Synonym
Neohesperidin dihydrochalcone, NHDC
IUPAC/Chemical Name
1-(4-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
InChi Key
ITVGXXMINPYUHD-JKDQZHIOSA-N
InChi Code
InChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27?,28+/m0/s1
SMILES Code
COC1=C(O)C=C(CCC(C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)C=C2O)=O)C=C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Neohesperidin dihydrochalcone (NHDC) is a semisynthetic glycoside chalcone, an artificial sweetener, and a derivative of neohesperidin.
In vitro activity:
Neohesperidin induces cell apoptosis in human breast adenocarcinoma MDA-MB-231 cells, which was possibly mediated by regulating the P53/Bcl-2/Bax pathway. MDA-MB-231 cells were subjected to treatment with neohesperidin. MTT and Trypan blue exclusion assays were applied to assess the cell viability. The morphological changes of cells were observed using an inverted microscope, and cell apoptosis was detected by flow cytometric analysis. Immunoblot analysis was conducted to evaluate the protein expressions of apoptosis-related genes, including P53, Bcl-2 and Bax. The results indicated that the proliferation of MDA-MB-231 cells was inhibited by the treatment with neohesperidin in a time- and dose-dependent manner. The IC50 values of neohesperidin at 24 and 48 h were 47.4 +/- 2.6 microM and 32.5 +/- 1.8 microM, respectively. The expressions of P53 and Bax in the neohesperidin-treated cells were significantly up-regulated, while that of Bcl-2 was down-regulated. Our study suggested that neohesperidin could induce apoptosis of MDA-MB-231 cells, a process which was associated with the activation of the Bcl-2/Bax-mediated signaling pathway.
Reference: Nat Prod Commun. 2012 Nov;7(11):1475-8. https://journals.sagepub.com/doi/pdf/10.1177/1934578X1200701116
In vivo activity:
KK-A(y) mice were used as the diabetic experimental model, whereas C57BL/6 mice were used as normal control for a 6-week study. Treatment of neohesperidin (NHP) significantly decreased fasting glucose, serum glucose, and glycosylated serum protein (GSP) in KK-A(y) mice. It significantly elevated oral glucose tolerance and insulin sensitivity and decreased insulin resistance in the diabetic mice. In addition, NHP significantly decreased serum triglycerides (TG), total cholesterol (TCH), leptin level, and liver index in the KK-A(y) mice. NHP also inhibited lipid accumulation in the liver and decreased the size of epididymal adipocyte in the KK-A(y) mice. Gene expression of stearoyl-CoA desaturase 1 (SCD-1) and fatty acid synthase (FAS) were significantly inhibited, whereas the expression of acyl-CoA oxidase (ACOX) was significantly induced by NHP treatment in the liver of KK-A(y) mice. In addition, elevated level of phosphorylation of hepatic AMPK was observed in NHP-treated mice. Therefore, the activation of the AMPK pathway and regulation of its target genes, including SCD-1, FAS, and ACOX, may play important roles in the hypoglycemic and hypolipidemic effects of NHP in vivo, and NHP may have great potential in the prevention of diabetes and its complications.
Reference: Food Funct. 2015 Mar;6(3):878-86. https://doi.org/10.1039/c4fo00993b
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
75.0 |
122.43 |
|
| Ethanol |
25.0 |
40.81 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
612.58
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Xu F, Zang J, Chen D, Zhang T, Zhan H, Lu M, Zhuge H. 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. PMID: 23285810.
2. Zhao T, Hu S, Ma P, Che D, Liu R, Zhang Y, Wang J, Li C, Ding Y, Fu J, An H, Gao Z, Zhang T. Neohesperidin suppresses IgE-mediated anaphylactic reactions and mast cell activation via Lyn-PLC-Ca2+ pathway. Phytother Res. 2019 Aug;33(8):2034-2043. doi: 10.1002/ptr.6385. Epub 2019 Jun 14. PMID: 31197891.
3. Jia S, Hu Y, Zhang W, Zhao X, Chen Y, Sun C, Li X, Chen K. 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. doi: 10.1039/c4fo00993b. PMID: 25620042.
4. Guo J, Fang Y, Jiang F, Li L, Zhou H, Xu X, Ning W. Neohesperidin inhibits TGF-β1/Smad3 signaling and alleviates bleomycin-induced pulmonary fibrosis in mice. Eur J Pharmacol. 2019 Dec 1;864:172712. doi: 10.1016/j.ejphar.2019.172712. Epub 2019 Oct 2. PMID: 31586469.
In vitro protocol:
1. Xu F, Zang J, Chen D, Zhang T, Zhan H, Lu M, Zhuge H. 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. PMID: 23285810.
2. Zhao T, Hu S, Ma P, Che D, Liu R, Zhang Y, Wang J, Li C, Ding Y, Fu J, An H, Gao Z, Zhang T. Neohesperidin suppresses IgE-mediated anaphylactic reactions and mast cell activation via Lyn-PLC-Ca2+ pathway. Phytother Res. 2019 Aug;33(8):2034-2043. doi: 10.1002/ptr.6385. Epub 2019 Jun 14. PMID: 31197891.
In vivo protocol:
1. Jia S, Hu Y, Zhang W, Zhao X, Chen Y, Sun C, Li X, Chen K. 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. doi: 10.1039/c4fo00993b. PMID: 25620042.
2. Guo J, Fang Y, Jiang F, Li L, Zhou H, Xu X, Ning W. Neohesperidin inhibits TGF-β1/Smad3 signaling and alleviates bleomycin-induced pulmonary fibrosis in mice. Eur J Pharmacol. 2019 Dec 1;864:172712. doi: 10.1016/j.ejphar.2019.172712. Epub 2019 Oct 2. PMID: 31586469.
1. Braune, A., Engst, W., and Blaut, M. Degradation of neohesperidin dihydrochalcone by human intestinal bacteria. J. Agric. Food Chem. 53(5), 1782-1790 (2005).
2. Shi, Q., Song, X., Fu, J., et al. Artificial sweetener neohesperidin dihydrochalcone showed antioxidative, anti-inflammatory and anti-apoptosis effects against paraquat-induced liver injury in mice. Int. Immunopharmacol. 29(2), 722-729 (2015).
3. Su, C., Xia, X., Shi, Q., et al. Neohesperidin dihydrochalcone versus CCl₄-induced hepatic injury through different mechanisms: The implication of free radical scavenging and Nrf2 activation. J. Agric. Food Chem. 63(22), 5468-5475 (2015).
