Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids
Zea mays (maize) is an important agricultural crop that produces a variety of valuable terpenoids, including several triterpenoids. However, no oxidosqualene cyclase (OSC) enzymes, which catalyze the first step in triterpenoid biosynthesis, have been identified in maize. Here, we identified a novel...
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| Format: | Article |
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KeAi Communications Co., Ltd.
2022-12-01
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| Series: | Synthetic and Systems Biotechnology |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405805X22000850 |
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| author | Zhenjun Fan Yan Wang Chengshuai Yang Zhihua Zhou Pingping Wang Xing Yan |
| author_facet | Zhenjun Fan Yan Wang Chengshuai Yang Zhihua Zhou Pingping Wang Xing Yan |
| author_sort | Zhenjun Fan |
| collection | DOAJ |
| description | Zea mays (maize) is an important agricultural crop that produces a variety of valuable terpenoids, including several triterpenoids. However, no oxidosqualene cyclase (OSC) enzymes, which catalyze the first step in triterpenoid biosynthesis, have been identified in maize. Here, we identified a novel OSC (ZmOSC1) in maize using a combination of genomic mining and phylogenetic analyses. To functionally characterize the candidate OSC, we constructed a yeast strain that produced high levels of 2,3-oxidosqualene. When ZmOSC1 was expressed in this strain, three compounds were detected and identified as hop-17(21)-en-3-ol, hopenol B and simiarenol, respectively. For their biosynthesis, we proposed a potential cyclization mechanism catalyzed by ZmOSC1 via the generation of a dammarenyl cation, followed by sequential cationic ring expansion, cyclization, cationic migration and further proton elimination. This study discovered and characterized an OSC from maize for the first time, and laid a foundation to produce three bioactive pentacyclic triterpenes, hop-17(21)-en-3-ol, hopenol B and simiarenol, using synthetic biology approaches. |
| first_indexed | 2024-04-11T06:21:58Z |
| format | Article |
| id | doaj.art-9317f9176d544cc89f542e740285e86e |
| institution | Directory Open Access Journal |
| issn | 2405-805X |
| language | English |
| last_indexed | 2024-04-11T06:21:58Z |
| publishDate | 2022-12-01 |
| publisher | KeAi Communications Co., Ltd. |
| record_format | Article |
| series | Synthetic and Systems Biotechnology |
| spelling | doaj.art-9317f9176d544cc89f542e740285e86e2022-12-22T04:40:33ZengKeAi Communications Co., Ltd.Synthetic and Systems Biotechnology2405-805X2022-12-017411671172Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoidsZhenjun Fan0Yan Wang1Chengshuai Yang2Zhihua Zhou3Pingping Wang4Xing Yan5CAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, China; University of Chinese Academy of Sciences, Beijing, 100049, ChinaCAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, ChinaCAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, ChinaCAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, China; University of Chinese Academy of Sciences, Beijing, 100049, ChinaCAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, China; Corresponding author.CAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, China; University of Chinese Academy of Sciences, Beijing, 100049, China; Corresponding author. CAS-Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Chinese Academy of Sciences, Shanghai, 200032, China.Zea mays (maize) is an important agricultural crop that produces a variety of valuable terpenoids, including several triterpenoids. However, no oxidosqualene cyclase (OSC) enzymes, which catalyze the first step in triterpenoid biosynthesis, have been identified in maize. Here, we identified a novel OSC (ZmOSC1) in maize using a combination of genomic mining and phylogenetic analyses. To functionally characterize the candidate OSC, we constructed a yeast strain that produced high levels of 2,3-oxidosqualene. When ZmOSC1 was expressed in this strain, three compounds were detected and identified as hop-17(21)-en-3-ol, hopenol B and simiarenol, respectively. For their biosynthesis, we proposed a potential cyclization mechanism catalyzed by ZmOSC1 via the generation of a dammarenyl cation, followed by sequential cationic ring expansion, cyclization, cationic migration and further proton elimination. This study discovered and characterized an OSC from maize for the first time, and laid a foundation to produce three bioactive pentacyclic triterpenes, hop-17(21)-en-3-ol, hopenol B and simiarenol, using synthetic biology approaches.http://www.sciencedirect.com/science/article/pii/S2405805X22000850Oxidosqualene cyclaseZea maysHop-17(21)-en-3-olHopenol BSimiarenol |
| spellingShingle | Zhenjun Fan Yan Wang Chengshuai Yang Zhihua Zhou Pingping Wang Xing Yan Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids Synthetic and Systems Biotechnology Oxidosqualene cyclase Zea mays Hop-17(21)-en-3-ol Hopenol B Simiarenol |
| title | Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids |
| title_full | Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids |
| title_fullStr | Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids |
| title_full_unstemmed | Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids |
| title_short | Identification of a novel multifunctional oxidosqualene cyclase from Zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids |
| title_sort | identification of a novel multifunctional oxidosqualene cyclase from zea mays sheds light on the biosynthetic pathway of three pentacyclic triterpenoids |
| topic | Oxidosqualene cyclase Zea mays Hop-17(21)-en-3-ol Hopenol B Simiarenol |
| url | http://www.sciencedirect.com/science/article/pii/S2405805X22000850 |
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