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Planta Med
DOI: 10.1055/a-2596-3029
Original Papers

Polycyclic Polyprenylated Acylphloroglucinols from Hypericum himalaicum

Guang-Hui Liu‡
1   Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
3   University of Chinese Academy of Sciences, Beijing, P. R. China
,
Fan Wu‡
1   Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
3   University of Chinese Academy of Sciences, Beijing, P. R. China
4   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, P. R. China
,
Xue-Yan Huo‡
2   School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, P. R. China
,
Hong-Bing Sun
1   Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
3   University of Chinese Academy of Sciences, Beijing, P. R. China
4   Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, P. R. China
,
Zhuo-Lin Jin
1   Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
3   University of Chinese Academy of Sciences, Beijing, P. R. China
,
Yu-Cheng Gu
5   Syngenta Jealottʼs Hill International Research Centre, Bracknell, United Kingdom
,
Da-Le Guo
2   School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, P. R. China
,
Yan Zhou
1   Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
› Author Affiliations
This work was supported by the Key Research and Development Program of Sichuan Province (China) (No. 2022YFS0511).
› Further Information
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Abstract

Six previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) with a vicinal diol moiety (1–6) were isolated from the whole plant of Hypericum himalaicum. Their structures were established through a comprehensive analysis of HRMS and 1D and 2D NMR data, while the absolute configurations were determined using the Mo2(OAc)4-induced circular dichroism (ICD), ECD, and NMR calculations. Compound 1 attenuated the secretion of NO, TNF-α, and IL-6, downregulated the protein expression of COX-2 and iNOS, and inhibited the release of ROS in LPS-induced RAW264.7 macrophages. Further investigation revealed that the anti-inflammatory effects may be attributed to the inhibition of the NF-κB and NLRP3 signaling pathways.

Highlights

  • Six new polycyclic polyprenylated acylphloroglucinols (PPAPs) with a vicinal diol moiety were isolated from the whole plant of Hypericum himalaicum.

  • The absolute configurations of vicinal diol were determined by the Mo2(OAc)4-induced circular dichroism (ICD).

  • Compound 1 may inhibit inflammation by blocking the NF-κB pathway and inhibiting NLRP3 inflammasome activation.

Keywords

Hypericum himalaicum - Hypericaceae - PPAPs - ICD - anti-inflammation

Supporting Information

    Spectroscopic information (NMR, HRMS, UV, IR, and Mo-induced CD) of compounds 1–6 is available as Supporting Information.

  • Supporting Information


Publication History

Received: 24 June 2024

Accepted after revision: 27 April 2025

Accepted Manuscript online:
28 April 2025

Article published online:
20 May 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

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