- Total Syntheses of (-)-Spirooliganones A and B and Their Diastereoisomers: Absolute Stereochemistry and Inhibitory Activity against Coxsackie Virus B3
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To investigate the effects of configuration on bioactivity, spirooliganones A and B and their six diastereoisomers (1-8) were synthesized in 11 steps. The key benzopyran core was assembled by intermolecular [4 + 2] hetero-Diels-Alder cycloaddition between (-)-sabinene and o-quinone methide, which was generated from the corresponding o-hydroxybenzyl alcohol. After establishing the absolute configuration, the inhibitory activities of spirooliganones 1-8 against Coxsackie virus B3 were evaluated, and the primary structure-activity relationships were analyzed. Compound 3 was the most potent compound, with an IC50 of 0.41 μM.
- Zhao, Nan,Ren, Xiaodong,Ren, Jinhong,Lü, Haining,Ma, Shuanggang,Gao, Rongmei,Li, Yuhuan,Xu, Song,Li, Li,Yu, Shishan
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p. 3118 - 3121
(2015/06/30)
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- Antiviral spirooliganones A and B with unprecedented skeletons from the roots of Illicium oligandrum
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Two novel spirooliganones A (1) and (2), a pair of spiro carbon epimers, with a rare dioxaspiro skeleton were isolated from the roots of Illicium oligandrum. The structures were fully determined by spectroscopic analysis and chemical methods, especially modified Mosher's method, and X-ray diffraction analysis. Spirooliganone B was found to exhibit more potent activities against coxsackie virus B3 and influenza virus A (H3N2) (IC50 3.70-5.05 μM) than spirooliganone A. The biosynthetic pathway involving a hetero-Diels-Alder reaction of the epimers was proposed.
- Ma, Shuang-Gang,Gao, Rong-Mei,Li, Yu-Huan,Jiang, Jian-Dong,Gong, Ning-Bo,Li, Li,Lue, Yang,Tang, Wen-Zhao,Liu, Yun-Bao,Qu, Jing,Lue, Hai-Ning,Li, Yong,Yu, Shi-Shan
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supporting information
p. 4450 - 4453
(2013/09/24)
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