Separation and Identification of Sucrose Esters from Turkish Tobacco Using Liquid Chromatography-Mass Spectrometry

Abstract

SUMMARYTetra-acylated sucrose esters (SE) in Turkish tobacco extracts have been separated and identified using liquid chromatography-mass spectrometry (LC-MS). An enriched fraction of SE from semi-preparative normal phase liquid chromatography of the methylene chloride extract was chosen for characterization. Several types of SE were observed that differed primarily in placement of the acyl functionality on either the glucose or the fructose fragment. In addition to acetyl, the other three observed acyl substitution patterns were governed by the presence of butyl, pentyl, and hexyl alkyl substituents. Within each type of SE, there were observed several homologs differing by a methylene moiety. Within each homolog, a number of isomeric components were found. The presence of unsaturation in one of the acyl alkyl substituents gave rise to another homologous series wherein isomers of the same mass were discovered. The information on the substitution pattern of SE using this new LC-MS approach was very similar to that obtained previously on tobacco samples employing gas chromatography-mass spectrometry (GC- RESUMEDes esters tetra-acylé de saccharose (SE) dans des extraits de tabac turc ont été séparés et identifiés par chromatographie liquide-spectrométrie de masse (LC-MS). Une fraction enrichie de SE obtenue par chromatographie liquide en phase normale semi-préparatoire de l'extrait de chlorure de méthylène a été choisie pour être caractérisé. Plusieurs types de SE ont été observés différant par la localisation de la fonction de l'acyl dans les fractions de glucose ou de fructose. En plus de l'acétyl, les trois autres schémas de substitution de l'acétyl ont été commandés par la présence de substituants butyl, pentyl et hexyl alkyl. Dans chaque type de SE plusieurs homologues ont été observés ayant un groupement méthylène différent. Dans chacun des homologues, un nombre de composants isomériques ont été trouvé. La présence de substituants acyl alkyl non saturé a induit

Ecological Roles and Biological Activities of Specialized Metabolites from the GenusNicotiana

“…There are several reports on the isolation and structural characterization of different types of SCE homologues from Nicotiana by silica gel column chromatography or HPTLC combined with spectroscopic methods, , LC–MS, − and LC–MS n . , The SCEs in the cuticular waxes of green tobacco are the major components of Turkish tobacco (N. tabacum) .…”

Identification and Quantification of Sucrose Esters in Various Turkish Tobaccos

“…The presence of unsaturation in one of the acyl alkyl substituents gave rise to another homologous series wherein isomers of the same mass were discovered. Supercritical CO 2 at various pressures and temperatures has been used to effect the fractionation of tetra-acyl sucrose esters (SE) from dried, ground Turkish tobacco without any further pretreatment of the matrix (15). It was determined that SE can not be extracted using low density CO 2 (150 atm, 60 /C, 0.62 gm/mL or 200 atm, 100 /C, 0.49 gm/mL), whereas other analytes which strongly interfere with the conventional solvent extraction of SE can be easily removed under the same conditions.…”

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

“…In addition to acetyl, the three acyl substitution patterns were governed by the presence of butyl, pentyl, and hexyl substituents. The presence of unsaturation in one of the acyl chains gave rise to another homologous series wherein isomers of the same mass were discovered (18,19). Our success with supercritical CO 2 for extraction has prompted us to now consider supercritical fluid chromatography for isolation of individual sucrose esters that are observed in "crude" extracts as opposed to conventional liquid chromatography.…”