Structurally intriguing rearranged bicyclogermacrene-type sesquiterpenoid from Aphania oligophylla

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2024-08-25 DOI:10.1016/j.tetlet.2024.155276

引用次数: 0

Abstract

An investigation on the aqueous ethanol extract of the powdered twigs of Aphania oligophylla has afforded a skeletal new sesquiterpenoid aphanoid A (1) and one new aromadendrane-type sesquiterpenoid aphanoid B (2), as well as six known sesquiterpenoids (3–8). Their structures including the absolute configurations were characterized based on spectroscopic data analysis and X-ray crystallography. Compound 1 featuring an unprecedented tricyclo[6.3.1.0^3,5]dodecane scaffold, is likely rearranged from the bicyclogermacrene-type sesquiterpenoid. Among those compounds, 2 at 10 μL showed moderate antimalarial effect.

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从寡叶樟中提取的结构奇特的重排双环革马烯类倍半萜化合物

通过对寡叶樟属植物小枝粉末的乙醇水提取物的研究，我们发现了一种骨架新的倍半萜类化合物 A（1）和一种新的芳香丹类倍半萜类化合物 B（2），以及六种已知的倍半萜类化合物（3-8）。通过光谱数据分析和 X 射线晶体学研究，确定了这些化合物的结构（包括绝对构型）。化合物 1 具有前所未有的三环[6.3.1.03,5]十二烷支架，很可能是由双环革马烯类倍半萜化合物重新排列而成。在这些化合物中，浓度为 10 μL 的 2 具有中等抗疟效果。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.