Rapid characterization of the sucrose esters from oriental tobacco using liquid chromatography/ion trap mass spectrometry

Ding, Li; Xie, Fuwei; Zhao, Ming; Xie, Jianping; Xu, Guowang

doi:10.1002/rcm.2664

Cited by 16 publications

(21 citation statements)

References 17 publications

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“…The overall fragmentation of these compounds is similar to that observed for saturated SEs, which suggests the same substitution pattern. The ions of the glucose moiety at m/z 483 and 497, together with the signal of the unsaturated C 6 acyl chain at m/z 97, indicated the presence of SEs similar to those reported earlier by Ding et al (2006). …”

Section: Identifi Cation Of N Tabacum Sucrose Esters By Gc-mssupporting

confidence: 86%

“…Einolf and Chan (1984) described the application of direct chemical ionization MS (DCI-MS) to Nicotiana SEs analysis, but extracts still had to be purifi ed by SPE (solid-phase extraction) before analysis. The LC/ ESI-MS-MS (liquid chromatography-electrospray ionization-tandem mass spectrometry) method was also developed by Ding et al (2006), but extracts from green leaves of tobacco were purifi ed and fractionated prior to analysis. To our knowledge, only a single LC/ESI-TOF MS-based method for SEs profi ling in crude plant extracts has been described to date (Weinhold and Baldwin, 2011).…”

Section: Introductionmentioning

confidence: 99%

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GC-MS and MALDI-TOF MS Profi ling of Sucrose Esters from Nicotiana tabacum and N. rustica

Haliński

Stepnowski²

2013

Zeitschrift Für Naturforschung C

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Matrix-assisted laser desorption/ionization-time-of-fl ight mass spectrometry (MALDI-TOF MS) has been applied for the fi rst time to the analysis of the sucrose esters from the surface of Nicotiana L. leaves. The profi les obtained for the model plant N. tabacum were similar to those from the gas chromatography-fl ame ionization detector (GC-FID) analysis. The most reproducible results were obtained using a dihydroxybenzoic acid (DHB) matrix. The main advantage of this method is that crude plant extracts can be analysed without sample clean-up. GC-MS analysis of Aztec tobacco (N. rustica) extracts revealed the presence of three types of sucrose esters. All identifi ed compounds had three C 4 − C 8 acyl chains substituting the glucose moiety, while the fructose part of the molecule was substituted with 0, 1, or 2 acetyl groups. MALDI-TOF MS analysis of the sucrose ester fraction revealed the presence of compounds not eluting from a GC column. Combining the data from both GC-MS and MALDI-TOF MS experiments, we obtained a full sucrose ester profi le, which is based on the molecular weight of the compounds and on the number of acyl chains in the molecule.

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Section: Identifi Cation Of N Tabacum Sucrose Esters By Gc-mssupporting

confidence: 86%

Section: Introductionmentioning

confidence: 99%

GC-MS and MALDI-TOF MS Profi ling of Sucrose Esters from Nicotiana tabacum and N. rustica

Haliński

Stepnowski²

2013

Zeitschrift Für Naturforschung C

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“…S1 and S2). Their mass spectra were consistent with a Suc ester structure containing C 8 BCFAs (identified as 6MeC7:0 or 5MeC7:0 by gas chromatography-flame ionization detection [GC-FID]) and, as in other Nicotiana species, acetate (Ding et al, 2006;Supplemental Table S1). For instance, the major acyl sugar (molecular weight 636; Supplemental Table S1) consisted of one C 8 BCFA esterified to both the Glc and Fru subunits and one acetate esterified to the Fru subunit (Supplemental Fig.…”

Section: Acyl Sugar and Fatty Acid Production In N Benthamiana And Smentioning

confidence: 53%

Transcriptomic and Reverse Genetic Analysesof Branched-Chain Fatty Acid and Acyl Sugar Production inSolanum pennelliiandNicotiana benthamiana

et al. 2008

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Acyl sugars containing branched-chain fatty acids (BCFAs) are exuded by glandular trichomes of many species in Solanaceae, having an important defensive role against insects. From isotope-feeding studies, two modes of BCFA elongation have been proposed: (1) fatty acid synthase-mediated two-carbon elongation in the high acyl sugar-producing tomato species Solanum pennellii and Datura metel; and (2) a-keto acid elongation-mediated one-carbon increments in several tobacco (Nicotiana) species and a Petunia species. To investigate the molecular mechanisms underlying BCFAs and acyl sugar production in trichomes, we have taken a comparative genomic approach to identify critical enzymatic steps followed by gene silencing and metabolite analysis in S. pennellii and Nicotiana benthamiana. Our study verified the existence of distinct mechanisms of acyl sugar synthesis in Solanaceae. From microarray analyses, genes associated with a-keto acid elongation were found to be among the most strongly expressed in N. benthamiana trichomes only, supporting this model in tobacco species. Genes encoding components of the branched-chain keto-acid dehydrogenase complex were expressed at particularly high levels in trichomes of both species, and we show using virus-induced gene silencing that they are required for BCFA production in both cases and for acyl sugar synthesis in N. benthamiana. Functional analysis by down-regulation of specific KAS I genes and cerulenin inhibition indicated the involvement of the fatty acid synthase complex in BCFA production in S. pennellii. In summary, our study highlights both conserved and divergent mechanisms in the production of important defense compounds in Solanaceae and defines potential targets for engineering acyl sugar production in plants for improved pest tolerance.

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“…In the previous article 24, characterization of SEs has been reported in detail. However, besides sucrose esters, low‐abundant glucose esters were also found.…”

Section: Resultsmentioning

confidence: 99%

Separation and detection of polar cuticular components from Oriental tobacco leaf by integration of normal‐phase liquid chromatography fractionation with reversed‐phase liquid chromatography‐mass spectrometry

Ding¹,

Xie²,

Xu³

et al. 2010

J of Separation Science

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Integration of normal-phase LC (NPLC) fractionation with RPLC-ESI/MS was established to detect the polar fractions of cuticular components from Oriental tobacco leaf. NPLC was selected for the fractionation of polar components of cuticular leaf extract, after being concentrated with rotary evaporator, each of the enriched fractions was further analyzed by RPLC-ESI/MS. In total, 83 compounds were finally detected including 45 cembranoids, 15 labdanoids, 20 sucrose esters, and 3 glucose esters (or fructose esters). Three cembranoids and seven labdanoids possibly are new diterpenoids. Glucose esters (or fructose esters) are also reported in Nicotiana tobacco for the first time.

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Rapid characterization of the sucrose esters from oriental tobacco using liquid chromatography/ion trap mass spectrometry

Cited by 16 publications

References 17 publications

GC-MS and MALDI-TOF MS Profi ling of Sucrose Esters from Nicotiana tabacum and N. rustica

GC-MS and MALDI-TOF MS Profi ling of Sucrose Esters from Nicotiana tabacum and N. rustica

Transcriptomic and Reverse Genetic Analysesof Branched-Chain Fatty Acid and Acyl Sugar Production inSolanum pennelliiandNicotiana benthamiana

Separation and detection of polar cuticular components from Oriental tobacco leaf by integration of normal‐phase liquid chromatography fractionation with reversed‐phase liquid chromatography‐mass spectrometry

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