ヒハツ果実に含まれる機能性食品・医薬用途の活性成分を特定(Researchers Identify Active Compounds in Piper Longum Fruits with Potential for Functional Foods and Medicine)

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2025-03-25 中国科学院(CAS)

中国科学院新疆理化技術研究所のハジ・アクバル・アイサ教授のチームは、ヒハツ(Piper longum)の果実から、抗炎症・抗糖尿病作用を持つ12組の二量体アミドアルカロイドのエナンチオマーを分離した。GNPSプラットフォームの分子ネットワーク解析により、既知化合物とは異なる新規クラスターを発見し、piperchabamide Hを手がかりにこれらを同定。構造は分光データ、電子円二色性(ECD)計算、X線解析で決定された。3種はマクロファージモデルで抗炎症活性を示し、他に糖代謝関連酵素への阻害効果も確認された。分子ドッキングと動力学解析により、標的酵素との安定した相互作用が示された。研究成果は機能性食品や医薬品開発への応用が期待される。

<関連情報>

抗炎症および抗糖尿病作用を有するPiper longum L.由来の二量体アミドアルカロイドエナンチオマー Dimeric Amide Alkaloid Enantiomers from Piper longum L. with Anti-Inflammatory and Antidiabetic Effects

Guanghui Gou,Liu Liu,Wenli Bao,Jun Li,and Haji Akber Aisa
Journal of Agricultural and Food Chemistry  Published: March 11, 2025
DOI:https://doi.org/10.1021/acs.jafc.4c13133

Abstract

ヒハツ果実に含まれる機能性食品・医薬用途の活性成分を特定(Researchers Identify Active Compounds in Piper Longum Fruits with Potential for Functional Foods and Medicine)

The fruit of Piper longum L. (Piperaceae), commonly used as a spice in various culinary applications, is renowned for its rich nutritional profile and potential medicinal properties. In this study, a molecular network-based dereplication strategy was employed to isolate 12 dimeric amide alkaloid enantiomers (112) from P. longum fruits, including eight pairs of cyclobutane-type dimers (18) and four pairs of cyclohexene-type dimers (912). Notably, five pairs of cyclobutane-type dimers, namely, piperlongramides E–I (15), and one pair of cyclohexene-type dimers, piperlongramide J (9), were identified as undescribed compounds. The structures of these compounds were elucidated by comprehensive spectroscopic data, electronic circular dichroism (ECD) calculations, and X-ray diffraction analysis. Additionally, these compounds, for the first time, were subjected to chiral resolution. In vitro bioactivity screening revealed that compounds (+)-10, (-)-10, and (+)-3 exhibited notable anti-inflammatory effects in an LPS-induced RAW 264.7 macrophage model, with IC50 values of 23.42 ± 1.04, 32.72 ± 0.54, and 33.52 ± 1.75 μM, respectively. Furthermore, compound (+)-3 also demonstrated significant inhibitory activity againstα-glucosidase, with an IC50 of 11.69 ± 0.91 μM. Compounds (+)-9, (+)-7, and (-)-9, exhibited promising inhibitory activity against PTP1B with IC50 values of 3.30 ± 0.09, 4.30 ± 0.18, and 4.37 ± 0.37 μM, respectively, indicating their potential antidiabetic effects. This study highlights the promising application of these amide alkaloid dimers in the development of functional foods and pharmaceutical products, thereby expanding the health-promoting potential of P. longum fruits.

有機化学・薬学
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