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

Open access


Isolation, fractionation, and identification of sucrose esters from aged oriental tobacco employing supercritical fluids have been completed. Underivatized sucrose ester-rich extracts were obtained using supercritical CO2 at densities greater than 0.73 g/mL. Lower density CO2 provided extracts with notable amounts of tobacco derived material; yet, no detectable sucrose ester content. Preparative supercritical fluid chromatography (SFC) provided for an additional purification of the sucrose ester-enriched fraction after column optimization. Structural assignments of the SFC fractions were facilitated using gas chromatography/mass spectrometry (GC/MS) accompanied by N, O-bis(trimethylsilyl)trifluoroacetamide-dimethylformamide (BSTFA-DMF) derivatization of the free hydroxyl groups and high performance-liquid chromatography/mass spectrometry (HPLC/MS). From a relative quantitative perspective regardless of tobacco type, sucrose esters having an acetyl group on C6 of the glucose function (Group III) were in higher concentration compared to both the concentration observed for sucrose ester of Group I (acetyl group on C3 of fructose) and sucrose ester of Group II (no acetyl group on either glucose or fructose). Saturated fatty acid constituents were found to range from a maximum total of 18 carbons to a minimum total of 13 carbons. Unsaturated and isomeric fatty acid homologues were detected within the Group II sucrose ester.

1. Schumacher, J.N.: The isolation of 6-O-acetyl-2,3,4,-tri-O-((+)-3-methylvaleryl)-beta-D-glucopyranose from tobacco; Carbohyd. Res. 13 (1970) 1-8.

2. Leffingwell, J.C. and D. Leffingwell: Chemical and sensory aspects of tobacco flavor; Rec. Adv. Tob. Sci. 14 (1988) 169-218.

3. Severson, R.F., A.W. Johnson, and D.M. Jackson: Cuticular constituents of tobacco: factors affecting their production and their role in insect and disease resistance and smoke quality; Rec. Adv. Tob. Sci. 11 (1985) 105-173.

4. Matsuzki, T., Y. Shinozaki, S. Suhara, M. Ninomiya, H. Shigematsu, and A. Koiwai: Isolation of glycolipids from the surface lipids of Nicotiana bigelovii and their distribution in Nicotiana species; Agric. Biol. Chem. 53 (1989) 3079-3082.

5. Severson, R.F., R.F. Arrendale, O.T. Chortyk, C.R. Green, F.A. Thomas, J.L. Stewart, and A.W. Johnson: Isolation and characterization of sucrose esters of the cuticular waxes of green tobacco leaf; J. Agric. Food Chem. 33 (1985) 870–875.

6. Arrendale, R.F., R.F. Severson, V.A. Sisson, C.E. Costello, J.A. Leary, D.S. Himmelsback, and H. van Halbeek: Characterization of the sucrose ester fraction from Nicotiana glutinosa; J. Agric. Food Chem. 38 (1990) 75–85.

7. Matsuzki, T., K. Koseki, and A. Koiwai: Germination and growth inhibition of surface lipids from Nicotiana species and identification of sucrose esters; Agric. Biol. Chem. 52 (1988) 1889–1897.

8. Matsuzki, T., Y. Shinozaki, S. Suhara, H. Shigematsu, and A. Koiwai: Isolation and characterization of tetra-and triacylglucose of Nicotiana miersii; Agric. Biol. Chem. 53 (1989) 3343–3345.

9. Matsuzki, T., Y. Shinozaki, S. Suhara, T. Tobita, H. Shigematsu, and A. Koiwai: Leaf surface glycolipids from Nicotiana acuminata and Nicotiana pauciflora: Agric. Biol. Chem. 55 (1991) 1417–1419.

10. Shinozaki, Y., T. Matsuzaki, S. Suhara, T. Tobita, H. Shigematsu, and A. Koiwai: New types of glycolipids from the surface lipids of Nicotiana umbratica; Agric. Biol. Chem. 55 (1991) 751–756.

11. Shinozaki, Y., T. Matsuzaki, H. Suzuki, H. Shige-matsu, and A. Koiwai: Surface glycolipids in shoot-forming culture of Nicotiana umbratica; Biosci. Bio-tech. Biochem. 56 (1992) 1482–1483.

12. Matsuzaki, T., Y. Shinozaki, M. Hagimori, T. Tobita, H. Shigematsu, and A. Koiwai: Novel glycerolipids and glycolipids from the surface lipids of Nicotiana benthamiana; Biosci. Biotech. Biochem. 56 (1992) 1565–1569.

13. Buta, J.G., W.R. Lusby, J.W. Neal, R.M. Waters, and G.W. Pittarelli: Sucrose esters from Nicotiana gossei active against the greenhouse whitefly trialeuroides vaporariorum; Phytochemistry 32 (1993) 859–864.

14. Severson, R.F., D.M. Jackson, A.W. Johnson, V.A. Sisson, and M.G. Stephenson: Ovipositional behavior of tobacco budworm and tobacco hormworm; in: Natural and Engineered Pest Management Agents, edited by P. Hedin, ACS Symp. Ser. 551, 1991, pp. 172–179.

15. Kandra, L. and G.J. Wagner: Studies of the site and mode of biosynthesis of tobacco trichrome exudates component; Archives Biochem. Biophys. 265 (1988) 425–432.

16. Danehower, D.A.: A rapid method for the isolation and quantification of the sucrose esters of tobacco; Tob. Intl. 189 (1987) 30–33.

17. Einolf, W.N. and W.H. Chan: Estimation of sucrose esters in tobacco by direct chemical ionization mass spectrometry; J. Agric. Food Chem. 32 (1984) 785–789.

18. Ashraf-Khorassani, M., N. Nazem, L.T. Taylor, and W.M. Coleman III: Separation and identification of sucrose esters from Turkish tobacco using liquid chro-matography-mass spectrometry; Beitr. Tabakforsch. Int. 21 (2005) 380–389.

19. Ashraf-Khorassani, M., N. Nazem, L.T. Taylor, and W.M. Coleman III: Identification and quantification of sucrose esters in various Turkish tobaccos; Beitr. Tabakforsch. Int. 21 (2005) 441–450.

20. Ashraf-Khorassani, M., N. Nazem, L.T. Taylor, and W.M. Coleman III: Isolation of tetra-acyl sucrose esters from Turkish tobacco using supercritical carbon dioxide and comparison with conventional solvent extraction; J. Agric. Food Chem. 53 (2005) 1866–1872.

21. Severson, R.F., O.T. Chortyk, M.G. Stephenson, D.H. Akey, J.W. Neal, G.W. Pittarelli, D.M. Jackson, and V.A Sisson: Characterization of natural pesticide from Nicotiana gossei; in: Bioregulators for Crop Protection and Pest Control; ACS Symp. Ser. 557, 1994, pp. 109–121.

22. Kanda, L., R.F. Severson, G.J. Wagner: Modified branched-chain amino acid pathways give rise to acyl acids of sucrose esters exuded from tobacco leaf trichomes; Eur. J. Biochem. 188 (1990) 385–394.

23. Leffingwell, J.C.: Leaf chemistry; in: Tobacco Pro-duction, Chemistry, and Technology; edited by D.L. Davis, and M.T. Nielson, Blackwell Science, Oxford, United Kingdom, 2001, pp.265–284.

Journal Information

CiteScore 2017: 0.63

SCImago Journal Rank (SJR) 2017: 0.309
Source Normalized Impact per Paper (SNIP) 2017: 0.403

Cited By


All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 112 108 4
PDF Downloads 75 73 10