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2025 , Vol. 15 >Issue 4: 40 - 40

DOI: https://doi.org/10.1007/s13659-025-00520-z

Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim.

  • Yulin Duan ,
  • Xiaoxia Gu ,
  • Xincai Hao ,
  • Guosheng Cao ,
  • Weiguang Sun ,
  • Changxing Qi ,
  • Yonghui Zhang
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  • 1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, Hubei, People's Republic of China;
    2. Department of Pharmacy, Wuhan No. 1 Hospital, Wuhan, 430022, People's Republic of China;
    3. Key Laboratory of Technology of Drug Preparation (Zhengzhou University), Ministry of Education of China;
    Key Laboratory of Henan Province for Drug Quality and Evaluation;
    Institute of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, 450001, China;
    4. Hubei Key Laboratory of Wudang Local Chinese Medicine Research, Hubei Engineering Technology Center for Comprehensive Utilization of Medicinal Plants, College of Pharmacy, Hubei University of Medicine, Shiyan, 442000, People's Republic of China;
    5. College of Pharmacy, Hubei University of Chinese Medicine, Wuhan, 430065, People's Republic of China;
    6. Hubei Shizhen Laboratory, Wuhan, 430065, People's Republic of China;
    7. Key Laboratory of Traditional Chinese Medicine Resource and Compound PrescriptionMinistry of Education, Hubei University of Chinese Medicine, Wuhan, 430065, People's Republic of China

收稿日期: 2025-03-06

  录用日期: 2025-05-13

  网络出版日期: 2025-06-19

基金资助

This work was financially supported by the National Key Research and Development Program of China (2021YFA0910500); National Natural Science Foundation of China (Nos. 32470422 and 32300335); the National Natural Science Foundation of Hubei Province (2023AFB791 and 2023AFB530); Knowledge Innovation Project of Wuhan Science and Technology Bureau (2023020201020534); Natural Science Foundation of Wuhan (2024040801020205); the Science and Technology Major Project of Hubei Province (2021ACA012); the National Key Research and Development Program (No.2023YFC2307004); the open foundation of Key Laboratory of Ethnomedicine (Minzu University of China), Ministry of Education (No. KLEM-KF202402); the open foundation of Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education (RDZH2024001); the open foundation of Hubei Key Laboratory of Wudang Local Chinese Medicine Research (Hubei University of Medicine) (WDCM2024002); the Fundamental Research Funds for the Central Universities (HUST: 2023JYCXJJ058).

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Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim.

  • Yulin Duan ,
  • Xiaoxia Gu ,
  • Xincai Hao ,
  • Guosheng Cao ,
  • Weiguang Sun ,
  • Changxing Qi ,
  • Yonghui Zhang
Expand
  • 1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, Hubei, People's Republic of China;
    2. Department of Pharmacy, Wuhan No. 1 Hospital, Wuhan, 430022, People's Republic of China;
    3. Key Laboratory of Technology of Drug Preparation (Zhengzhou University), Ministry of Education of China;
    Key Laboratory of Henan Province for Drug Quality and Evaluation;
    Institute of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, 450001, China;
    4. Hubei Key Laboratory of Wudang Local Chinese Medicine Research, Hubei Engineering Technology Center for Comprehensive Utilization of Medicinal Plants, College of Pharmacy, Hubei University of Medicine, Shiyan, 442000, People's Republic of China;
    5. College of Pharmacy, Hubei University of Chinese Medicine, Wuhan, 430065, People's Republic of China;
    6. Hubei Shizhen Laboratory, Wuhan, 430065, People's Republic of China;
    7. Key Laboratory of Traditional Chinese Medicine Resource and Compound PrescriptionMinistry of Education, Hubei University of Chinese Medicine, Wuhan, 430065, People's Republic of China

Received date: 2025-03-06

  Accepted date: 2025-05-13

  Online published: 2025-06-19

Supported by

This work was financially supported by the National Key Research and Development Program of China (2021YFA0910500); National Natural Science Foundation of China (Nos. 32470422 and 32300335); the National Natural Science Foundation of Hubei Province (2023AFB791 and 2023AFB530); Knowledge Innovation Project of Wuhan Science and Technology Bureau (2023020201020534); Natural Science Foundation of Wuhan (2024040801020205); the Science and Technology Major Project of Hubei Province (2021ACA012); the National Key Research and Development Program (No.2023YFC2307004); the open foundation of Key Laboratory of Ethnomedicine (Minzu University of China), Ministry of Education (No. KLEM-KF202402); the open foundation of Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education (RDZH2024001); the open foundation of Hubei Key Laboratory of Wudang Local Chinese Medicine Research (Hubei University of Medicine) (WDCM2024002); the Fundamental Research Funds for the Central Universities (HUST: 2023JYCXJJ058).

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摘要

Four previously undescribed polyprenylated acylphloroglucinols, hyperisenins A–D (1–4), along with two known analogues (5 and 6), were obtained from the aerial part of Hypericum seniawinii Maxim. Compounds 1 and 2 were two highly degraded polyprenylated acylphloroglucinols with a cyclohexanone-monocyclic skeleton, while compound 3 was the first example of O-prenylated acylphloroglucinols with a 6/6/6 ring system. Their structures were identified by analyzing NMR, HRESIMS data, and quantum chemical calculations. The biosynthetic pathway of 1 and 2 might originate from bicyclic polyprenylated acylphloroglucinols via a series of complex retro-Claisen, keto-enol tautomerism, and intramolecular cyclization. The bioassay results showed that 4 exhibited quorum sensing inhibitory activity against Pseudomonas aeruginosa, which could decrease the activation of the rhl system, and significantly reduce rhamnolipid levels at a concentration of 100 μM, and the mechanism might be the ability to bind 4 to lasR and pqsR.

关键词： Polyprenylated Acylphloroglucinols; Hypericum seniawinii Maxim.; Quorum sensing inhibitory; Pseudomonas aeruginosa

本文引用格式

Yulin Duan , Xiaoxia Gu , Xincai Hao , Guosheng Cao , Weiguang Sun , Changxing Qi , Yonghui Zhang . Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim.[J]. 应用天然产物, 2025 , 15(4) : 40 -40 . DOI: 10.1007/s13659-025-00520-z

Abstract

Four previously undescribed polyprenylated acylphloroglucinols, hyperisenins A–D (1–4), along with two known analogues (5 and 6), were obtained from the aerial part of Hypericum seniawinii Maxim. Compounds 1 and 2 were two highly degraded polyprenylated acylphloroglucinols with a cyclohexanone-monocyclic skeleton, while compound 3 was the first example of O-prenylated acylphloroglucinols with a 6/6/6 ring system. Their structures were identified by analyzing NMR, HRESIMS data, and quantum chemical calculations. The biosynthetic pathway of 1 and 2 might originate from bicyclic polyprenylated acylphloroglucinols via a series of complex retro-Claisen, keto-enol tautomerism, and intramolecular cyclization. The bioassay results showed that 4 exhibited quorum sensing inhibitory activity against Pseudomonas aeruginosa, which could decrease the activation of the rhl system, and significantly reduce rhamnolipid levels at a concentration of 100 μM, and the mechanism might be the ability to bind 4 to lasR and pqsR.

Key words： Polyprenylated Acylphloroglucinols; Hypericum seniawinii Maxim.; Quorum sensing inhibitory; Pseudomonas aeruginosa

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