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Cuevaenes C-E:来自链霉菌 LZ35ΔgdmAI 的三种新的三烯羧酸衍生物。

Cuevaenes C-E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI.

机构信息

Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan, Shandong 250012, P. R. China.

出版信息

Beilstein J Org Chem. 2014 Apr 15;10:858-862. doi: 10.3762/bjoc.10.82. eCollection 2014.

DOI:10.3762/bjoc.10.82
PMID:24778741
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3999817/
Abstract

Two pairs of geometrical isomers - cuevaenes A (1) and C (3) as well as cuevaenes D (4) and E (5) - and cuevaene B (2) were isolated from gdmAI-disrupted Streptomyces sp. LZ35. The constitution of cuevaene C (3) was found to be identical to cuevaene A (1) by means of NMR spectroscopy and high resolution mass spectrometry. However, the relative configurations of the triene side chain moieties were determined to be different. It was established on the basis of spectroscopic data that cuevaenes D (4) and E (5) are amides and geometrical isomers. Cuevaenes A-C (1-3) displayed moderate activity against Gram-positive bacteria (e.g., Bacillus subtilis strain ATCC 11060) and modest activity against fungi (e.g., Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4). However, cuevaenes D (4) and E (5) showed no inhibitory activity against any of the tested microbes.

摘要

从 gdmAI 敲除的链霉菌 sp. LZ35 中分离得到两对几何异构体 - 库埃瓦烯 A(1)和 C(3)以及库埃瓦烯 D(4)和 E(5)- 和库埃瓦烯 B(2)。通过 NMR 光谱和高分辨质谱发现,库埃瓦烯 C(3)的结构与库埃瓦烯 A(1)相同。然而,三烯侧链部分的相对构型被确定为不同。基于光谱数据确定,库埃瓦烯 D(4)和 E(5)是酰胺和几何异构体。库埃瓦烯 A-C(1-3)对革兰氏阳性菌(例如枯草芽孢杆菌 ATCC 11060 株)表现出中等活性,对真菌(例如,串珠镰刀菌 S68 株和立枯丝核菌 GXE4 株)表现出适度的活性。然而,库埃瓦烯 D(4)和 E(5)对测试的微生物均没有抑制活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bd6/3999817/4094a2f453f6/Beilstein_J_Org_Chem-10-858-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bd6/3999817/3ca98691ea53/Beilstein_J_Org_Chem-10-858-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bd6/3999817/4094a2f453f6/Beilstein_J_Org_Chem-10-858-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bd6/3999817/3ca98691ea53/Beilstein_J_Org_Chem-10-858-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bd6/3999817/4094a2f453f6/Beilstein_J_Org_Chem-10-858-g003.jpg

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