Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409
Two new phenylspirodrimanes, stachybotrins K and L (<b>1</b> and <b>2</b>), together with eight known analogues (<b>3</b>–<b>10</b>), were isolated from deep-sea-derived <i>Stachybotrys</i> sp. MCCC 3A00409. Their structures were determined...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/29/7/1685 |
| _version_ | 1827286647475011584 |
|---|---|
| author | Xinhua Ma Min Wu Zhenwei Chen Fan Cao Tianhua Zhong Zhuhua Luo Zongze Shao Yonghong Zhang Limin Chen Zhiqiang Zhang |
| author_facet | Xinhua Ma Min Wu Zhenwei Chen Fan Cao Tianhua Zhong Zhuhua Luo Zongze Shao Yonghong Zhang Limin Chen Zhiqiang Zhang |
| author_sort | Xinhua Ma |
| collection | DOAJ |
| description | Two new phenylspirodrimanes, stachybotrins K and L (<b>1</b> and <b>2</b>), together with eight known analogues (<b>3</b>–<b>10</b>), were isolated from deep-sea-derived <i>Stachybotrys</i> sp. MCCC 3A00409. Their structures were determined by extensive NMR data and mass spectroscopic analysis. Absolute configurations of new compounds were determined through a comparison of their circular dichroism (CD) spectra with other reported compounds. The possible reversal effects of all compounds were assayed in the resistant cancer cell lines. Stachybotrysin B (<b>8</b>) can reverse multidrug resistance (MDR) in ABCB1-overexpression cells (KBv200, Hela/VCR) at the non-cytotoxic concentration. Doxorubicin accumulation assay and molecular-docking analysis reveal that the mechanism of its reversal MDR effect may be related to the increase in the intracellular concentration of substrate anticancer drugs. |
| first_indexed | 2024-04-24T10:38:05Z |
| format | Article |
| id | doaj.art-8fd11cf17496475ba8079ff3b4606010 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-24T10:38:05Z |
| publishDate | 2024-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8fd11cf17496475ba8079ff3b46060102024-04-12T13:23:45ZengMDPI AGMolecules1420-30492024-04-01297168510.3390/molecules29071685Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409Xinhua Ma0Min Wu1Zhenwei Chen2Fan Cao3Tianhua Zhong4Zhuhua Luo5Zongze Shao6Yonghong Zhang7Limin Chen8Zhiqiang Zhang9Fujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaFujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaFujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaFujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaKey Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Sources, Xiamen 361005, ChinaKey Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Sources, Xiamen 361005, ChinaKey Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Sources, Xiamen 361005, ChinaFujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaFujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaFujian Provincial Key Laboratory of Pharmacology of Natural Medicine, School of Pharmacy, Fujian Medical University, Fuzhou 350122, ChinaTwo new phenylspirodrimanes, stachybotrins K and L (<b>1</b> and <b>2</b>), together with eight known analogues (<b>3</b>–<b>10</b>), were isolated from deep-sea-derived <i>Stachybotrys</i> sp. MCCC 3A00409. Their structures were determined by extensive NMR data and mass spectroscopic analysis. Absolute configurations of new compounds were determined through a comparison of their circular dichroism (CD) spectra with other reported compounds. The possible reversal effects of all compounds were assayed in the resistant cancer cell lines. Stachybotrysin B (<b>8</b>) can reverse multidrug resistance (MDR) in ABCB1-overexpression cells (KBv200, Hela/VCR) at the non-cytotoxic concentration. Doxorubicin accumulation assay and molecular-docking analysis reveal that the mechanism of its reversal MDR effect may be related to the increase in the intracellular concentration of substrate anticancer drugs.https://www.mdpi.com/1420-3049/29/7/1685deep-sea fungus<i>Stachybotrys</i>phenylspirodrimanesmultidrug resistance (MDR)reversal MDR effects |
| spellingShingle | Xinhua Ma Min Wu Zhenwei Chen Fan Cao Tianhua Zhong Zhuhua Luo Zongze Shao Yonghong Zhang Limin Chen Zhiqiang Zhang Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409 Molecules deep-sea fungus <i>Stachybotrys</i> phenylspirodrimanes multidrug resistance (MDR) reversal MDR effects |
| title | Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409 |
| title_full | Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409 |
| title_fullStr | Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409 |
| title_full_unstemmed | Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409 |
| title_short | Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus <i>Stachybotrys</i> sp. 3A00409 |
| title_sort | phenylspirodrimane with moderate reversal effect of multidrug resistance isolated from the deep sea fungus i stachybotrys i sp 3a00409 |
| topic | deep-sea fungus <i>Stachybotrys</i> phenylspirodrimanes multidrug resistance (MDR) reversal MDR effects |
| url | https://www.mdpi.com/1420-3049/29/7/1685 |
| work_keys_str_mv | AT xinhuama phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT minwu phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT zhenweichen phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT fancao phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT tianhuazhong phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT zhuhualuo phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT zongzeshao phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT yonghongzhang phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT liminchen phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 AT zhiqiangzhang phenylspirodrimanewithmoderatereversaleffectofmultidrugresistanceisolatedfromthedeepseafungusistachybotrysisp3a00409 |