Homosecoiridoid Alkaloids with Amino Acid Units from the Flower Buds of Lonicera japonica

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• 作者：Yang Yu ; Chenggen Zhu ; Sujuan Wang ; Weixia Song ; Yongchun Yang ; Jiangong Shi
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：December 27, 2013
• 年：2013
• 卷：76
• 期：12
• 页码：2226-2233
• 全文大小：337K
• ISSN：1520-6025

文摘

Nine new homosecoiridoid alkaloids, named lonijaposides O鈥揥 (1鈥?b>9), along with 19 known compounds, were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their structures and absolute configurations were determined by spectroscopic data analysis and chemical methods. Lonijaposides O鈥揥 have structural features that involve amino acid units sharing the N atom with a pyridinium (1鈥?b>5) or nicotinic acid (6鈥?b>9) moiety. The absolute configurations of the amino acid units were determined by oxidation of each pyridinium ring moiety with potassium ferricyanide, hydrolysis of the oxidation product, and Marfey鈥檚 analysis of the hydrolysate. This procedure was validated by oxidizing and hydrolyzing synthetic model compounds. The phenylalanine units in compounds 4, 5, and 9 have the d-configuration, and the other amino acid units in 1鈥?b>3 and 6鈥?b>8 possess the l-configuration. Compounds 1, 4, 6, and 9 and the known compounds 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 5鈥?O-methyladenosine exhibited antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2) with IC₅₀ values of 3.4鈥?1.6 渭M, and 4 inhibited Coxsackie virus B3 replication with an IC₅₀ value of 12.3 渭M.