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<p>A phytochemical study on the 70% ethanol extract of the stem bark of Vietnamese <i>Ceiba pentandra</i> (L.) Gaertn led to the isolation of the three new sesquiterpene alkaloids pentandralactams A (<b>1</b>), B (<b>2</b>), and C (<b>3</b>), along with the six known compounds thespesilactam (<b>4</b>), isohemigossylic acid lactone-2-methyl ether (<b>5</b>), alanense H (<b>6</b>), hibiscolactone A (<b>7</b>), 11-hydroxy-2-O-methylhibiscolactone A (<b>8</b>), and vavain 3′-O-<i>β</i>-D-glucoside (<b>9</b>). Their structures were elucidated through extensive spectroscopic analyses, including HR-ESI-MS, and 1D and 2D NMR. All isolates were tested for their ability to inhibit NO production in LPS-induced RAW 264.7 cells. The sesquiterpene alkaloids pentandralactams A–C (<b>1 − 3</b>) exhibited potent NO inhibition with IC<sub>50</sub> values of 8.03, 9.79, and 11.28 µM, respectively. In silico, compound <b>1</b> demonstrated the strongest binding affinity with iNOS enzyme with extensive π-π stacking, hydrophobic interactions, and a key hydrogen bond, without any unfavorable contacts. Compound <b>2</b> formed multiple hydrogen bonds in addition to π-π interactions, contributing to stable binding, though its broader interaction distribution may slightly affect its specificity. Compound <b>3</b> also engaged in essential π-π and hydrophobic contacts but exhibited an unfavorable acceptor-acceptor interaction with ASN370, potentially reducing its efficacy. These results highlight the potential of <i>C. pentandra</i>-derived compounds for further development as anti-inflammatory agents.</p> Graphical abstract <p></p>

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New pentandralactams from Vietnamese Ceiba pentandra (L.) Gaertn. and their anti-inflammatory activity via NO production inhibition

  • 期刊论文

  • 发表日期：

    2026年5月13日

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  • Chuong Nguyen Ngoc,
  • Manh Hung Tran,
  • Thuy Mi Pham Lam,
  • Hieu Thi Hong Nguyen,
  • Minh-Anh Nguyen Ngo Le,
  • Trong Tuan Vo

摘要

A phytochemical study on the 70% ethanol extract of the stem bark of Vietnamese Ceiba pentandra (L.) Gaertn led to the isolation of the three new sesquiterpene alkaloids pentandralactams A (1), B (2), and C (3), along with the six known compounds thespesilactam (4), isohemigossylic acid lactone-2-methyl ether (5), alanense H (6), hibiscolactone A (7), 11-hydroxy-2-O-methylhibiscolactone A (8), and vavain 3′-O-β-D-glucoside (9). Their structures were elucidated through extensive spectroscopic analyses, including HR-ESI-MS, and 1D and 2D NMR. All isolates were tested for their ability to inhibit NO production in LPS-induced RAW 264.7 cells. The sesquiterpene alkaloids pentandralactams A–C (1 − 3) exhibited potent NO inhibition with IC50 values of 8.03, 9.79, and 11.28 µM, respectively. In silico, compound 1 demonstrated the strongest binding affinity with iNOS enzyme with extensive π-π stacking, hydrophobic interactions, and a key hydrogen bond, without any unfavorable contacts. Compound 2 formed multiple hydrogen bonds in addition to π-π interactions, contributing to stable binding, though its broader interaction distribution may slightly affect its specificity. Compound 3 also engaged in essential π-π and hydrophobic contacts but exhibited an unfavorable acceptor-acceptor interaction with ASN370, potentially reducing its efficacy. These results highlight the potential of C. pentandra-derived compounds for further development as anti-inflammatory agents.

Graphical abstract