Exploring the Sponge Consortium Plakortis symbiotica–Xestospongia deweerdtae as a Potential Source of Antimicrobial Compounds and Probing the Pharmacophore for Antituberculosis Activity of Smenothiazole A by Diverted Total Synthesis,Journal of Natural Products

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Exploring the Sponge Consortium Plakortis symbiotica–Xestospongia deweerdtae as a Potential Source of Antimicrobial Compounds and Probing the Pharmacophore for Antituberculosis Activity of Smenothiazole A by Diverted Total Synthesis
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-07-25 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00300
Carlos Jiménez-Romero ₁ , Joanna E. Rode ₂ , Yeiry M. Pérez ₁ , Scott G. Franzblau ₃ , Abimael D. Rodríguez ₁

Affiliation

Fractionation of the bioactive CHCl₃–MeOH (1:1) extracts obtained from two collections of the sponge consortium Plakortis symbiotica–Xestospongia deweerdtae from Puerto Rico provided two new plakinidone analogues, designated as plakinidone B (2) and plakinidone C (3), as well as the known plakinidone (1), plakortolide F (4), and smenothiazole A (5). The structures of 1–5 were characterized on the basis of 1D and 2D NMR spectroscopic, IR, UV, and HRMS analysis. The absolute configurations of plakinidones 2 and 3 were established through chemical correlation methods, VCD/ECD experiments, and spectroscopic data comparisons. When assayed in vitro against Mycobacterium tuberculosis H₃₇Rv, none of the plakinidones 1–3 displayed significant activity, whereas smenothiazole A (5) was the most active compound, exhibiting an MIC value of 4.1 μg/mL. Synthesis and subsequent biological screening of 8, a dechlorinated version of smenothiazole A, revealed that the chlorine atom in 5 is indispensable for anti-TB activity.

中文翻译：

探索海绵状共生菌Pakkortis symbiotica–Xestospongia deweerdtae作为抗菌化合物的潜在来源，并通过转移总合成探索Smenothiazole A的抗结核药性

从波多黎各的两个共生性海绵体Plakortis symbiotica – Xestospongia deweerdtae的两个集合中分离出具有生物活性的CHCl ₃ -MeOH（1：1）提取物，提供了两个新的plakinidone类似物，分别称为plakinidone B（2）和plakinidone C（3），以及已知的Plakinidone（1），Plakortolide F（4）和Smenothiazole A（5）。的结构1 - 5进行了表征1D和2D NMR光谱学，IR，UV，和HRMS分析的基础上。plakinidones 2和3的绝对构型通过化学相关方法，VCD / ECD实验和光谱数据比较建立。当在体外测定对结核分枝杆菌ħ ₃₇ RV，没有plakinidones的1 - 3显示显著活性，而smenothiazole A（5）是最活跃的化合物，表现出4.1微克/毫升的MIC的值。合成和随后的生物筛选，即8的次氯代噻唑A的脱氯版本，表明5中的氯原子对于抗结核病活性是必不可少的。

更新日期：2017-07-25

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