Bioactive Limonoid Constituents of Munronia henryi

• Published in: Journal of natural products (Washington, D.C.) Vol. 78; no. 4; pp. 811 - 821
• Main Authors: 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
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 24.04.2015; Amer Chemical Soc
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Antiviral Agents - chemistry; Antiviral Agents - isolation & purification; Antiviral Agents - pharmacology; Chemistry, Medicinal; Crystallography, X-Ray; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; HL-60 Cells; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; Limonins - chemistry; Limonins - isolation & purification; Limonins - pharmacology; Meliaceae - chemistry; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; Tobacco Mosaic Virus - drug effects; CHEMISTRY; MOSAIC-VIRUS; CHEMICAL-CONSTITUENTS; A-J; LEAVES; SKELETON
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np501057f

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.