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双抗素的结构与绝对构型:一种来自忍冬(忍冬科)的新型天然环过氧化物。

The structure and absolute configuration of Shuangkangsu: a novel natural cyclic peroxide from Lonicera japonica (Thunb.).

作者信息

Yu De-Quan, Chen Ruo-Yun, Huang Long-Jiang, Xie Feng-Zhi, Ming Dong-Sheng, Zhou Kun, Li Hong-Yuan, Tong Kui-Min

机构信息

The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Peking Union Medical College, Beijing, China.

出版信息

J Asian Nat Prod Res. 2008 Sep-Oct;10(9-10):851-6. doi: 10.1080/10286020802144677.

DOI:10.1080/10286020802144677
PMID:18985497
Abstract

A novel cyclic peroxide, shuangkangsu (1), has been obtained from the water extract of the buds of Lonicera japonica (Thunb.). The structure was elucidated as 5,8-divinyl-1,4-dihydro-1,4-di-O-beta-d-glucopyranosyl-2,3-dioxane (1) on the basis of the spectral data. Its absolute stereochemistry was determined to be (1S, 4S) by comparison of its CD curves with those of its optically pure analogs 2 and 3, which were synthesized from the phthalaldehyde. The absolute configurations of 2 and 3 were determined to be (1R, 4R) and (1S, 4S) by X-ray analysis and CD spectra, respectively. Compound 1 showed significant antiviral activities against influenza virus in chicken embryo and respiratory syncytial virus in cells.

摘要

从忍冬(Thunb.)芽的水提取物中获得了一种新型环状过氧化物双抗素(1)。根据光谱数据,其结构被确认为5,8-二乙烯基-1,4-二氢-1,4-二-O-β-D-吡喃葡萄糖基-2,3-二氧六环(1)。通过将其圆二色光谱曲线与由邻苯二甲醛合成的光学纯类似物2和3的曲线进行比较,确定其绝对立体化学为(1S,4S)。通过X射线分析和圆二色光谱分别确定2和3的绝对构型为(1R,4R)和(1S,4S)。化合物1在鸡胚中对流感病毒以及在细胞中对呼吸道合胞病毒显示出显著的抗病毒活性。

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The structure and absolute configuration of Shuangkangsu: a novel natural cyclic peroxide from Lonicera japonica (Thunb.).双抗素的结构与绝对构型:一种来自忍冬(忍冬科)的新型天然环过氧化物。
J Asian Nat Prod Res. 2008 Sep-Oct;10(9-10):851-6. doi: 10.1080/10286020802144677.
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