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Leaf Chemistry Reprinted from Tobacco: Production, Chemistry, And Technology, D. Layten Davis and Mark T. Nielson, Eds., Blackwell Science (Pub.), 1999 Chapter 8 leaf Chemistry BA Basic Chemical Constituents of Tobacco Leaf and Differences among Tobacco Types J.C. Leffingwell Leffingwell and Associates Canton, Georgia, USA INTRODUCTION multitude of nitrogenous chemicals important in the development of aroma and flavor quality. Dawson In 1960, a little over 200 chemical constituents had (1952) has suggested a concept based on the Krebs cycle been identified in tobacco leaf of all types and less than to account for inherited and culturally induced varia­ 450 had been reported in smoke. Today, approximately tions in gross tobacco composition. Using this concept, 3000 have been identified and characterized in tobacco he rationally suggested that for tobaccos where the leaf and some 4000 in smoke. Estimates are that the nitrogen supply is abundant, such as in cigar and burley total number of chemical constituents in leaf exceeds tobacco production, there should be an abundant for­ 4000 and there are over 6000 in tobacco smoke. It is not mation of protein, amino acids and nicotine. For the purpose of this section to comprehensively review Oriental tobacco, where growth is maintained with all of the known constituents, but rather to provide an limited supplies of nitrogen nutrients and water, there is insight into the known composition and chemistry of an accumulation oface tate in the Krebs cycle resulting in tobacco types that impact tobacco quality and differ­ the biosynthesis ofterpenoids via mevalonic acid as well entiate tobacco types. Emphasis will be placed on the as a higher production ofca rbohydrates, 'aromatic' acids major tobaccos utilized commercially: Virginia (flue­ and resins at the expense of nitrogen constituents. Flue­ cured), air-cured (burley and cigar) and Oriental. cured tobacco is intermediate in that the phytochemistry The physical and chemical properties of leaf tobacco during the plant's life cycle is balanced by a moderate are influenced by genetics, agricultural practices, soil supply ofnitrogen which is depleted as the plant reaches type and nutrients, weather conditions, plant disease, maturity. stalk position, harvesting and curing procedures. A Examination of representative analyses of the major change in any of these factors can markedly alter the cigarette tobacco types as presented by Harlan and chemical composition of leaf and thus affect smoking Moseley ( 1955) (Table 8.1) provides an overview of the quality (Tso, 1972; Tso, 1990). major differences in aged flue-cured, burley, Maryland It is now generally accepted that the metabolic and Oriental tobaccos. carbon- nitrogen balance in li ving plants is due to Although average reducing sugar content in flue­ continuing transformations based on the Krebs tri­ cured and Oriental cigarette tobaccos today rarely runs carboxylic acid cycle. In the Krebs cycle, carbon dioxide as high as reported in Table 8.1 , the basic analytical from air is assimilated through photosynthesis in the trends still remain valid. T hus, in air-cured burley, tobacco leaf while inorganic nitrogen (nitrate and/or Maryland and cigar tobaccos the carbohydrates have ammonia) is assimilated through the roots from the soil. been virtually depleted via metabolism of the living Soil nitrate is converted to ammonia which is utilized in cells, whereas the protein and ex-amino nitrogen are the Krebs cycle to form amino acids which serve as a obviously higher than in flue-cured or Oriental nitrogen pool for the formation and transformation of a tobaccos. Conversely, the flue-cured and Oriental 265 266 Tobacco: Production, Chemistry and Technology LeafCho Table 8.1 Composition of cigarette tobaccos: representative analyses of cigarette tobaccos (leaf web after Table 8 .. aging, moisture-free basis). tobacco weight). Component (%)' Flue-cured, type 13 2 Burley, type 31 Maryland, type 32 Oriental Constitue Total volatile bases as ammonia 0.282 0.621 0.366 0.289 Starch Nicotine 1.93 2.91 1.27 1.05 Free redu Ammonia 0.019 0.159 0.130 0.105 Levulose Glutamine as ammonia 0.033 0.035 0.041 0.020 Sucrose Asparagine as ammonia 0.025 0.111 0.016 0.058 Crude fib• ()(-Amino nitrogen as ammonia 0.065 0.203 0.075 0.118 Total nitre Protein nitrogen as ammonia 0.91 1.77 1.61 1.19 Protein ni Nitrate nitrogen as N0 3 trace 1.70 0.087 trace Nicotine Total nitrogen as ammonia 1.97 3.96 2.80 2.65 Ash pH 5.45 5.80 6.60 4.90 Calcium Total volatile acids as acetic acid 0.153 0.103 0.090 0.194 Oxalic ac Formic acid 0.059 0.027 0.022 0.079 Citric acic Malic acid 2.83 6.75 2.43 3.87 Malic acio Citric acid 0.78 8.22 2.98 1.03 Resins Oxalic acid 0.81 3.04 2.79 3.16 Pectinic a Volatile oils 0.148 0.141 0.140 0.248 pH of tob Alcohol-soluble resins 9.08 9.27 8.94 11.28 Reducing sugars as dextrose 22.09 0.21 0.21 12.39 Source: Bao Pectin as calcium pectate 6.91 9.91 12.41 6.77 Crude fiber 7.88 9.29 21.79 6.63 Ash 10.81 24.53 21.98 14.78 I 20 Calcium as CaO 2.22 8.01 4.79 4.22 Potassium as K20 2.47 5.22 4.40 2.33 Magnesium as MgO 0.36 1.29 1.03 0.69 Chlorine as Cl 0.84 0.71 0.26 0.69 f: 15 Phosphorus as P2 0 5 0.51 0.57 0.53 0.47 Sulfur as S0 "E 4 1.23 1.98 3.34 1.40 <ll Alkalinity of water-soluble ash 3 0 15.9 36.2 36.9 22.5 cf 1 In %except for pH and alkalinity. .r: 10 2 Blend of Macedonia, Smyrna, and Samsun types. 0 3 Milliliters of 1 N acid per 100 g tobacco. ~ (/) Source: Harlan and Moseley (1955). 5 tobaccos possess significant amounts of reducing during flue-curing which causes enzyme inactivation. sugars (which are virtually absent in the air-cured Nevertheless, considerable change has occurred (Table 0 tobaccos) and lesser amounts of protein and a-amino 8.2) in the leaf (during the period after priming and nitrogen. Substantial changes in the chemical compo­ early stages of curing) as starch loss occurs via enzy­ sition of tobacco leaf occur following harvest and matic hydrolysis with a concomitant increase in redu­ during subsequent processes. cing sugar (Bacon, et al., 1952). This is illustrated for Fig. 8.1 I the starch depletion during cure of Virginia tobacco Virginia tc: CARBOHYDRATES: STARCH, SUGARS, (Fig. 8.1) and the concurrent generation of reducing SUGAR ESTERS, CELLULOSE, AND sugars (Long & Weybrew, 1981) (Fig. 8.2). Starch• PECTIN In burley tobacco the starch accumulation during saccharid· growth is only about 25% the amount in Virginia has appr (a) Starch and sugars tobacco (W eybrew & Hamann, 1977) and this is nearly pectin, v depleted completely during the catabolic respiration of approx1m In flue-cured tobacco, respiration in the primed leaf is the plant while air-curing leaving negligible sucrose, Gohnston arrested by the controlled desiccative dehydration and reducing sugars in the cured leaf. estimated • nd Technology Leaf Chemistry: Basic Chemical Constituents & Differences among Tobacco Types 267 Eaf web after Table 8.2 Changes in composition of Virginia tobacco during the flue-curing process (% of dry weight). ?r--------------.,7 Oriental 2 Constituents Green Yellowed Cured 0.289 Starch 29.30 12.40 5.52 1.05 Free reducing sugars 6.68 15.92 16.47 0.105 Levulose 2.87 7.06 7.06 5 0.020 Sucrose 1.73 5.22 7.30 0.058 Crude fiber 7.28 7.16 7.24 0.118 Total nitrogen 1.08 1.04 1.05 1.19 Protein nitrogen 0.65 0.56 0.51 trace Nicotine 1.10 1.02 0.97 3 2.65 Ash 9.23 9.24 9.25 • 4.90 Calcium 1.37 1.37 1.37 0.194 Oxalic acid 0.96 0.92 0.85 0.079 Citric acid 0.40 0.37 0.38 3.87 Malic acid 8.62 9.85 8.73 1.03 Resins 7.05 6.53 6.61 0 30 60 90 120 150 3.16 Pectinic acid 10.99 10.22 8.48 Hours - Rue Curing 0.248 pH of tobacco 5.55 5.64 5.55 11.28 Fig. 8.2 Change in lamina reducing sugars during flue­ Source: Bacon, eta/. (1952). 12.39 curing of Virginia tobacco (adapted from Long & Weybrew, 6.77 1981). 6.63 14.78 4.22 glucose units, while the amylopectin has about 26 2.33 0.69 glucose units. 0.69 15 15 0.47 c Q) (b) Sugar esters 1.40 u 22.5 The first report of sugar esters in Oriental tobacco ~ 10 10 .s::: came in 1970 with the isolation, structure elucidation s~ and synthesis of 6-0-acetyl-2,3,4-tri-0-[( + )-3- (/) methylvaleryl]-beta-o-glucopyranose (a glucose tet­ raester) by Schumacher (1970). This and the more 5 5 predominant sucrose tetraesters (STE) of lower car­ boxylic acids (Fig. 8.3) are now considered to be some vme inactivation. of the most important aroma precursors responsible for i occurred (Table 0 Oriental flavor (Leffingwell & Leffingwell, 1988). fter priming and 0 30 60 90 120 150 In 1981, Severson, et. al., found that the cuticular occurs via enzy­ Hours - Flue Curing waxes of a tobacco budworm resistant tobacco con­ increase in redu­ tained a series of STE which are the probable pre­ Fig.
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