Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer <i>Streptomyces</i> sp. CPCC 204095, 7,12-dihydroisatropolone C (H<sub>2</sub>ITC) is discovered and identified as a...
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MDPI AG
2022-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/9/2882 |
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| author | Jiachang Liu Xiaoyan Liu Jie Fu Bingya Jiang Shufen Li Linzhuan Wu |
| author_facet | Jiachang Liu Xiaoyan Liu Jie Fu Bingya Jiang Shufen Li Linzhuan Wu |
| author_sort | Jiachang Liu |
| collection | DOAJ |
| description | Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer <i>Streptomyces</i> sp. CPCC 204095, 7,12-dihydroisatropolone C (H<sub>2</sub>ITC) is discovered and identified as a mixture of two interchangeable diastereomers differing in the C-6 configuration. As a major metabolite in the mycelial growth period of <i>Streptomyces</i> sp. CPCC 204095, H<sub>2</sub>ITC can be oxidized spontaneously to isatropolone C (ITC), suggesting H<sub>2</sub>ITC is the physiological precursor of ITC. Characterization of H<sub>2</sub>ITC makes us propose dihydrotropolone-ring construction in the biosynthesis of isatropolones. |
| first_indexed | 2024-03-10T03:53:58Z |
| format | Article |
| id | doaj.art-b667a3f1a3f6485cb8b12ecf5bdf6c4c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:53:58Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b667a3f1a3f6485cb8b12ecf5bdf6c4c2023-11-23T08:51:02ZengMDPI AGMolecules1420-30492022-04-01279288210.3390/molecules27092882Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone BiosynthesisJiachang Liu0Xiaoyan Liu1Jie Fu2Bingya Jiang3Shufen Li4Linzhuan Wu5NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, ChinaNHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, ChinaNHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, ChinaNHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, ChinaNHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, ChinaNHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, ChinaIsatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer <i>Streptomyces</i> sp. CPCC 204095, 7,12-dihydroisatropolone C (H<sub>2</sub>ITC) is discovered and identified as a mixture of two interchangeable diastereomers differing in the C-6 configuration. As a major metabolite in the mycelial growth period of <i>Streptomyces</i> sp. CPCC 204095, H<sub>2</sub>ITC can be oxidized spontaneously to isatropolone C (ITC), suggesting H<sub>2</sub>ITC is the physiological precursor of ITC. Characterization of H<sub>2</sub>ITC makes us propose dihydrotropolone-ring construction in the biosynthesis of isatropolones.https://www.mdpi.com/1420-3049/27/9/2882<i>Streptomyces</i>7,12-dihydroisatropolone Cspontaneous oxidation |
| spellingShingle | Jiachang Liu Xiaoyan Liu Jie Fu Bingya Jiang Shufen Li Linzhuan Wu Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis Molecules <i>Streptomyces</i> 7,12-dihydroisatropolone C spontaneous oxidation |
| title | Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis |
| title_full | Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis |
| title_fullStr | Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis |
| title_full_unstemmed | Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis |
| title_short | Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis |
| title_sort | dihydroisatropolone c from i streptomyces i and its implication in tropolone ring construction for isatropolone biosynthesis |
| topic | <i>Streptomyces</i> 7,12-dihydroisatropolone C spontaneous oxidation |
| url | https://www.mdpi.com/1420-3049/27/9/2882 |
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