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

被引：12

作者：

Xie, Shuangshuang ^{[1
]}

Qi, Changxing ^{[1
]}

Duan, Yulin ^{[1
]}

Hao, Xincai ^{[2
]}

Guo, Yi ^{[1
]}

Deng, Mengyi ^{[1
]}

Qiao, Yuben ^{[1
]}

Shi, Zhengyi ^{[1
]}

Tao, Li ^{[1
]}

Cao, Yunfang ^{[1
]}

Gu, Lianghu ^{[1
]}

Zhou, Yuan ^{[1
]}

Zhang, Yonghui ^{[1
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Pharm, Tongji Med Coll, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China

[2] Hubei Univ Med, Hubei Key Lab Wudang Local Chinese Med Res, Hubei Engn Technol Ctr Comprehens Utilizat Med Pl, Coll Pharm, Shiyan 442000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 03期

基金：

中国国家自然科学基金;

关键词：

BENZOYLPHLOROGLUCINOL DERIVATIVES; ADAMANTYL SKELETON;

D O I：

10.1039/c9qo01158g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 mu M, respectively.

引用

页码：464 / 471

页数：8

共 33 条

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NATURAL PRODUCTS AND BIOPROSPECTING, 2022, 12 (01)
[32] Nardochinoids A-C, Three Dimeric Sesquiterpenoids with Specific Fused-Ring Skeletons from Nardostachys chinensis
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[33] The absolute configurations of hyperilongenols A-C: rare 12,13-seco-spirocyclic polycyclic polyprenylated acylphloroglucinols with enolizable β,β′-tricarbonyl systems from Hypericum longistylum Oliv. (vol 6, pg 1491, 2019)
Zhang, Na
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