Harnessing Plant Trichome Biochemistry for the Production of Useful Compounds

Tissier, Alain

doi:10.1002/9781118801512.ch14

Cited by 4 publications

(8 citation statements)

References 141 publications

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“…Taken together with the identification of the presently reported diTPSs and CPTs, it is likely that the trichomes are the site of diterpenoid biosynthesis in the Eremophila species examined here. This is in agreement with the known role of glandular trichomes in specialised terpenoid biosynthesis in plants [69][70][71].…”

Section: Involvement Of Trichomes In the Biosynthesis Of Diterpenoidssupporting

confidence: 91%

Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species

et al. 2020

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Background: Eremophila R.Br. (Scrophulariaceae) is a diverse genus of plants with species distributed across semi-arid and arid Australia. It is an ecologically important genus that also holds cultural significance for many Indigenous Australians who traditionally use several species as sources of medicines. Structurally unusual diterpenoids, particularly serrulatane and viscidane-types, feature prominently in the chemical profile of many species and recent studies indicate that these compounds are responsible for much of the reported bioactivity. We have investigated the biosynthesis of diterpenoids in three species: Eremophila lucida, Eremophila drummondii and Eremophila denticulata subsp. trisulcata. Results: In all studied species diterpenoids were localised to the leaf surface and associated with the occurrence of glandular trichomes. Trichome-enriched transcriptome databases were generated and mined for candidate terpene synthases (TPS). Four TPSs with diterpene biosynthesis activity were identified: ElTPS31 and ElTPS3 from E. lucida were found to produce (3Z,7Z,11Z)-cembratrien-15-ol and 5-hydroxyviscidane, respectively, and EdTPS22 and EdtTPS4, from E. drummondii and E. denticulata subsp. trisulcata, respectively, were found to produce 8,9-dihydroserrulat-14-ene which readily aromatized to serrulat-14-ene. In all cases, the identified TPSs used the cisoid substrate, nerylneryl diphosphate (NNPP), to form the observed products. Subsequently, cis-prenyl transferases (CPTs) capable of making NNPP were identified in each species. Conclusions: We have elucidated two biosynthetic steps towards three of the major diterpene backbones found in this genus. Serrulatane and viscidane-type diterpenoids are promising candidates for new drug leads. The identification of an enzymatic route to their synthesis opens up the possibility of biotechnological production, making accessible a ready source of scaffolds for further modification and bioactivity testing.

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Section: Involvement Of Trichomes In the Biosynthesis Of Diterpenoidssupporting

confidence: 91%

Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species

et al. 2020

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“…Insect control can potentially also be pursued using metabolic engineering of volatiles (Paul et al ., ; Sun et al ., ; Abbas et al ., ; Tissier, ). In an attempt to change the resistance of chrysanthemum against aphids, Hu et al .…”

Section: Agricultural Importance Of Vocsmentioning

confidence: 99%

The role of volatiles in plant communication

et al. 2019

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SummaryVolatiles mediate the interaction of plants with pollinators, herbivores and their natural enemies, other plants and micro‐organisms. With increasing knowledge about these interactions the underlying mechanisms turn out to be increasingly complex. The mechanisms of biosynthesis and perception of volatiles are slowly being uncovered. The increasing scientific knowledge can be used to design and apply volatile‐based agricultural strategies.

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“…In particular, two isomers (12,20) of o-coumaric acid glucoside (trans-and cis-melilotoside), previously reported in A. annua tea infusions [19], were detected at high levels in the leaves together with other hydroxycinnamate esters that include feruloyl moieties, such as two feruloylquinic acid isomers (19,21), one diferuloylquinic acid isomer (63) and ve caffeoylferuloylquinic acid isomers, one characterizing mostly the leaves (50) and the other ones the stems (45,51,54,59). Also, caffeoyl-(9, 15), dicaffeoyl- (33,34,37,38,40,61) and tricaffeoyl-(60, 65, 68) quinic acids were well represented in both leaves and stems within this species. Among the coumarins, the stems reported the highest levels of methoxycoumarin-O-hexoside (10).…”

Section: Metabolic Pro Les Of Artemisia Spp Methanolic Extractsmentioning

confidence: 85%

“…Another peculiarity of this species was the high relative levels of various tricaffeoylhexaric acid isomers (35,44,48,57), including those acylated to isobutyric acid moieties commonly found in other Asteraceae species (69, 70, 72); [20] and other tricaffeoyl acid esters (73, 76) that were particularly high in the stems. The leaves and stems were also characterized by many different isomers of dicaffeoyl (18, 28, 33,34,37,38,40,41,55) and tricaffeoyl (60, 65, 68) quinic acid, by dicaffeoylquinic acid hexoside (25) and coumaroylcaffeoylquinic acid isomers (47,52), while neochlorogenic acid (3) levels were higher in the leaves of this species. Other characteristic metabolites of A. verlotiorum leaves were represented by hexose (1) and pentose (5) esters of a dihydroxybenzoic acid, by quercetin-O-caffeoylhexoside (43) and by four avone glycosides, which included apigenin-O-hexoside-deoxyhexoside (31), apigenin-7-O-glucoside (39) and two dihydroxymethoxy avone-O-hexoside isomers (49,56), the latter best represented in the stems.…”

Section: Metabolic Pro Les Of Artemisia Spp Methanolic Extractsmentioning

confidence: 88%

“…2B) were strongly characterized by the glycosides of different coumarins including esculetin hexoside (6), coumarin-O-hexoside (8), methoxycoumarin-O-hexoside (10) and dimethoxycoumarin-O-hexoside (13). These organs present major peaks attributed to caffeoylquinic acids (9,15) and various isomers of dicaffeoylquinic acid (28, 34,37,38,40). Less represented hydroxycinnamic acid derivatives include dicaffeoylquinic acid hexoside (25), caffeoylpentoside (17) and three isomers of tricaffeoylquinic acid (60, 65, 68), which were mostly abundant in the leaves.…”

Section: Metabolic Pro Les Of Artemisia Spp Methanolic Extractsmentioning

confidence: 99%

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Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds

Negri,

Pietrolucci,

Andreatta

et al. 2023

Preprint

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Species from genus Artemisia are widely distributed throughout temperate regions of the northern hemisphere and many cultures have a long-standing traditional use of these plants as herbal remedies, liquors, cosmetics, spices, etc. Nowadays, the discovery of new plant-derived products to be used as food supplements or drugs has been pushed by the exploitation of bioprospection approaches. Often driven by the knowledge derived from the ethnobotanical use of plants, bioprospection explores the existing biodiversity through integration of modern omics techniques with targeted bioactivity assays. In this work we set up a bioprospection plan to investigate the phytochemical diversity and the potential bioactivity of five Artemisiaspecies with recognized ethnobotanical tradition (A. absinthium, A. alba, A. annua, A. verlotiorum and A. vulgaris), growing wild in the natural areas of the Verona province. We characterized the specialized metabolomes of the species (including sesquiterpenoids from the artemisinin biosynthesis pathway) through an LC-MS based untargeted approach and, in order to identify potential bioactive metabolites, we correlated their composition with the in vitro antioxidant activity. We propose as potential bioactive compounds several isomers of caffeoyl and feruloyl quinic acid esters (e.g. dicaffeoylquinic acids, feruloylquinic acids and caffeoylferuloylquinic acids), which strongly characterize the most antioxidant species A. verlotiorum and A. annua. Morevoer, in this study we report for the first time the occurrence of sesquiterpenoids from the artemisinin biosynthesis pathway in the species A. alba.

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Harnessing Plant Trichome Biochemistry for the Production of Useful Compounds

Cited by 4 publications

References 141 publications

Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species

Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species

The role of volatiles in plant communication

Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds

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