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Int. J. Mol. Sci. 2016, 17(4), 591; doi:10.3390/ijms17040591

Hepatoprotective Limonoids from Andiroba (Carapa guianensis)

Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan
Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan
Laboratory of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
Authors to whom correspondence should be addressed.
Academic Editor: Maurizio Battino
Received: 15 January 2016 / Revised: 9 April 2016 / Accepted: 14 April 2016 / Published: 19 April 2016
(This article belongs to the Section Bioactives and Nutraceuticals)
View Full-Text   |   Download PDF [489 KB, uploaded 21 April 2016]   |  


Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 13 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (117) isolated from the seed and/or flower oils of C. guianensis were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of 13 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-α; however, these compounds did not decrease the cytotoxicity caused by d-GalN. In addition, the structural requirements of limonoids (117) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated. View Full-Text
Keywords: hepatoprotective effect; limonoid; andiroba; Carapa guianensis; Meliaceae; structural requirement hepatoprotective effect; limonoid; andiroba; Carapa guianensis; Meliaceae; structural requirement

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Ninomiya, K.; Miyazawa, S.; Ozeki, K.; Matsuo, N.; Muraoka, O.; Kikuchi, T.; Yamada, T.; Tanaka, R.; Morikawa, T. Hepatoprotective Limonoids from Andiroba (Carapa guianensis). Int. J. Mol. Sci. 2016, 17, 591.

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