Cajuputones A–C, β‐triketone flavanone hybrids from the branches and leaves of Melaleuca cajuputi,Chemistry & Biodiversity

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Cajuputones A–C, β‐triketone flavanone hybrids from the branches and leaves of Melaleuca cajuputi
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2020-10-27 , DOI: 10.1002/cbdv.202000706
Wen-Jun Xu ₁ , Xin Xie ₁ , Lin Wu ₁ , Xiao-Meng Tian ₁ , Cheng-Cheng Wang ₂ , Ling-Yi Kong ₃ , Jun Luo ₁

Affiliation

Three new β‐triketone flavanone hybrids, cajuputones A–C were obtained from Melaleuca cajuputi (the Australian ‘tea tree’). The structures of cajuputones A–C were elucidated by 1D/2D NMR spectroscopy and HR‐ESI‐MS analyses; and their absolute configurations were established by electric circular dichroism (ECD) calculations using TDDFT method. Structurally, cajuputones A–C feature a rare 6/6/6/6 oxatetracyclic ring system fused between an acylphloroglucinol‐derived β‐triketone and a pinocembrin or strobopinin moiety via an angle‐type pyran‐like motif. DFT‐based conformational optimization in chloroform explained the similarity of the 1D NMR data of cajuputones B and C (C‐2 epimers).

中文翻译：

Cajuputones A-C, 来自白千层枝叶的β-三酮黄烷酮杂合体

从 Melaleuca cajuputi（澳大利亚“茶树”）中获得了三种新的 β-三酮黄烷酮杂种 cajuputones A-C。cajuputones A-C的结构通过1D/2D NMR光谱和HR-ESI-MS分析得到阐明；并且它们的绝对构型是通过使用 TDDFT 方法通过电圆二色性 (ECD) 计算建立的。在结构上，cajuputones A-C 具有罕见的 6/6/6/6 氧杂四环系统，通过角型吡喃样基序在酰基间苯三酚衍生的 β-三酮和松香蛋白或 strobopinin 部分之间融合。氯仿中基于 DFT 的构象优化解释了 cajuputones B 和 C（C-2 差向异构体）的 1D NMR 数据的相似性。

更新日期：2020-10-27

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