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2-Alkylquinolone alkaloid biosynthesis in the medicinal plant Evodia rutaecarpa involves collaboration of two novel type III polyketide synthases
http://hdl.handle.net/10110/00019283
http://hdl.handle.net/10110/0001928339b0e031-32d2-458e-b1bc-6c2d1534dcae
名前 / ファイル | ライセンス | アクション |
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J.Biol.CHem_292_9117to9135_Matsui (6.1 MB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2019-02-25 | |||||
タイトル | ||||||
タイトル | 2-Alkylquinolone alkaloid biosynthesis in the medicinal plant Evodia rutaecarpa involves collaboration of two novel type III polyketide synthases | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Matsui, Takashi
× Matsui, Takashi× Kodama, Takeshi× Mori, Takahiro× Tadakoshi, Tetsuhiro× Noguchi, Hiroshi× Abe, Ikuro× Morita, Hiroyuki |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | 2-Alkylquinolone (2AQ) alkaloids are pharmaceutically and biologically important natural products produced by both bacteria and plants, with a wide range of biological effects, including antibacterial, cytotoxic, anticholinesterase, and quorum-sensing signaling activities. These diverse activities and 2AQ occurrence in vastly different phyla have raised much interest in the biosynthesis pathways leading to their production. Previous studies in plants have suggested that type III polyketide synthases (PKSs) might be involved in 2AQ biosynthesis, but this hypothesis is untested. To this end, we cloned two novel type III PKSs, alkyldiketide-CoA synthase (ADS) and alkylquinolone synthase (AQS), from the 2AQ-producing medicinal plant, Evodia rutaecarpa (Rutaceae). Functional analyses revealed that collaboration of ADS and AQS produces 2AQ via condensations of N-methylanthraniloyl-CoA, a fatty acyl-CoA, with malonyl-CoA. We show that ADS efficiently catalyzes the decarboxylative condensation of malonyl-CoA with a fatty acyl-CoA to produce an alkyldiketide-CoA, whereas AQS specifically catalyzes the decarboxylative condensation of an alkyldiketide acid with N-methylanthraniloyl-CoA to generate the 2AQ scaffold via C–C/C–N bond formations. Remarkably, the ADS and AQS crystal structures at 1.80 and 2.20 Å resolutions, respectively, indicated that the unique active-site architecture with Trp-332 and Cys-191 and the novel CoA-binding tunnel with Tyr-215 principally control the substrate and product specificities of ADS and AQS, respectively. These results provide additional insights into the catalytic versatility of the type III PKSs and their functional and evolutionary implications for 2AQ biosynthesis in plants and bacteria. | |||||
書誌情報 |
Journal of Biological Chemistry 巻 292, p. 9117-9135, 発行日 2017-04-14 |
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ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0021-9258 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1083-351X | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | info:doi/10.1074/jbc.M117.778977 | |||||
権利 | ||||||
権利情報 | This research was originally published in the Journal of Biological Chemistry. Takashi Matsui, Takeshi Kodama, Takahiro Mori, Tetsuhiro Tadakoshi, Hiroshi Noguchi, Ikuro Abe. 2-Alkylquinolone alkaloid biosynthesis in the medicinal plant. J. Biol. Chem. 2017; 292:9117-9135. © the American Society for Biochemistry and Molecular Biology or © the Author(s). | |||||
フォーマット | ||||||
内容記述タイプ | Other | |||||
内容記述 | application/pdf | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
資源タイプ(DSpace) | ||||||
内容記述タイプ | Other | |||||
内容記述 | Article | |||||
関係URI | ||||||
識別子タイプ | URI | |||||
関連識別子 | https:/doi.org/10.1074/jbc.M117.778977 | |||||
関連名称 | 出版社版 |