Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim.
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 cyclohexan...
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| Language: | English |
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SpringerOpen
2025-06-01
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| Series: | Natural Products and Bioprospecting |
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| Online Access: | https://doi.org/10.1007/s13659-025-00520-z |
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| author | Yulin Duan Xiaoxia Gu Xincai Hao Guosheng Cao Weiguang Sun Changxing Qi Yonghui Zhang |
| author_facet | Yulin Duan Xiaoxia Gu Xincai Hao Guosheng Cao Weiguang Sun Changxing Qi Yonghui Zhang |
| author_sort | Yulin Duan |
| collection | DOAJ |
| description | 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. Graphical Abstract |
| format | Article |
| id | doaj-art-ab45baaeaf254228a01f6a707deba037 |
| institution | OA Journals |
| issn | 2192-2195 2192-2209 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | SpringerOpen |
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| series | Natural Products and Bioprospecting |
| spelling | doaj-art-ab45baaeaf254228a01f6a707deba0372025-08-20T02:10:35ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092025-06-0115111210.1007/s13659-025-00520-zDiscovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim.Yulin Duan0Xiaoxia Gu1Xincai Hao2Guosheng Cao3Weiguang Sun4Changxing Qi5Yonghui Zhang6Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Wudang Local Chinese Medicine Research, Hubei Engineering Technology Center for Comprehensive Utilization of Medicinal Plants, College of Pharmacy, Hubei University of MedicineCollege of Pharmacy, Hubei University of Chinese MedicineHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyAbstract 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. Graphical Abstracthttps://doi.org/10.1007/s13659-025-00520-zPolyprenylated AcylphloroglucinolsHypericum seniawinii Maxim.Quorum sensing inhibitoryPseudomonas aeruginosa |
| spellingShingle | 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. Natural Products and Bioprospecting Polyprenylated Acylphloroglucinols Hypericum seniawinii Maxim. Quorum sensing inhibitory Pseudomonas aeruginosa |
| title | Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim. |
| title_full | Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim. |
| title_fullStr | Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim. |
| title_full_unstemmed | Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim. |
| title_short | Discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from Hypericum seniawinii Maxim. |
| title_sort | discovery of structurally diverse polyprenylated acylphloroglucinols with quorum sensing inhibitory activity from hypericum seniawinii maxim |
| topic | Polyprenylated Acylphloroglucinols Hypericum seniawinii Maxim. Quorum sensing inhibitory Pseudomonas aeruginosa |
| url | https://doi.org/10.1007/s13659-025-00520-z |
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