Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities

被引：0
作者：
Mana Sampei
Midori A. Arai
Masami Ishibashi
机构：
[1] Chiba University,Graduate School of Pharmaceutical Sciences
来源：
Journal of Natural Medicines | 2018年 / 72卷
关键词：
Lignan glycoside; Antioxidant activity; Total synthesis; Natural product;
D O I：
暂无
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学科分类号：
摘要：
Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization step. To determine the stereochemistry of 1, we synthesized the natural product (±)-isolariciresinol (18) from alcohol 17. Comparison of the spectral data showed good agreement. Glycosylation was investigated using four different glycosyl donors. Only the Koenigs–Knorr condition using silver trifluoromethanesulfonate with 1,1,3,3-tetramethylurea provided the glycosylated product. Deprotection and purification using reverse-phase high-performance liquid chromatography gave schizandriside (1) and its diastereomer saracoside (2). Synthesized 1, 2 and 18 showed antioxidant activity with IC50 = 34.4, 28.8, 53.0 μM, respectively.
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页码：651 / 654
页数：3
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