<p>A series of novel sulfur-containing cyclic lipopeptides named thioamycolamides F–I (<b>1</b>–<b>4</b>), with thiazoline, sulfoxide/sulfide, and fatty acid moieties, was discovered by applying GNPS molecular networking technology against combined-culture broth of <i>Amycolatopsis</i> sp. 26-4 and <i>Tsukamurella pulmonis</i> TP-B0596. Planar structural elucidation was accomplished by HRMS and 1D/2D NMR spectroscopic data analyses. The absolute configuration was determined by the highly sensitive advanced Marfey’s method developed by our group, electronic circular dichroism (ECD) spectroscopy, chemical synthesis, and Gaussian calculation. Moreover, compound <b>2</b> exhibited cytotoxicity against human cervix adenocarcinoma HeLa S3 cells with an IC<sub>50</sub> of 24.0 μM.</p><p></p>

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Combination of combined-culture of Amycolatopsis sp. with Tsukamurella pulmonis and GNPS molecular networking reveals novel sulfur-containing cyclic lipopeptides thioamycolamides F–I

  • Chengqian Pan,
  • Lei Zhang,
  • Takefumi Kuranaga,
  • Hiroyasu Onaka,
  • Naoya Shinzato,
  • Hideaki Kakeya

摘要

A series of novel sulfur-containing cyclic lipopeptides named thioamycolamides F–I (14), with thiazoline, sulfoxide/sulfide, and fatty acid moieties, was discovered by applying GNPS molecular networking technology against combined-culture broth of Amycolatopsis sp. 26-4 and Tsukamurella pulmonis TP-B0596. Planar structural elucidation was accomplished by HRMS and 1D/2D NMR spectroscopic data analyses. The absolute configuration was determined by the highly sensitive advanced Marfey’s method developed by our group, electronic circular dichroism (ECD) spectroscopy, chemical synthesis, and Gaussian calculation. Moreover, compound 2 exhibited cytotoxicity against human cervix adenocarcinoma HeLa S3 cells with an IC50 of 24.0 μM.