Cytotoxic limonoids from Trichilia americana leaves.
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.
Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
Kai-Long
KL
Ji
Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303, People's Republic of China.
Ping
P
Zhang
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
Xiao-Nian
XN
Li
Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303, People's Republic of China.
Juan
J
Guo
Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303, People's Republic of China.
Hua-Bin
HB
Hu
Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303, People's Republic of China.
Chun-Fen
CF
Xiao
Department of Pharmaceutical Sciences, Computational Chemical Genomics Screening Center, School of Pharmacy and Drug Discovery Institute, University of Pittsburgh, Pittsburgh, PA 15261, USA.
Xiang-Qun
XQ
Xie
Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303, People's Republic of China. Electronic address: xyk@xtbg.org.cn.
You-Kai
YK
Xu
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029582:Meliaceae / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D036701:Limonins; C414666:cedrelone
Cedrelone limonoids; Cytotoxicity; Meliaceae; Trichilia americana