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A Cryptic Plant Terpene Cyclase Producing Unconventional 18-and 14-Membered Macrocyclic C-25 and C-20 Terpenoids with Immunosuppressive Activity
Chen,Yue-Gui; Li,De-Sen; Ling,Yi; Liu,Yan-Chun; Zuo,Zhi-Li; Gan,Li-She; Luo,Shi-Hong; Hua,Juan; Chen,Ding-Yuan; Xu,Fan; Li,Man; Guo,Kai; Liu,Yan; Gershenzon,Jonathan; Li,Sheng-Hong
2021
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
Volume60Issue:48Pages:25468-25476
AbstractA versatile terpene synthase (LcTPS2) producing unconventional macrocyclic terpenoids was characterized from Leucosceptrum canum. Engineered Escherichia coli and Nicotiana benthamiana expressing LcTPS2 produced six 18-/14-membered sesterterpenoids including five new ones and two 14-membered diterpenoids. These products represent the first macrocyclic sesterterpenoids from plants and the largest sesterterpenoid ring system identified to date. Two variants F516A and F516G producing approximately 3.3- and 2.5-fold, respectively, more sesterterpenoids than the wild-type enzyme were engineered. Both 18- and 14-membered ring sesterterpenoids displayed significant inhibitory activity on the IL-2 and IFN-gamma production of T cells probably via inhibition of the MAPK pathway. The findings will contribute to the development of efficient biocatalysts to create bioactive macrocyclic sesterterpenoids, and also herald a new potential in the well-trodden territory of plant terpenoid biosynthesis.
Keywordenzyme engineering immunosuppressive activity Leucosceptrum canum macrocyclic terpenoids sesterterpene synthase GERANYLFARNESYL DIPHOSPHATE SYNTHASE GLANDULAR TRICHOMES LEUCOSCEPTRUM-CANUM SCALE INSECT SESTERTERPENOIDS CONVERSION EVOLUTION PRECURSOR HARBOR
DOI10.1002/anie.202110842
WOS IDWOS:000711812800001
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/73451
Collection中国科学院昆明植物研究所
Affiliation1.Chengdu Univ Tradit Chinese Med, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Peoples R China
2.Chengdu Univ Tradit Chinese Med, Innovat Inst Chinese Med & Pharm, Chengdu 611137, Peoples R China
3.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
4.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
5.Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China
6.Max Planck Inst Chem Ecol, D-07745 Jena, Germany
7.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Chen,Yue-Gui,Li,De-Sen,Ling,Yi,et al. A Cryptic Plant Terpene Cyclase Producing Unconventional 18-and 14-Membered Macrocyclic C-25 and C-20 Terpenoids with Immunosuppressive Activity[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021,60(48):25468-25476.
APA Chen,Yue-Gui.,Li,De-Sen.,Ling,Yi.,Liu,Yan-Chun.,Zuo,Zhi-Li.,...&Li,Sheng-Hong.(2021).A Cryptic Plant Terpene Cyclase Producing Unconventional 18-and 14-Membered Macrocyclic C-25 and C-20 Terpenoids with Immunosuppressive Activity.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,60(48),25468-25476.
MLA Chen,Yue-Gui,et al."A Cryptic Plant Terpene Cyclase Producing Unconventional 18-and 14-Membered Macrocyclic C-25 and C-20 Terpenoids with Immunosuppressive Activity".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60.48(2021):25468-25476.
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