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<p>Twelve new sesquiterpenoids, sanguisorbaols A–L (<b>1–12</b>), along with twenty-five known compounds (<b>13–37</b>), were isolated from the roots of <i>Sanguisorba officinalis</i>. Structures were determined through comprehensive analysis of HRESIMS, 1D and 2D NMR spectroscopic data, ECD and NMR calculations, and X-ray crystallographic analysis. Among them, compounds <b>1–6</b> were identified as new patchoulol-type sesquiterpenoids bearing hydroxyl groups at different positions, the further structural elucidation revealed that compounds <b>5</b> and <b>6</b> are nor-patchoulol-type sesquiterpenoids due to the absence of the C-11 carbon atom. Compounds <b>7–11</b> were characterized as guaiane-type sesquiterpenoids incorporating a [5,7]-bicyclic framework, among which <b>7</b> and <b>8</b> constitute a pair of C-11 epimers. Notably, compound <b>12</b> possesses a rare bicyclo[4.3.1]decane core scaffold. All the patchoulol-type sesquiterpenoids reported here were obtained for the first time from the genus <i>Sanguisorba</i>, and a plausible biosynthetic pathway was proposed. Furthermore, the anti-melanogenic bioactivity of all isolates was assessed using IBMX-stimulated B16F10 melanoma cells. Compounds <b>3–5</b>, <b>8–10</b>, <b>12–14</b>, <b>17</b>, <b>19</b>, <b>21</b>, <b>22</b>, <b>25–27</b>, <b>29</b>, <b>31</b>, <b>32</b> and <b>34</b> demonstrated significant inhibitory activity against melanogenesis at concentrations ranging from 6.25 to 50 μM. These results highlighted the potential of <i>S. officinalis</i> as a natural anti-melanogenesis agent for skin-whitening or for the treatment of hyperpigmentation disorders.</p> Graphical Abstract <p></p>

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New patchoulol- and guaiane-type sesquiterpenoids from Sanguisorba officinalis with anti-melanogenic activity

  • 期刊论文

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  • 发表日期：

    2026年5月12日

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  • Long-Long Wu,
  • Jia-Rui Wu,
  • Kai-Xian Chen,
  • Liu-Qiang Zhang,
  • Yi-Ming Li

摘要

Twelve new sesquiterpenoids, sanguisorbaols A–L (1–12), along with twenty-five known compounds (13–37), were isolated from the roots of Sanguisorba officinalis. Structures were determined through comprehensive analysis of HRESIMS, 1D and 2D NMR spectroscopic data, ECD and NMR calculations, and X-ray crystallographic analysis. Among them, compounds 1–6 were identified as new patchoulol-type sesquiterpenoids bearing hydroxyl groups at different positions, the further structural elucidation revealed that compounds 5 and 6 are nor-patchoulol-type sesquiterpenoids due to the absence of the C-11 carbon atom. Compounds 7–11 were characterized as guaiane-type sesquiterpenoids incorporating a [5,7]-bicyclic framework, among which 7 and 8 constitute a pair of C-11 epimers. Notably, compound 12 possesses a rare bicyclo[4.3.1]decane core scaffold. All the patchoulol-type sesquiterpenoids reported here were obtained for the first time from the genus Sanguisorba, and a plausible biosynthetic pathway was proposed. Furthermore, the anti-melanogenic bioactivity of all isolates was assessed using IBMX-stimulated B16F10 melanoma cells. Compounds 3–5, 8–10, 12–14, 17, 19, 21, 22, 25–27, 29, 31, 32 and 34 demonstrated significant inhibitory activity against melanogenesis at concentrations ranging from 6.25 to 50 μM. These results highlighted the potential of S. officinalis as a natural anti-melanogenesis agent for skin-whitening or for the treatment of hyperpigmentation disorders.

Graphical Abstract