Structurally diverse deformed phenanthrenes from Strophioblachia fimbricalyx with cytotoxic activities by inducing cell apoptosis
Copyright © 2024 Elsevier Ltd. All rights reserved..
A group of phenanthrene derivatives with different deformed types, including four previously undescribed derivatives (1-4), an undescribed natural product (5) and five known compounds (6-10), were isolated from the leaves and stems of Strophioblachia fimbricalyx by molecular networking based on UPLC-MS/MS method. Their structures were established by 1D/2D NMR spectroscopy, HRESIMS, quantum chemistry calculation, and single crystal X-ray diffraction. In biogenic pathways, series of deformed phenanthrenes were all suspected to be derived from 6/6/6 tricyclic phenanthrenes with a gem-dimethyl unit in one ring as characteristic components of Strophioblachia. Fimbricalyxone (1) and trigoxyphin M (6) with a 6/6/5 tricyclic carbon skeleton were reported for the first time from the genus and fimbricalyxanhydride C (2) is the first example of anhydride type bearing a rare 8,9-oxycycle. All the isolates were evaluated for their cytotoxic activity against three tumor cell lines, and compounds 8 and 10 exhibited significant activity with IC50 values of 4.65-9.02 μM, and the structure-activity relationship of the deformed phenanthrenes was discussed. In addition, the X-ray structure of 8 and 10 and the antineoplastic activity of 10 are reported herein for the first time. Trigohowilol G (10) inhibiting the proliferation of A549 cells might be related to cell cycle distribution and the induction of S phase arrest, and it induced cell apoptosis through Bad/Bax/Cleaved PARP1 pathway.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:221 |
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| Enthalten in: |
Phytochemistry - 221(2024) vom: 15. Apr., Seite 114035 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yang, Changshui [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 08.04.2024 Date Revised 08.04.2024 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.phytochem.2024.114035 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a A group of phenanthrene derivatives with different deformed types, including four previously undescribed derivatives (1-4), an undescribed natural product (5) and five known compounds (6-10), were isolated from the leaves and stems of Strophioblachia fimbricalyx by molecular networking based on UPLC-MS/MS method. Their structures were established by 1D/2D NMR spectroscopy, HRESIMS, quantum chemistry calculation, and single crystal X-ray diffraction. In biogenic pathways, series of deformed phenanthrenes were all suspected to be derived from 6/6/6 tricyclic phenanthrenes with a gem-dimethyl unit in one ring as characteristic components of Strophioblachia. Fimbricalyxone (1) and trigoxyphin M (6) with a 6/6/5 tricyclic carbon skeleton were reported for the first time from the genus and fimbricalyxanhydride C (2) is the first example of anhydride type bearing a rare 8,9-oxycycle. All the isolates were evaluated for their cytotoxic activity against three tumor cell lines, and compounds 8 and 10 exhibited significant activity with IC50 values of 4.65-9.02 μM, and the structure-activity relationship of the deformed phenanthrenes was discussed. In addition, the X-ray structure of 8 and 10 and the antineoplastic activity of 10 are reported herein for the first time. Trigohowilol G (10) inhibiting the proliferation of A549 cells might be related to cell cycle distribution and the induction of S phase arrest, and it induced cell apoptosis through Bad/Bax/Cleaved PARP1 pathway | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Activity relationship | |
| 650 | 4 | |a Cell cycle arrest | |
| 650 | 4 | |a Deformed phenanthrenes | |
| 650 | 4 | |a Molecular networking | |
| 650 | 4 | |a Strophioblachia fimbricalyx | |
| 650 | 4 | |a Structure | |
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| 650 | 7 | |a Phenanthrenes |2 NLM | |
| 650 | 7 | |a Antineoplastic Agents |2 NLM | |
| 700 | 1 | |a Jiang, Houli |e verfasserin |4 aut | |
| 700 | 1 | |a Mao, Haoyu |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yue |e verfasserin |4 aut | |
| 700 | 1 | |a Cao, Yinxue |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yanyan |e verfasserin |4 aut | |
| 700 | 1 | |a Yu, Hongyan |e verfasserin |4 aut | |
| 700 | 1 | |a Lv, Mengying |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Hairong |e verfasserin |4 aut | |
| 700 | 1 | |a Dong, Xiaoyun |e verfasserin |4 aut | |
| 700 | 1 | |a Tao, Li |e verfasserin |4 aut | |
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