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Antiviral Triterpenes from the Twigs and Leaves of Lyonia ovalifolia

Lv, Xiao-Jing, Li, Yong, Ma, Shuang-Gang, Qu, Jing, Liu, Yun-Bao, Li, Yu-Huan, Zhang, Dan, Li, Li, Yu, Shi-Shan
Journal of natural products 2016 v.79 no.11 pp. 2824-2837
inhibitory concentration 50, Enterovirus, nuclear magnetic resonance spectroscopy, X-ray diffraction, antiviral properties, Human alphaherpesvirus 1, Influenza A virus, triterpenoids, leaves, spectral analysis, branches, herpes simplex, Lyonia ovalifolia, glycosides, circular dichroism spectroscopy
Eleven new 9,10-seco-cycloartan triterpene glycosides (1–11), seven new lanostane triterpene glycosides (12–18), and two new ursane triterpenoids (19–20) were isolated from the twigs and leaves of Lyonia ovalifolia. The structures of these compounds were elucidated by extensive MS and NMR spectroscopic analysis. The absolute configuration of compound 1a (the aglycone of 1) was established by X-ray crystallography, and that of C-24 in compounds 2, 7, and 12 was established by Mo₂(OAc)₄-induced electronic circular dichroism experiments. All compounds were evaluated for their antiviral [herpes simplex virus-1 (HSV-1), influenza A/95–359 (A/95–359), and Coxsackie B3 (CVB3)] activity. Compounds 1, 1a, 2a, 12a, 13, and 16 exhibited potent activity against HSV-1, with IC₅₀ values from 2.1 to 14.3 μM, while compounds 1a, 2a, 12a, 13, and 12–2a exhibited potent activity against A/95–359, with IC₅₀ values from 2.1 to 11.1 μM. In turn, compounds 1, 1a, 2a, 12a, and 13 exhibited potent activity against CVB3, with IC₅₀ values from 2.1 to 11.1 μM.