A chemical study of <i>burley</i> tobacco flavour (<i>nicotiana tabacum</i><scp>L</scp>.) VI. Identification and Synthesis of Four Irregular Terpenoids Related to Solanone, Including a ‘Prenylsolanone’

Demole, E.; Enggist, Paul

doi:10.1002/hlca.19750580614

Cited by 16 publications

(4 citation statements)

References 16 publications

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“…This peak #1 was annotated to be norsolanadione by deconvolution analysis. Norsolanadione is a product derived from the autooxidation of solanone, which is an unsaturated ketone and commonly used as a fragrant additive [18]. On the other hand, a peak (labeled with peak #5) was detected in samples of India and Brazil but not in ones of North Carolina.…”

Section: Comparison Of Volatile Profiles In Curedmentioning

confidence: 99%

Integration of GC-MS Based Non-Targeted Metabolic Profiling with Headspace Solid Phase Microextraction Enhances the Understanding of Volatile Differentiation in Tobacco Leaves from North Carolina, India and Brazil

Ma¹,

Gandra²,

Sharma³

et al. 2012

AJPS

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In this report, gas chromatography-mass spectrometry (GC-MS) based non-targeted metabolomics is used to develop appropriate headspace solid phase microextractions (HS-SPME) to enhance the understanding of volatile complexity of flue-cured tobacco leaves. Non-targeted metabolic profiling of GC-MS shows that the extraction condition of HS-SPME at 100˚C for 30 min provides a better metabolite profile than other extraction conditions tested. GC-MS and principal component analyses (PCA) show that among five types of fibers tested, 100 μm polydimethylsiloxane (PMDS), 65 μm polydimethylsiloxane/divinylbenzene (PMDS/DVB) and 75 μm carboxen/polydimethylsiloxane (CAR/ PMS) provide a better reproducible metabolite profile. Based on an appropriate PDMS extraction condition optimized, we use GC-MS analysis and PCA to compare metabolite profiles in flue-cured leaves of tobacco plants grown in North Carolina, India and Brazil, respectively. The resulting data of PCA show that the global metabolic profiles in North Carolina samples are separated from those in Brazil and India samples, two groups of which are characterized by a partially overlapped pattern. Several peaks that were differentially accumulated in samples were annotated to known metabolites by deconvolution analysis, such as norsolanadione, solavetivone and rishitin. Norsolanadione is detected only in Brazil samples. Solavetivone is detected in samples of India and Brazil but not in those of North Carolina. Rishitin is detected in samples of North Carolina and India but not in Brazil samples. These data indicate that not only can a non-targeted metabolic profiling approach enhance the understanding of volatile complexity, but also can identify marker volatile metabolites in tobacco leaves produced in different growth regions.

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Section: Comparison Of Volatile Profiles In Curedmentioning

confidence: 99%

Integration of GC-MS Based Non-Targeted Metabolic Profiling with Headspace Solid Phase Microextraction Enhances the Understanding of Volatile Differentiation in Tobacco Leaves from North Carolina, India and Brazil

Ma¹,

Gandra²,

Sharma³

et al. 2012

AJPS

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“…The large coupling constant (16.0 Hz) observed for signals due to H-5 and H-6 of both 1 and 5 suggested trans configuration for the C 5 =C 6 double bond. The configuration of C-7, the carbon bearing the iso -propyl group, is assumed to be S based on the large coupling constant (9.5 Hz) observed for H-6 and H-7 similar to the structurally related compound, 5 E ,7 S -isopropyl-4-methyl-10-oxo-undecen-4-olide ( 6 ) (Aasen, Hlubucek, & Enzell, 1975a; Coates, Ghisalberti, & Jefferies 1977; Demole & Enggist, 1975), and on biogenetic considerations (Aasen, Junker, & Enzell, 1975b; Zhang et al, 2003). Based on the above reasoning and the observed HMBC correlations (Figure 1), the structure of tricinonoic acid was elucidated as 5 E ,7 S -isopropyl-4-methylene-10-oxo-undec-4-enoic acid ( 1 ).…”

Section: Resultsmentioning

confidence: 99%

Tricinonoic acid and tricindiol, two new irregular sesquiterpenes from an endophytic strain ofFusarium tricinctum

Bashyal

Gunatilaka

2010

Natural Product Research

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Two new rare irregular sesquiterpenes, tricinonoic acid (1) and tricindiol (2), and the known furanopyrrolidones, NG-391 (3) and NG-393 (4), have been isolated from an EtOAc extract of Fusarium tricinctum, a fungus endophytic in the root tissue of the Sonoran desert plant, Rumex hymenosepalus. The structures of 1 and 2 were elucidated on the basis of their high-resolution mass, 1D and 2D NMR spectroscopic data. A possible biosynthetic route to 1 and 2 from farnesyl diphosphate is proposed.

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“…The sample targets in Scheme IV have both been synthesized in the laboratory. 20 The olefin package in LHASA suggests a route (among others) to phenylsolanone (16) which is at least as inventive as the published synthesis. For ocimene (17), LHASA finds the published route and a large number of other reasonable pathways as well.…”

Section: Methodsmentioning

confidence: 99%

Computer-assisted synthetic analysis. Performance of long-range strategies for stereoselective olefin synthesis

Corey¹,

Long²

1978

J. Org. Chem.

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A chemical study of burley tobacco flavour (nicotiana tabacumL.) VI. Identification and Synthesis of Four Irregular Terpenoids Related to Solanone, Including a ‘Prenylsolanone’

Abstract: The preparation and study of RurJcy totncco condcnsrrtc subfractions I33-PN-a to -i will bc describcd in a future paper.

Cited by 16 publications

References 16 publications

Integration of GC-MS Based Non-Targeted Metabolic Profiling with Headspace Solid Phase Microextraction Enhances the Understanding of Volatile Differentiation in Tobacco Leaves from North Carolina, India and Brazil

Integration of GC-MS Based Non-Targeted Metabolic Profiling with Headspace Solid Phase Microextraction Enhances the Understanding of Volatile Differentiation in Tobacco Leaves from North Carolina, India and Brazil

Tricinonoic acid and tricindiol, two new irregular sesquiterpenes from an endophytic strain ofFusarium tricinctum

Computer-assisted synthetic analysis. Performance of long-range strategies for stereoselective olefin synthesis

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