Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406
Six new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (<b>1a</b>) and B (<b>1b</b>), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (<b>6</b>), 10<i>R</i>-15-methylpseurotin A (<...
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MDPI AG
2021-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/1/4 |
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| author | Li-Hong Yan Xiao-Ming Li Lu-Ping Chi Xin Li Bin-Gui Wang |
| author_facet | Li-Hong Yan Xiao-Ming Li Lu-Ping Chi Xin Li Bin-Gui Wang |
| author_sort | Li-Hong Yan |
| collection | DOAJ |
| description | Six new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (<b>1a</b>) and B (<b>1b</b>), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (<b>6</b>), 10<i>R</i>-15-methylpseurotin A (<b>7</b>), 1,4,23-trihydroxy-hopane-22,30-diol (<b>10</b>), and sphingofungin I (<b>11</b>), together with six known compounds (<b>2</b>–<b>5</b> and <b>8</b>–<b>9</b>), were isolated and identified from the deep-sea sediment-derived fungus <i>Aspergillus fumigatus</i> SD-406. Their structures were determined by detailed spectroscopic analysis of NMR and MS data, chiral HPLC analysis of the acidic hydrolysate, X-ray crystallographic analysis, <i>J</i>-based configuration analysis, and quantum chemical calculations of ECD, OR, and NMR (with DP4+ probability analysis). Among the compounds, <b>1a</b>/<b>1b</b> represent a pair of novel scaffolds derived from indole diketopiperazine by cleavage of the amide bond following aromatization to give a pyridine ring. Compounds <b>1</b>, <b>4</b>, <b>6</b>, <b>7</b>, <b>10</b> and <b>11</b> showed inhibitory activities against pathogenic bacteria and plant pathogenic fungus, with MIC values ranging from 4 to 64 μg/mL. |
| first_indexed | 2024-03-10T01:05:03Z |
| format | Article |
| id | doaj.art-02fc351bfd154855a653220db5d8cc44 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T01:05:03Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-02fc351bfd154855a653220db5d8cc442023-11-23T14:27:13ZengMDPI AGMarine Drugs1660-33972021-12-01201410.3390/md20010004Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406Li-Hong Yan0Xiao-Ming Li1Lu-Ping Chi2Xin Li3Bin-Gui Wang4CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaCAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaSix new metabolites, including a pair of inseparable mixtures of secofumitremorgins A (<b>1a</b>) and B (<b>1b</b>), which differed in the configuration of the nitrogen atom, 29-hydroxyfumiquinazoline C (<b>6</b>), 10<i>R</i>-15-methylpseurotin A (<b>7</b>), 1,4,23-trihydroxy-hopane-22,30-diol (<b>10</b>), and sphingofungin I (<b>11</b>), together with six known compounds (<b>2</b>–<b>5</b> and <b>8</b>–<b>9</b>), were isolated and identified from the deep-sea sediment-derived fungus <i>Aspergillus fumigatus</i> SD-406. Their structures were determined by detailed spectroscopic analysis of NMR and MS data, chiral HPLC analysis of the acidic hydrolysate, X-ray crystallographic analysis, <i>J</i>-based configuration analysis, and quantum chemical calculations of ECD, OR, and NMR (with DP4+ probability analysis). Among the compounds, <b>1a</b>/<b>1b</b> represent a pair of novel scaffolds derived from indole diketopiperazine by cleavage of the amide bond following aromatization to give a pyridine ring. Compounds <b>1</b>, <b>4</b>, <b>6</b>, <b>7</b>, <b>10</b> and <b>11</b> showed inhibitory activities against pathogenic bacteria and plant pathogenic fungus, with MIC values ranging from 4 to 64 μg/mL.https://www.mdpi.com/1660-3397/20/1/4<i>Aspergillus fumigatus</i>deep-sea sediment-derived fungusalkaloidstriterpenoidantimicrobial activity |
| spellingShingle | Li-Hong Yan Xiao-Ming Li Lu-Ping Chi Xin Li Bin-Gui Wang Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406 Marine Drugs <i>Aspergillus fumigatus</i> deep-sea sediment-derived fungus alkaloids triterpenoid antimicrobial activity |
| title | Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406 |
| title_full | Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406 |
| title_fullStr | Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406 |
| title_full_unstemmed | Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406 |
| title_short | Six New Antimicrobial Metabolites from the Deep-Sea Sediment-Derived Fungus <i>Aspergillus fumigatus</i> SD-406 |
| title_sort | six new antimicrobial metabolites from the deep sea sediment derived fungus i aspergillus fumigatus i sd 406 |
| topic | <i>Aspergillus fumigatus</i> deep-sea sediment-derived fungus alkaloids triterpenoid antimicrobial activity |
| url | https://www.mdpi.com/1660-3397/20/1/4 |
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