<p>Four triterpenes with the unprecedented pentacyclic skeletons were isolated from <i>Limax maximus</i>, the traditional medicine of the Zhuang ethnic group in Guangxi. Notably, compounds <b>1</b>−<b>4</b> were characterized by rare&#xa0;7/6/5 tricyclic ring moiety linked to 6/5 bicyclic moiety via three carbon chain. The structures of compounds <b>1</b>−<b>4</b> were elucidated by comprehensive spectroscopic analysis. The absolute configurations of compounds <b>1</b>−<b>2</b> were determined by single-crystal X-ray diffraction analysis using Cu Kα radiation. Biogenetically, compound <b>1</b> could be derived from the tetraepoxysqualenes, via cyclisation and hydroxylation reactions. Bioactivity assay results showed that compound <b>4</b> significantly inhibited LPS-induced NO production in RAW 264.7 cells at 25&#xa0;µM with inhibition of NO production by 47%.</p> Graphical Abstract <p></p>

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Unprecedented triterpenes with anti-inflammatory activity from Limax maximus

  • Ya-feng Wang,
  • Pei-de Tang,
  • Rui-jie He,
  • Zhang-bin Liu,
  • Yong-qiong Wei,
  • Jun Ruan,
  • Bing-yuan Yang,
  • Yong-lin Huang

摘要

Four triterpenes with the unprecedented pentacyclic skeletons were isolated from Limax maximus, the traditional medicine of the Zhuang ethnic group in Guangxi. Notably, compounds 14 were characterized by rare 7/6/5 tricyclic ring moiety linked to 6/5 bicyclic moiety via three carbon chain. The structures of compounds 14 were elucidated by comprehensive spectroscopic analysis. The absolute configurations of compounds 12 were determined by single-crystal X-ray diffraction analysis using Cu Kα radiation. Biogenetically, compound 1 could be derived from the tetraepoxysqualenes, via cyclisation and hydroxylation reactions. Bioactivity assay results showed that compound 4 significantly inhibited LPS-induced NO production in RAW 264.7 cells at 25 µM with inhibition of NO production by 47%.

Graphical Abstract