<p>Sixteen previously undiscovered guaiane-type sesquiterpene dimers, xylanins A–P (<b>1–16</b>), along with six known analogues (<b>17–22</b>), were isolated from the branches and leaves of <i>Xylopia vielana</i> with chromatographic techniques. Their structures including absolute configurations were determined by high-resolution electrospray ionization mass spectrometry (HR-ESI–MS), nuclear magnetic resonance (NMR) data, electron circular dichroism (ECD) spectra, as well as X-ray crystallographic analysis. In cytotoxicity test, we found that five compounds (<b>6</b>, <b>7</b>, <b>8</b>, <b>9</b> and <b>12</b>) had cytotoxic activities in vitro against the human pancreatic cancer (PANC-1) and human prostate cancer (PC-3) cell lines. Of these compounds, compound <b>8</b> showed a relatively greater cytotoxic effect against PANC-1 cell lines with half maximal inhibitory concentration (IC<sub>50</sub>) value of 1.06&#xa0;μM. Flow cytometry analysis showed that the apoptosis rate of PANC-1 cells increased with increasing concentrations of compound <b>8</b>, and also demonstrated that the cell cycle of PANC-1 cells was arrested at S phase by the treatment of compound <b>8</b>. By the invasion test, compound <b>8</b> was found to restrain the invasion of PANC-1 cells. In autophagy assay, we observed increased microtubule-associated protein 1 light chain 3 <b>(</b>LC3) by immunofluorescence in the compound <b>8</b>-treated group.</p> Graphical Abstract <p></p>

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Xylanins A–P, sixteen new guaiane-type dimers from the branches and leaves of Xylopia vielana with anti-proliferative activity against PANC-1 cell line

  • Xianglian Jiang,
  • Ting Zhang,
  • Fancheng Meng,
  • Min Chen,
  • Guowei Wang

摘要

Sixteen previously undiscovered guaiane-type sesquiterpene dimers, xylanins A–P (1–16), along with six known analogues (17–22), were isolated from the branches and leaves of Xylopia vielana with chromatographic techniques. Their structures including absolute configurations were determined by high-resolution electrospray ionization mass spectrometry (HR-ESI–MS), nuclear magnetic resonance (NMR) data, electron circular dichroism (ECD) spectra, as well as X-ray crystallographic analysis. In cytotoxicity test, we found that five compounds (6, 7, 8, 9 and 12) had cytotoxic activities in vitro against the human pancreatic cancer (PANC-1) and human prostate cancer (PC-3) cell lines. Of these compounds, compound 8 showed a relatively greater cytotoxic effect against PANC-1 cell lines with half maximal inhibitory concentration (IC50) value of 1.06 μM. Flow cytometry analysis showed that the apoptosis rate of PANC-1 cells increased with increasing concentrations of compound 8, and also demonstrated that the cell cycle of PANC-1 cells was arrested at S phase by the treatment of compound 8. By the invasion test, compound 8 was found to restrain the invasion of PANC-1 cells. In autophagy assay, we observed increased microtubule-associated protein 1 light chain 3 (LC3) by immunofluorescence in the compound 8-treated group.

Graphical Abstract