Isolation and structural elucidation of β-tocopherol derivatives from Dryopteris crassirhizoma

Isolation and structural elucidation of β-tocopherol derivatives from Dryopteris crassirhizoma
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粗鳞毛蕨中 β-生育酚衍生物的分离和结构解析

DOI:
10.1016/j.indcrop.2021.114010
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发表时间:
2021-11
影响因子:
5.9
通讯作者:
Guocai Wang
Guocai Wang
中科院分区:
农林科学1区
文献类型:
--
作者:
Nenghua Chen;Wen Li;Jihui Zhang;Weibin Xu;Zhongnan Wu;Yaolan Li;Yubo Zhang;Qingwen Zhang;Guocai Wang

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粗茎鳞毛蕨(Dryopteris crassirhizomaNakai)为鳞毛蕨科(Dryopteridaceae)的一种粗茎木本蕨类植物,主要分布于我国北方和东北地区。它在园艺和医药应用方面具有重要价值。从粗茎鳞毛蕨(Dryopteriscrassirhizoma)根茎中分离得到5个β-生育酚衍生物,即粗茎鳞毛蕨醇(drycrassperols)A-E(1-5),具有3种骨架结构。化合物1 - 2的基本结构是苯酚基序通过吡喃环与植基型二萜稠合,化合物3 - 4具有前所未有的四环体系,其中4-甲基环己酮被引入1的基本单元。有趣的是,化合物5是一个新的二聚体,由两个单体通过吡喃环形成一个五环系统。这些结构通过综合的光谱数据和量子化学电子圆二色性(ECD)计算进行了阐明。重要的是,化合物1表现出与阳性对照利巴韦林相当的抗呼吸道合胞病毒活性,IC 50值为6.50 ± 1.25 μM。本研究表明,D.β-生育酚衍生物在医药工业中具有新的潜在应用。
Dryopteris crassirhizomaNakai (Dryopteridaceae), a thick-stemmed wood fern, is a semi-evergreen plant mainly distributed in North and Northeast China. It is of great value in horticultural and medicinal applications. In this study, five β-tocopherol derivatives, drycrasspherols A–E (1–5), with three kinds of skeletons, were isolated from the rhizomes ofDryopteris crassirhizoma. Compounds1–2represent the basic architecture featuring a phenol motif fused with the phytyl-type diterpene via a pyran ring, compounds3–4possess an unprecedented tetracyclic system in which a 4-methylcyclohexanone is incorporated into the base unit of1. Interestingly, compound5is a novel dimer constructed from two monomers via a pyran ring to form a pentacyclic system. These structures were elucidated by comprehensive spectroscopic data and quantum chemical electronic circular dichroism (ECD) calculations. Importantly, compound1exhibited the comparable anti-respiratory syncytial virus activity with an IC50value of 6.50 ± 1.25 μM to the positive control ribavirin. This study suggested the rhizomes ofD. crassirhizomaas well as the β-tocopherol derivatives had new potential applications in pharmaceutical industry.
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