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MedKoo Cat#: 471011 | Name: Narirutin
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Description:

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

Narirutin has anti-inflammatory and antidepressant-like activities

Chemical Structure

Narirutin
Narirutin
CAS#14259-46-2

Theoretical Analysis

MedKoo Cat#: 471011

Name: Narirutin

CAS#: 14259-46-2

Chemical Formula: C27H32O14

Exact Mass: 580.1790

Molecular Weight: 580.54

Elemental Analysis: C, 55.86; H, 5.56; O, 38.58

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 2 weeks
25mg USD 750.00 2 weeks
50mg USD 1,250.00 2 weeks
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Related CAS #
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Synonym
Narirutin, Isonaringenin, Isonaringin, Naringenin 7-beta-rutinoside, Naringenin 7-O-rutinoside, (2S)-Narirutin
IUPAC/Chemical Name
(S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
InChi Key
HXTFHSYLYXVTHC-AJHDJQPGSA-N
InChi Code
InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
SMILES Code
C[C@@H]1O[C@H]([C@@H]([C@@H]([C@H]1O)O)O)OC[C@H]2O[C@H]([C@@H]([C@H]([C@@H]2O)O)O)Oc3cc4c(C(C[C@@H](c5ccc(O)cc5)O4)=O)c(O)c3
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
>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
2934.99.03.00
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C20M02C19
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Narirutin is a shikimate kinase inhibitor with anti-tubercular potency.
In vitro activity:
Narirutin suppressed the growth of MDA-MB-231 and MCF-7 in a dose-proportional manner. Unexpectedly, narirutin suppressed the proliferation of normal cells (24.51%) at 100 μM. Further, narirutin inhibits the activity of LOX-5 in cell-free (18.18 ± 3.93 μM) and cell-based (48.13 ± 7.04 μM) test systems while moderately affecting COX-2, CATD, ODC and DHFR activity. Reference: Biochim Biophys Acta Gen Subj. 2023 Mar 1:130340. https://pubmed.ncbi.nlm.nih.gov/36868290/
In vivo activity:
The present study was aimed to investigate whether NR (narirutin) confers an antidepressant-like effect in mice exposed to a chronic mild stress (CMS) model of depression. The results showed that NR treatment for 1 week significantly alleviated the depressive-like behaviours of CMS-exposed mice, as indicated by restored decreased sucrose preference and shortened floating time in the forced swimming test. Moreover, NR treatment significantly blocked the CMS-induced anxiety-like behaviors, including increased time spent in the central zone in the open field test, and shortened the latency to feeding in the novelty suppressed feeding test. Reference: Neuroreport. 2018 Oct 17;29(15):1264-1268. https://pubmed.ncbi.nlm.nih.gov/30028378/
Solvent mg/mL mM
Solubility
DMF 20.0 34.45
DMF:PBS (pH 7.2) (1:1) 0.5 0.86
DMSO 78.3 134.93
Ethanol 1.0 1.72
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 580.54 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.

Recalculate based on batch purity %
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. Singh S, Maurya AK, Meena A, Mishra N, Luqman S. Narirutin downregulates lipoxygenase-5 expression and induces G0/G1 arrest in triple-negative breast carcinoma cells. Biochim Biophys Acta Gen Subj. 2023 Mar 1:130340. doi: 10.1016/j.bbagen.2023.130340. Epub ahead of print. PMID: 36868290. 2. Yang H, Shan Z, Guo W, Wang Y, Cai S, Li F, Huang Q, Liu JA, Cheung CW, Cai S. Reversal of Peripheral Neuropathic Pain by the Small-Molecule Natural Product Narirutin via Block of Nav1.7 Voltage-Gated Sodium Channel. Int J Mol Sci. 2022 Nov 27;23(23):14842. doi: 10.3390/ijms232314842. PMID: 36499167; PMCID: PMC9738487. 3. Li Y, Du Y, Yang J, Xiu Z, Yang N, Zhang J, Gao Y, Li B, Shi H. Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model. Neuroreport. 2018 Oct 17;29(15):1264-1268. doi: 10.1097/WNR.0000000000001102. PMID: 30028378. 4. Funaguchi N, Ohno Y, La BL, Asai T, Yuhgetsu H, Sawada M, Takemura G, Minatoguchi S, Fujiwara T, Fujiwara H. Narirutin inhibits airway inflammation in an allergic mouse model. Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70. doi: 10.1111/j.1440-1681.2007.04636.x. PMID: 17600554.
In vitro protocol:
1. Singh S, Maurya AK, Meena A, Mishra N, Luqman S. Narirutin downregulates lipoxygenase-5 expression and induces G0/G1 arrest in triple-negative breast carcinoma cells. Biochim Biophys Acta Gen Subj. 2023 Mar 1:130340. doi: 10.1016/j.bbagen.2023.130340. Epub ahead of print. PMID: 36868290. 2. Yang H, Shan Z, Guo W, Wang Y, Cai S, Li F, Huang Q, Liu JA, Cheung CW, Cai S. Reversal of Peripheral Neuropathic Pain by the Small-Molecule Natural Product Narirutin via Block of Nav1.7 Voltage-Gated Sodium Channel. Int J Mol Sci. 2022 Nov 27;23(23):14842. doi: 10.3390/ijms232314842. PMID: 36499167; PMCID: PMC9738487.
In vivo protocol:
1. Li Y, Du Y, Yang J, Xiu Z, Yang N, Zhang J, Gao Y, Li B, Shi H. Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model. Neuroreport. 2018 Oct 17;29(15):1264-1268. doi: 10.1097/WNR.0000000000001102. PMID: 30028378. 2. Funaguchi N, Ohno Y, La BL, Asai T, Yuhgetsu H, Sawada M, Takemura G, Minatoguchi S, Fujiwara T, Fujiwara H. Narirutin inhibits airway inflammation in an allergic mouse model. Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70. doi: 10.1111/j.1440-1681.2007.04636.x. PMID: 17600554.
1: Li Y, Du Y, Yang J, Xiu Z, Yang N, Zhang J, Gao Y, Li B, Shi H. Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model. Neuroreport. 2018 Jul 18. doi: 10.1097/WNR.0000000000001102. [Epub ahead of print] PubMed PMID: 30028378. 2: Chakraborty S, Basu S. Multi-functional activities of citrus flavonoid narirutin in Alzheimer's disease therapeutics: An integrated screening approach and in vitro validation. Int J Biol Macromol. 2017 Oct;103:733-743. doi: 10.1016/j.ijbiomac.2017.05.110. Epub 2017 May 19. PubMed PMID: 28528948. 3: Liu LN, Wang Y, Jin HY, Ma SC, Liu JP. Application of immunoaffinity purification technology as the pretreatment technology for traditional Chinese medicine: Its application to analysis of hesperidin and narirutin in traditional Chinese medicine preparations containing Citri reticulatae Pericarpium. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 15;1021:122-128. doi: 10.1016/j.jchromb.2015.10.005. Epub 2015 Oct 22. PubMed PMID: 26526495. 4: Park HY, Ha SK, Eom H, Choi I. Narirutin fraction from citrus peels attenuates alcoholic liver disease in mice. Food Chem Toxicol. 2013 May;55:637-44. doi: 10.1016/j.fct.2013.01.060. Epub 2013 Feb 13. PubMed PMID: 23416143. 5: Ha SK, Park HY, Eom H, Kim Y, Choi I. Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation. Food Chem Toxicol. 2012 Oct;50(10):3498-504. doi: 10.1016/j.fct.2012.07.007. Epub 2012 Jul 17. PubMed PMID: 22813871. 6: Lee S, Khoo CS, Pearson JL, Hennell JR, Bensoussan A. Liquid chromatographic determination of narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the raw herb and of the dried aqueous extract. J AOAC Int. 2009 May-Jun;92(3):789-96. PubMed PMID: 19610369. 7: Funaguchi N, Ohno Y, La BL, Asai T, Yuhgetsu H, Sawada M, Takemura G, Minatoguchi S, Fujiwara T, Fujiwara H. Narirutin inhibits airway inflammation in an allergic mouse model. Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70. PubMed PMID: 17600554. 8: Zhang J, Brodbelt JS. Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst. 2004 Dec;129(12):1227-33. Epub 2004 Oct 26. PubMed PMID: 15565223. 9: Manach C, Morand C, Gil-Izquierdo A, Bouteloup-Demange C, Rémésy C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr. 2003 Feb;57(2):235-42. PubMed PMID: 12571654. 10: Puig DG, Pérez ML, Fuster MD, Ortuño A, Sabater F, Porras I, Lidón AG, Del Río JA. Effect of ethylene on naringin, narirutin and nootkatone accumulation in grapefruit. Planta Med. 1995 Jun;61(3):283-5. PubMed PMID: 17238080.

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TASP0434299

TASP0434299