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<p>Twenty-eight prenylated acylphloroglucinols, including the new hypulatones C–F (<b>1</b>–<b>4</b>), have been isolated from the fruits of <i>Hypericum patulum</i> and structurally characterized. Compound <b>1</b> represents a rare meroterpenoid formed through the addition of a prenylated acylphloroglucinol unit and a sesquiterpenoid moiety. Spirocyclic polycyclic polyprenylated acylphloroglucinol <b>2</b> contains six chiral centers, and its relative configuration was established based on <sup>1</sup>H–<sup>1</sup>H coupling constants, conformational analysis, and NOE correlations. The cytotoxic activities of all isolates against two human carcinoma cell lines (Huh-7 and Panc-1) were evaluated using the CCK-8 assay. Bioassay results indicated that compounds <b>6</b>, <b>8</b>, and <b>15</b> exhibited moderate antiproliferative activity.</p> Graphical Abstract <p></p>

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Prenylated acylphloroglucinols from the fruits of Hypericum patulum

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年4月23日

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  • Yu-Feng Qiu,
  • Yi Zhou,
  • Cheng Chen,
  • Juan Huang,
  • Xing-Wei Yang

摘要

Twenty-eight prenylated acylphloroglucinols, including the new hypulatones C–F (1–4), have been isolated from the fruits of Hypericum patulum and structurally characterized. Compound 1 represents a rare meroterpenoid formed through the addition of a prenylated acylphloroglucinol unit and a sesquiterpenoid moiety. Spirocyclic polycyclic polyprenylated acylphloroglucinol 2 contains six chiral centers, and its relative configuration was established based on 1H–1H coupling constants, conformational analysis, and NOE correlations. The cytotoxic activities of all isolates against two human carcinoma cell lines (Huh-7 and Panc-1) were evaluated using the CCK-8 assay. Bioassay results indicated that compounds 6, 8, and 15 exhibited moderate antiproliferative activity.

Graphical Abstract