Nothofagin

Names

[ Name ]:
Nothofagin

[Synonym ]:
Nothofagin
(1S)-1,5-Anhydro-1-{2,4,6-trihydroxy-3-[3-(4-hydroxyphenyl)propanoyl]phenyl}-D-glucitol
D-Glucitol, 1,5-anhydro-1-C-[2,4,6-trihydroxy-3-[3-(4-hydroxyphenyl)-1-oxopropyl]phenyl]-, (1S)-
1-(3-beta-D-Glucopyranosyl-2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone

Biological Activity

[Description]:

Nothofagin, a dihydrochalcone, is isolated from rooibos (Aspalathus linearis)[1]. Nothofagin downregulates NF-κB translocation through blocking calcium influx. Nothofagin has antioxidant activity and ameliorates various inflammatory responses such as the septic response and vascular inflammation[2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Inflammation/Immunology

[In Vitro]

Nothofagin pre-treatment (0.1, 1, 10 μM) decreases the level of histamine release in RBL-2H3 and RPMCs cells. The production of cytokines are downregulated bynothofagin pre-treatment Nothofagin (TNF-α: 1-10 μM; IL-4: 0.1-10 μM, IL-6: 1-10 μM)[1]. Pre-treatment of DNPHSA-stimulated RBL-2H3 with Nothofagin (10 μM) markedly suppresses the phosphorylation of Lyn, Syk, and Akt[1]. Nothofagin (30 μM; for 6 hours) results in inhibited formation of LPS-induced (100 ng/mL; 4 hours) paracellular gaps with the formation of dense F-actin rings in HUVECs[2]. Nothofagin suppresses IgE-mediated mast cell degranulation both in vitro and in vivo[1].

[In Vivo]

Nothofagin (1 mg/kg; orally; once a day; for 7 days) significantly increases the urinary volume of both normotensive (NTR) and spontaneously hypertensive rats (SHR)[3]. Animal Model: Male Wistar normotensive and spontaneously hypertensive rats (3-4 months old) [3] Dosage: 1 mg/kg Administration: Orally; once a day; for 7 days Result: Significantly increased the urinary volume of both NTR and SHR.

[References]

[1]. Wonhwa Lee, et al. Anti-inflammatory Effects of Aspalathin and Nothofagin From Rooibos (Aspalathus Linearis) In Vitro and In Vivo. Inflammation. 2015 Aug;38(4):1502-16.

[2]. Byeong-Cheol Kang, et al. Nothofagin Suppresses Mast Cell-Mediated Allergic Inflammation. Chem Biol Interact. 2019 Jan 25;298:1-7.

[3]. Camila Leandra Bueno de Almeida, et al. Prolonged Diuretic and Saluretic Effect of Nothofagin Isolated From Leandra Dasytricha (A. Gray) Cogn. Leaves in Normotensive and Hypertensive Rats: Role of Antioxidant System and Renal Protection. Chem Biol Interact. 2018 Jan 5;279:227-233.

Chemical & Physical Properties

[ Density]:
1.594±0.06 g/cm3

[ Boiling Point ]:
711.5±0.0 °C at 760 mmHg

[ Melting Point ]:
92-110 ºC (decomp)

[ Molecular Formula ]:
C₂₁H₂₄O₁₀

[ Molecular Weight ]:
436.409

[ Flash Point ]:
249.4±0.0 °C

[ Exact Mass ]:
436.136932

[ LogP ]:
0.90

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

[ Index of Refraction ]:
1.709

[ Water Solubility ]:
Very slightly soluble (0.92 g/L) (25 ºC)

Related Compounds

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