| A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway | |
Yang, Yan-Long1,2 ; Zhou, Hui1,2; Du, Gang1,2; Feng, Ke-Na1,2; Feng, Tao1,3; Fu, Xiao-Li1; Liu, Ji-Kai1,3; Zeng, Ying1; Ji-Kai Liu, Ying Zeng
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| 2016-04-25 | |
| 发表期刊 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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| 卷号 | 55期号:18页码:5463-5466 |
| 摘要 | 综合运用有机化学以及生化与分子生物学技术，通过前体指导的生物合成，进一步研究了褐盖韧革菌中结构多样的混源萜类化合物的生物合成机制。首次在基因与酶学水平上确定了参与其中氧化脱羧关键反应的单氧化酶VibMO1，从而证实了长久以来的推测：异戊烯基取代的对苯二酚类化合物（有时也称之为混源萜meroterpenoids）很可能来源于异戊烯基取代的对羟基苯甲酸的氧化脱羧。单氧化酶VibMO1的发现，还为真核生物辅酶Q形成过程中催化类似反应的酶基因鉴定提供了重要线索。同时，该研究还证明了由异戊烯基对羟基苯甲醇通过发散生物合成途径(a divergent pathway)形成韧革菌素类混源萜，其中3-取代的γ丁内酯类化合物Vibralactone G (8)新颖的生物合成途径，还是首次在天然产物化学中报道。研究结果加深了对次生代谢产物结构多样性产生机制的认识，为天然产物的生物合成研究开辟了新的视野。; The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted gamma-butyrolactones from a shikimate origin. |
| 关键词 | Biosynthesis Decarboxylation Enzymes Meroterpenoid Natural Products |
| 学科领域 | 天然产物有机化学 ; 生物有机化学 |
| DOI | 10.1002/anie.201510928 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000375113300008 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/25396 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 通讯作者 | Ji-Kai Liu, Ying Zeng |
| 作者单位 | 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.South Cent Univ Nationalities, Sch Pharmaceut Sci, Wuhan 430074, Peoples R China |
| 推荐引用方式 GB/T 7714 | Yang, Yan-Long,Zhou, Hui,Du, Gang,et al. A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2016,55(18):5463-5466. |
| APA | Yang, Yan-Long.,Zhou, Hui.,Du, Gang.,Feng, Ke-Na.,Feng, Tao.,...&Ji-Kai Liu, Ying Zeng.(2016).A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,55(18),5463-5466. |
| MLA | Yang, Yan-Long,et al."A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55.18(2016):5463-5466. |
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