant reduction in activities of two useful markers of liver damage, AST and ALT. The relative levels of NF-κB, IL-6, IL-1β and TNF-α protein in the liver of PQ-treated mice are inhibited by neohesperidin dihydrochalcone[3]. The embryotoxicity/teratogenicity of neohesperidin dihydrochalcone is examined in Wistar Crl:(WI)WU BR rats. No adverse effects are observed at neohesperidin dihydrochalcone levels of up to 5% of the diet, the highest dose level tested, at which the rats consumed about 3.3 g/kg body weight/day[4].

[Cell Assay]

WST-8 dye is used in the cell viability assay. HIT-T15 and HUVEC cells are grown and maintained in Dulbecco’s modified Eagle’s medium, supplemented with 10% fetal bovine calf serum. 1000 cells in each well are incubated with various concentrations of neohesperidin dihydrochalcone (50, 100, 500 μM, 1 mM) and other compounds. After treating HIT-T15 and HUVEC cells with 500 μM HOCl, WST-8 dye is added to each well, and the absorbance is detected at 420 nm with microplate reader[1].

[Animal admin]

Rats: The embryotoxicity/teratogenicity of neohesperidin dihydrochalcone is examined in Wistar Crl:(WI)WU BR rats. The study is comprised of four groups of 28 mated female rats each, i.e., a control group (0% neohesperidin dihydrochalcone) and three treatment groups (1.25, 2.5, and 5% neohesperidin dihydrochalcone). The general condition and behavior of the animals are observed twice daily. Body weight is determined on days 0, 7, 14, and 21 of gestation. Food consumption is determined during three consecutive periods (days 0-7, 7-14, and 14-21 of gestation)[4]. [3]Mice: Neohesperidin dihydrochalcone is dissolved in a 0.5% CMC vehicle. Mice are randomized into four groups. The control group receives equal volume of vehicles throughout. The PQ group receives saline once daily for 6 consecutive days. One hour after final saline treatment, mice are injected with PQ (75 mg/kg body weight). The neohesperidin dihydrochalcone group receives a daily dose of 200 mg/kg body weight by oral gavage for 6 consecutive days. One hour after final neohesperidin dihydrochalcone treatment, mice are injected with PQ (75 mg/kg body weight)[3].

[References]

[1]. Choi JM, et al. Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acid-induced DNA strand breakage, protein degradation, and cell death. Biol Pharm Bull. 2007 Feb;30(2):324-30.

[2]. Kashani-Amin E, et al. Neohesperidin dihydrochalcone: presentation of a small molecule activator of mammalian alpha-amylase as an allosteric effector. FEBS Lett. 2013 Mar 18;587(6):652-8.

[3]. Shi Q, et al. Artificial sweetener neohesperidin dihydrochalcone showed antioxidative, anti-inflammatory and anti-apoptosis effects against paraquat-induced liver injury in mice. Int Immunopharmacol. 2015 Dec;29(2):722-9.

[4]. Waalkens-Berendsen DH, et al. Embryotoxicity and teratogenicity study with neohesperidin dihydrochalcone in rats. Regul Toxicol Pharmacol. 2004 Aug;40(1):74-9.

[Related Small Molecules]

Entrectinib | Repotrectinib | 3,4-Dimethoxycinnamic acid

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
927.1±65.0 °C at 760 mmHg

[ Melting Point ]:
156-158 °C(lit.)

[ Molecular Formula ]:
C₂₈H₃₆O₁₅

[ Molecular Weight ]:
612.576

[ Flash Point ]:
302.6±27.8 °C

[ Exact Mass ]:
612.205444

[ PSA ]:
245.29000

[ LogP ]:
3.09

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

[ Index of Refraction ]:
1.684

[ Storage condition ]:
−20°C

[ Water Solubility ]:
Insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ5785000

CHEMICAL NAME :: Glucopyranoside, 3,5-dihydroxy-4-(3-hydroxy-4-methoxyhydrocinnamoyl)ph enyl- 2-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-

CAS REGISTRY NUMBER :: 20702-77-6

LAST UPDATED :: 199312

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C28-H36-O15

MOLECULAR WEIGHT :: 612.64

WISWESSER LINE NOTATION :: T6OTJ B1 CQ DQ EQ FO- CT6OTJ BOR CQ EQ DV2R CQ DO1&& DQ EQ F1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 365 mg/kg/13W-C

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 89,69,1981

Safety Information

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

[ Hazard Codes ]:
C

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LZ5785000

[ HS Code ]:
2932999099

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro.

Chem. Biol. Interact. 213 , 51-9, (2014)

The purpose of this study was to investigate the possible hepatoprotective effects of neohesperidin dihydrochalcone (NHDC) on carbon tetrachloride (CCl4)-induced acute oxidative injury in vivo and in ...

Determination of high-intensity sweeteners in river water and wastewater by solid-phase extraction and liquid chromatography-tandem mass spectrometry.

J. Chromatogr. A. 1393 , 106-14, (2015)

High-intensity sweeteners have been suggested as potential organic contaminants due to their widespread use in food, drugs and sanitary products. As a consequence, they are introduced into the environ...

Neohesperidin dihydrochalcone: presentation of a small molecule activator of mammalian alpha-amylase as an allosteric effector.

FEBS Lett. 587(6) , 652-8, (2013)

Flavonoids and their precursor trans-chalcone have been reported as inhibitors of mammalian alpha-amylase. With regard to this background, neohesperidin dihydrochalcone (NHDC) effect was investigated ...