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从 Leucosceptrum canum 中分离得到具有对映环戊烯酮的免疫抑制白藜芦醇型倍半萜。

Immunosuppressive leucosceptrane-type sesterterpenoids with antipodal cyclopentenones isolated from Leucosceptrum canum.

机构信息

State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, PR China.

College of Bioscience and Biotechnology, Shenyang Agricultural University, Shenyang, 110866, PR China.

出版信息

Phytochemistry. 2025 Jan;229:114305. doi: 10.1016/j.phytochem.2024.114305. Epub 2024 Oct 16.

Abstract

Ten undescribed leucosceptrane-type sesterterpenoids with antipodal cyclopentenone moieties were isolated from the leaves of Leucosceptrum canum. Their structures including absolute configurations were elucidated by comprehensive spectroscopic analyses (including 1D and 2D NMR, and HRMS) and ECD calculations. In vitro immunosuppressive effects of these sesterterpenoids against the proliferation of T cells and the secretion of cytokine IFN-γ were evaluated. Among them, 11α-H-leucosceptroid C, 5,13-dehydro-11α-H-leucosceptroid C, 5,13-dehydro-11β-hydroxy-leucosceptroid C, and 5,13-dehydro-11α-hydroxy-leucosceptroid C significantly inhibited IFN-γ secretion with IC values of 12.55-23.62 μM. More remarkable inhibitory effects against IFN-γ secretion were observed for 5,13-dehydro-11β-hydroxy-leucosceptroid D, leucosceptroid U, 14-epi-leucosceptroid U, leucosceptroid V, and 14-epi-leucosceptroid V, with IC values of 4.32-9.47 μM.

摘要

从白毛银背藤的叶子中分离得到了 10 种具有对映环戊烯酮部分的新型白头翁烷型倍半萜。通过全面的光谱分析(包括 1D 和 2D NMR 和 HRMS)和 ECD 计算确定了它们的结构包括绝对构型。评估了这些倍半萜对 T 细胞增殖和细胞因子 IFN-γ分泌的体外免疫抑制作用。其中,11α-H-白头翁素 C、5,13-去氢-11α-H-白头翁素 C、5,13-去氢-11β-羟基白头翁素 C 和 5,13-去氢-11α-羟基白头翁素 C 显著抑制 IFN-γ 的分泌,IC 值为 12.55-23.62 μM。5,13-去氢-11β-羟基白头翁素 D、白头翁素 U、14-表-白头翁素 U、白头翁素 V 和 14-表-白头翁素 V 对 IFN-γ 分泌的抑制作用更为显著,IC 值为 4.32-9.47 μM。

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