Wilsonglucinols A–C, homoadamantane-type polycyclic polyprenylated acylphloroglucinols with unusual fused epoxy ring skeletons from Hypericum wilsonii

文献情報

出版日 2019-12-17

DOI 10.1039/C9QO01158G

インパクトファクター 5.281

著者

Shuangshuang Xie, Changxing Qi, Yulin Duan, Xincai Hao, Yi Guo, Mengyi Deng, Yuben Qiao, Zhengyi Shi, Li Tao, Yunfang Cao, Lianghu Gu, Yuan Zhou, Yonghui Zhang

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要旨

Wilsonglucinols A–C (1–3), three new polycyclic polyprenylated acylphloroglucinols (PPAPs) possessing novel homoadamantane architectures based on unusual epoxy-ring-fused systems, along with four new analogues, wilsonglucinols D–G (4–7), were isolated from the aerial parts of Hypericum wilsonii. The structures of the new compounds were determined using a combination of NMR, HRESIMS data, electronic circular dichroism (ECD) comparisons, and X-ray crystallography. Structurally, wilsonglucinol A (1) features a new hexahydrofuro[2,3-c][1,2]dioxine motif, and wilsonglucinols B (2) and C (3) possess unusual decahydro-1,8:6a,10-dimethanocycloocta[1,2-b:1,8-b′]difuran fragments. More significantly, an in vitro bioassay showed that 1, 3, and 9 exhibited moderate immunosuppressive activities against the proliferation of murine splenocytes stimulated by anti-CD3/anti-CD28 monoclonal antibodies, with IC50 values of 9.7, 9.3, and 7.1 μM, respectively.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Wilsonglucinols A–C, homoadamantane-type polycyclic polyprenylated acylphloroglucinols with unusual fused epoxy ring skeletons from Hypericum wilsonii

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