Quantitation of the major cuticular components from green leaf of different tobacco types

Severson, Ray F.; Arrendale, Richard F.; Chortyk, O. T.; Johnson, Albert W.; Jackson, D. Michael; Gwynn, G. R.; Chaplin, J. F.; Stephenson, M. G.

doi:10.1021/jf00123a037

Cited by 110 publications

(93 citation statements)

References 4 publications

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“…The molecular species distributions for the alkane and MAG fractions for tobacco plants transformed with the 35STAtGPAT5 construct are given in Supplemental Table S1. The alkane distribution is very similar to that reported by Severson et al (1984) and is annotated accordingly. The bis-TMSi derivatives of branched-chain b-MAG species have very similar mass spectra to their straight-chain isomers, but elute ahead at distinctive fractional equivalent carbon numbers.…”

Section: Surface Mags Are Produced In 35stgpat5-expressing Tobacco Plsupporting

confidence: 80%

“…Both straight and branched-chain acyl groups were present in the MAGs. This parallels the presence of iso-and anteiso-C27-C33 branched-chain hydrocarbons reported for tobacco epicuticular waxes (Severson et al, 1984). The molecular species distributions for the alkane and MAG fractions for tobacco plants transformed with the 35STAtGPAT5 construct are given in Supplemental Table S1.…”

Section: Surface Mags Are Produced In 35stgpat5-expressing Tobacco Plsupporting

confidence: 74%

“…For molecular identification, a Hewlett-Packard 5890 GC-coupled MSD 5972 mass analyzer was used with the mass analyzer set in electron impact mode (70 eV) and scanning from 40 to 700 atomic mass units. Tobacco leaf epicuticular wax analysis was conducted as above, except that leaves were dipped in dichloromethane instead of chloroform (Severson et al, 1984).…”

Section: Cuticular Wax Analysismentioning

confidence: 99%

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Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

et al. 2007

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The interface between plants and the environment is provided for aerial organs by epicuticular waxes that have been extensively studied. By contrast, little is known about the nature, biosynthesis, and role of waxes at the root-rhizosphere interface. Waxes isolated by rapid immersion of Arabidopsis (Arabidopsis thaliana) roots in organic solvents were rich in saturated C18-C22 alkyl esters of p-hydroxycinnamic acids, but also contained significant amounts of both a-and b-isomers of monoacylglycerols with C22 and C24 saturated acyl groups and the corresponding free fatty acids. Production of these compounds in root waxes was positively correlated to the expression of sn-glycerol-3-P acyltransferase5 (GPAT5), a gene encoding an acyltransferase previously shown to be involved in aliphatic suberin synthesis. This suggests a direct metabolic relationship between suberin and some root waxes. Furthermore, when ectopically expressed in Arabidopsis, GPAT5 produced very-longchain saturated monoacylglycerols and free fatty acids as novel components of cuticular waxes. The crystal morphology of stem waxes was altered and the load of total stem wax compounds was doubled, although the major components typical of the waxes found on wild-type plants decreased. These results strongly suggest that GPAT5 functions in vivo as an acyltransferase to a glycerol-containing acceptor and has access to the same pool of acyl intermediates and/or may be targeted to the same membrane domain as that of wax synthesis in aerial organs.

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Section: Surface Mags Are Produced In 35stgpat5-expressing Tobacco Plsupporting

confidence: 80%

Section: Surface Mags Are Produced In 35stgpat5-expressing Tobacco Plsupporting

confidence: 74%

Section: Cuticular Wax Analysismentioning

confidence: 99%

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Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

et al. 2007

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“…This fraction contained only a trace amount of nicotine and did not contain N-hydroxyacylnornicotine. The internal nicotine and nornicotine content of homogenized leaves was chloroform extracted, the chloroform evaporated, the alkaloid residue TLC purified, (19). We observed that CH2Cl2 extracts nicotine and N-hydroxyacylnornicotine (Fig.…”

Section: Methodsmentioning

confidence: 97%

The Biosynthesis of a Novel Nicotine Alkaloid in the Trichomes of Nicotiana stocktonii

Zádor¹,

Jones²

1986

Plant Physiol.

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N-Hydroxyacylnornicotine, newly discovered from fresh plant tissue, was found entirely in the trichome exudate produced at the epidermis of the aerial part of Nicotiana stocktonii. Nicotine and nornicotine, but not N-hydroxyacylnornicotine, were present inside of the trichomes as well as other internal parts of the plant. Only nicotine was found in bleeding sap squeezed from cut roots or stems. Feeding of leaves with 2'-'4C-labeled nicotine primarily yielded labeled nicotine, nornicotine, and Nhydroxyacylnoraicotine. When similarly labeled nornicotine was fed to leaves as a precursor, a labeled N-hydroxyacylnornicotine was obtained, with a higher specific activity than with the 12'-4Cinicotine feeding.Based on these results, a synthesis route is suggested where nicotine is converted in the leaf to nornicotine, followed by trichome conversion of nornicotine to N-hydroxyacylnornicotine, and rapid secretion of this product.

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“…of the foliage of Nicotiana tabacum, the host plant of this insect (14). Analysis of the spectra obtained for secretions from pupal Delphastus catalinae revealed partial structures representing sesquiterpenoids, including a humulene derivative and acetylated derivatives of known germacrenediols (15), as well as a large group of polyketide-like fragments, which, based on HMBC data, appeared to be attached to highly unsaturated heterocyclic moieties.…”

mentioning

confidence: 99%

2D NMR-spectroscopic screening reveals polyketides in ladybugs

Deyrup

Eckman²,

McCarthy³

et al. 2011

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

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Small molecules of biological origin continue to yield the most promising leads for drug design, but systematic approaches for exploring nature's cache of structural diversity are lacking. Here, we demonstrate the use of 2D NMR spectroscopy to screen a library of biorationally selected insect metabolite samples for partial structures indicating the presence of new chemical entities. This NMRspectroscopic survey enabled detection of novel compounds in complex metabolite mixtures without prior fractionation or isolation. Our screen led to discovery and subsequent isolation of two families of tricyclic pyrones in Delphastus catalinae, a tiny ladybird beetle that is employed commercially as a biological pest control agent. The D. catalinae pyrones are based on 23-carbon polyketide chains forming 1,11-dioxo-2,6,10-trioxaanthracene and 4,8-dioxo-1,9,13-trioxaanthracene derivatives, representing ring systems not previously found in nature. This study highlights the utility of 2D NMR-spectroscopic screening for exploring nature's structure space and suggests that insect metabolomes remain vastly underexplored.

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Quantitation of the major cuticular components from green leaf of different tobacco types

Cited by 110 publications

References 4 publications

Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

Monoacylglycerols Are Components of Root Waxes and Can Be Produced in the Aerial Cuticle by Ectopic Expression of a Suberin-Associated Acyltransferase

The Biosynthesis of a Novel Nicotine Alkaloid in the Trichomes of Nicotiana stocktonii

2D NMR-spectroscopic screening reveals polyketides in ladybugs

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