Hypersonins A–D, Polycyclic Polyprenylated Acylphloroglucinols with a 1,2-seco-Homoadamantane Architecture from Hypericum wilsonii

Hypersonins A–D (1–4), four 1,2-seco-homoadamantane type polycyclic polyprenylated acylphloroglucinols (PPAPs) possessing a new bicyclo[4.3.1]­decane-3-methoxycarbonyl architecture, were obtained from Hypericum wilsonii. The structures of hypersonins A–D were identified by spectroscopic data, electr...

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Published inJournal of natural products (Washington, D.C.) Vol. 83; no. 6; pp. 1804 - 1809
Main Authors Xie, Shuangshuang, Tan, Xiaosheng, Liu, Yaping, Duan, Yulin, Chen, Gang, Feng, Hao, Sun, Lingjuan, Huang, Yingying, Guo, Yi, Shi, Zhengyi, Zhou, Yuan, Qi, Changxing, Zhang, Yonghui
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.06.2020
Amer Chemical Soc
Subjects
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
BENZOYLPHLOROGLUCINOL DERIVATIVES
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Summary:Hypersonins A–D (1–4), four 1,2-seco-homoadamantane type polycyclic polyprenylated acylphloroglucinols (PPAPs) possessing a new bicyclo[4.3.1]­decane-3-methoxycarbonyl architecture, were obtained from Hypericum wilsonii. The structures of hypersonins A–D were identified by spectroscopic data, electronic circular dichroism comparison, and X-ray crystallographic data. Hypersonins A–D are the first seco-homoadamantane-type PPAPs with cleavage at the C-1–C-2 bond. Hypersonin A (1) showed moderate inhibitory activity to anti-CD3/anti-CD28 monoclonal antibody-induced proliferation of murine splenocytes, with an IC50 value of 8.3 ± 0.2 μM.
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ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.9b01187