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三锥栗 CF,四种新型具有 1,2-裂石竹烷型碳骨架的柠檬苦素类化合物,来自三锥栗的果实。

Trichiconlides CF, four new limonoids with 1,2-seco phragmalin-type carbon skeleton from the fruits of Trichilia connaroides.

机构信息

Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China; State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People's Republic of China.

Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.

出版信息

Fitoterapia. 2018 Mar;125:72-77. doi: 10.1016/j.fitote.2017.12.023. Epub 2017 Dec 26.

DOI:10.1016/j.fitote.2017.12.023
PMID:29288024
Abstract

Phytochemical investigation of the fruits from Trichilia connaroides led to the isolation of four rare 1,2-seco phragmalin-type limonoids (1-4) with C-7/28 δ-lactone ring along with two known triterpenoids (5-6). An oxygen bridge between C-1 and C-2 formed an rare 9-oxa-tricyclo[3.3.2.1]undecane-2-ene moiety in structure of 1 and 2, and 3-4 possessed a bicyclo[5.2.1]decane skeleton. Their structures were established based on extensive spectroscopic methods and their absolute configurations of 1 were confirmed by TDDFT/ECD calculation and comparative analysis. Compounds 5-6 showed moderate inhibitory effects on Hela tumor cell lines with inhibition ratio values of 83.8% and 87.1% at concentration 40μM, respectively.

摘要

从 Trichilia connaroides 的果实中进行的植物化学研究导致分离出四种罕见的 1,2-裂环法呢基型 limonoids(1-4),它们具有 C-7/28 δ-内酯环以及两种已知的三萜(5-6)。在 1 和 2 的结构中,C-1 和 C-2 之间形成了一个含氧桥,形成了一个罕见的 9-氧代三环[3.3.2.1]十一烷-2-烯部分,而 3-4 则具有双环[5.2.1]癸烷骨架。它们的结构是基于广泛的光谱方法确定的,并且通过 TDDFT/ECD 计算和比较分析确定了 1 的绝对构型。化合物 5-6 在 40μM 浓度下对 Hela 肿瘤细胞系表现出中等抑制作用,抑制率分别为 83.8%和 87.1%。

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