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裂环甜没药酸B和C:从刚果Entandrophragma congoënse(楝科)根部分离出的两种新型3,4-裂环羽扇豆烷三萜类化合物的鉴定

seco-Tiaminic acids B and C: Identification of two novel 3,4-seco-tirucallane triterpenoids isolated from the root of Entandrophragma congoënse (Meliaceae).

作者信息

Happi Gervais Mouthé, Talontsi Ferdinand Mouafo, Laatsch Hartmut, Zühlke Sebastian, Ngadjui Bonaventure Tchaleu, Spiteller Michael, Kouam Simeon Fogue

机构信息

Department of Chemistry, Higher Teachers' Training College, University of Yaoundé I, P. O. Box 47, Yaoundé, Cameroon; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany.

Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany.

出版信息

Fitoterapia. 2018 Jan;124:17-22. doi: 10.1016/j.fitote.2017.10.004. Epub 2017 Oct 5.

DOI:10.1016/j.fitote.2017.10.004
PMID:28987553
Abstract

Chemical investigation of the roots of Entandrophragma congoënse (Meliaceae) led to the isolation of two new 3,4-seco-tirucallane triterpenes, namely seco-tiaminic acids B and C (1 and 2) together with nine known compounds: 3,4-secotirucalla-21-formyl-23-oxo-4(28),7,24-trien-3-oic acid (3), methyl angolensate (4), molucensin N (5), molucensin O (6), piscidinol A (7), 7α,20(S)-dihydroxy-4,24(28)-ergostadien-3-one (8), 24-methylene-cholest-5-en-3β,7α-diol (9), entilin A (10), and entilin B (11). Their structures were determined using extensive spectroscopic methods including 1D and 2D NMR, HRMS, and CD analyses; new results were compared to existing data in the literature. The two newly identified seco-tiaminic acids showed moderate antiplasmodial and cytotoxic activities against a chloroquine-sensitive strain of the malaria parasite (Plasmodium falciparum NF54) and were cytotoxic toward an L6 rat skeletal myoblast cell line, respectively.

摘要

对刚果Entandrophragma(楝科)根进行化学研究,从中分离出两种新的3,4-裂环羽扇烷三萜,即裂环硫胺酸B和C(1和2),以及九种已知化合物:3,4-裂环羽扇烷-21-甲酰基-23-氧代-4(28),7,24-三烯-3-酸(3)、安哥拉酸甲酯(4)、莫鲁新N(5)、莫鲁新O(6)、鲷毒素A(7)、7α,20(S)-二羟基-4,24(28)-麦角甾二烯-3-酮(8)、24-亚甲基胆甾-5-烯-3β,7α-二醇(9)、恩替林A(10)和恩替林B(11)。通过包括一维和二维核磁共振、高分辨质谱和圆二色分析在内的广泛光谱方法确定了它们的结构;将新结果与文献中的现有数据进行了比较。这两种新鉴定的裂环硫胺酸分别对氯喹敏感的疟原虫(恶性疟原虫NF54)菌株表现出中等抗疟活性和细胞毒性,并且对L6大鼠骨骼肌成肌细胞系具有细胞毒性。

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