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Profiling of Glycerides in Tobacco Seeds

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Profiling of Glycerides in Tobacco Seeds 2010_TSRC59_Moldoveanu.pdf Profiling of Glycerides in Tobacco Seeds S. C. Moldoveanu, Y. Chang, R. J. Reynolds Tobacco Co. TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Purpose of this work 2010_TSRC59_Moldoveanu.pdf • Establish a protocol for the extraction of tobacco seed oil. • Develop a technique for performing chemical analysis of tobacco seed oil. • Evaluate differences in the chemistry of tobacco seed oil from different tobacco species (Nicotiana tabacum, N. rustica, N. langsdorfii, N. suaveolens, N. sylvestris ), and from three types of N. tabacum (flue-cured, burley, and Oriental). • Compare tobacco seed oil with the oil from several reference oils. TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Extraction procedure 2010_TSRC59_Moldoveanu.pdf • Tobacco seeds (0.200 ±0.001 g) and ~2.5 g of diatomaceous earth were ground using a mortar and pestle. • The sample was transferred into a 22-mL, stainless-steel extraction cell of an accelerated solvent extraction instrument, ASE 350 (Dionex). • The extraction was performed in hexane at 105 oC in three cycles of 10 min each. • The oils from the extracts were submitted for analysis. TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Seed oil extraction yield (%) and relative standard deviation of the measurement 2010_TSRC59_Moldoveanu.pdf (RSD%) Tobacco type Average RSD% Nicotiana tabacum , flue-cured 38.10% 0.48% “ burley 39.20% 3.39% “ oriental 39.45% 0.78% N. glutinosa 36.95% 0.21% N. alata 30.73% 0.39% N. langsdorfii 29.47% 0.18% N. sylvestris 38.08% 0.81% N. suaveolens 36.83% 0.60% 29.20% 2.40% N. rustica TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Analysis procedures 2010_TSRC59_Moldoveanu.pdf • Profile of fatty acids from the glycerides after hydrolysis and derivatization as trimethylsilyl derivatives (TMS). • Quantitation of individual fatty acids. • Profile of as is glycerides (unmodified) in the oil using a GC/MS technique. • Quantitation of individual glycerides. • Corroborate results from free acids analysis with those from glyceride analysis. TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Chromatogram of TMS derivatives of fatty acids from a commercial cooking 2010_TSRC59_Moldoveanu.pdf oil hydrolysate sample. Abundance 27.82 1.8e+07 1.6e+07 1.4e+07 1.2e+07 16.41 1e+07 8000000 27.35 6000000 23.13 4000000 28.50 2000000 27.27 14.61 21.03 23.30 31.70 34.63 0 14.0 16.0 18.0 20.0 22.0 24.0 26.0 28.0 30.0 32.0 34.0 Time--> TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Peak identification and relative peak area for the chromatogram of TMS derivatives of fatty acids 2010_TSRC59_Moldoveanu.pdf from a commercial cooking oil hydrolysate sample. No Compound Ret. time MW Symbol Area % . 1 Glycerin 3TMS 10.74 308.64 0.15 2 Unknown 14.61 ? 0.24 3 Internal standard (I.S.) 16.41 4 Column bleed 21.03 5 Palmitic acid TMS 23.13 328.613 C16:0 9.52 6 Palmitoleic acid TMS 23.30 326.597 C16:1 Z-9 0.07 7 Stearic acid TMS 27.27 356.667 C18:0 2.56 8 Oleic acid TMS 27.35 354.651 C18:1 Z-9 20.33 9 Elaidic acid TMS (trans-9-C18:1) 27.49 354.651 C18:1 E-9 2.09 10 Linoleic acid TMS 27.82 352.635 C18:2 Z,Z-9,12 59.72 11 Linolenic acid TMS 28.50 350.62 C18:3 Z,Z,Z-6,9,12 4.99 12 Arachidic acid TMS 31.70 384.721 C20:0 0.13 13 11-Eicosenoic acid TMS 31.80 382.705 C20:1 Z-11 0.06 14 Docosanoic acid TMS (behenic) 34.63 412.78 C22:0 0.14 TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Calibration of free acids as TMS derivatives 2010_TSRC59_Moldoveanu.pdf 0.7 y = 3.4409x y = 0.7292x y = 0.3433x R2 = 0.9971 R2 = 0.9972 R2 = 0.9952 0.6 y = 1.3998x 2 R = 0.9941 y = 0.2970x 2 0.5 R = 0.9965 Palmitic 0.4 Linoleic Linolenic mg/mL 0.3 Oleic Stearic 0.2 0.1 0 0 0.5 1 1.5 2 Normalized peak area TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Quantitative results regarding the % weight of free fatty acids reported to the weight of oil sample 2010_TSRC59_Moldoveanu.pdf Oil * Palmitic Linoleic Linolenic Oleic Stearic TOTAL Olive 11.8 12.27 - 66.46 3.16 93.69 Safflower 5.50 74.04 - 11.78 2.15 93.47 Sunflower 6.15 56.24 - 26.98 2.46 91.83 Corn 11.07 49.11 1.21 31.44 2.08 94.91 Soybean 9.66 55.76 7.37 18.14 2.77 93.70 Canola 6.14 20.93 5.12 58.76 2.75 93.72 Linseed 4.54 13.44 62.19 11.77 1.76 93.70 Palm 36.88 12.88 - 39.8 4.83 94.39 Cottonseed 15.73 54.76 0.02 19.96 2.32 92.79 Coconut 6.23 2.90 - 5.87 1.69 16.69 Lard 19.84 21.33 1.35 37.65 7.14 87.31 Peanut 13.80 17.61 0.87 44.48 2.70 79.46 Menhaden 12.75 0.17 0.36 6.77 1.76 21.81 Commercial cooking 8.71 51.47 5.21 24.26 4.04 93.69 Commercial grape seed 6.88 69.12 0.98 14.55 3.60 95.13 Very good agreement with data published in the literature * TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Quantitative results regarding the % weight of free fatty acids reported to the weight of oil sample 2010_TSRC59_Moldoveanu.pdf Oil Palmitic Linoleic Linolenic Oleic Stearic TOTAL N tabacum , flue-cured (USA) 8.63 69.71 0.36 12.68 2.12 93.50 N tabacum , flue-cured (India) 10.73 62.86 1.00 15.53 3.59 93.71 N tabacum , burley 9.12 65.46 1.82 13.70 2.71 92.81 N tabacum , oriental 8.77 67.88 0.24 13.99 2.81 93.69 N. glutinosa 7.99 65.01 0.17 18.02 2.42 93.61 N. alata 7.83 68.89 1.92 11.97 3.09 93.70 N. langsdorfii 8.15 67.90 1.72 13.43 2.49 93.69 N. sylvestris 8.35 66.54 3.82 12.88 2.10 93.69 N. suaveolens 8.26 31.30 27.88 23.42 2.84 93.71 9.24 68.96 4.75 10.02 1.73 94.70 N. rustica TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Chromatogram of glycerides from a flue cured seed oil generated using MS detection 2010_TSRC59_Moldoveanu.pdf Abundance 19.02 1800000 1600000 Flue-cured (USA) 1400000 21.25 1200000 1000000 18.67 20.77 800000 600000 20.43 17.22 20.32 400000 18.45 20.02 200000 16.93 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Peak identification for the flue-cured seed oil chromatogram 2010_TSRC59_Moldoveanu.pdf No. Compound MW Ret. time Rel. % 1 Dipalmitostearin 835 16.93 0.42 2 Dipalmitolinolein 831 17.22 2.87 3 Palmitooleostearin 861 18.35 1.12 4 Palmito stearin linolein 859 18.45 1.22 5 Palmito olein linolein 857 18.67 9.09 6 Palmito dilinolein 855 19.02 23.88 7 Distearinolinolein 887 19.66 0.46 8 Distearinolinolein 887 19.91 0.67 9 Distearinoolein 889 20.02 1.45 10 Triolein/Petroselin 885 20.32 5.47 11 Triolein 885 20.43 5.43 12 Dilinoleino olein 881 20.77 16.98 13 Trilinolein 879 21.25 30.94 TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Mass spectrum of palmito-linoleo-olein (the correct position of substituents is unknown) 2010_TSRC59_Moldoveanu.pdf Abundance 262 O 100 palm ityl 90 55 O O 80 linoleyl 70 41 69 O 60 oleyl 81 95 O 50 40 O 30 109 577 313 20 123 339 10 135 164 239 601 367 393 449 503 0 m/z--> 50 100 150 200 250 300 350 400 450 500 550 600 m/z--> TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed The structures of several diagnostic ions in the spectrum of palmito-linoleo-olein. 2010_TSRC59_Moldoveanu.pdf .+ O CH2 O O O O ion m/z = 601 ion m/z = 575 O .+ H2C O .+ O CH2 O ion m/z = 339 OH O O .+ CH ion m/z = 577 O O ion m/z = 262 + . O OH TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Abundance 2010_TSRC59_Moldoveanu.pdf 19.02 1800000 1600000 1400000 21.25 1200000 Flue-cured 1000000 18.67 20.77 800000 600000 20.43 17.22 20.32 400000 18.45 20.02 200000 16.93 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> Abundance 19.02 1800000 1600000 18.67 1400000 Cotton seed 1200000 1000000 17.22 800000 600000 20.77 21.25 400000 18.45 16.93 20.45 200000 15.97 0 14.0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Abundance 2010_TSRC59_Moldoveanu.pdf 19.02 1800000 1600000 1400000 21.25 1200000 Flue-cured 1000000 18.67 20.77 800000 600000 20.43 17.22 20.32 400000 18.45 20.02 200000 16.93 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> Abundance 20.77 1800000 21.25 1600000 19.02 1400000 1200000 18.67 Sunflower seed 1000000 800000 600000 20.45 400000 18.45 17.22 200000 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Abundance 19.02 2010_TSRC59_Moldoveanu.pdf 1800000 1600000 1400000 21.25 1200000 Flue-cured 1000000 18.67 20.77 800000 600000 20.43 17.22 20.32 400000 18.45 20.02 200000 16.93 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> Abundance 18.67 19.02 1.1e+07 17.22 1e+07 9000000 17.40 Animal Fat 8000000 7000000 6000000 5000000 19.15 20.25 4000000 17.62 20.54 18.37 3000000 15.88 19.85 2000000 20.91 1000000 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Abundance 19.02 1800000 1600000 2010_TSRC59_Moldoveanu.pdf 1400000 21.25 1200000 Flue-cured 1000000 18.67 20.77 800000 600000 20.43 17.22 20.32 400000 18.45 20.02 200000 16.93 0 15.0 16.0 17.0 18.0 19.0 20.0 21.0 22.0 23.0 24.0 25.0 Time--> Abundance 2000000 1800000 19.02 21.25 1600000 1400000 Burley 1200000 1000000 20.
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