Investigation of the Physical and Bioactive Properties of Bromo- and Iodo-Containing Sponge-Derived Compounds Possessing an Oxyphenylethanamine Core,Journal of Natural Products

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Investigation of the Physical and Bioactive Properties of Bromo- and Iodo-Containing Sponge-Derived Compounds Possessing an Oxyphenylethanamine Core
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-16 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00694
Erin P. McCauley ₁ , Hanh Lam ₂ , Nicholas Lorig-Roach ₁ , Justin Luu ₂ , Cameron Lloyd ₂ , Karen Tenney ₁ , Halina Pietraszkiewicz ₃ , Cristina Diaz ₄ , Frederick A. Valeriote ₃ , Victoria Auerbuch ₂ , Phillip Crews ₁

Affiliation

This research set out to identify compounds from marine sponges that can act as bacterial virulence blockers. Extracts from a total of 80 sponges collected from throughout Indonesia were screened in a high-throughput NF-κB-based screen that identifies compounds capable of inhibiting the bacterial type III secretion system (T3SS) in Yersinia pseudotuberculosis. An extract that was shown to inhibit T3SS-driven NF-κB expression was obtained from an Iotrochota cf. iota sponge and was the source of seven new bromo- and iodo-containing compounds, all of which contain a 2-(4-oxyphenyl)ethan-1-amine core. Five were determined to be new compounds and named enisorines A–E (1–5). The remaining two were determined to be new hemibastadinol analogues named (+)-1-O-methylhemibastadinol 2 (6) and (+)-1-O-methylhemibastadinol 4 (7). All seven compounds inhibited T3SS-dependent YopE secretion and did not affect the growth or metabolic activity of Y. pseudotuberculosis. The most potent inhibitors of T3SS activity were enisorine C (3), enisorine E (5), and (+)-1-O-methylhemibastadinol 2 (6), all of which inhibited YopE secretion by >50% at 30 μM.

中文翻译：

具有氧苯基乙胺核的含溴和碘的海绵衍生化合物的物理和生物活性性质的研究

这项研究着手从可以用作细菌毒力阻滞剂的海洋海绵中鉴定出化合物。在整个基于NF-κB的高通量筛选中筛选了从整个印度尼西亚收集的总共80个海绵的提取物，该筛选确定了能够抑制假结核耶尔森氏菌细菌III型分泌系统（T3SS）的化合物。从Iotrochota cf.获得了显示出抑制T3SS驱动的NF-κB表达的提取物。丝毫海绵是七个新溴源和化合物，所有这些都含有2-（4-氧苯基）含碘乙-1-胺核心。五个被确定为新的化合物，命名为enisorines A-E（1 - 5）。测定剩余的两个被命名为新hemibastadinol类似物（+） - 1- Ö -methylhemibastadinol 2（6）和（+） - 1- Ö -methylhemibastadinol 4（7）。所有这七个化合物均抑制T3SS依赖性YopE分泌，并且不影响假结核耶尔森氏菌的生长或代谢活性。T3SS活性最有效的抑制剂是enisorine C（3），enisorine E（5）和（+）-1- O- methylhemibastadinol 2（6），所有这些抑制剂均在30μM下抑制YopE分泌> 50％。

更新日期：2017-11-16

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