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诃子变种绒毛诃子中的五个新木脂素:Termitomenins A-E。

Termitomenins A-E: Five new lignans from Terminalia chebula var. tomentella (Kurz) C. B. Clarke.

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.

出版信息

Fitoterapia. 2020 Jun;143:104571. doi: 10.1016/j.fitote.2020.104571. Epub 2020 Mar 21.

Abstract

An elaborated phytochemical study on the fresh fruits of Terminalia chebula var. tomentella (Combretaceae) led to the isolation of five new lignans, including three tetrahydrofuran (1-3) and two furofuran (4 and 5) derivatives, namely termitomenins A-E (1-5), along with 10 known ones. All of them were obtained from the titled plant for the first time. Their structures were determined by extensive spectroscopic analysis, including 1D/2D NMR, MS, UV, IR, electronic circular dichroism (ECD), time-dependent density functional theory (TDDFT) calculation of ECD spectra, and single crystal X-ray diffraction in case of 3. Compounds 1-15 exhibited certain anti-inflammatory activities. Interestingly, compounds 6 (IC = 18.17 ± 0.57  μM) and 7 (IC = 13.66 ± 0.38 μM) which contain an aldehyde group displayed stronger NO inhibitory activity than the positive control L-NMMA (IC = 42.34 ± 0.66 μM).

摘要

对诃子变种绒毛诃子(使君子科)的新鲜果实进行了详细的植物化学研究,从中分离得到了 5 个新的木脂素,包括 3 个四氢呋喃(1-3)和 2 个呋喃(4 和 5)衍生物,即诃子脂素 A-E(1-5),以及 10 个已知化合物。所有这些化合物均首次从该植物中获得。通过广泛的光谱分析,包括 1D/2D NMR、MS、UV、IR、电子圆二色性(ECD)、基于时间密度泛函理论(TDDFT)的 ECD 光谱计算和单晶 X 射线衍射,确定了它们的结构。化合物 1-15 表现出一定的抗炎活性。有趣的是,含有醛基的化合物 6(IC=18.17±0.57μM)和 7(IC=13.66±0.38μM)比阳性对照 L-NMMA(IC=42.34±0.66μM)具有更强的 NO 抑制活性。

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