Hyparillums A and B: polycyclic polyprenylated acylphloroglucinols from Hypericum patulum

IF 4 2区医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE

Chinese Journal of Natural Medicines Pub Date : 2024-03-01 DOI:10.1016/S1875-5364(24)60599-6

Yulin DUAN , Zhengyi SHI , Fei SONG , Zhangrong HOU , Xiaosheng TAN , Yeting ZHANG , Xincai HAO , Gang CHEN , Changxing QI , Yonghui ZHANG

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引用次数: 0

Abstract

Hyparillums A (1) and B (2), two previously unidentified polycyclic polyprenylated acylphloroglucinols (PPAPs) with intricate architectures, were isolated from Hypericum patulum Thunb. Hyparillum A was the first PPAP with eight-carbon rings based on an unprecedented 6/6/5/6/6/5/6/4 octocyclic system featuring a rare heptacyclo[10.8.1.1^1,10.0^3,8.0^8,21.0^12,19.0^14,17]docosane core. In contrast, hyparillum B featured a novel heptacyclic architecture (6/6/5/6/6/5/5) based on a hexacyclo[9.6.1.1^1,9.0^3,7.0^7,18.0^11,16]nonadecane motif. Furthermore, hyparillums A and B demonstrated promising inhibitory effects on the proliferation of murine splenocytes stimulated by anti-CD3/anti-CD28 monoclonal antibodies and lipopolysaccharide, exhibiting half-maximal inhibitory concentration (IC₅₀) values ranging from 6.13 ± 0.86 to 12.69 ± 1.31 μmol·L⁻¹.

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金丝桃 A 和 B：来自金丝桃的多环多烯酰化酰基氯葡萄糖醇

从金丝桃（Hypericum patulum Thunb.）中分离出了 Hyparillums A (1) 和 B (2)，这是两种以前未被发现的具有复杂结构的多环多烯酰化酰基氯葡萄糖醇（PPAPs）。金丝桃 A 是第一种具有八碳环的 PPAP，其基础是前所未有的 6/6/5/6/6/5/6/4 八环体系，具有罕见的七环[10.8.1.11,10.03,8.08,21.012,19.014,17]二十二烷核心。与此相反，副菌群 B 具有一种基于六环[9.6.1.11,9.03,7.07,18.011,16]壬烷基团的新型七环结构（6/6/5/6/5/5）。此外，拟南芥 A 和 B 在抗-CD3/抗-CD28 单克隆抗体和脂多糖的刺激下，对小鼠脾细胞的增殖具有良好的抑制作用，其半最大抑制浓度 (IC50) 值范围为 6.13 ± 0.86 至 12.69 ± 1.31 μmol-L-1。

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来源期刊

Chinese Journal of Natural Medicines INTEGRATIVE & COMPLEMENTARY MEDICINE-PHARMACOLOGY & PHARMACY

CiteScore

7.50

自引率

4.30%

发文量

2235

期刊介绍： The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM). Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.