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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Profiling of Glycerides in Tobacco Seeds S. C. Moldoveanu, Y. Chang, R. J. Reynolds Tobacco Co. TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Purpose of this work 2010_TSRC59_Moldoveanu.pdf • Establish a protocol for the extraction of tobacco seed oil.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 TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Extraction procedure 2010_TSRC59_Moldoveanu.pdf • Tobacco seeds (0.200 ±0.001 g) and ~2.5 g of diatomaceous earth were ground using a mortar and pestle.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 TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Seed oil extraction yield (%) and relative standard deviation of the measurement 2010_TSRC59_Moldoveanu.pdf (RSD%) Tobacco type Average RSD% Nicotiana tabacum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29.47% 0.18% N. sylvestris 38.08% 0.81% N. suaveolens 36.83% 0.60% 29.20% 2.40% N. rustica TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Analysis procedures 2010_TSRC59_Moldoveanu.pdf • Profile of fatty acids from the glycerides after hydrolysis and derivatization as trimethylsilyl derivatives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 TSRC2010(64) - Document not peer-reviewed by CORESTATSRC2010(64) - Document not peer-reviewed Chromatogram of TMS derivatives of fatty acids from a commercial cooking 2010_TSRC59_Moldoveanu.pdf oil hydrolysate sample.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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  • Characteristics, Composition and Oxidative Stability of Lannea Microcarpa Seed and Seed Oil

    Characteristics, Composition and Oxidative Stability of Lannea Microcarpa Seed and Seed Oil

    Molecules 2014, 19, 2684-2693; doi:10.3390/molecules19022684 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Characteristics, Composition and Oxidative Stability of Lannea microcarpa Seed and Seed Oil Patrice Bazongo 1, Imaël Henri Nestor Bassolé 1,*, Søren Nielsen 2, Adama Hilou 3, Mamoudou Hama Dicko 1 and Vijai K. S. Shukla 2 1 Laboratoire de Biochimie Alimentaire, Enzymologie, Biotechnologie Industrielle et Bioinformatique (Laboratoire BAEBIB), Department of Biochemistry and Microbiology, Université de Ouagadougou, Ouagadougou 03 03 BP 7021, Burkina Faso; E-Mails: [email protected] (P.B.); [email protected] (M.H.D.) 2 International Food Science Centre (IFSC A/S), Sønderskovvej, Lystrup 7 DK-8520, Denmark; E-Mails: [email protected] (S.N.); [email protected] (V.K.S.S.) 3 Laboratoire de Biochimie et Chimie Appliquées (LABIOCA), UFR/SVT, Université de Ouagadougou, Ouagadougou 09 09 BP 848, Burkina Faso; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +226-7812-5004. Received: 13 November 2013; in revised form: 6 December 2013 / Accepted: 9 December 2013 / Published: 24 February 2014 Abstract: The proximate composition of seeds and main physicochemical properties and thermal stability of oil extracted from Lannea microcarpa seeds were evaluated. The percentage composition of the seeds was: ash (3.11%), crude oil (64.90%), protein (21.14%), total carbohydrate (10.85%) and moisture (3.24%). Physicochemical properties of the oil were: refractive index, 1.473; melting point, 22.60°C; saponification value, 194.23 mg of KOH/g of oil; iodine value, 61.33 g of I2/100 g of oil; acid value, 1.21 mg of KOH/g of oil; peroxide value, 1.48 meq of O2/kg of oil and oxidative stability index, 43.20 h.
  • Encapsulation and Protection of Omega-3-Rich Fish Oils Using Food-Grade Delivery Systems

    Encapsulation and Protection of Omega-3-Rich Fish Oils Using Food-Grade Delivery Systems

    foods Review Encapsulation and Protection of Omega-3-Rich Fish Oils Using Food-Grade Delivery Systems Vishnu Kalladathvalappil Venugopalan 1 , Lekshmi Ramadevi Gopakumar 2, Ajeeshkumar Kizhakkeppurath Kumaran 2, Niladri Sekhar Chatterjee 2, Vishnuja Soman 3, Shaheer Peeralil 2, Suseela Mathew 2, David Julian McClements 4,* and Ravishankar Chandragiri Nagarajarao 2 1 Centre for Marine Living Resources and Ecology (CMLRE), Ministry of Earth Sciences, Kochi 682508, India; [email protected] 2 Central Institute of Fisheries Technology (CIFT), Indian Council for Agricultural Research, Matsyapuri P.O, Kochi 682029, India; [email protected] (L.R.G.); [email protected] (A.K.K.); [email protected] (N.S.C.); [email protected] (S.P.); [email protected] (S.M.); [email protected] (R.C.N.) 3 Department of Chemical Oceanography, School of Marine Sciences, Cochin University of Science and Technology, Cochin 682016, India; [email protected] 4 Department of Food Science, University of Massachusetts, Amherst, MA 01003, USA * Correspondence: [email protected] Abstract: Regular consumption of adequate quantities of lipids rich in omega-3 fatty acids is claimed to provide a broad spectrum of health benefits, such as inhibiting inflammation, cardiovascular diseases, diabetes, arthritis, and ulcerative colitis. Lipids isolated from many marine sources are a rich source of long-chain polyunsaturated fatty acids (PUFAs) in the omega-3 form which are claimed to have particularly high biological activities. Functional food products designed to enhance Citation: Venugopalan, V.K.; human health and wellbeing are increasingly being fortified with these omega-3 PUFAs because Gopakumar, L.R.; Kumaran, A.K.; of their potential nutritional and health benefits.
  • Nutritional Indices for Assessing Fatty Acids: a Mini-Review

    Nutritional Indices for Assessing Fatty Acids: a Mini-Review

    International Journal of Molecular Sciences Review Nutritional Indices for Assessing Fatty Acids: A Mini-Review Jiapeng Chen 1 and Hongbing Liu 1,2,* 1 Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; [email protected] 2 Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao 266237, China * Correspondence: [email protected]; Tel.: +86-0532-82031823 Received: 30 June 2020; Accepted: 6 August 2020; Published: 8 August 2020 Abstract: Dietary fats are generally fatty acids that may play positive or negative roles in the prevention and treatment of diseases. In nature, fatty acids occur in the form of mixtures of saturated fatty acid (SFA), monounsaturated fatty acid (MUFA), and polyunsaturated fatty acid (PUFA), so their nutritional and/or medicinal values must be determined. Herein, we do not consider the P P P P P classic indices, such as SFA, MUFA, PUFA, n-6 PUFA, n-3 PUFA, and n-6 PUFA/n-3 PUFA; instead, we summarize and review the definitions, implications, and applications of indices used in recent years, including the PUFA/SFA, index of atherogenicity (IA), the index of thrombogenicity (IT), the hypocholesterolemic/hypercholesterolemic ratio (HH), the health-promoting index (HPI), the unsaturation index (UI), the sum of eicosapentaenoic acid and docosahexaenoic acid (EPA + DHA), fish lipid quality/flesh lipid quality (FLQ), the linoleic acid/α-linolenic acid (LA/ALA) ratio, and trans fatty acid (TFA). Of these nutritional indices, IA and IT are the most commonly used to assess the composition of fatty acids as they outline significant implications and provide clear evidence.