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从(豆科)布氏红豆中分离得到的两种具有细胞毒活性的新紫檀烷和一种新的吡喃衍生物:蒙杜勒内酯的核磁共振谱归属修订

Two new pterocarpans and a new pyrone derivative with cytotoxic activities from (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone.

作者信息

Ngnintedo Dominique, Fotso Ghislain W, Kuete Victor, Nana Frederic, Sandjo Louis P, Karaosmanoğlu Oğuzhan, Sivas Hülya, Keumedjio Felix, Kirsch Gilbert, Ngadjui Bonaventure T, Andrae-Marobela Kerstin

机构信息

Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, Yaoundé, Cameroon.

Department of Biochemistry, Faculty of Science, University of Dschang, Dschang, Cameroon ; Department of Biology, Science Faculty, Anadolu University, Eskişehir, Turkey.

出版信息

Chem Cent J. 2016 Oct 5;10:58. doi: 10.1186/s13065-016-0204-x. eCollection 2016.

Abstract

BACKGROUND

is a genus related to which comprises only three species. Compared to , which has been phytochemically and pharmacologically studied, species have only few or no reports on their chemical constituents. Moreover, no studies on the cytotoxic activities of its secondary metabolites have been previously documented.

RESULTS

From the non polar fractions of the roots bark of (syn ), two new pterocarpans: seputhecarpan C and seputhecarpan D and a new pyrone derivative, ptycholopyrone A were isolated. Alongside, five known compounds identified as 3-α,α-dimethylallyl-4-methoxy-6-styryl-α-pyrone or mundulea lactone , glyasperin F , seputhecarpan A , seputheisoflavone and 5--methyl-myo-inositol or sequoyitol were also obtained. Their structures were established by the mean means of spectroscopic data in conjunction to those reported in literature. The NMR assignment of the major compound mundulea lactone is revised in this paper. In addition, the cytotoxicity of the isolated metabolites was evaluated on two lung cancer cell lines A549 and SPC212. was not active while compounds displayed antiproliferative effects against the two carcinoma cell lines with IC values below 75 µM. IC values below 10 µM were obtained for and on SPC212 cells.

CONCLUSION

Based on the obtained results, turns to be a rich source of phenolic metabolites among them some bearing prenyl moieties. This study reports for the first time the isolation of pyrone derivatives and from genus. The cytotoxicity observed for the isolate is also reported for the first time and shows that and could be chemically explored in order to develop a hit candidate against lung cancer. Graphical abstractTwo new pterocarpans and a new pyrone derivative with cytotoxic activities from ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone.

摘要

背景

[某属]与[另一属]相关,该属仅包含三个物种。与已进行植物化学和药理学研究的[另一属]相比,[该属]物种的化学成分报道很少或没有报道。此外,此前尚无关于其次生代谢产物细胞毒性活性的研究记录。

结果

从[某种植物](同物异名[具体名称])根皮的非极性部分中,分离出两种新的紫檀烷:seputhecarpan C([具体结构简式])和seputhecarpan D([具体结构简式])以及一种新的吡喃酮衍生物ptycholopyrone A([具体结构简式])。同时,还获得了五种已知化合物,分别鉴定为3-α,α-二甲基烯丙基-4-甲氧基-6-苯乙烯基-α-吡喃酮或mundulea内酯([具体结构简式])、glyasperin F([具体结构简式])、seputhecarpan A([具体结构简式])、seputheisoflavone([具体结构简式])和5--甲基-myo-肌醇或红杉醇([具体结构简式])。它们的结构通过光谱数据并结合文献报道得以确定。本文对主要化合物mundulea内酯([具体结构简式])的核磁共振归属进行了修订。此外,对分离得到的代谢产物在两种肺癌细胞系A549和SPC212上进行了细胞毒性评估。[某化合物]无活性,而化合物[具体化合物]对两种癌细胞系显示出抗增殖作用,IC值低于75 μM。在SPC212细胞上,[具体化合物]和[具体化合物]的IC值低于10 μM。

结论

基于所得结果,[某种植物]是酚类代谢产物的丰富来源,其中一些含有异戊烯基部分。本研究首次报道了从[该属]中分离出吡喃酮衍生物[具体名称]和[具体名称]。首次报道了分离物的细胞毒性,表明[具体化合物]和[具体化合物]可进行化学探索,以开发针对肺癌的候选药物。图形摘要从扭叶决明(豆科)中分离出具有细胞毒性活性的两种新紫檀烷和一种新吡喃酮衍生物:mundulea内酯的核磁共振归属修订。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c33/5050614/37d410a92fb5/13065_2016_204_Figa_HTML.jpg

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