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Limonin

Limonin is a furanolactone found in fruits in the Citrus family. Limonin exhibits antioxidative, anti-inflammatory, hepatoprotective, anticancer, antiviral, anti-parasitic, and immunomodulatory activities. In animal models of hepatic ischemia/reperfusion, limonin upregulates expression of IL-10 and downregulates expression of toll-like receptors 2 and 4 (TLR2, TLR4), MyD88, TRIF, TNF-α, and NF-κB. In colon adenocarcinoma cells, limonin induces mitochondria-dependent apoptosis and inhibits proliferation. Additionally, limonin inhibits expression of HIV-1 and HTLV-1 in infected cells. This compound also exhibits larvicidal activity against species of Aedes and decreases NF-κB activation and CD4+ T cell stimulation in vitro.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18940312

Cas No.

1180-71-8

Purity

≥98%

Formula

C26H30O8

Formula Wt.

470.52

Chemical Name

8-(3-furyl)decahydro-2,2,4a,8a-tetramethyl-11H,13H- oxireno-[d]pyrano[4,3:3,3a]isobenzofuro[5,4-f][2]- benzopyran-4,6,13-(2H,5aH)-trione

Synonym

Evodine; Limonoic acid di-δ-lactone; limonoic acid 3,19:16,17-dilactone; Citrolimonin

Melting Point

298-300°C

Solubility

Soluble in ethanol, acetic acid, or DMSO. Slightly soluble in water.

Appearance

White Solid

Mahmoud MF, Gamal S, El-Fayoumi HM. Limonin attenuates hepatocellular injury following liver ischemia and reperfusion in rats via toll-like receptor dependent pathway. Eur J Pharmacol. 2014 Oct 5;740:676-82. PMID: 24967531.

Hafeez F, Akram W, Shaalan EA. Mosquito larvicidal activity of citrus limonoids against Aedes albopictus. Parasitol Res. 2011 Jul;109(1):221-9. PMID: 21212981.

Chidambara Murthy KN, Jayaprakasha GK, et al. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. J Agric Food Chem. 2011 Mar 23;59(6):2314-23. PMID: 21338095.

Balestrieri E, Pizzimenti F, Ferlazzo A, et al. Antiviral activity of seed extract from Citrus bergamia towards human retroviruses. Bioorg Med Chem. 2011 Mar 15;19(6):2084-9. PMID: 21334901.

Kim W, Fan YY, Smith R, et al. Dietary curcumin and limonin suppress CD4+ T-cell proliferation and interleukin-2 production in mice. J Nutr. 2009 May;139(5):1042-8. PMID: 19321585.

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