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来源于青葙的具有独特共轭 Δ 二烯和高度氧化侧链的甾烷型甾体化合物。

Stigmastane-type steroids with unique conjugated Δ diene and highly oxygenated side chains from the twigs of Vernonia amygdalina.

机构信息

Fujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen, 361005, PR China.

Fujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen, 361005, PR China.

出版信息

Phytochemistry. 2019 Feb;158:67-76. doi: 10.1016/j.phytochem.2018.10.036. Epub 2018 Nov 24.

DOI:10.1016/j.phytochem.2018.10.036
PMID:30476898
Abstract

Veramyosides A-J, eleven undescribed stigmastane-type steroids, including one aglycone and ten glycosides, along with three known homologues were isolated from the twigs of Vernonia amygdalina Delile (compositae). All compounds featured a stigmastane-type steroid skeleton with a unique conjugated Δ diene segment and highly oxygenated side chains with a γ-lactone or an α, β-unsaturated five-membered lactone ring. The structures of veramyosides A-J and their absolute configurations were unambiguously elucidated by HR-ESI-MS, extensive NMR spectroscopy, in situ dimolybdenum CD methods, modified Mosher's method, quantum chemical calculation of their ECD curves, and CD comparison methods on basis of their biogenetic pathway. In addition, all isolates were investigated for their effects on RXRα transcription, and their effects on the NF-κB signaling pathway were also evaluated.

摘要

我们从 Vernonia amygdalina Delile(菊科)的小枝中分离得到了 11 种未描述的甾体化合物,包括一种苷元和 10 种糖苷,以及 3 种已知同系物。所有化合物均具有甾体骨架,带有独特的共轭 Δ 二烯片段和高度氧化的侧链,具有γ-内酯或α,β-不饱和五元内酯环。通过高分辨电喷雾质谱(HR-ESI-MS)、广泛的 NMR 光谱、原位二钼 CD 方法、改进的莫舍尔法、ECD 曲线的量子化学计算以及基于生物合成途径的 CD 比较方法,明确阐明了 veramyosides A-J 的结构及其绝对构型。此外,还研究了所有分离物对 RXRα 转录的影响,并评估了它们对 NF-κB 信号通路的影响。

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