New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp.
Two new dipyrroloquinones, namely talaroterreusinones A (<b>1</b>) and B (<b>2</b>), together with four known secondary metabolites, terreusinone A (<b>3</b>), penicillixanthone A (<b>4</b>), isorhodoptilometrin (<b>5</b>), and chrysomutani...
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MDPI AG
2023-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/23/7847 |
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| author | Dandan Zhang Xiaoqing Wang Bo Liu Shuhui Li Yanlei Wang Tao Guo Yi Sun |
| author_facet | Dandan Zhang Xiaoqing Wang Bo Liu Shuhui Li Yanlei Wang Tao Guo Yi Sun |
| author_sort | Dandan Zhang |
| collection | DOAJ |
| description | Two new dipyrroloquinones, namely talaroterreusinones A (<b>1</b>) and B (<b>2</b>), together with four known secondary metabolites, terreusinone A (<b>3</b>), penicillixanthone A (<b>4</b>), isorhodoptilometrin (<b>5</b>), and chrysomutanin (<b>6</b>), were isolated from the solid culture of the endophytic fungus <i>Talaromyces</i> sp. by integrating mass spectrometry-based metabolic profiling and a bioassay-guided method. Their planar structures and stereochemistry were elucidated by comprehensive spectroscopic analysis including NMR and MS. The absolute configuration at C-1″ of terreusinone A (<b>1</b>) was established by applying the modified Mosher’s method. Compounds <b>1</b>–<b>6</b> were evaluated for anti-inflammatory activity and cytotoxicity. As a result, <b>1</b>–<b>3</b> inhibited the LPS-stimulated NO production in macrophage RAW264.7 cells, with IC<sub>50</sub> values of 20.3, 30.7, and 20.6 µM, respectively. Penicillixanthone A (<b>4</b>) exhibited potent cytotoxic activity against Hep G2 and A549 cell lines, with IC<sub>50</sub> values of 117 nM and 212 nM, respectively, and displayed significant antitumour effects in A549 cells by inhibiting the PI3K-Akt-mTOR signalling pathway. |
| first_indexed | 2024-03-09T01:46:16Z |
| format | Article |
| id | doaj.art-b0eb683dea0a4edb90c7e4b1a472dafc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T01:46:16Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b0eb683dea0a4edb90c7e4b1a472dafc2023-12-08T15:22:31ZengMDPI AGMolecules1420-30492023-11-012823784710.3390/molecules28237847New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp.Dandan Zhang0Xiaoqing Wang1Bo Liu2Shuhui Li3Yanlei Wang4Tao Guo5Yi Sun6Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100010, ChinaInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100010, ChinaInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100010, ChinaInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100010, ChinaInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100010, ChinaHenan Engineering Research Center of Medicinal and Edible Chinese Medicine Technology, Henan University of Chinese Medicine, Zhengzhou 450046, ChinaInstitute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100010, ChinaTwo new dipyrroloquinones, namely talaroterreusinones A (<b>1</b>) and B (<b>2</b>), together with four known secondary metabolites, terreusinone A (<b>3</b>), penicillixanthone A (<b>4</b>), isorhodoptilometrin (<b>5</b>), and chrysomutanin (<b>6</b>), were isolated from the solid culture of the endophytic fungus <i>Talaromyces</i> sp. by integrating mass spectrometry-based metabolic profiling and a bioassay-guided method. Their planar structures and stereochemistry were elucidated by comprehensive spectroscopic analysis including NMR and MS. The absolute configuration at C-1″ of terreusinone A (<b>1</b>) was established by applying the modified Mosher’s method. Compounds <b>1</b>–<b>6</b> were evaluated for anti-inflammatory activity and cytotoxicity. As a result, <b>1</b>–<b>3</b> inhibited the LPS-stimulated NO production in macrophage RAW264.7 cells, with IC<sub>50</sub> values of 20.3, 30.7, and 20.6 µM, respectively. Penicillixanthone A (<b>4</b>) exhibited potent cytotoxic activity against Hep G2 and A549 cell lines, with IC<sub>50</sub> values of 117 nM and 212 nM, respectively, and displayed significant antitumour effects in A549 cells by inhibiting the PI3K-Akt-mTOR signalling pathway.https://www.mdpi.com/1420-3049/28/23/7847<i>Talaromyces</i> sp.endophytic fungusdipyrroloquinoneanti-inflammatorycytotoxic activity |
| spellingShingle | Dandan Zhang Xiaoqing Wang Bo Liu Shuhui Li Yanlei Wang Tao Guo Yi Sun New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp. Molecules <i>Talaromyces</i> sp. endophytic fungus dipyrroloquinone anti-inflammatory cytotoxic activity |
| title | New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp. |
| title_full | New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp. |
| title_fullStr | New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp. |
| title_full_unstemmed | New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp. |
| title_short | New Dipyrroloquinones from a Plant-Derived Endophytic Fungus <i>Talaromyces</i> sp. |
| title_sort | new dipyrroloquinones from a plant derived endophytic fungus i talaromyces i sp |
| topic | <i>Talaromyces</i> sp. endophytic fungus dipyrroloquinone anti-inflammatory cytotoxic activity |
| url | https://www.mdpi.com/1420-3049/28/23/7847 |
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