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<p>The combined-culture of actinomycetes with mycolic acid-containing bacteria (MACB) <i>Tsukamurella pulmonis</i> TP-B0596 is a promising strategy to produce cryptic metabolites in actinomycetes. In this study, <i>Streptomyces</i> sp. 23-50 was identified as an appropriate strain for co-culturing with <i>T. pulmonis</i> TP-B0596 using <i>on</i>-<i>gel</i> combined-culture screening of 160 strains of actinomycetes. A new pyranonaphthoquinone, actinoquinonal A (<b>1</b>), along with two known congeners, compound <b>2</b> and mevashuntin (<b>3</b>), were isolated from the combined-culture of <i>Streptomyces</i> sp. 23-50 with <i>T. pulmonis</i> TP-B0596 based on global natural product social (GNPS) molecular networking. The planar structures of <b>1</b>–<b>3</b> were elucidated by analyzing 2D nuclear magnetic resonance (NMR) and LC-MS/MS spectral data, and the absolute configurations of <b>1</b> and <b>3</b> were unambiguously determined by comparing experimental and calculated ECD spectra. Moreover, the combined-culture characteristic metabolites, including <b>3</b>, were enhanced when <i>Streptomyces</i> sp. 23-50 was cultured in the presence of pravastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A&#xa0;(HMG-CoA) reductase in the mevalonate pathway, suggesting that <i>T. pulmonis</i> TP-B0596 triggered a shunt in the mevalonate pathway of <i>Streptomyces</i> sp. 23-50. Notably, compounds <b>1</b> and <b>3</b> exhibited cytotoxicity against human cervical epithelioid carcinoma HeLa S3 (IC<sub>50</sub> = 60.5 μM for <b>1</b>, 0.67 μM for <b>3</b>) and human colorectal cancer HT29 cells (IC<sub>50</sub> = 101.9 μM for <b>1</b>, 0.45 μM for <b>3</b>).</p><p></p>

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A new pyranonaphthoquinone, actinoquinonal A, and its congeners from the combined-culture of Streptomyces sp. 23–50 and Tsukamurella pulmonis TP-B0596

  • 期刊论文

  • 发表日期：

    2025年4月22日

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  • Kazuki Yanagisawa,
  • Kensuke Kaneko,
  • Hiroaki Ikeda,
  • Sumika Iwata,
  • Atsuya Muranaka,
  • Hiroyuki Koshino,
  • Noeka Nagao,
  • Susumu Watari,
  • Shinichi Nishimura,
  • Naoya Shinzato,
  • Hiroyasu Onaka,
  • Hideaki Kakeya

摘要

The combined-culture of actinomycetes with mycolic acid-containing bacteria (MACB) Tsukamurella pulmonis TP-B0596 is a promising strategy to produce cryptic metabolites in actinomycetes. In this study, Streptomyces sp. 23-50 was identified as an appropriate strain for co-culturing with T. pulmonis TP-B0596 using on-gel combined-culture screening of 160 strains of actinomycetes. A new pyranonaphthoquinone, actinoquinonal A (1), along with two known congeners, compound 2 and mevashuntin (3), were isolated from the combined-culture of Streptomyces sp. 23-50 with T. pulmonis TP-B0596 based on global natural product social (GNPS) molecular networking. The planar structures of 1–3 were elucidated by analyzing 2D nuclear magnetic resonance (NMR) and LC-MS/MS spectral data, and the absolute configurations of 1 and 3 were unambiguously determined by comparing experimental and calculated ECD spectra. Moreover, the combined-culture characteristic metabolites, including 3, were enhanced when Streptomyces sp. 23-50 was cultured in the presence of pravastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase in the mevalonate pathway, suggesting that T. pulmonis TP-B0596 triggered a shunt in the mevalonate pathway of Streptomyces sp. 23-50. Notably, compounds 1 and 3 exhibited cytotoxicity against human cervical epithelioid carcinoma HeLa S3 (IC50 = 60.5 μM for 1, 0.67 μM for 3) and human colorectal cancer HT29 cells (IC50 = 101.9 μM for 1, 0.45 μM for 3).