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Bioactive Limonoid Constituents of Munronia henryi

Yan, Ying, Zhang, Jian-Xin, Huang, Tao, Mao, Xin-Ying, Gu, Wei, He, Hong-Ping, Di, Ying-Tong, Li, Shun-Lin, Chen, Duo-Zhi, Zhang, Yu, Hao, Xiao-Jiang
Journal of natural products 2015 v.78 no.4 pp. 811-821
X-ray diffraction, antiviral properties, cytotoxicity, heptane, humans, inhibitory concentration 50, limonoids, mass spectrometry, neoplasms, nuclear magnetic resonance spectroscopy, oxygen, viruses
Fourteen new limonoids, munronins A–N (1–14), and eight known limonoids (15–22) were isolated from the whole plants of Munronia henryi. The structures of the new compounds were elucidated by 2D NMR spectroscopy and mass spectrometry, and the structure of 8 was confirmed by single-crystal X-ray diffraction analysis. Compound 1 represents the first limonoid found with a novel 7-oxabicyclo[2.2.1]heptane moiety produced by incorporating C-11 and C-14 via an oxygen atom. All compounds were evaluated for their anti-tobacco mosaic virus (TMV) activity and in vitro cytotoxicity against the human cancer HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Among them, compounds 2, 8, 9, 10, 11, 12, 18, and 20 showed significant anti-TMV activity, with IC₅₀ values in the range 19.6–44.4 μg/mL. Compounds 1 and 18 exhibited cytotoxic effects for all five cancer cell lines, with IC₅₀ values between 0.4 and 4.8 μM.