Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C
Racemic dinaphthalenone derivatives, (±)-asperlone A (1) and (±)-asperlone B (2), and two new azaphilones, 6′-hydroxy-(R)-mitorubrinic acid (3) and purpurquinone D (4), along with four known compounds, (−)-mitorubrinic acid (5), (−)-mitorubrin (6), purpurquinone A (7) and orsellinic acid (8), were i...
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-01-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/13/1/366 |
| _version_ | 1811301229877264384 |
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| author | Ze'en Xiao Shao'e Lin Chunbing Tan Yongjun Lu Lei He Xishan Huang Zhigang She |
| author_facet | Ze'en Xiao Shao'e Lin Chunbing Tan Yongjun Lu Lei He Xishan Huang Zhigang She |
| author_sort | Ze'en Xiao |
| collection | DOAJ |
| description | Racemic dinaphthalenone derivatives, (±)-asperlone A (1) and (±)-asperlone B (2), and two new azaphilones, 6′-hydroxy-(R)-mitorubrinic acid (3) and purpurquinone D (4), along with four known compounds, (−)-mitorubrinic acid (5), (−)-mitorubrin (6), purpurquinone A (7) and orsellinic acid (8), were isolated from the cultures of Aspergillus sp. 16-5C. The structures were elucidated using comprehensive spectroscopic methods, including 1D and 2D NMR spectra and the structures of 1 further confirmed by single-crystal X-ray diffraction analysis, while the absolute configuration of 3 and 4 were determined by comparing their optical rotation and CD with those of the literature, respectively. Compounds 1, 2 and 6 exhibited potent inhibitory effects against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with IC50 values of 4.24 ± 0.41, 4.32 ± 0.60 and 3.99 ± 0.34 μM, respectively. |
| first_indexed | 2024-04-13T07:05:09Z |
| format | Article |
| id | doaj.art-1b67653e50fd44ee8f2f29a037035d84 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-13T07:05:09Z |
| publishDate | 2015-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-1b67653e50fd44ee8f2f29a037035d842022-12-22T02:57:01ZengMDPI AGMarine Drugs1660-33972015-01-0113136637810.3390/md13010366md13010366Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5CZe'en Xiao0Shao'e Lin1Chunbing Tan2Yongjun Lu3Lei He4Xishan Huang5Zhigang She6School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Life Sciences and Biomedical Center, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Life Sciences and Biomedical Center, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaRacemic dinaphthalenone derivatives, (±)-asperlone A (1) and (±)-asperlone B (2), and two new azaphilones, 6′-hydroxy-(R)-mitorubrinic acid (3) and purpurquinone D (4), along with four known compounds, (−)-mitorubrinic acid (5), (−)-mitorubrin (6), purpurquinone A (7) and orsellinic acid (8), were isolated from the cultures of Aspergillus sp. 16-5C. The structures were elucidated using comprehensive spectroscopic methods, including 1D and 2D NMR spectra and the structures of 1 further confirmed by single-crystal X-ray diffraction analysis, while the absolute configuration of 3 and 4 were determined by comparing their optical rotation and CD with those of the literature, respectively. Compounds 1, 2 and 6 exhibited potent inhibitory effects against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with IC50 values of 4.24 ± 0.41, 4.32 ± 0.60 and 3.99 ± 0.34 μM, respectively.http://www.mdpi.com/1660-3397/13/1/366marine fungiAspergillus sp.asperlonesazaphilonesMptpB inhibitor |
| spellingShingle | Ze'en Xiao Shao'e Lin Chunbing Tan Yongjun Lu Lei He Xishan Huang Zhigang She Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C Marine Drugs marine fungi Aspergillus sp. asperlones azaphilones MptpB inhibitor |
| title | Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C |
| title_full | Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C |
| title_fullStr | Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C |
| title_full_unstemmed | Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C |
| title_short | Asperlones A and B, Dinaphthalenone Derivatives from a Mangrove Endophytic Fungus Aspergillus sp. 16-5C |
| title_sort | asperlones a and b dinaphthalenone derivatives from a mangrove endophytic fungus aspergillus sp 16 5c |
| topic | marine fungi Aspergillus sp. asperlones azaphilones MptpB inhibitor |
| url | http://www.mdpi.com/1660-3397/13/1/366 |
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