Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification
Chemical epigenetic modification on a marine-derived fungus <i>Aspergillus terreus</i> RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extrac...
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MDPI AG
2020-08-01
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| Online Access: | https://www.mdpi.com/1420-3049/25/17/3927 |
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| author | Jing-Shuai Wu Xiao-Hui Shi Ya-Hui Zhang Chang-Lun Shao Xiu-Mei Fu Xin Li Guang-Shan Yao Chang-Yun Wang |
| author_facet | Jing-Shuai Wu Xiao-Hui Shi Ya-Hui Zhang Chang-Lun Shao Xiu-Mei Fu Xin Li Guang-Shan Yao Chang-Yun Wang |
| author_sort | Jing-Shuai Wu |
| collection | DOAJ |
| description | Chemical epigenetic modification on a marine-derived fungus <i>Aspergillus terreus</i> RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-<b>1</b>, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (<b>1</b>), together with two new benzyl pyrones, asperpyranones A (<b>2</b>) and B (<b>3</b>). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-<b>1</b>, (+)-<b>1</b>, (−)-<b>1</b>, and <b>2</b> displayed the antifungal activities against <i>Candida albicans</i> with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC<sub>50</sub> values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound <b>2</b> exhibited antibacterial activity against <i>Pseudomonas aeruginosa</i> with the MIC value of 32 μg/mL. |
| first_indexed | 2024-03-10T16:46:01Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T16:46:01Z |
| publishDate | 2020-08-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9b6be2cdcd254508b6e66c45b22e16732023-11-20T11:38:57ZengMDPI AGMolecules1420-30492020-08-012517392710.3390/molecules25173927Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic ModificationJing-Shuai Wu0Xiao-Hui Shi1Ya-Hui Zhang2Chang-Lun Shao3Xiu-Mei Fu4Xin Li5Guang-Shan Yao6Chang-Yun Wang7Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, ChinaChemical epigenetic modification on a marine-derived fungus <i>Aspergillus terreus</i> RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-<b>1</b>, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (<b>1</b>), together with two new benzyl pyrones, asperpyranones A (<b>2</b>) and B (<b>3</b>). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-<b>1</b>, (+)-<b>1</b>, (−)-<b>1</b>, and <b>2</b> displayed the antifungal activities against <i>Candida albicans</i> with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC<sub>50</sub> values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound <b>2</b> exhibited antibacterial activity against <i>Pseudomonas aeruginosa</i> with the MIC value of 32 μg/mL.https://www.mdpi.com/1420-3049/25/17/3927marine-derived fungus<i>Aspergillus terreus</i>chemical epigenetic modificationbenzyl furanonebenzyl pyrone |
| spellingShingle | Jing-Shuai Wu Xiao-Hui Shi Ya-Hui Zhang Chang-Lun Shao Xiu-Mei Fu Xin Li Guang-Shan Yao Chang-Yun Wang Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification Molecules marine-derived fungus <i>Aspergillus terreus</i> chemical epigenetic modification benzyl furanone benzyl pyrone |
| title | Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification |
| title_full | Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification |
| title_fullStr | Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification |
| title_full_unstemmed | Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification |
| title_short | Benzyl Furanones and Pyrones from the Marine-Derived Fungus <i>Aspergillus terreus</i> Induced by Chemical Epigenetic Modification |
| title_sort | benzyl furanones and pyrones from the marine derived fungus i aspergillus terreus i induced by chemical epigenetic modification |
| topic | marine-derived fungus <i>Aspergillus terreus</i> chemical epigenetic modification benzyl furanone benzyl pyrone |
| url | https://www.mdpi.com/1420-3049/25/17/3927 |
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