Neohesperidin | CAS#13241-33-3 | flavonoid

MedKoo Cat#: 330110 | Name: Neohesperidin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Neohesperidin is a flavonoid found in citrus fruit peel that has diverse biological activities. Neohesperidin Exerts Lipid-Regulating Effects in vitro and in vivo via Fibroblast Growth Factor 21 and AMP-Activated Protein Kinase/Sirtuin Type 1/Peroxisome Proliferator-Activated Receptor Gamma Coactivator 1α Signaling Axis. Neohesperidin suppresses osteoclast differentiation, bone resorption and ovariectomised-induced osteoporosis in mice.

Chemical Structure

Neohesperidin

CAS#13241-33-3

Theoretical Analysis

MedKoo Cat#: 330110

Name: Neohesperidin

CAS#: 13241-33-3

Chemical Formula: C28H34O15

Exact Mass: 610.1898

Molecular Weight: 610.57

Elemental Analysis: C, 55.08; H, 5.61; O, 39.31

Price and Availability

Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 550.00	2 Weeks

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Synonym

Neohesperidin; Hesperetin 7-O-neohesperidoside; Hesperetin 7-neohesperidoside; NSC 31048; NSC31048; NSC-31048;

IUPAC/Chemical Name

(S)-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-(3-hydroxy-4-methoxyphenyl)chroman-4-one

InChi Key

ARGKVCXINMKCAZ-UZRWAPQLSA-N

InChi Code

InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1

SMILES Code

O=C1C2=C(O)C=C(O[C@H]3[C@H](O[C@@]4([H])[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)[C@@H](O)[C@H](O)[C@@H](CO)O3)C=C2O[C@H](C5=CC=C(OC)C(O)=C5)C1

Appearance

Solid powder

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

>2 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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C20M02C18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

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

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
Solubility
	DMSO	5.0	8.20

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 610.57 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:

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: Du L, Jiang Z, Xu L, Zhou N, Shen J, Dong Z, Shen L, Wang H, Luo X. Microfluidic reactor for lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives and their antimicrobial activity research. Carbohydr Res. 2018 Jan 2;455:32-38. doi: 10.1016/j.carres.2017.11.008. Epub 2017 Nov 21. PubMed PMID: 29161612. 2: Wu H, Liu Y, Chen X, Zhu D, Ma J, Yan Y, Si M, Li X, Sun C, Yang B, He Q, Chen K. Neohesperidin Exerts Lipid-Regulating Effects in vitro and in vivo via Fibroblast Growth Factor 21 and AMP-Activated Protein Kinase/Sirtuin Type 1/Peroxisome Proliferator-Activated Receptor Gamma Coactivator 1α Signaling Axis. Pharmacology. 2017;100(3-4):115-126. doi: 10.1159/000452492. Epub 2017 May 30. PubMed PMID: 28554169. 3: Tan Z, Cheng J, Liu Q, Zhou L, Kenny J, Wang T, Lin X, Yuan J, Quinn JMW, Tickner J, Hong G, Qin A, Zhao J, Xu J. Neohesperidin suppresses osteoclast differentiation, bone resorption and ovariectomised-induced osteoporosis in mice. Mol Cell Endocrinol. 2017 Jan 5;439:369-378. doi: 10.1016/j.mce.2016.09.026. Epub 2016 Sep 21. PubMed PMID: 27664516. 4: Xia X, Fu J, Song X, Shi Q, Su C, Song E, Song Y. Neohesperidin dihydrochalcone down-regulates MyD88-dependent and -independent signaling by inhibiting endotoxin-induced trafficking of TLR4 to lipid rafts. Free Radic Biol Med. 2015 Dec;89:522-32. doi: 10.1016/j.freeradbiomed.2015.08.023. Epub 2015 Oct 8. PubMed PMID: 26453923. 5: Shi Q, Song X, Fu J, Su C, Xia X, Song E, Song Y. 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):722-729. doi: 10.1016/j.intimp.2015.09.003. Epub 2015 Sep 9. PubMed PMID: 26362205. 6: Su C, Xia X, Shi Q, Song X, Fu J, Xiao C, Chen H, Lu B, Sun Z, Wu S, Yang S, Li X, Ye X, Song E, Song Y. Neohesperidin Dihydrochalcone versus CCl₄-Induced Hepatic Injury through Different Mechanisms: The Implication of Free Radical Scavenging and Nrf2 Activation. J Agric Food Chem. 2015 Jun 10;63(22):5468-75. doi: 10.1021/acs.jafc.5b01750. Epub 2015 May 28. PubMed PMID: 25978654. 7: Ho SL, Poon CY, Lin C, Yan T, Kwong DW, Yung KK, Wong MS, Bian Z, Li HW. Inhibition of β-amyloid Aggregation By Albiflorin, Aloeemodin And Neohesperidin And Their Neuroprotective Effect On Primary Hippocampal Cells Against β-amyloid Induced Toxicity. Curr Alzheimer Res. 2015;12(5):424-33. PubMed PMID: 25938872. 8: Kashani-Amin E, Ebrahim-Habibi A, Larijani B, Moosavi-Movahedi AA. Effect of neohesperidin dihydrochalcone on the activity and stability of alpha-amylase: a comparative study on bacterial, fungal, and mammalian enzymes. J Mol Recognit. 2015 Oct;28(10):605-13. doi: 10.1002/jmr.2473. Epub 2015 Mar 25. PubMed PMID: 25808616. 9: 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. PubMed PMID: 25620042. 10: Gong N, Zhang B, Yang D, Gao Z, Du G, Lu Y. Development of new reference material neohesperidin for quality control of dietary supplements. J Sci Food Agric. 2015 Jul;95(9):1885-91. doi: 10.1002/jsfa.6893. Epub 2014 Oct 6. PubMed PMID: 25170574. 11: Hamdan DI, Mahmoud MF, Wink M, El-Shazly AM. Effect of hesperidin and neohesperidin from bittersweet orange (Citrus aurantium var. bigaradia) peel on indomethacin-induced peptic ulcers in rats. Environ Toxicol Pharmacol. 2014 May;37(3):907-15. doi: 10.1016/j.etap.2014.03.006. Epub 2014 Mar 15. PubMed PMID: 24691249. 12: Hu L, Li L, Xu D, Xia X, Pi R, Xu D, Wang W, Du H, Song E, Song Y. Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro. Chem Biol Interact. 2014 Apr 25;213:51-9. doi: 10.1016/j.cbi.2014.02.003. Epub 2014 Feb 14. PubMed PMID: 24530446. 13: Wang X, Pan Y, Jianshe M, Shi S, Zheng X, Xiang Z. Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, bioavailability and tissue distribution of neohesperidin dihydrochalcone in rats. Xenobiotica. 2014 Jun;44(6):555-61. doi: 10.3109/00498254.2013.861950. Epub 2013 Nov 25. PubMed PMID: 24274324. 14: Wang JJ, Cui P. Neohesperidin attenuates cerebral ischemia-reperfusion injury via inhibiting the apoptotic pathway and activating the Akt/Nrf2/HO-1 pathway. J Asian Nat Prod Res. 2013 Sep;15(9):1023-37. doi: 10.1080/10286020.2013.827176. Epub 2013 Aug 16. PubMed PMID: 23952707. 15: Kashani-Amin E, Larijani B, Ebrahim-Habibi A. 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. doi: 10.1016/j.febslet.2013.01.022. Epub 2013 Feb 1. PubMed PMID: 23376024. 16: 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. PubMed PMID: 23285810. 17: Zhang J, Sun C, Yan Y, Chen Q, Luo F, Zhu X, Li X, Chen K. Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells. Food Chem. 2012 Dec 1;135(3):1471-8. doi: 10.1016/j.foodchem.2012.06.004. Epub 2012 Jun 13. PubMed PMID: 22953882. 18: Zhang J, Zhu X, Luo F, Sun C, Huang J, Li X, Chen K. Separation and purification of neohesperidin from the albedo of Citrus reticulata cv. Suavissima by combination of macroporous resin and high-speed counter-current chromatography. J Sep Sci. 2012 Jan;35(1):128-36. doi: 10.1002/jssc.201100695. Epub 2011 Nov 21. PubMed PMID: 22102373. 19: Tong L, Zhou D, Gao J, Zhu Y, Sun H, Bi K. Simultaneous determination of naringin, hesperidin, neohesperidin, naringenin and hesperetin of Fractus aurantii extract in rat plasma by liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal. 2012 Jan 25;58:58-64. doi: 10.1016/j.jpba.2011.05.001. Epub 2011 May 11. PubMed PMID: 22018980. 20: Lee JH, Lee SH, Kim YS, Jeong CS. 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. doi: 10.1002/ptr.2840. PubMed PMID: 19367677.