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浆果楝中的异常三萜类化合物和甾体及其生物活性。

Unusual triterpenoids and steroids from Cipadessa baccifera and their biological activities.

作者信息

Zhang De-Yu, Liu Han-Fei, Jiang Tai-Bai, Chen Chao, Lou Hua-Yong, Pan Wei-Dong, Li Jin-Yu

机构信息

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China; Natural Products Research Center of Guizhou Province, Guiyang 550014, PR China.

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China.

出版信息

Fitoterapia. 2023 Dec;171:105708. doi: 10.1016/j.fitote.2023.105708. Epub 2023 Oct 20.

Abstract

Five undescribed triterpenoids and steroids (1-5), as well as ten known compounds, were purified from the branches and leaves of Cipadessa baccifera. Notably, 1 and 2 are rare cipadesin-type limonoids with an unusual 8,30-epoxide ring and 1,8-ether linkage, respectively. Compound 5 possessed pregnane steroid skeleton with an uncommon 5/6/6/6/5-fused ring system. Their structures were constructed by extensive spectroscopic analysis (NMR, IR, UV, and HRESIMS), and their absolute configurations were confirmed by ECD calculations and quantum chemical calculations. All the isolates were in vitro assayed for their antimicrobial potentials against 6 pathogenic microorganisms and antiproliferation activities against five human cancer cell lines. As a result, compounds 5, 12, 13, and 14 exhibited moderate antibacterial activities (MIC: 25-50 μg/mL). Moreover, 5 showed cytotoxicity against five cancer cell lines with IC values ranging from 8.0 to 19.9 μM.

摘要

从浆果楝的枝叶中分离得到5个未报道的三萜类和甾体类化合物(1-5)以及10个已知化合物。值得注意的是,化合物1和2分别是罕见的具有不寻常的8,30-环氧环和1,8-醚键的浆果楝素型柠檬苦素。化合物5具有孕甾烷甾体骨架,带有罕见的5/6/6/6/5稠环体系。通过广泛的光谱分析(NMR、IR、UV和HRESIMS)确定了它们的结构,并通过ECD计算和量子化学计算确定了它们的绝对构型。对所有分离物进行了体外抗6种致病微生物的抗菌活性和对5种人类癌细胞系的抗增殖活性测试。结果,化合物5、12、13和14表现出中等抗菌活性(MIC:25-50μg/mL)。此外,化合物5对5种癌细胞系具有细胞毒性,IC值范围为8.0至19.9μM。

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