| Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids | |
Yan, Yijun1; Yang, Jing1 ; Yu, Zhiyin1; Yu, Mingming1; Ma, Ya-Tuan1; Wang, Li1; Su, Can1; Luo, Jianying1; Horsman, Geoffrey P.2; Huang, Sheng-Xiong1
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| 2016-10-07 | |
| 发表期刊 | NATURE COMMUNICATIONS
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| 卷号 | 7期号:1页码:1 |
| 摘要 | The pyridine ring is a potent pharmacophore in alkaloid natural products. Nonetheless, its biosynthetic pathways are poorly understood. Rubrolones A and B are tropolone alkaloid natural products possessing a unique tetra-substituted pyridine moiety. Here, we report the gene cluster and propose a biosynthetic pathway for rubrolones, identifying a key intermediate that accumulates upon inactivation of sugar biosynthetic genes. Critically, this intermediate was converted to the aglycones of rubrolones by non-enzymatic condensation and cyclization with either ammonia or anthranilic acid to generate the respective pyridine rings. We propose that this non-enzymatic reaction occurs via hydrolysis of the key intermediate, which possesses a 1,5-dione moiety as an amine acceptor capable of cyclization. This study suggests that 1,5-dione moieties may represent a general strategy for pyridine ring biosynthesis, and more broadly highlights the utility of non-enzymatic diversification for exploring and expanding natural product chemical space. |
| DOI | 10.1038/ncomms13083 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000385588000001 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/33643 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Wilfrid Laurier Univ, Dept Chem & Biochem, Waterloo, ON N2L 3C5, Canada |
| 推荐引用方式 GB/T 7714 | Yan, Yijun,Yang, Jing,Yu, Zhiyin,et al. Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids[J]. NATURE COMMUNICATIONS,2016,7(1):1. |
| APA | Yan, Yijun.,Yang, Jing.,Yu, Zhiyin.,Yu, Mingming.,Ma, Ya-Tuan.,...&Huang, Sheng-Xiong.(2016).Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids.NATURE COMMUNICATIONS,7(1),1. |
| MLA | Yan, Yijun,et al."Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids".NATURE COMMUNICATIONS 7.1(2016):1. |
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| ncomms13083.pdf（1066KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | 浏览 下载 | |
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