(E)-Naringenin chalcone

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(E)-Naringenin chalcone is an orally active anti-allergic agent. (E)-Naringenin chalcone also has antioxidant, anti-inflammatory activities. (E)-Naringenin chalcone can improve adipocyte functions. (E)-Naringenin chalcone inhibits histamine release from rat peritoneal mast cell.

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(E)-Naringenin chalcone Chemical Structure

CAS No. : 25515-46-2

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Other Forms of (E)-Naringenin chalcone:

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Biological Activity
Purity & Documentation
References
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Description

Cellular Effect

Cell Line	Type	Value	Description	References
MCF7	IC₅₀	> 10 μM Compound: 2b	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 26690274]
MDA-MB-231	IC₅₀	> 10 μM Compound: 2b	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by MTT assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by MTT assay	[PMID: 26690274]

In Vitro

(E)-Naringenin chalcone (25-125 μg/mL, 10 min) inhibits histamine release from rat peritoneal mast cells, with an IC₅₀ value of 68 μg/mL^[1].
(E)-Naringenin chalcone (25-50 μM, 8 days) improves adipocyte (3T3-L1) functions by enhancing adiponectin production^[2].
(E)-Naringenin chalcone (25-100 μM, 24 h) stimulates the activity of PPARγ in NIH-3T3 cells^[2].
(E)-Naringenin chalcone (0-200 μM 24 h) inhibits the production of TNF-alpha, MCP-1, and nitric oxide (NO) by LPS-stimulated RAW 264 macrophages^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

RT-PCR^[2]

Cell Line:	3T3-L1 adipocytes
Concentration:	25-100 μM
Incubation Time:	8 days
Result:	Increased adiponectin mRNA levels up to 8.0-fold in a dose-dependent manner.

Western Blot Analysis^[4]

Cell Line:	RAW 264 macrophages
Concentration:	0,25, 50, 100, 200 μM
Incubation Time:	24 h
Result:	Suppressed the degradation of IκB-α.

In Vivo

(E)-Naringenin chalcone (0.8 mg/kg, oral administration) shows anti-allergic effect in type I allergic mice^[1].
(E)-Naringenin chalcone (0.8 mg/kg, oral administration) suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells in allergic airway inflammatory mice^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Mouse type I allergic model^[1]
Dosage:	0.8 mg/kg
Administration:	Oral administration
Result:	Inhibited the ear-swelling response, with the inhibitory ratio of 46.7%.

Animal Model:	Allergic airway inflammation induced in mice^[3]
Dosage:	0.8 mg/kg
Administration:	Oral administration, daily
Result:	Decreased cell numbers of the infiltrating leukocyte and eosinophils. Decreased Muc5ac and gob-5 expression in the lungs.

Molecular Weight

272.26

Formula

C₁₅H₁₂O₅

CAS No.

25515-46-2

SMILES

OC(C=C1)=CC=C1/C=C/C(C2=C(C=C(O)C=C2O)O)=O

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Taichi Yamamoto, et al. Anti-allergic activity of naringenin chalcone from a tomato skin extract. Biosci Biotechnol Biochem. 2004 Aug;68(8):1706-11. [Content Brief]

[2]. Taro Horiba, et al. Naringenin chalcone improves adipocyte functions by enhancing adiponectin production. Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14. [Content Brief]

[3]. Chiaki Iwamura, et al. Naringenin chalcone suppresses allergic asthma by inhibiting the type-2 function of CD4 T cells. Allergol Int. 2010 Mar;59(1):67-73. [Content Brief]

[4]. Shizuka Hirai, et al. Inhibitory effect of naringenin chalcone on inflammatory changes in the interaction between adipocytes and macrophages. Life Sci. 2007 Sep 29;81(16):1272-9. [Content Brief]