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<p>Two previously undescribed specialized metabolites, erecricins F (<b>1</b>) and G (<b>2</b>), along with two known metabolites, erectumins A (<b>3</b>) and B (<b>4</b>), were isolated from the aerial parts of <i>Hypericum erectum</i> Thunb. (Hypericaceae). Detailed spectroscopic analyses revealed erecricin F (<b>1</b>) to be a C<sub>30</sub> meroterpene with four isoprene units, and erecricin G (<b>2</b>) to be a prenylated acylphloroglucinol biogenetically related to <b>1</b>. The relative configurations of erecricins F (<b>1</b>) and G (<b>2</b>) were assigned by NOESY analysis and GIAO NMR calculation, while their absolute configurations were deduced by comparison of the ECD spectra with TDDFT calculated spectra. The relative configurations of <b>3</b> and <b>4</b> were also elucidated by the similar method as for <b>1</b> and <b>2</b>. Erecricins F (<b>1</b>) and G (<b>2</b>) and erectumins A (<b>3</b>) and B (<b>4</b>) were evaluated for their inhibitory effect against IL-1<i>β</i> release from LPS-stimulated murine microglial cells and anti-ferroptosis activity using human hepatoma Hep3B cells.</p> Graphical Abstract <p></p>

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Meroterpenes and prenylated acylphloroglucinol from the aerial parts of Hypericum erectum

  • 期刊论文

  • 发表日期：

    2025年2月18日

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  • Rena Takizawa,
  • Chiaki Nagata,
  • Sang-Yong Kim,
  • Daisuke Tsuji,
  • Mareshige Kojoma,
  • Reiko Akagi,
  • Yoshiki Kashiwada,
  • Naonobu Tanaka

摘要

Two previously undescribed specialized metabolites, erecricins F (1) and G (2), along with two known metabolites, erectumins A (3) and B (4), were isolated from the aerial parts of Hypericum erectum Thunb. (Hypericaceae). Detailed spectroscopic analyses revealed erecricin F (1) to be a C30 meroterpene with four isoprene units, and erecricin G (2) to be a prenylated acylphloroglucinol biogenetically related to 1. The relative configurations of erecricins F (1) and G (2) were assigned by NOESY analysis and GIAO NMR calculation, while their absolute configurations were deduced by comparison of the ECD spectra with TDDFT calculated spectra. The relative configurations of 3 and 4 were also elucidated by the similar method as for 1 and 2. Erecricins F (1) and G (2) and erectumins A (3) and B (4) were evaluated for their inhibitory effect against IL-1β release from LPS-stimulated murine microglial cells and anti-ferroptosis activity using human hepatoma Hep3B cells.

Graphical Abstract