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4. Characterization of defensive cadinenes and a novel sesquiterpene synthase responsible for their biosynthesis from the invasive Eupatorium adenophorum.

Author

Liu, Yan, Luo, Shi‐Hong, Hua, Juan, Li, De‐Sen, Ling, Yi, Luo, Qian, and Li, Sheng‐Hong

Subjects
NICOTIANA benthamiana, EUPATORIUM, BEET armyworm, BIOSYNTHESIS, NUCLEAR magnetic resonance, NATURAL products
Abstract

Summary: Eupatorium adenophorum is a malignant invasive plant possessing extraordinary defense potency, but its chemical weaponry and formation mechanism have not yet been extensively investigated.We identified six cadinene sesquiterpenes, including two volatiles (amorpha‐4,7(11)‐diene and (–)‐amorph‐4‐en‐7‐ol) and four nonvolatiles (9‐oxo‐10,11‐dehydroageraphorone, muurol‐4‐en‐3,8‐dione, 9‐oxo‐ageraphorone and 9β‐hydroxy‐ageraphorone), as the major constitutive and inducible chemicals of E. adenophorum. All cadinenes showed potent antifeedant activity against a generalist insect Spodoptera exigua, indicating that they have significant defensive roles.We cloned and functionally characterized a sesquiterpene synthase from E. adenophorum (EaTPS1), catalyzing the conversion of farnesyl diphosphate to amorpha‐4,7(11)‐diene and (–)‐amorph‐4‐en‐7‐ol, which were purified from engineered Escherichia coli and identified by extensive nuclear magnetic resonance (NMR) spectroscopy. EaTPS1 was highly expressed in the aboveground organs, which was congruent with the dominant distribution of cadinenes, suggesting that EaTPS1 is likely involved in cadinene biosynthesis. Mechanical wounding and methyl jasmonate negatively regulated EaTPS1 expression but caused the release of amorpha‐4,7(11)‐diene and (–)‐amorph‐4‐en‐7‐ol. Nicotiana benthamiana transiently expressing EaTPS1 also produced amorpha‐4,7(11)‐diene and (–)‐amorph‐4‐en‐7‐ol, and showed enhanced defense function.The findings presented here uncover the role and formation of the chemical defense mechanism of E. adenophorum – which probably contributes to the invasive success of this plant – and provide a tool for manipulating the biosynthesis of biologically active cadinene natural products. [ABSTRACT FROM AUTHOR]

Published
2021
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5. An extremely promiscuous terpenoid synthase from the Lamiaceae plant Colquhounia coccineavar. molliscatalyzes the formation of sester-/di-/sesqui-/mono-terpenoids

Author

Li, De-Sen, Hua, Juan, Luo, Shi-Hong, Liu, Yan-Chun, Chen, Yue-Gui, Ling, Yi, Guo, Kai, Liu, Yan, and Li, Sheng-Hong

Abstract

Terpenoids are the largest class of natural products with complex structures and extensive bioactivities; their scaffolds are generated by diverse terpenoid synthases (TPSs) from a limited number of isoprenoid diphosphate precursors. Promiscuous TPSs play important roles in the evolution of terpenoid chemodiversity, but they remain largely unappreciated. Here, an extremely promiscuous terpenoid synthase (CcTPS1) of the TPS-b subfamily was cloned and functionally characterized from a leaf-specific transcriptome of the Lamiaceae plant Colquhounia coccineavar. mollis. CcTPS1 is the first sester-/di-/sesqui-/mono-TPS identified from the plant kingdom, accepting C25/C20/C15/C10diphosphate substrates to generate a panel of sester-/di-/sesqui-/mono-terpenoids. Engineered Escherichia coliexpressing CcTPS1produced three previously unreported terpenoids (two sesterterpenoids and a diterpenoid) with rare cyclohexane-containing skeletons, along with four sesquiterpenoids and one monoterpenoid. Their structures were elucidated by extensive nuclear magnetic resonance spectroscopy. Nicotiana benthamianatransiently expressing CcTPS1also produced the diterpenoid and sesquiterpenoids, demonstrating the enzyme’s promiscuity in planta. Its highly leaf-specific expression pattern combined with detectable terpenoid products in leaves of C. coccineavar. mollisand N. benthamianaexpressing CcTPS1suggested that CcTPS1 was mainly responsible for diterpenoid and sesquiterpenoid biosynthesis in plants. CcTPS1expression and the terpenoid products could be induced by methyl jasmonate, suggesting their possible role in plant–environment interaction. CcTPS1 was localized to the cytosol and may differ from mono-TPSs in subcellular compartmentalization and substrate tolerance. These findings will greatly aid our understanding of plant TPS evolution and terpenoid chemodiversity; they also highlight the enormous potential of transcriptome mining and heterologous expression for the exploration of unique enzymes and natural products hidden in plants.

Published
2021
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