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寄生蜜茱萸(奥斯贝克)科斯滕茎皮中的倍半萜类化合物和倍半萜二聚体

Sesquiterpenoids and sesquiterpenoid dimers from the stem bark of Dysoxylum parasiticum (osbeck) kosterm.

作者信息

Naini Al Arofatus, Mayanti Tri, Harneti Desi, Maharani Rani, Farabi Kindi, Herlina Tati, Supratman Unang, Fajriah Sofa, Kuncoro Hadi, Azmi Mohamad Nurul, Shiono Yoshihito, Jungsuttiwong Siriporn, Chakthong Suda

机构信息

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas, Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia; Central Laboratory, Universitas Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia.

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas, Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia; Study Centre of Natural Product Chemistry and Synthesis, Faculty of Mathematics and Natural, Sciences, Universitas Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia.

出版信息

Phytochemistry. 2023 Jan;205:113477. doi: 10.1016/j.phytochem.2022.113477. Epub 2022 Oct 22.

Abstract

Two undescribed sesquiterpenoids, namely dysoticans A and B, and three undescribed sesquiterpenoid dimers, namely dysoticans C-E, together with six analogs, were isolated from the stem bark of Dysoxylum parasiticum (Osbeck) Kosterm. (Meliaceae), growing in West Java, Indonesia. Their structures were elucidated based on extensive spectroscopic analysis and theoretical simulations of ECD spectra and C NMR shifts. Dysoticans A and B possessed undescribed cadinanes with minor modifications, while C and D featured unprecedented pseudo-sesquiterpenoid dimers through O-ether linkages of cadinanes and guaianes, respectively. Dysotican E was also characterized as the true-sesquiterpenoid dimer featuring eudesmane-germacrene hybrid framework from the Meliaceae family. Furthermore, A-C and E showed moderate activities against the human breast cancer MCF-7 and cervical cancer HeLa cell lines with IC values ranging from 22.15 to 45.14 μM. D selectively exhibited significant cytotoxicity against the HeLa cell line with an IC value of 13.00 ± 0.13 μM.

摘要

从生长在印度尼西亚西爪哇的寄生地黄连(Dysoxylum parasiticum (Osbeck) Kosterm.)(楝科)的茎皮中分离出两种未描述的倍半萜类化合物,即寄生地黄连素A和B,以及三种未描述的倍半萜二聚体,即寄生地黄连素C - E,还有六种类似物。基于广泛的光谱分析以及ECD光谱和碳核磁共振化学位移的理论模拟,阐明了它们的结构。寄生地黄连素A和B具有略有修饰的未描述的杜松烷类化合物,而C和D分别通过杜松烷类化合物和愈创木烷类化合物的O - 醚键形成了前所未有的假倍半萜二聚体。寄生地黄连素E也被表征为具有楝科桉叶烷 - 吉马烯杂化骨架的真正倍半萜二聚体。此外,A - C和E对人乳腺癌MCF - 7和宫颈癌HeLa细胞系表现出中等活性,IC值范围为22.15至45.14 μM。D对HeLa细胞系选择性地表现出显著的细胞毒性,IC值为13.00 ± 0.13 μM。

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