Cytotoxic limonoids from Trichilia americana leaves

Phytochemistry
Kai-Long JiYou-Kai Xu

Abstract

Ten cedrelone limonoids were isolated from the leaves of Trichilia americana. These compounds include americanolides A-D (1-4), 1,2-dihydrodeacetylhirtin (5), 1α-hydroxy-1,2-dihydrodeacetylhirtin (6), 1α-hydroxy-1,2-dihydrohirtin (7), 1α-methoxy-1,2-dihydrodeacetylhirtin (8), 11β-hydroxy-12α-propanoyloxycedrelone (9), and 1α,11β-dihydroxy-1,2-dihydrocedrelone (10), as well as two previously reported compounds, deacetylhirtin (11) and hirtin (12). Their structures were characterized on the basis of spectroscopic studies, and the assignment of the absolute configuration of americanolide A (1) was supported by single-crystal X-ray diffraction studies. The cytotoxic activities of all isolated compounds were also evaluated against five human tumour cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) using an MTS assay. Compounds 11 and 12 showed significant cytotoxicity with IC50 values ranging from 0.1 to 0.5 μM, and compounds 5, 6, 7, 8, 9, and 10 exhibited potent or selective cytotoxic activity with IC50 values ranging from 1.0 to 39.6 μM.

References

Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Feb 1, 2008·Journal of Applied Crystallography·Rob W W HooftAnthony L Spek
Jan 28, 2011·Journal of Natural Products·Qiang ZhangXiao-Jiang Hao
Sep 8, 2011·Chemical Reviews·Qin-Gang Tan, Xiao-Dong Luo
Oct 8, 2013·Journal of Natural Products·Jin-Biao XuJian-Min Yue
Mar 13, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kai-Long JiYou-Kai Xu
Jul 31, 2014·Journal of Natural Products·Kai-Long JiYou-Kai Xu

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Citations

Oct 19, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nicholas A Eddy, Pranjali Ichalkaranje
Jul 19, 2019·Natural Product Research·Kai-Long JiYou-Kai Xu
Feb 15, 2020·Natural Product Reports·Robert A Hill, Joseph D Connolly
Apr 5, 2018·Frontiers in Chemistry·Haishan LiuWeiming Zhu
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ivan LimachiOlov Sterner
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mariela Gonzalez-RamirezOlov Sterner

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