Cytotoxic limonoids from Trichilia americana leaves

• Published in: Phytochemistry (Oxford) Vol. 118; pp. 61 - 67
• Main Authors: Ji, Kai-Long, Zhang, Ping, Li, Xiao-Nian, Guo, Juan, Hu, Hua-Bin, Xiao, Chun-Fen, Xie, Xiang-Qun, Xu, You-Kai
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.10.2015; Elsevier
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biochemistry & Molecular Biology; Cedrelone limonoids; Crystallography, X-Ray; Cytotoxicity; Drug Screening Assays, Antitumor; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; Limonins - chemistry; Limonins - isolation & purification; Limonins - pharmacology; Meliaceae; Meliaceae - chemistry; Molecular Conformation; Molecular Structure; Plant Leaves - chemistry; Plant Sciences; Science & Technology; Trichilia americana; Cytotoxicity; Cedrelone limonoids; Meliaceae; Trichilia americana; TETRANORTRITERPENOIDS; NITRIC-OXIDE PRODUCTION; CONNAROIDES; ANTIFEEDANT; EXTRACT
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2015.08.014

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.