Synthesis, Biological Investigation, and Structural Revision of Sielboldianin A,Journal of Natural Products

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Synthesis, Biological Investigation, and Structural Revision of Sielboldianin A
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-03-19 00:00:00 , DOI: 10.1021/acs.jnatprod.8b00020
Renate Kristianslund ₁ , Marius Aursnes ₁ , Jørn E. Tungen ₁ , Carl H. Görbitz ₂ , Trond V. Hansen ₁

Affiliation

The two ar-bisabol sesquiterpenoids (+)-sielboldianin A (1) and (+)-sielboldianin B (2) were isolated from the stem bark of the plant Fraxinus sielboldiana and belong to a medicinally interesting class of natural products used in traditional Chinese medicine. Herein the total synthesis of the proposed structure of (+)-sielboldianin A (1) is reported using an organocatalyzed enantioselective bromolactonization protocol. X-ray analysis of a key intermediate together with specific rotation values and NOESY data of the synthesized product enabled the revision of the absolute configuration of the natural product (+)-sielboldianin A to (7R,10R). Studies on the antioxidant effects using two cell-based assays were conducted. These studies revealed that the enantiomer of 1 exhibited antioxidant effects with IC₅₀ values of 18 ± 3 μM in a cellular lipid peroxidation antioxidant activity assay. Moreover, (−)-1 showed strong protective effects against reactive oxygen species in a cell-based antioxidant activity assay (IC₅₀ = 31 ± 5 μM). In addition, the two ar-sesquiterpenoids (−)-boivinianin B and (−)-gossoronol showed no effect in either assay. No cytotoxic activity in the K562 cancer cell line was observed for the three sesquiterpenoids tested (IC₅₀ > 50 μM).

中文翻译：

Sielboldianin A的合成，生物学研究和结构修订

从植物Fraxinus sielboldiana的茎皮中分离出两个ar- bisabol倍半萜类（+）-sielboldianin A（1）和（+）-sielboldianin B（2），它们属于传统医学中医学上令人感兴趣的天然产物类别药物。在本文中，使用有机催化的对映选择性溴化内酯化方案报道了（+）-山茱dian素A（1）的拟议结构的总合成。对关键中间体进行X射线分析，以及合成产品的比旋光度值和NOESY数据，可以将天然产物（+）-西番莲单宁A的绝对构型修正为（7 R，10 R）。使用两种基于细胞的测定法进行了抗氧化作用的研究。这些研究表明，在细胞脂质过氧化抗氧化活性测定中，对映异构体1表现出抗氧化作用，IC ₅₀值为18±3μM。此外，（-）- 1在基于细胞的抗氧化剂活性测定中显示出对活性氧的强大保护作用（IC ₅₀ = 31±5μM）。另外，两种ar-倍半萜类化合物（-）-博维宁宁B和（-）-棉酚在两种测定中均未显示作用。对于三种测试的倍半萜类化合物，未观察到K562癌细胞系的细胞毒性活性（IC ₅₀ > 50μM）。

更新日期：2018-03-19

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