A feedback insensitive isopropylmalate synthase affects acylsugar composition in cultivated and wild tomato

Ning, Jing; Moghe, Gaurav D.; Leong, Bryan J.; Kim, Jeongwoon; Ofner, Itai; Wang, Zhenzhen; Adams, Christopher J.; Jones, A. Daniel; Zamir, Dani

doi:10.1104/pp.15.00474

Cited by 73 publications

(191 citation statements)

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“…Published studies revealed major differences in trichome metabolite accumulation (15,25,26,29) in several introgression lines (ILs), which have regions of the S. pennellii LA0716 genome substituted in place of the S. lycopersicum M82 genome (31). Rescreening the ILs by liquid chromatography-time of flight mass spectrometry (LC-ToF MS) identified a more subtle phenotype: accumulation of two lowabundance species in IL4-1 not seen in the M82 parent (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…1C). Sl-ASAT2 RNAi lines were generated in M82, and reduced total acylsugar levels were observed for 24 of 29 independent transgenic lines (SI Appendix, Deep RNA-seq analysis revealed that both Sl-ASAT1 and Sl-ASAT2 mRNAs are highly enriched in M82 tomato trichomes (26), and trichome-enriched expression of Sl-ASAT1 and Sl-ASAT2 in M82 stem trichomes and Sp-ASAT2 in S. pennellii LA0716 leaf trichomes were confirmed by RT-PCR (SI Appendix, Figs. S1C and S2D).…”

Section: Sl-asat2mentioning

confidence: 99%

“…Recent work on acylsucrose biosynthesis in trichomes of the tomato clade revealed that this relatively closely related group of plants produces a surprisingly diverse group of acylsucroses in tip cells of the long hair-like type I/IV trichomes (14,(24)(25)(26). The genetic and biochemical mechanisms underlying some of this phenotypic diversity have begun to be revealed.…”

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confidence: 99%

“…Protective properties against herbivores have made increasing total acylsugars or altering acyl chain types a target for breeding insect-resistant cultivated tomatoes (Solanum lycopersicum) (16-18). In addition, synthetic sucrose esters mimicking natural acylsugars have been applied as safe, biodegradable insecticidal compounds (19-21) and also have commercial value in the food, cosmetic, and pharmaceutical industries (22,23).Recent work on acylsucrose biosynthesis in trichomes of the tomato clade revealed that this relatively closely related group of plants produces a surprisingly diverse group of acylsucroses in tip cells of the long hair-like type I/IV trichomes (14,(24)(25)(26). The genetic and biochemical mechanisms underlying some of this phenotypic diversity have begun to be revealed.…”

mentioning

confidence: 99%

“…The genetic and biochemical mechanisms underlying some of this phenotypic diversity have begun to be revealed. For example, 2-methylpropanoic acid (iC4) and 3-methylbutanoic acid (iC5) acyl chain variation in Solanum pennellii accessions is influenced by variation in the activity of a set of truncated isopropylmalate synthase 3 (IPMS3) enzymes (26). Differences in patterns of Solanum habrochaites acylsucrose acetylation (24) and acyl chain length and position variation (25) are due to genetic variation in two BAHD [BEAT, AHCT, HCBT, DAT (27,28)] acyltransferases.…”

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confidence: 99%

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In vitro reconstruction and analysis of evolutionary variation of the tomato acylsucrose metabolic network

Fan

Miller

Schilmiller

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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Plant glandular secreting trichomes are epidermal protuberances that produce structurally diverse specialized metabolites, including medically important compounds. Trichomes of many plants in the nightshade family (Solanaceae) produce O-acylsugars, and in cultivated and wild tomatoes these are mixtures of aliphatic esters of sucrose and glucose of varying structures and quantities documented to contribute to insect defense. We characterized the first two enzymes of acylsucrose biosynthesis in the cultivated tomato Solanum lycopersicum. These are type I/IV trichome-expressed BAHD acyltransferases encoded by Solyc12g006330─or S. lycopersicum acylsucrose acyltransferase 1 (Sl-ASAT1)─and Solyc04g012020 (Sl-ASAT2). These enzymes were used-in concert with two previously identified BAHD acyltransferases-to reconstruct the entire cultivated tomato acylsucrose biosynthetic pathway in vitro using sucrose and acyl-CoA substrates.Comparative genomics and biochemical analysis of ASAT enzymes were combined with in vitro mutagenesis to identify amino acids that influence CoA ester substrate specificity and contribute to differences in types of acylsucroses that accumulate in cultivated and wild tomato species. This work demonstrates the feasibility of the metabolic engineering of these insecticidal metabolites in plants and microbes.Solanum | glandular trichomes | acylsugar | specialized metabolism | genotype to phenotype P lants are masters of metabolism, producing hundreds of thousands of small molecules known as specialized metabolites, which vary widely in structure, abundance, and physical and biological properties. These metabolites tend to be produced by enzymes that evolve faster than those that produce "central" metabolites such as amino acids, nucleotides, sugars, and cofactors (1-3), and the pathways and metabolic intermediates involved in biosynthesis of many specialized metabolites remain mysterious. Despite the growing availability of genomic DNA sequences, understanding the genetic and biochemical mechanisms that contribute to this phenotypic diversity and plasticity presents enduring and major challenges in plant biochemistry. It is of great interest to understand and manipulate the biosynthesis of these biologically active molecules.Specialized metabolites typically are produced in a cell-or tissue-specific manner and are generally limited in their taxonomic distribution. Glandular secreting trichomes provide an example of such a differentiated structure; these epidermal "hairs" produce a variety of metabolites of importance to humans, including aromatic flavor components (e.g., in hops for beer and Mediterranean herbs for cooking), psychoactive cannabinoids in Cannabis, and the antimalarial drug artemisinin in Artemisia annua (4, 5).Some trichome-produced metabolites have documented direct and indirect antiherbivore activities (4, 6-8). For example, acylsugars are a group of structurally related specialized metabolites produced in plants of the nightshade family-the Solanaceae (9, 10). Characterized examples ...

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Section: Resultsmentioning

confidence: 99%

Section: Sl-asat2mentioning

confidence: 99%

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In vitro reconstruction and analysis of evolutionary variation of the tomato acylsucrose metabolic network

Fan

Miller

Schilmiller

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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106

233

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Identification of BAHD acyltransferases associated with acylinositol biosynthesis in Solanum quitoense (naranjilla)

et al. 2022

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Plants make a variety of specialized metabolites that can mediate interactions with animals, microbes, and competitor plants. Understanding how plants synthesize these compounds enables studies of their biological roles by manipulating their synthesis in vivo as well as producing them in vitro. Acylsugars are a group of protective metabolites that accumulate in the trichomes of many Solanaceae family plants.Acylinositol biosynthesis is of interest because it appears to be restricted to a subgroup of species within the Solanum genus. Previous work characterized a triacylinositol acetyltransferase involved in acylinositol biosynthesis in the Andean fruit plant Solanum quitoense (lulo or naranjilla). We characterized three additional S. quitoense trichome expressed enzymes and found that virus-induced gene silencing of each caused changes in acylinositol accumulation. pH was shown to influence the stability and rearrangement of the product of ASAT1H and could potentially play a role in acylinositol biosynthesis. Surprisingly, the in vitro triacylinositol products of these enzymes are distinct from those that accumulate in planta. This suggests that additional enzymes are required in acylinositol biosynthesis. These characterized S. quitoense enzymes, nonetheless, provide opportunities to test the biological impact and properties of these triacylinositols in vitro.

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The trichome-specific acetolactate synthase NtALS1 gene, is involved in acylsugar biosynthesis in tobacco (Nicotiana tabacum L.)

Chang

Chen

Yang

et al. 2020

Planta

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A feedback insensitive isopropylmalate synthase affects acylsugar composition in cultivated and wild tomato

Cited by 73 publications

References 78 publications

In vitro reconstruction and analysis of evolutionary variation of the tomato acylsucrose metabolic network

In vitro reconstruction and analysis of evolutionary variation of the tomato acylsucrose metabolic network

Identification of BAHD acyltransferases associated with acylinositol biosynthesis in Solanum quitoense (naranjilla)

The trichome-specific acetolactate synthase NtALS1 gene, is involved in acylsugar biosynthesis in tobacco (Nicotiana tabacum L.)

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