Alkaloids from the Root of Isatis indigotica

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• 作者：Minghua Chen ; Lishe Gan ; Sheng Lin ; Xiaoliang Wang ; Li Li ; Yuhuan Li ; Chenggen Zhu ; Yanan Wang ; Bingya Jiang ; Jiandong Jiang ; Yongchun Yang ; Jiangong Shi
• 刊名：Journal of Natural Products
• 出版年：2012
• 出版时间：June 22, 2012
• 年：2012
• 卷：75
• 期：6
• 页码：1167-1176
• 全文大小：360K
• 年卷期：v.75,no.6(June 22, 2012)
• ISSN：1520-6025

文摘

Seventeen new alkaloids (1鈥?b>17) and 14 known analogues have been isolated from an aqueous extract of the root of Isatis indigotica. The structures and absolute configurations of these compounds were determined by extensive spectroscopic data analysis, including 2D NMR, single-crystal X-ray crystallography using anomalous scattering of Cu K伪 radiation, and electronic circular dichroism spectra calculations based on the quantum-mechanical time-dependent density functional theory. Compounds 1, 2, and 3 are the first examples of natural products with unique linkages between a molecule of 2-(4-methoxy-1H-indol-3-yl)acetonitrile and 2-(1H-indol-3-yl)acetonitrile, 2-(4-methoxy-1H-indol-3-yl)acetonitrile, and 4-hydroxyphenylethane, respectively. Compounds (鈭?-4 and (+)-4 represent the first natural products with the pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline skeleton. Some structural assignments for the new alkaloids suggest that the assignments made for certain previously reported alkaloids require revision. Compounds 1鈥?b>3 and arvelexin (18) show antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2), with IC₅₀ values of 3.70鈥?2.35 渭M, and 17 inhibits Coxsackie virus B3 replication with an IC₅₀ of 6.87 渭M.