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<p>Four previously undescribed polyprenylated acylphloroglucinols, hyperisenins A–D (<b>1</b>–<b>4</b>), along with two known analogues (<b>5</b> and <b>6</b>), were obtained from the aerial part of <i>Hypericum seniawinii</i> Maxim. Compounds <b>1</b> and <b>2</b> were two highly degraded polyprenylated acylphloroglucinols with a cyclohexanone-monocyclic skeleton, while compound <b>3</b> was the first example of <i>O</i>-prenylated acylphloroglucinols with a 6/6/6 ring system. Their structures were identified by analyzing NMR, HRESIMS data, and quantum chemical calculations. The biosynthetic pathway of <b>1</b> and <b>2</b> might originate from bicyclic polyprenylated acylphloroglucinols via a series of complex retro-Claisen, keto − enol tautomerism, and intramolecular cyclization. The bioassay results showed that <b>4</b> exhibited quorum sensing inhibitory activity against <i>Pseudomonas aeruginosa</i>, which could decrease the activation of the <i>rhl</i> system, and significantly reduce rhamnolipid levels at a concentration of 100&#xa0;µM, and the mechanism might be the ability to bind <b>4</b> to lasR and pqsR.</p> Graphical Abstract <p></p>

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Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim.

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年6月19日

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  • Yulin Duan,
  • Xiaoxia Gu,
  • Xincai Hao,
  • Guosheng Cao,
  • Weiguang Sun,
  • Changxing Qi,
  • Yonghui Zhang

摘要

Four previously undescribed polyprenylated acylphloroglucinols, hyperisenins A–D (1–4), along with two known analogues (5 and 6), were obtained from the aerial part of Hypericum seniawinii Maxim. Compounds 1 and 2 were two highly degraded polyprenylated acylphloroglucinols with a cyclohexanone-monocyclic skeleton, while compound 3 was the first example of O-prenylated acylphloroglucinols with a 6/6/6 ring system. Their structures were identified by analyzing NMR, HRESIMS data, and quantum chemical calculations. The biosynthetic pathway of 1 and 2 might originate from bicyclic polyprenylated acylphloroglucinols via a series of complex retro-Claisen, keto − enol tautomerism, and intramolecular cyclization. The bioassay results showed that 4 exhibited quorum sensing inhibitory activity against Pseudomonas aeruginosa, which could decrease the activation of the rhl system, and significantly reduce rhamnolipid levels at a concentration of 100 µM, and the mechanism might be the ability to bind 4 to lasR and pqsR.

Graphical Abstract