Isolation and characterization of the sucrose esters of the cuticular waxes of green tobacco leaf

Severson, R. F.; Arrendale, R. F.; Chortyk, O. T.; Green, C. R.; Thome, F. A.; Stewart, J.L.; Johnson, Albert W.

doi:10.1021/jf00065a026

Cited by 104 publications

(91 citation statements)

References 3 publications

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“…Components were derivatized using bis(trimethy1si-lyl)trifluoroacetamide/N,N-dimethylformamide (1 : 1) and analyzed by capillary gas chromatography/mass spectrometry. For compositional analysis of sucrose ester acids, the sucrose ester fraction was hydrolyzed, free acids were converted to their butyl esters and these were analyzed by capillary gas chromatography [15].…”

Section: Determination Of Surface Constituentsmentioning

confidence: 99%

Modified branched‐chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes

Kandra

Severson

Wagner

1990

European Journal of Biochemistry

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A major diversion of carbon from branched-chain amino acid biosynthesis/catabolism to form acyl moieties of sucrose esters (6-~-acety~-~,~,~-tr~-~-acy~-a-~-g~ucopyranosy~-~-~-fructofuranos~des) was observed to be associated with specialized trichome head cells which secrete large amounts of sucrose esters. Surface chemistry and acetyl and acyl substituent groups of tobacco (T.I. 1068) sucrose esters were identified and quantified by gas chromatography/mass spectrometry. Sucrose esters were prominent surface constituents and 3-methylvaleric acid, 2-and 3-methylbutyric acid, and methylpropionic acid accounted for 60%, 25% and 9%, respectively, of total C3 -C7 acyl substituents. Radiolabeled Thr, Ile, Val, Leu, pyruvate and Asp, metabolites of branched-chain amino acid pathways, were compared with radioactively labeled acetate and sucrose as donors of carbon to sucrose, acetyl and acyl components of sucrose esters using epidermal peels with undisturbed trichomes. Preparations of biosynthetically competent trichome heads (site of sucrose ester formation) were also examined. Results indicate that 3-methylvaleryl and 2-methylbutyryl groups are derived from the Thr pathway of branched-chain amino acid metabolism, 3-methylbutyryl and methylpropionyl groups are formed via the pyruvate pathway, and that acetyl groups are principally formed directly via acetyl-CoA. Arguments are presented which rule out participation of fatty acid synthase in the formation of prominent acyl acids.Results suggest that the shunting of carbon away from the biosynthesis of Val, Leu and Ile may be due to a low level of amino acid utilization in protein synthesis in specialized glandular head cells of trichomes. This would result in the availability of corresponding 0x0 acids for CoA activation and esterification to form sucrose esters. Preliminary evidence was found for the involvement of cycling reactions in 0x0-acid-chain lengthening and for utilization of pyruvate-derived 2-oxobutyrate to form straight-chain acyl substituents.

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Section: Determination Of Surface Constituentsmentioning

confidence: 99%

Modified branched‐chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes

Kandra

Severson

Wagner

1990

European Journal of Biochemistry

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“…A presença desses aleloquímicos, no acesso selvagem de tomateiro Lycopersicon pennellii 'LA-716', confere resistência a um grande número de pragas, inclusive àquelas consideradas pragas-chave na cultura do tomateiro. Sua presença também foi identificada em outras espécies do gênero Lycopersicon, bem como em outros gêneros da família Solanaceae, inclusive Solanum, Nicotiana e Datura (Severson et al, 1985;King et al, 1990;Shinozaki et al, 1991). Esse grupo de fitoquímicos pode atuar de modo a impedir a oviposição e a alimentação ou, ainda, a exercer efeito deletério no desenvolvimento de determinadas fases dos artrópodos-praga (Goffreda et al, 1989;Liedl et al, 1995;Resende et al, 2002aResende et al, , 2006Baldin et al, 2005).…”

Section: Introductionunclassified

Herança de acilaçúcares em genótipos de tomateiro provenientes de cruzamento interespecífico

Gonçalves

Maluf

Cardoso

et al. 2007

Pesq. agropec. bras.

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Resumo -O objetivo deste trabalho foi determinar a herança da produção de acilaçúcares em genótipos de tomateiro, em uma população segregante (F 2 ) do terceiro retrocruzamento, para Lycopersicon esculentum Mill. 'TOM-584', a partir da espécie L. pennellii 'LA-716'. A determinação do teor de acilaçúcares foi realizada com metodologia para determinação de açúcares redutores. Os dados foram utilizados para verificação da herança monogênica, sob diferentes graus de dominância (GD) presumidos, por meio do teste qui-quadrado. Para verificar a existência de efeitos aditivos e não aditivos de um gene maior e de possíveis poligenes, utilizou-se o método da máxima verossimilhança. Para os diferentes GD testados, na faixa compreendida entre -0,7 e -0,4, a hipótese de herança monogênica não pôde ser descartada, o que indica a ação de alelo recessivo, com dominância incompleta na expressão de alto teor de acilaçúcares. Por meio de modelos genéticos pela função de verossimilhança, a hipótese de herança monogênica foi confirmada. Plantas de tomateiro, com boa resistência a artrópodos-praga, mediada pelo aleloquímico acilaçúcar, podem ser obtidas com eficiência em populações de retrocruzamentos, a partir do cruzamento interespecífico L. esculentum x L. pennellii.Termos para indexação: Lycopersicon esculentum, Lycopersicon pennellii, seleção, aleloquímico, resistência à praga. Inheritance of tomato leaflet acylsugar contents in genotypes derived from an interspecific crossAbstract -The objective of this work was to determine the inheritance of acylsugar contents in tomato genotypes, from the F 2 generation of the third backcross of L. esculentum Mill. 'TOM-584', after the original cross with the wild accession L. pennellii 'LA-716'. Acylsugar contents in tomato leaflets were measured according to a methodology for reducing sugars determination. The data obtained were evaluated with chi-square tests of monogenic hypotheses of inheritance, under different presumed degrees of dominance, and also under genetic models with the maximum likelihood function, in which presence of a major gene and possible polygenes with additive and non additive effects were tested. For the different presumed degrees of dominance (DD) tested in an array between -0.7 and -0.4, the hypotheses of monogenic inheritance could not be rejected, indicating that high acylsugar contents are controlled by a recessive allele in a locus with incomplete dominance. Genetic models tested under the maximum likelihood function also confirmed the hypothesis of monogenic inheritance. Tomato plants with adequate levels of acylsugar-mediated resistance to arthropod pests can be efficiently obtained in backcross populations, derived from the interspecific cross L. esculentum x L. pennellii.Index terms: Lycopersicon esculentum, Lycopersicon pennellii, selection, allelochemicals, pest resistance. IntroduçãoAlgumas espécies do gênero Lycopersicon apresentam elevada resistência a artrópodos-praga e apresentam potencial para utilização em programas de melhoramento genético que vis...

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“…The acylsugars identified thus far consist of short to medium (C2-C12) chain length aliphatic acids in normal (straight chain), iso (branched at the penultimate carbon), or anteiso (branched at the antepenultimate carbon) configuration esterified to Suc or Glc ( Fig. 1A; Severson et al, 1985;Burke et al, 1987;King et al, 1990;Walters and Steffens, 1990). Acylsugars contribute to direct defense against a wide variety of insect herbivores (Rodriguez et al, 1993;Juvik et al, 1994;Chortyk et al, 1997;Puterka et al, 2003), and substitutions in either the sugar or acyl chain component alter their insecticidal activity (Puterka et al, 2003).…”

mentioning

confidence: 99%

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

Ning

Moghe²,

Leong³

et al. 2015

Plant Physiol.

177

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Acylsugars are insecticidal specialized metabolites produced in the glandular trichomes of plants in the Solanaceae family. In the tomato clade of the Solanum genus, acylsugars consist of aliphatic acids of different chain lengths esterified to sucrose, or less frequently to glucose. Through liquid chromatography-mass spectrometry screening of introgression lines, we previously identified a region of chromosome 8 in the Solanum pennellii LA0716 genome (IL8-1/8-1-1) that causes the cultivated tomato Solanum lycopersicum to shift from producing acylsucroses with abundant 3-methylbutanoic acid acyl chains derived from leucine metabolism to 2-methylpropanoic acid acyl chains derived from valine metabolism. We describe multiple lines of evidence implicating a trichome-expressed gene from this region as playing a role in this shift. S. lycopersicum M82 SlIPMS3 (Solyc08g014230) encodes a functional end product inhibition-insensitive version of the committing enzyme of leucine biosynthesis, isopropylmalate synthase, missing the carboxyl-terminal 160 amino acids. In contrast, the S. pennellii LA0716 IPMS3 allele found in IL8-1/8-1-1 encodes a nonfunctional truncated IPMS protein. M82 transformed with an SlIPMS3 RNA interference construct exhibited an acylsugar profile similar to that of IL8-1-1, whereas the expression of SlIPMS3 in IL8-1-1 partially restored the M82 acylsugar phenotype. These IPMS3 alleles are polymorphic in 14 S. pennellii accessions spread throughout the geographical range of occurrence for this species and are associated with acylsugars containing varying amounts of 2-methylpropanoic acid and 3-methylbutanoic acid acyl chains.

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Isolation and characterization of the sucrose esters of the cuticular waxes of green tobacco leaf

Cited by 104 publications

References 3 publications

Modified branched‐chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes

Modified branched‐chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes

Herança de acilaçúcares em genótipos de tomateiro provenientes de cruzamento interespecífico

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

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