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<p>Two pairs of undescribed alkaloid enantiomers, (+)-/(−)-ormohenins A (<b>1</b>) and B (<b>2</b>), were isolated from the seeds of <i>Ormosia henryi</i> Prain, along with four undescribed alkaloids (<b>3</b>, <b>4</b>,<b> 7</b> and <b>8</b>) and seven known ones (<b>5</b>, <b>6</b>, <b>9</b>–<b>13</b>). Compounds <b>1</b>–<b>6</b> belong to the ormosanine-type alkaloids, compounds <b>7</b>, <b>9</b>, and <b>11</b> are of the lupinine-type, compounds <b>8</b> and <b>10</b> are classified as anagyrine-type alkaloids, <b>12</b> and <b>13</b> are cytisine-type alkaloids. The chemical structures of <b>1</b>–<b>13</b> were elucidated through comprehensive NMR and MS data analyses. Furthermore, the racemates (±)-<b>1</b> and (±)-<b>2</b> were successfully resolved into their respective optically pure enantiomers using a chiral HPLC system. The absolute configurations of compounds <b>1–3</b> were determined using single-crystal X-ray diffraction and corroborated by DFT calculations of specific rotations. The absolute configurations of <b>4</b>, <b>7</b>, and <b>8</b> were assigned by the experimental electronic circular dichroism (ECD) with those predicted using TDDFT calculations. Compound <b>12</b> exhibited significant acetylcholinesterase (AChE) inhibitory activity with the IC<sub>50</sub> value of 6.581 ± 1.203&#xa0;μM. The neuroprotective effects of these compounds against A<i>β</i><sub>25-35</sub> induced cell damage in PC12 cells were investigated, and compounds<b> 3</b>, <b>9</b>, and <b>12</b> exhibited significant neuroprotective effects against A<i>β</i><sub>25-35</sub> induced PC12 cell damage, with the EC<sub>50</sub> values of 7.99–15.49&#xa0;μM, respectively.</p> Graphical Abstract <p></p>

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(+)-/(−)-Ormohenins A and B, two pairs of ormosanine-type enantiomers and their derivatives with neuroprotective activity from Ormosia henryi Prain

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  • 发表日期：

    2025年8月25日

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  • Ming Cheng,
  • Xian-Si Zeng,
  • Zhao-Yun Yin,
  • Xiao-Yan Xie,
  • Jia-Wen Zhu,
  • Jian-Feng Wang,
  • Ying-Kun Sheng,
  • Jin-Biao Xu

摘要

Two pairs of undescribed alkaloid enantiomers, (+)-/(−)-ormohenins A (1) and B (2), were isolated from the seeds of Ormosia henryi Prain, along with four undescribed alkaloids (3, 4, 7 and 8) and seven known ones (5, 6, 9–13). Compounds 1–6 belong to the ormosanine-type alkaloids, compounds 7, 9, and 11 are of the lupinine-type, compounds 8 and 10 are classified as anagyrine-type alkaloids, 12 and 13 are cytisine-type alkaloids. The chemical structures of 1–13 were elucidated through comprehensive NMR and MS data analyses. Furthermore, the racemates (±)-1 and (±)-2 were successfully resolved into their respective optically pure enantiomers using a chiral HPLC system. The absolute configurations of compounds 1–3 were determined using single-crystal X-ray diffraction and corroborated by DFT calculations of specific rotations. The absolute configurations of 4, 7, and 8 were assigned by the experimental electronic circular dichroism (ECD) with those predicted using TDDFT calculations. Compound 12 exhibited significant acetylcholinesterase (AChE) inhibitory activity with the IC50 value of 6.581 ± 1.203 μM. The neuroprotective effects of these compounds against Aβ25-35 induced cell damage in PC12 cells were investigated, and compounds 3, 9, and 12 exhibited significant neuroprotective effects against Aβ25-35 induced PC12 cell damage, with the EC50 values of 7.99–15.49 μM, respectively.

Graphical Abstract