Glabralides A – C, three novel meroterpenoids from Sarcandra glabra

Glabralides A – C, three novel meroterpenoids from Sarcandra glabra
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Glabralides A – C,来自草珊瑚的三种新型类萜

DOI:
10.1016/j.tet.2017.12.001
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发表时间:
2018-01
期刊:
影响因子:
2.1
通讯作者:
Fei Wang
Fei Wang
中科院分区:
化学3区
文献类型:
--
作者:
Wan-qiu Yang;Ping Hai;Han Xiao;Yuan Gao;Yun-hai Tao;De-ren Miao;Fei Wang

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Glabralides A–C (1–3),是从草珊瑚全株中分离出的三种新型类萜,包括两种前所未有的骨架。 Glabralide A (1) 代表查耳酮偶联单萜的独特骨架,带有具有五个手性中心的双环 [2.2.2] 辛烯核心单元。通过光谱方法(包括二维核磁共振实验)建立结构,并使用圆二色(CD)光谱确定绝对构型。 1 的合理生物发生途径表明 α-水芹烯通过 Diels-Alder 环化与查耳酮缀合,而 3 则暗示 α-水芹烯和邻羟基苯乙酸酯通过罕见的自由基加成和阳离子环化进行环化。
Glabralides A–C (1–3), three novel meroterpenoids including two unprecedented skeletons were isolated from the whole plants of Sarcandra glabra. Glabralide A (1) represented a unique skeleton of the chalcone-coupled monoterpenoid, bearing a bicyclo [2.2.2] octene core unit with five chiral centers. The structures were established by spectroscopic methods, including 2D NMR experiments, and the absolute configurations were determined using circular dichroic (CD) spectra. The plausible biogenetic pathway for 1 suggested that α-phellandrene was conjugated with chalcone by Diels-Alder cyclization, and for 3 implied that α-phellandrene and o-hydroxy phenylacetate cyclized by an uncommon radical addition and cationic cyclization.
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