2010Journal of Natural ProductsRequires access

Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica

Jing‐Jy Cheng, Lijie Zhang, Huiling Cheng, Chun‐Tang Chiou, I‐Jung Lee, Yao‐Haur Kuo

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Abstract

Six hexacyclic triterpene acids (1-6), named euscaphic acids A-F, and eight known triterpene acid compounds (7-14) were isolated from an ethanolic extract of twigs of Euscaphis japonica. Compounds 8 and 10 were isolated for the first time from a natural source. Triterpenes 1-6 possess hexacyclic skeletons with a 13α,27-cyclopropane ring. Structural elucidation of compounds 1-6 was established by spectroscopic methods, especially 2D NMR techniques ((1)H-(1)H COSY, HMQC, HMBC, and NOESY). Compounds 3, 4, and 14 showed significant cytotoxicity against different cancer cell lines [IC50 = 2.54 (NCI-H460), 3.61 (MCF-7), and 3.27 μM (CEM) for 3, 4, and 14, respectively].

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What this paper is about

Six hexacyclic triterpene acids (1-6), named euscaphic acids A-F, and eight known triterpene acid compounds (7-14) were isolated from an ethanolic extract of twigs of Euscaphis japonica. Compounds 8 and 10 were isolated for the first time from a natural source. Triterpenes 1-6 possess hexacyclic skeletons with a 13α,27-cyclopropane ring. Structural elucidation of compounds 1-6 was established by spectroscopic methods, especially 2D NMR techniques ((1)H-(1)H COSY, HMQC, HMBC, and NOESY). Compounds 3, 4, and 14 showed significant cytotoxicity against different cancer cell lines [IC50 = 2.54 (NCI-H460), 3.61 (MCF-7), and 3.27 μM (CEM) for 3, 4, and 14, respectively].

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Available abstract

Six hexacyclic triterpene acids (1-6), named euscaphic acids A-F, and eight known triterpene acid compounds (7-14) were isolated from an ethanolic extract of twigs of Euscaphis japonica. Compounds 8 and 10 were isolated for the first time from a natural source. Triterpenes 1-6 possess hexacyclic skeletons with a 13α,27-cyclopropane ring. Structural elucidation of compounds 1-6 was established by spectroscopic methods, especially 2D NMR techniques ((1)H-(1)H COSY, HMQC, HMBC, and NOESY). Compounds 3, 4, and 14 showed significant cytotoxicity against different cancer cell lines [IC50 = 2.54 (NCI-H460), 3.61 (MCF-7), and 3.27 μM (CEM) for 3, 4, and 14, respectively].

Key concepts: Triterpene, Stereochemistry, Cyclopropane, Two-dimensional nuclear magnetic resonance spectroscopy, Terpene, Chemistry, Japonica, Cancer cell lines

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