Academic Journal
Kaurepenoid A, a 2-nor-ent-kaurane diterpenoid with P-glycoprotein-mediated reversal of multidrug resistance activity from the fungus Bipolaris sp.
| Τίτλος: | Kaurepenoid A, a 2-nor-ent-kaurane diterpenoid with P-glycoprotein-mediated reversal of multidrug resistance activity from the fungus Bipolaris sp. |
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| Συγγραφείς: | Shen Y; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Ding N; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Zheng M; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China; Department of Pharmacy, Union Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430022, China., Guo T; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Gu X; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Liang Y; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China; Department of Pharmacy, The Central Hospital of Wuhan, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430014, China., Chen C; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China., Li Q; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: liqin2023@hust.edu.cn., Zhang Y; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: zhangyh@mails.tjmu.edu.cn., Zhu H; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: zhuhucheng@hust.edu.cn. |
| Πηγή: | Chinese journal of natural medicines [Chin J Nat Med] 2026 Oct; Vol. 24 (10), pp. 1251-1261. |
| Τύπος έκδοσης: | Journal Article |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Science Press Country of Publication: China NLM ID: 101504416 Publication Model: Print Cited Medium: Internet ISSN: 1875-5364 (Electronic) Linking ISSN: 18755364 NLM ISO Abbreviation: Chin J Nat Med Subsets: MEDLINE |
| Imprint Name(s): | Publication: <2009-> : Beijing : Science Press ; Elsevier Original Publication: Nanjing : Ke xue chu ban she |
| Ιατρικοί όροι (MeSH): | Diterpenes, Kaurane*/chemistry , Diterpenes, Kaurane*/pharmacology , Diterpenes, Kaurane*/isolation & purification , ATP Binding Cassette Transporter, Subfamily B, Member 1*/metabolism , ATP Binding Cassette Transporter, Subfamily B, Member 1*/genetics , Drug Resistance, Multiple*/drug effects , Bipolaris*/chemistry, Drug Resistance, Neoplasm/drug effects ; Molecular Structure ; Humans ; Cell Line, Tumor |
| Περίληψη: | Chemical research on the fungus Bipolaris sp. led to the identification of seven ent-kaurane diterpenoids, kaurepenoids A-G (1-7), marking the first isolation of such diterpenoids from this genus. Kaurepenoids A-F (1-6) represent the first 2-nor-ent-kaurane diterpenoids with a fused 5/6/6/5 tetracyclic ring system. Kaurepenoid G (7) bears a rare 2,3-epoxy-ent-kaurane skeleton. Their structures and absolute configurations were elucidated by NMR, ECD calculations, and single-crystal X-ray diffraction analyses. Putative biosynthetic pathways for kaurepenoids A-F were proposed. Furthermore, the derivatization of both kaurepenoids B and C as starting materials afforded five derivatives (8-12). Among these compounds, kaurepenoid A could increase the efficacy of anticancer drug paclitaxel (PTX) by 204-fold at 20 μmol·L-1. Mechanistic investigation demonstrated that kaurepenoid A could inhibit the transport function of P-glycoprotein (P-gp) rather than affecting its expression, and the possible recognition mechanism was predicted by molecular docking. (Copyright © 2026 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.) |
| Contributed Indexing: | Keywords: Bipolaris sp.; Derivatization; Ent-kaurane; Multidrug resistance; P-glycoprotein |
| Substance Nomenclature: | 0 (Diterpenes, Kaurane) 0 (ATP Binding Cassette Transporter, Subfamily B, Member 1) |
| Entry Date(s): | Date Created: 20260930 Date Completed: 20260930 Latest Revision: 20260930 |
| Update Code: | 20261001 |
| DOI: | 10.1016/S1875-5364(26)61218-6 |
| PMID: | 42816037 |
| Βάση Δεδομένων: | MEDLINE |
| ISSN: | 1875-5364 |
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| DOI: | 10.1016/S1875-5364(26)61218-6 |