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Cytotoxic limonoids from Trichilia americana leaves
Twelve cedrelone limonoids, two previously known, were isolated and characterized from Trichilia americana leaves. Eight of the isolated limonoids displayed potent cytotoxicity against five tumour cell lines. [Display omitted] •Twelve cedrelone limonoids, two known, were isolated from Trichilia amer...
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Published in: | Phytochemistry (Oxford) 2015-10, Vol.118, p.61-67 |
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Main Authors: | , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | Twelve cedrelone limonoids, two previously known, were isolated and characterized from Trichilia americana leaves. Eight of the isolated limonoids displayed potent cytotoxicity against five tumour cell lines. [Display omitted]
•Twelve cedrelone limonoids, two known, were isolated from Trichilia americana.•The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction.•Cytotoxicity against five human tumour cell lines was assessed by MTS assay.•The two previously known limonoids showed significant cytotoxicity (IC50⩽0.5μM).
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 0.5μM, and compounds 5, 6, 7, 8, 9, and 10 exhibited potent or selective cytotoxic activity with IC50 values ranging from 1.0 to 39.6μM. |
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ISSN: | 0031-9422 1873-3700 |
DOI: | 10.1016/j.phytochem.2015.08.014 |