Discovery of a non-stereoselective cytochrome P450 catalyzing either 8 alpha- or 8 beta-hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis
文献类型：期刊论文
| 作者 | Gou, Junbo1,2; Hao, Fuhua3; Huang, Chongyang3; Kwon, Moonhyuk4; Chen, Fangfang2; Li, Changfu2; Liu, Chaoyang3; Ro, Dae-Kyun4; Tang, Huiru3,5; Zhang, Yansheng2 |
| 刊名 | PLANT JOURNAL
 |
| 出版日期 | 2018 |
| 卷号 | 93期号:1页码:92-106 |
| 关键词 | C12 8-fused STLs cytochrome P450 (CYP) germacrene A acid C8-hydroxylase Inula hupehensis inunolide sesquiterpene lactones (STLs) |
| ISSN号 | 0960-7412 |
| DOI | 10.1111/tpj.13760 |
| 英文摘要 | Sesquiterpene lactones (STLs) are C15 terpenoid natural products with alpha-methylene gamma-lactone moiety. A large proportion of STLs in Asteraceae species is derived from the central precursor germacrene A acid (GAA). Formation of the lactone rings depends on the regio-(C6 or C8) and stereoselective (alpha- or beta-)hydroxylations of GAA, producing STLs with four distinct stereo-configurations (12,6 alpha-, 12,6-, 12, 8 alpha-, and 12,8 beta-olide derivatives of GAA) in nature. Curiously, two configurations of STLs (C12,8 alpha and C12,8 beta) are simultaneously present in the Chinese medicinal plant, Inula hupehensis. However, how these related yet distinct STL stereo-isomers are co-synthesized in I. hupehensis remains unknown. Here, we describe the functional identification of the I. hupehensis cytochrome P450 (CYP71BL6) that can catalyze the hydroxylation of GAA in either 8 alpha-or 8 beta-configuration, resulting in the synthesis of both 8 alpha- and 8 beta-hydroxyl GAAs. Of these two products, only 8 alpha-hydroxyl GAA spontaneously lactonizes to the C12,8 alpha-STL while the 8 beta-hydroxyl GAA remains stable without lactonization. Chemical structures of the C12,8 alpha-STL, named inunolide, and 8 beta-hydroxyl GAA were fully elucidated by nuclear magnetic resonance analysis and mass spectrometry. The CYP71BL6 displays 63-66% amino acid identity to the previously reported CYP71BL1/2 catalyzing GAA 6aor 8 beta-hydroxylation, indicating CYP71BL6 shares the same evolutionary lineage with other stereoselective cytochrome P450s, but catalyzes hydroxylation in a non-stereoselective manner. We observed that the CYP71BL6 transcript abundance correlates closely to the accumulation of C12,8-STLs in I. hupehensis. The identification of CYP71BL6 provides an insight into the biosynthesis of STLs in Asteraceae. |
| 资助项目 | National Natural Science Foundation of China[31370339] ; National Natural Science Foundation of China[81230090] ; National Natural Science Foundation of China[81520108030] ; Ministry of Science and Technology of China[2011YQ120035] ; Natural Sciences and Engineering Research Council of Canada (NSERC) ; Next-Generation Bio-Green 21 Program (SSAC) from Rural Development Administration, Republic of Korea[PJ01105501] ; Basic Science Research Programme through the National Research Foundation of Korea (NRF) - Ministry of Education[2017R1A6A3A03003409] |
| WOS研究方向 | Plant Sciences |
| 语种 | 英语 |
| WOS记录号 | WOS:000418228000008 |
| 出版者 | WILEY |
| 源URL | [http://202.127.146.157/handle/2RYDP1HH/3366]  |
| 专题 | 中国科学院武汉植物园 |
| 通讯作者 | Tang, Huiru; Zhang, Yansheng |
| 作者单位 | 1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Chinese Acad Sci, Wuhan Bot Garden, CAS Key Lab Plant Germplasm Enhancement & Special, Wuhan 430074, Hubei, Peoples R China 3.Univ Chinese Acad Sci, Wuhan Inst Phys & Math, Natl Ctr Magnet Resonance Wuhan,Key Lab Magnet Re, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan 430071, Hubei, Peoples R China 4.Univ Calgary, Dept Biol Sci, 2500 Univ Dr NW, Calgary, AB T2N 1N4, Canada 5.Fudan Univ, Collaborat Innovat Ctr Genet & Dev, State Key Lab Genet Engn, Shanghai 200438, Peoples R China |
| 推荐引用方式 GB/T 7714 | Gou, Junbo,Hao, Fuhua,Huang, Chongyang,et al. Discovery of a non-stereoselective cytochrome P450 catalyzing either 8 alpha- or 8 beta-hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis[J]. PLANT JOURNAL,2018,93(1):92-106. |
| APA | Gou, Junbo.,Hao, Fuhua.,Huang, Chongyang.,Kwon, Moonhyuk.,Chen, Fangfang.,...&Zhang, Yansheng.(2018).Discovery of a non-stereoselective cytochrome P450 catalyzing either 8 alpha- or 8 beta-hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis.PLANT JOURNAL,93(1),92-106. |
| MLA | Gou, Junbo,et al."Discovery of a non-stereoselective cytochrome P450 catalyzing either 8 alpha- or 8 beta-hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis".PLANT JOURNAL 93.1(2018):92-106. |
入库方式： OAI收割
来源：武汉植物园
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