Skip to main content
SpringerLink
Log in
SpringerLink
Log in

Isoprenoids and Alkaloids of Tobacco

  • Chapter
Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

Apart from cotton and food-providing plants, tobacco is the major cultivated plant in the world. It is grown in some one hundred countries and the annual production is of the order of five million tons. In view of its economic importance both in producing and consuming countries, it is not surprising that the chemistry of tobacco has attracted the attention of many investigators. More recently, health aspects and the desire to produce a tobacco substitute to counter future tobacco shortages have given further impetus to chemical research on this plant.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Aasen, A. J., S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 35. Two isomeric 5,6-epoxy-3-hydroxy-7-megastigmen-9-ones from Nicotiana tabacum L. Beiträge zur Tabakforsch. 8, 366 (1976).

    CAS  Google Scholar 

  2. Aasen, A. J., S.-O. Almqvist, T. Nishida, J. R. Hlubucek, and C. R. Enzell: To be published.

    Google Scholar 

  3. Aasen, A. J., and C. R. Enzell: Tobacco chemistry 30. The absolute configuration of 11-nor-8-hydroxy-9-drimanone, a constituent of Greek Nicotiana tabacum L. Acta Chem. Scand. B28, 1239 (1974).

    Google Scholar 

  4. Aasen, A. J., and C. R. Enzell: Tobacco chemistry 32. The absolute configuration of norsolanadione, (5S)-5-isopropyl-3E-nonen-2,8-dione, a nor-thunberganoid of Nicotiana tabacum L. Acta Chem. Scand. B29, 528 (1975).

    CAS  Google Scholar 

  5. Aasen, A. J., C. R. Enzell, and T. Chuman: Tobacco chemistry 33. (6S)-3-Methyl-6-isopropyl-9-oxo-2E,4E-decadienoic acid from Turkish Nicotiana tabacum L. Assignment of absolute configuration. Agr. Biol. Chem. 39, 2085 (1975).

    CAS  Google Scholar 

  6. Aasen, A. J., J. R. Hlubucek, S.-O. Almqvist, B. Kimland, and C. R. Enzell: Tobacco chemistry 20. Structure and synthesis of three new tobacco constituents of probable isoprenoid origin. Acta Chem. Scand. 27, 2405 (1973).

    CAS  Google Scholar 

  7. Aasen, A. J., J. R. Hlubucek, and C. R. Enzell: Tobacco chemistry 24. (9R)-9-Hydroxy-4-megastigmen-3-one, a new tobacco constituent. Acta Chem. Scand. B28,285(1974).

    Google Scholar 

  8. Aasen, A. J., J. R. Hlubucek, and C. R. Enzell: Tobacco chemistry 27. The structures of four stereoisomeric 8,12ξ-epoxylabd-14-en-13ξ-ols isolated from Greek Nicotiana tabacum L. Acta Chem. Scand. B29, 589(1975).

    Google Scholar 

  9. Aasen, A. J., J. R. Hlubucek, and C. R. Enzell: Tobacco chemistry 29. (7S)-10-oxo-4ξ-methyl-7-isopropyl-5E-undecen-4-olide, a new thunbergane-type nor-isoprenoid isolated from Greek Nicotiana tabacum L. Acta Chem. Scand. B29, 677 (1975).

    Google Scholar 

  10. Aasen, A. J., N. Junker, C. R. Enzell, J.-E. Berg, and A. M. Pilotti: Tobacco chemistry 36. Absolute configuration of tobacco thunberganoids. Tetrahedron Letters 2607 (1975).

    Google Scholar 

  11. Aasen, A. J., B. Kimland, S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 9. 5-Methoxy-6,7-dimethylbenzofuran, a new tobacco constituent. Acta Chem. Scand. 25, 3182 (1971).

    CAS  Google Scholar 

  12. Aasen, A. J., B. Kimland, S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 13. 8, 13-Epoxylabd-14-en-12-one and 8, 13 β-epoxylabd-14-en-12-one, two new diterpenoids from tobacco. Acta Chem. Scand. 26, 832 (1972).

    CAS  Google Scholar 

  13. Aasen, A. J., B. Kimland, S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 15. New tobacco constituents — the structures of five isomeric megastigmatrienones. Acta Chem. Scand. 26, 2573 (1972).

    CAS  Google Scholar 

  14. Aasen, A. J., B. Kimland, and C. R. Enzell: Tobacco chemistry 7. Structure and synthesis of 3-oxo-α-ionol, a new tobacco constituent. Acta Chem. Scand. 25, 1481 (1971).

    Google Scholar 

  15. Aasen, A. J., B. Kimland, and C. R. Enzell: Tobacco chemistry 11. Total synthesis of 5-methoxy-6,7-dimethylbenzo-furan, a new tobacco constituent. Acta Chem. Scand. 25, 3537 (1971).

    CAS  Google Scholar 

  16. Tobacco chemistry 18. Absolute configuration of (9R)-9-hydroxy-4,7E-megastigmadien-3-one (3-oxo-α-ionol). Acta Chem. Scand. 27, 2107 (1973).

    Google Scholar 

  17. Aasen, A. J., B. Kimland, J. R. Hlubucek, and C. R. Enzell: Unpublished result.

    Google Scholar 

  18. Aasen, A. J., T. Nishida, C. R. Enzell, and M. Devreux: Tobacco chemistry 37. The absolute configuration of prenylsolanone, (9S)-6,12-dimethyl-9-isopropyltrideca-5E,10E. 12-trien-2-one, a nor-thunberganoid of Nicotiana tabacum L. Acta Chem. Scand. 30, 178(1976).

    Google Scholar 

  19. Aasen, A. J., Å. Pilotti, C. R. Enzell, J.-E. Berg, and A.-M. Pilotti: To be published.

    Google Scholar 

  20. Aasen, A. J., C. H. G. Vogt, and C. R. Enzell: Tobacco chemistry 28. Structure and synthesis of drim-8-en-7-one, a new tobacco constituent. Acta Chem. Scand. B29, 51 (1975).

    Google Scholar 

  21. Almqvist, S.-O., A. J. Aasen, J. R. Hlubucek, B. Kimland, and C. R. Enzell: Tobacco chemistry 23. Structures and syntheses of four new nor-isoprenoid furans from tobacco. Acta Chem. Scand. B28, 528 (1974).

    Google Scholar 

  22. Ayers, J. E., M. J. Fishwick, D. G. Land, and T. Swain: Off-flavour of dehydrated carrot stored in oxygen. Nature 203, 81 (1964).

    CAS  Google Scholar 

  23. Bailey, J. A., R. S. Burden, and G. G. Vincent: Capsidiol: an antifungal compound produced in Nicotiana tabacum and Nicotiana clevelandii following infection with tobacco necrosis virus. Phytochem. 14, 597 (1975).

    CAS  Google Scholar 

  24. Baldwin, J. E., H. H. Basson, and H. Krauss Jr.: The cleavage of aromatic nuclei with singlet oxygen: Significance in biosynthetic processes. Chem. Commun. 984 (1968).

    Google Scholar 

  25. Bayley, W. C, A. K. Boose, R. M. Ikeda, R. H. Newman, H. V. Secor, and C. Varsel: The isolation from tobacco of 2-hydroxy-2,6,6-trimethylcyclohexylidene acetic acid-γ-lactone and its synthesis. J. Organ. Chem. 33, 2819 (1968).

    Google Scholar 

  26. Becket, A. H., P. Jenner, and J. W. Gorrod: Characterization of the diastereo-isomers of nicotine-l-N-oxide, a metabolite of nicotine, and other possible oxidation products by nuclear magnetic resonance spectroscopy. Xenobiotica 3, 557 (1973).

    Google Scholar 

  27. Bodn Á. R. I., and L. Nagy: Pyridine content of tobacco. Z. Untersuch. Lebensm. 74, 302 (1937).

    Google Scholar 

  28. Bolt, A. J. N.: 1′-Hexanoylnornicotine and 1′-octanoylnornicotine from tobacco. Phytochem. 11, 2341 (1972).

    CAS  Google Scholar 

  29. Bolt, A. J. N., and R. E. Clarke: Cholesterol glucoside in tobacco. Phytochem. 9, 819 (1970).

    CAS  Google Scholar 

  30. Bondarovich, H. A., P. Friedel, V. Krampl, J. A. Renner, F. W. Shephard, and M. Gianturco: Volatile constituents of coffee. Pyrazines and other compounds. J. Agric. Food Chem. 15, 1093 (1967).

    CAS  Google Scholar 

  31. Booth, J., and E. Boyland: The metabolism of nicotine into two optically-active stereoisomers of nicotine-1′-oxide by animal tissues in vitro and by cigarette smokers. Biochem. Pharmacol. 19, 733 (1970).

    CAS  Google Scholar 

  32. Brandänge, S., and L. Lindblom: ITN-vinyl as N-H protecting group — a convenient synthesis of myosmine. Acta Chem. Scand. B30, 93 (1976).

    Google Scholar 

  33. Breuer, E., and D. Melumad: A one-step synthesis of nicotine from cyclopropyl 3-pyridyl ketone. Tetrahedron Letters 3595 (1969).

    Google Scholar 

  34. Burden, R. S., J. A. Bailey, and G. G. Vincent: Glutinosone, a new antifungal sesquiterpene from Nicotiana glutinosa infected with tobacco mosaic virus. Phytochem 14, 221 (1975).

    CAS  Google Scholar 

  35. Burden, R. S., and H. F. Taylor: The structure and chemical transformations of xanthoxin. Tetrahedron Letters 4071 (1970).

    Google Scholar 

  36. Cambie, R. C, K. N. Joblin, and A. F. Preston: Chemistry of the Podocarpaceae. XXX. Conversion of 8α,13-epoxylabd-14-ene into a compound with an ambergris-type odour. Austral. J. Chem. 24, 583 (1971).

    CAS  Google Scholar 

  37. Cambie, R. C., K. N. Joblin, and A. F. Preston: Chemistry of the Podocarpaceae. XXXIV. Some oxidation products of (13R)-labda-8(17),14-dien-13-ol (manool). Austral. J. Chem. 24, 2365 (1971).

    CAS  Google Scholar 

  38. Carruthers, W., and J. R. Plimmer: Sterols in green tobacco leaf. Chem. and Ind. 48 (1959).

    Google Scholar 

  39. Chakraborty, M. K., and J. A. Weybrew: The chemistry of tobacco trichomes. Tob. Sci. 7, 122 (1963).

    CAS  Google Scholar 

  40. Chan, H. W.-S.: Singlet oxygen analogs in biological systems. Coupled oxygenation of 1,3-diens by soybean lipoxidase. J. Amer. Chem. Soc. 93, 2357 (1971).

    CAS  Google Scholar 

  41. Chirkova, M. A., A. K. Dzizenko, and V. A. Pentegova: Neutral substances of the resin of Abies sibirica. II. Structure of a diterpenic hydroxy ketone. Khim. Prir. Soedin. 3, 86 (1967).

    CAS  Google Scholar 

  42. Chuman, T., H. Kaneko, T. Fukuzumi, and M. Noguchi: Isolation of two terpenoid acids, 4-isopropyl-7-methyl-5E,7-octadienoic acid and 3-isopropyl-6-methyl-4E,6-heptadienoic acid from Turkish tobacco. Agr. Biol. Chem. 38, 2295 (1974).

    CAS  Google Scholar 

  43. Chuman, T., H. Kaneko, T. Fukuzumi, and M. Noguchi: Acidic aroma constituents of Turkish tobacco. Terpenoid acids related to tobacco thunberganoids. Agr. Biol. Chem. 40, 587 (1976).

    CAS  Google Scholar 

  44. Chuman, T., and M. Noguchi: Isolation of a new terpenoid acid 2-methyl-5-iso-propyl-1-cyclopentene-l-carboxylic acid from Turkish tobacco. Agr. Biol. Chem. 39, 567 (1975).

    CAS  Google Scholar 

  45. Isolation of new terpenoid acids (—)-3-methyl-6-isopropyl-9-oxo-2E,4E-deca-dienoic acid and 3-isopropyl-6-oxo-2E-heptenoic acid from Turkish tobacco. Agr. Biol. Chem. In press.

    Google Scholar 

  46. Colledge, A., W. W. Reid, and R. Russell: The diterpenoids of Nicotiana species and their potential technological significance. Chem. and Ind. 570 (1975).

    Google Scholar 

  47. Comes, R. A., M. T. Core, M. D. Edmonds, W. B. Edwards, and R. W. Jenkins: Preparation of carbon-14 labelled tobacco constituents. II. The synthesis of dl-nicotine (2′-14C). J. Label. Compounds 9, 253 (1973).

    CAS  Google Scholar 

  48. Cornforth, J. W., B. V. Milborrow, and G. Ryback: Synthesis of (±)abscisin II. Nature 206, 715 (1965).

    CAS  Google Scholar 

  49. Courtney, J. L., and S. Mcdonald: A new C-20 α,β-unsaturated aldehyde (3,7,13-trimethyl-10-isopropyl-2,6,ll,13-tetradecatetraen-l-al) from tobacco. Tetrahedron Letters 459 (1967).

    Google Scholar 

  50. Creasy, P. J., and M. J. Saxby: Steam volatile acids of Latakia tobacco leaf. Phytochem. 8, 2427 (1969).

    CAS  Google Scholar 

  51. Dauben, W. G., W. E. Thiessen, and P. R. Resnick: Cembrene, a fourteen-membered ring diterpene hydrocarbon. J. Amer. Chem. Soc. 84, 2015 (1962).

    CAS  Google Scholar 

  52. Dawes, I. W., and R. A. Edwards: Methyl-substituted pyrazines as volatile reaction products of heated aqueous aldose, amino acid mixtures. Chem. and Ind. 2203 (1966).

    Google Scholar 

  53. Dwson, R. F.: On biogenesis of nornicotine and anabasine. J. Amer. Chem. Soc. 67, 503 (1945).

    Google Scholar 

  54. Dwson, R. F.: Advances in enzymology, New York 8, 203 (1948).

    Google Scholar 

  55. Dwson, R. F.: Alkaloid biogenesis. III. Specificity of the nicotine-nornicotine conversion. J. Amer. Chem. Soc. 73, 4218 (1951).

    Google Scholar 

  56. Dawson, R. F., D. R. Christman, A. D’Adamo, M. L. Solt, and A. P. Wolf: The biosynthesis of nicotine from isotopically labelled nicotinic acids. J. Amer. Chem. Soc. 82, 2628 (1960).

    CAS  Google Scholar 

  57. Dawson, R. F., D. R. Christman, and R. CH. Anderson: Alkaloid biogenesis. IV. The non-availability of nicotinic acid-[carboxyl-C14] and its ethyl ester for nicotine biosynthesis. J. Amer. Chem. Soc. 75, 5114 (1953).

    CAS  Google Scholar 

  58. Decker. K., H. Eberwein, F. A. Gries, und M. Brühmüller: Über den Abbau des Nikotins durch Bakterienenzyme. VI. L-6-Hydroxynicotin als erstes Zwischenprodukt. Biochem. Z. 334, 227 (1961).

    CAS  Google Scholar 

  59. Decker, K., und R. Sammeck: Enzymchemische Untersuchungen zum Nikotinabbau in der Kaninchenleber. Biochem. Z. 340, 326 (1964).

    CAS  Google Scholar 

  60. Demole, E.: Private communication.

    Google Scholar 

  61. Demole, E.: Chemistry of Burley tobacco flavor Nicotiana tabacum L.). Novel constituents and newer syntheses. VI. International Congress of Essentials Oils. San Francisco U.S.A. 1974.

    Google Scholar 

  62. Demole, E., et D. Berthet: Identification de la damascénone et de la β-damascone dans le tabac Burley. Helv. Chim. Acta 54, 681 (1971).

    CAS  Google Scholar 

  63. A chemical study of Burley tobacco flavour (Nicotiana tabacum L.). I. Volatile to medium volatile constituents. Helv. Chim. Acta 55, 1866 (1972).

    Google Scholar 

  64. A chemical study of Burley tobacco flavour A chemical study of Burley tobacco flavour Nicotiana tabacum L.). II. Medium volatile, free acidic constituents. Helv. Chim. Acta 55, 1898 (1972).

    Google Scholar 

  65. Demole, E., and C. Demole: A chemical study of Burley tobacco flavour (Nicotiana tabacum L.) V. Identification and synthesis of the novel terpenoid alkaloids 1,3,6,6-tetramethyl-5,6,7,8-tetrahydro-isoquinolin-8-one and 3,6,6-trimethyl-5,6-dihydro-7H-2-pyrindin-7-one. Helv. Chim. Acta 58, 523 (1975).

    CAS  Google Scholar 

  66. Demole, E., and C. Demole: A chemical study of Burley tobacco flavour (Nicotiana tabacum L.). VII. Identification and synthesis of twelve irregular terpenoids related to solanone including 7,8-dioxabicyclo[3.2.1] octane and 4,9-dioxabicyclo[3.3.1]nonane derivatives. Helv. Chim. Acta 58, 1867 (1975).

    CAS  Google Scholar 

  67. Demole, E., C. Demole, and D. Berthet: A chemical study of Burley tobacco flavour (Nicotiana tabacum L.). III. Structure determination and synthesis of 5-(4-methyl-2-furyl)-6-methylheptan-2-one (“Solanofuran”) and of 3,4,7-trimethyl-1, 6-dioxa-spiro[4.5]dec-3-en-2-one (“Spiroxabovolide”). Two new flavour components of Burley tobacco. Helv. Chim. Acta 56, 265 (1973).

    CAS  Google Scholar 

  68. Demole, E., C. Demole, and D. Berthet: A chemical study of Burley tobacco flavour (Nicotiana tabacum L.). IV. Identification of seven new solanone metabolites including 7,8-dioxabicyclo[3.2.1]oc-tane and 4,9-dioxabicyclo[3.3.1]nonane derivatives. Helv. Chim. Acta 57, 192 (1974).

    CAS  Google Scholar 

  69. Demole, E., and P. Enggist: Novel synthesis of 3,5,5-trimethyl-4-(2-butenylidene)-cyclohex-2-en-1-one, a major constituent of Burley tobacco flavour. Helv. Chim. Acta 57, 2087 (1974).

    CAS  Google Scholar 

  70. Demole, E., and P. Enggist: A chemical study of Burley tobacco flavour (Nicotiana tabacum L.). VI. Identification and synthesis of four irregular terpenoids related to solanone, including a prenyl-solanone. Helv. Chim. Acta 58, 1602 (1975).

    CAS  Google Scholar 

  71. Dewey, L. J., R. U. Byerrum, and C. D. Ball: Biosynthesis of the pyrrolidine ring of nicotine. Biochim. Biophys. Acta 18, 141 (1955).

    CAS  Google Scholar 

  72. Drew, M. G. B., D. H. Templeton, and A. Zalkin: The crystal and molecular structure of cembrene. Acta Cryst. B25, 261 (1969).

    Google Scholar 

  73. Duffield, A. M., H. Budzikiewicz, and C. Djerassi: Mass spectrometry in structural and stereochemical problems. LXXII. A study of the fragmentation processes of some tobacco alkaloids. J. Amer. Chem. Soc. 87, 2926 (1965).

    CAS  Google Scholar 

  74. Dymicky, M., and R. L. Stedman: Composition studies on tobacco. IV. Ergosterol, γ-sitosterol and a partially characterized steroidal glycoside from flue-cured leaves. Tob. Sci. 3, 4 (1959).

    CAS  Google Scholar 

  75. Composition studies on tobacco. IX. Campesterol from flue-cured leaves. Tob. Sci. 3, 179 (1959).

    Google Scholar 

  76. Eddy, C. R., and A. Eisner: Infrared spectra of nicotine and some of its derivatives. Anal.Chem. 26, 1428 (1954).

    CAS  Google Scholar 

  77. Egger, K., A. G. Dabbagh, und H. Nitsche: Überführung von Neoxanthin in Diadinochrom. Tetrahedron Letters 2995 (1969).

    Google Scholar 

  78. Ehrenstein, M.: Zur Kenntnis der Alkaloide des Tabaks. Chem. Ber. 64, 627 (1931).

    Google Scholar 

  79. Enzell, C. R.: Mass spectrometric studies of carotenoids. J. Pure and Applied Chem. 20, 497 (1969).

    CAS  Google Scholar 

  80. Enzell, C. R., B. Kimland, and L.-E. Gunnarsson: Tobacco Chemistry 5. Nor-solanesene, a C44-isoprenoid hydrocarbon from tobacco. Tetrahedron Letters 1983 (1971).

    Google Scholar 

  81. Eppenberger, U., L. Hirth, und G. Ourisson: Anaerobische Cyclisierung von Squalen-2,3-epoxyd zu Cycloartenol in Gewebekulturen von Nicotiana tabacum L. Eur. J. Biochem. 8, 180 (1969).

    CAS  Google Scholar 

  82. Erickson, R. E., C. H. Schunk, N. R. Trenner, B. H. Arison, and K. Folkers: Coenzyme Q. XL The structure of solanesol. J. Amer. Chem. Soc. 81, 4999 (1959).

    CAS  Google Scholar 

  83. Etoh, H., K. Ina, and M. Iguchi: Photosensitized oxygenation of α-pyran derived from β-ionone. Agr. Biol. Chem. 37, 2241 (1973).

    CAS  Google Scholar 

  84. Feeney, J., and F. W. Hemming: Nuclear magnetic resonance spectrometry of naturally occurring polyprenols. Analyt. Biochem. 20, 1 (1967).

    CAS  Google Scholar 

  85. Fikensher, L. H.: Nicotine, an alkaloid in Erythroxylum coca. Pharm. Weekblad 93, 932 (1958).

    Google Scholar 

  86. Firn, R. D., and J. Friend: Enzymic production of the plant growth inhibitor xanthoxin. Planta 103, 263 (1972).

    CAS  Google Scholar 

  87. Flament, I., B. Willhalm, et M. Stoll: Recherches sur les arômes. Sur l’arôme du cacao. III. Helv. Chim. Acta 50, 2233 (1967).

    CAS  Google Scholar 

  88. Foote, C. S., and M. Brenner: Chemistry of singlet oxygen. VIII. An unusual allenic oxygenation product. Tetrahedron Letters 6041 (1968).

    Google Scholar 

  89. Frankenburg, W. G., and A. M. Gottscho: Nicotinic acid in processed cigar tobacco. Arch. Biochem. Biophys. 21, 247 (1949).

    CAS  Google Scholar 

  90. Frankenburg, W. G., and A. M. Gottscho: Myosmine in cigar tobacco. Arch. Biochem. Biophys. 23, 333 (1949).

    Google Scholar 

  91. Frankenburg, W. G., and A. M. Gottscho: The chemistry of tobacco fermentation. I. Conversion of the alkaloids. B. The formation of oxynicotine. J. Amer. Chem. Soc. 77, 5728 (1955).

    CAS  Google Scholar 

  92. Frankenburg, W. G., A. M. Gottscho, E. W. Mayaud, and T.-C. Tso: The chemistry of tobacco fermentation: I. Conversion of the alkaloids. A. The formation of 3-pyridyl methyl ketone and of 2,3′-dipyridyl. J. Amer. Chem. Soc. 74, 4309 (1952).

    CAS  Google Scholar 

  93. Frankenburg, W. G., A. M. Gottscho, and A. A. Vaitekunas: Biochemical conversions of some tobacco alkaloids. Tob. Sci. 2, 9 (1958).

    CAS  Google Scholar 

  94. Frankenburg, W. G., A. M. Gottscho, A. A. Vaitekunas, and R. M. Zacharius: The chemistry of tobacco fermentation. I. Conversion of the alkaloids. C. The formation of 3-pyridyl propyl ketone, nicotinamide and N-methylnicotinamide. J. Amer. Chem. Soc. 77, 5730 (1955).

    CAS  Google Scholar 

  95. Frankenburg, W. G., and A. A. Vaitekunas: Chemical studies on nicotine degradation by microorganisms derived from the surface of tobacco seeds. Arch. Biochem. Biophys. 58, 509 (1955).

    CAS  Google Scholar 

  96. Frankenburg, W. G., and A. A. Vaitekunas: The chemistry of tobacco fermentation. I. Conversion of the alkaloids. D. Identification of cotinine in fermented leaves. J. Amer. Chem. Soc. 79, 149 (1957).

    CAS  Google Scholar 

  97. Fredrickson, J. D.: ß-Amyrenyl esters of tobacco. 20th Tobacco Chemists’ Research Conference, Winston-Salem, N. C., 1966.

    Google Scholar 

  98. Fujimori, T., R. Kasuga, H. Kaneko, and M. Noguchi: Isolation of 3-(4,8,12-trimethyl-tridecyl)-furan (“Phytofuran”) from Burley tobacco. Agr. Biol. Chem. 38, 2293 (1974).

    CAS  Google Scholar 

  99. Fujimori, T., R. Kasuga, H. Kaneko, and M. Noguchi: A new acetylenic diol, 3-hydroxy-7,8-dehydro-β-ionol from Burley Nicotiana tabacum L. Phytochem. 14, 2095 (1975).

    CAS  Google Scholar 

  100. Fujimori, T., R. Kasuga, M. Noguchi, and H. Kaneko: Isolation of R-(—)-3-hydroxy-β-ionone from Burley tobacco. Agr. Biol. Chem. 38, 891 (1974).

    CAS  Google Scholar 

  101. Fukuzumi, T., H. Kaneko, and H. Takahara: Studies on the chemical constituents of tobacco leaves. III. Isolation of (—)-2-isopropyl-5-oxo-hexanoic acid from Turkish tobacco leaves and absolute configuration of solanone. Agr. Biol. Chem. 31, 607 (1967).

    CAS  Google Scholar 

  102. Fukuzumi, T., H. Takahara, H. Kaneko, and I. Onishi: Isolation of hydroxy acids from Turkish tobacco leaves. Agr. Biol. Chem. 29, 967 (1965).

    CAS  Google Scholar 

  103. Fukuzumi, T., H. Takahara, H. Kaneko, and I. Onishi: Isolation of 2-isopropylmalic acid from Turkish tobacco. Nippon Nogeikagaku Kaisha 39, 204 (1965).

    CAS  Google Scholar 

  104. Gherna, R. L., S. H. Richardson, and S. C. Rittenberg: The bacterial oxidation of nicotine. VI. The metabolism of 2,6-dihydroxypseudooxynicotine. J. Biol. Chem. 240, 3669 (1965).

    CAS  Google Scholar 

  105. Gilbertson, T. J.: Biosynthesis of the piperidine nucleus: metabolism of D- and L-lysine-2-14C by Nicotiana glauca. Phytochem. 11, 1737 (1972).

    CAS  Google Scholar 

  106. Giles, J. A., and J. N. Schumacher: Turkish tobacco — I. Isolation and characterization of α-and α-levantenolide. Tetrahedron 14, 246 (1961).

    CAS  Google Scholar 

  107. Giles, J. A., J. N. Schumacher, S. S. Mims, and E. Bernasek: Turkish tobacco — II. Isolation and characterization of 12α-hydroxy-13-epimanoyloxide. Tetrahedron 18, 169 (1962).

    CAS  Google Scholar 

  108. Giles, J. A., J. N. Schumacher, and G. W. Young: Turkish tobacco — III. Isolation and characterization of α2-levantanolide. Tetrahedron 19, 107 (1963).

    CAS  Google Scholar 

  109. Gloger, M., und K. Decker: Zum Mechanismus der Induktion nikotinabbauender Enzyme in Arthrobacter oxydans. Zeitschrift Naturforsch. 24B, 1016 (1969).

    Google Scholar 

  110. Goldman, I. M., J. Seibl, I. Flament, F. Gautschi, M. Winter, B. Willhalm, et M. Stoll: Recherches sur les arômes. Sur l’arôme de café. II Pyrazines et pyridines. Helv. Chim. Acta 50, 694 (1967).

    CAS  Google Scholar 

  111. Gray, J. G., S. D. Kung, S. G. Wildman, and S. J. Sheen: Origin of Nicotiana tabacum L., detected by polypeptide composition of fraction I protein. Nature 252, 226 (1974).

    CAS  Google Scholar 

  112. Gries, F. A., K. Decker, und M. Brühmüller: Über den Abbau des Nikotins durch Bakterienenzyme. V. Abbau des L-6-Hydroxy-Nicotins zu [γ-Methylaminopropyl]-[6-hydroxy-pyridyl-(3)]-keton. Hoppe Seylers Z. Physiol. Chem. 325, 229 (1961).

    CAS  Google Scholar 

  113. Griffiths, W. T., D. R. Threlfall, and T. W. Goodwin: Observations on the nature and biosynthesis of terpenoid quinones and related compounds in tobacco shoots. Eur. J.Biochem. 5, 124 (1968).

    Google Scholar 

  114. Grunwald, C: Phytosterols in tobacco leaves at various stages of physiological maturity. Phytochem. 14, 79 (1975).

    CAS  Google Scholar 

  115. Gupta, R. N., and I. D. Spenser: Biosynthesis of the piperidine nucleus: the occurrence of two pathways from lysine. Phytochem. 9, 2329 (1970).

    CAS  Google Scholar 

  116. Gutcho, S.: Tobacco flavoring substances and methods 1972. Noyes Data Corp. U.S.A., pp. 65, 66.

    Google Scholar 

  117. Haines, P. G., and A. Eisner: Identification of pseudooxynicotine and its conversion to N-methylmyosmine. J. Amer. Chem. Soc. 72, 1719 (1950).

    CAS  Google Scholar 

  118. Hewlins, M. J. E., J. D. Ehrhardt, L. Hirth, and G. Ourisson: Conversion of [14C]-cycloartenol and [14C]-lanosterol into phytosterols by cultures of Nicotiana tabacum. Eur. J. Biochem. 8, 184 (1969).

    CAS  Google Scholar 

  119. Hlubucek, J. R., A. J. Aasen, S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 21. Three new volatile tobacco constituents of probable isoprenoid origin. Acta Chem. Scand. 27, 2232 (1973).

    CAS  Google Scholar 

  120. Hlubucek, J. R., A. J. Aasen, S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 22. Structures and synthesis of a nor-and a seco-terpenoid of the drimane series isolated from tobacco. Acta Chem. Scand. B28, 18 (1974).

    Google Scholar 

  121. Tobacco chemistry 26. Synthesis of 14, 15-bisnor-8-hydroxylabd-11E-en-13-one, a new tobacco constituent. Acta Chem. Scand. B28, 131 (1974).

    Google Scholar 

  122. Hlubucek, J. R., A. J. Aasen, S.-O. Almqvist, and C. R. Enzell: Tobacco chemistry 25. Two new drimane sesquiterpene alcohols from Greek Nicotiana tabacum L. Acta Chem. Scand. B28, 289 (1974).

    Google Scholar 

  123. Hlubucek, J. R., A. J. Aasen, B. Kimland, and C. R. Enzell: New volatile constituents of Greek Nicotiana tabacum. Phytochem. 12, 2555 (1973).

    CAS  Google Scholar 

  124. Hochstein, L. I., and S. C. Rittenberg: Bacterial oxidation of nicotine. II. Isolation of the first oxidative product and its identification as (l)-6-hydroxynicotine. J. Biol. Chem. 234, 156 (1959).

    CAS  Google Scholar 

  125. Bacterial oxidation of nicotine. Iii. Isolation and identification of 6-hydroxy-pseudooxynicotine. J. Biol. Chem. 235, 795 (1960).

    Google Scholar 

  126. Hoffman, D., S. S. Hecht, R. M. Ornaf, and E. L. Wynder: ITN’-nitrosonornicotine in tobacco. Science 186, 265 (1974).

    Google Scholar 

  127. Holmes, P. E., S. C. Rittenberg, and H. J. Knackmuss: The bacterial oxidation of nicotine. Synthesis of 2,3,6-trihydroxypyridine and accumulation and partial characterization of the product of 2,6-dihydroxypyridine oxidation. J. Biol. Chem. 247, 7628 (1972).

    Google Scholar 

  128. Hu, M. W., W. E. Bodinell, and D. Hoffmann: Chemical studies on tobacco smoke. XXIII. Synthesis of carbon-14 labelled myosmine, nornicotine and N’-nitro-sonornicotine. J. Label. Compounds 10, 79 (1974).

    CAS  Google Scholar 

  129. Huber, C.: Vorläufige Notiz über einige Derivate des Nikotins. Liebigs Ann. Chem. 141, 271 (1867).

    Google Scholar 

  130. Huber, C.: Vorläufige Mitteilung. Chem. Ber. 3, 849 (1870).

    Google Scholar 

  131. Hudson, C. S., and A. Neuberger: The stereochemical formulas of the hydroxy-proline and allohydroxyproline enantiomorphs and some related substances. J. Organ. Chem. 15, 24 (1950).

    Google Scholar 

  132. Il’in, G. S.: The interrelationship among the chief tobacco alkaloids. Biokhimiya (USSR) 13, 193 (1948).

    CAS  Google Scholar 

  133. Irvine, W. J., and M. J. Saxby: Steam volatile amines of Latakia tobacco leaf. Phytochem. 8, 473 (1969).

    CAS  Google Scholar 

  134. Isoe, S., S. B. Hyeon, S. Katsumura, and T. Sakan: Photo-oxygenation of caro-tenoids. II. The absolute configuration of loliolide and dihydroactinidiolide. Tetrahedron Letters 2517 (1972).

    Google Scholar 

  135. Isoe, S., S. B. Hyeon, and T. Sakan: Photo-oxygenation of carotenoids. I. The formation of dihydroactinidiolide and β-ionone from β-carotene. Tetrahedron Letters 279 (1969).

    Google Scholar 

  136. Isoe, S., S. Katsumura, S. B. Hyeon, and T. Sakan: Biogenetic type synthesis of grasshopper ketone and loliolide and a possible biogenesis of allenic carotenoids. Tetrahedron Letters 1089 (1971).

    Google Scholar 

  137. Isoe, S., S. Katsumura, and T. Sakan: The synthesis of damascenone and β-damascone and the possible mechanism of their formation from carotenoids. Helv. Chim. Acta 56, 1514 (1973).

    Google Scholar 

  138. Johnson, R. R., and J. A. Nicholson: The structure, chemistry and synthesis of solanone — anomalous terpenoid ketone from tobacco. J. Organ. Chem. 30, 2918 (1965).

    Google Scholar 

  139. Kallianos, A. G., and R. E. Means: Isoprenoid ketones in tobacco. CORESTA/ TCRC joint conference, Williamsburg, Va., Oct. 22–28, 1972. Abstr. 13, Coresta Information Bulletin 1972.

    Google Scholar 

  140. Kallianos, A. G., F. A. Shelburne, R. E. Means, R. K. Stevens, R. E. Lax, and J. D. Mold: Identification of the D-glucosides of stigmasterol, sitosterol and campesterol in tobacco and cigarette smoke. Biochem. J. 87, 596 (1963).

    CAS  Google Scholar 

  141. Kaneko, H.: The aroma of cigar tobacco. Part II. Isolation of norambreinolide from cigar tobacco. Agr. Biol. Chem. 35, 1461 (1971).

    CAS  Google Scholar 

  142. Kaneko, H., and M. Harada: 4-Hydroxy-β-damascone and 4-hydroxy-dihydro-β-damascone from cigar tobacco. Agr. Biol. Chem. 36, 168 (1972).

    CAS  Google Scholar 

  143. Aroma of cigar tobacco. III. Isolation and synthesis of R-(+)-3-isopropyl-5-hydroxypentanoic acid lactone. Agr. Biol. Chem. 36, 658 (1972).

    Google Scholar 

  144. Kaneko, H., and K. Hosfflmo: Isolation from cigar tobacco leaves of tetrahydro-actinidiolide (2-hydroxy-2,6,6-trimethylcyclohexyl acetic acid γ-lactone). Agr. Biol. Chem. 33, 969 (1969).

    CAS  Google Scholar 

  145. Kaneko, H., and K. Ijichi: The aroma of cigar tobacco. Part I. Isolation of 2-hydroxy-2,6,6-trimethylcyclohexylidene-l-acetic acid lactone (dihydroactinidiolide) from ether extract of cigar leaves. Agr. Biol. Chem. 32, 1337 (1968).

    CAS  Google Scholar 

  146. Karrer, P., und R. Widmer: Konfiguration des Nikotins. Optisch aktive Hygrin-säure. Helv. Chim. Acta 8, 364 (1925).

    CAS  Google Scholar 

  147. Kato, T., M. Tanemura, T. Suzuki, and Y. Kitahara: Biogenetic-type synthesis of α-and β-levantenolides. Chem. Commun. 28 (1970).

    Google Scholar 

  148. Kearns, D. R.: Physical and chemical properties of singlet molecular oxygen. Chem. Rev. 71, 395 (1971).

    CAS  Google Scholar 

  149. Kimland, B., A. J. Aasen, S.-O. Almqvist, P. Arpino, and C. R. Enzell: Tobacco chemistry 16. Volatile acids of sun-cured Greek tobacco. Phytochem. 12, 835 (1973).

    CAS  Google Scholar 

  150. Kimland, B., A. J. Aasen, and C. R. Enzell: Tobacco chemistry 12. Volatile neutral constituents of Greek tobacco. Acta Chem. Scand. 26, 1281 (1972).

    CAS  Google Scholar 

  151. Kimland, B., A. J. Aasen, and C. R. Enzell: Tobacco chemistry 10. Volatile neutral constituents of Greek tobacco. Acta Chem. Scand. 26, 2177 (1972).

    CAS  Google Scholar 

  152. Kimland, B., R. A. Ajppleton, A. J. Aasen, J. Roeraade, and C. R. Enzell: Tobacco Chemistry 6. Neutral oxygen-containing volatile constituents of Greek tobacco. Phytochem. 11, 309 (1972).

    Google Scholar 

  153. Kinzer, G. W., T. F. Page, and R. R. Johnson: Structure of two solanone precursors from tobacco. J. Organ. Chem. 31, 1797 (1966).

    CAS  Google Scholar 

  154. Kisaki, T., S. Mizusaki, and E. Tamaki: γ-Methylaminobutyraldehyde, a new intermediate in nicotine biosynthesis. Arch. Biochem. Biophys. 117, 677 (1966).

    CAS  Google Scholar 

  155. Kisaki, T., S. Mizusaki, and E. Tamaki: Phytochemical studies on tobacco alkaloids. XL A new alkaloid in Nicotiana tabacum roots. Phytochem. 7, 323 (1968).

    CAS  Google Scholar 

  156. Kisaki, T., and E. Tamaki: Phytochemical studies on the tobacco alkaloids. I. Optical rotatory power of nicotine. Arch. Biochem. Biophys. 92, 351 (1961).

    CAS  Google Scholar 

  157. Phytochemical studies of the tobacco alkaloids. III. Observations on the interconversion of dl-nicotine and dl-nornicotine in excised tobacco leaves. Arch. Biochem. Biophys. 94, 252 (1961).

    Google Scholar 

  158. Phytochemical studies on the tobacco alkaloids. X. Degradation of the tobacco alkaloids and their optical rotatory changes in tobacco plants. Phytochem. 5, 293 (1966).

    Google Scholar 

  159. Kobayashi, H., and S. Akiyoshi: Thunbergene, a macrocyclic diterpene. Bull. Chem. Soc. Japan 35, 1044 (1962).

    CAS  Google Scholar 

  160. Terpenoids. VI. Structure of thunbergene. Bull. Chem. Soc. Japan 36, 823 (1963).

    Google Scholar 

  161. Koehler, P. E., M. E. Mason, and J. A. Newell: Formation of pyrazine compounds in sugar-amino acid model systems. J. Agric. Food Chem. 17, 393 (1969).

    CAS  Google Scholar 

  162. Koehler, P. E., and G. V. Odell: Factors affecting the formation of pyrazine compounds in sugar-amine reactions. J. Agric. Food Chem. 18, 895 (1970).

    CAS  Google Scholar 

  163. Kofler, M., A. Langemann, R. Rü Egg, U. Gloor, U. Schwieter, J. Wü Rsch, O. Wiss, und O. Isler: Struktur und Partialsynthese des pflanzlichen Chinons mit isoprenoider Seitenkette. Helv. Chim. Acta 42, 2252(1959).

    Google Scholar 

  164. Korte, F., und H.-J. Schulze-Steinen: Acyl-lacton-Umlagerung XXII. Umlagerung von α-Aroyl-pyrrolidonen in konz. Salzsäure zu Pyrrollinderivaten. Chem. Ber. 95, 2444 (1962).

    CAS  Google Scholar 

  165. Kuffner, F., and N. Faderl: Constitution of nicotelline. Monatsh. Chem. 87, 71 (1956).

    CAS  Google Scholar 

  166. Kurata, S., Y. Inouye, and H. Kakisawa: Synthesis of dihydroactinidiolide and a trimethyloctalenedione. Tetrahedron Letters 5153 (1973).

    Google Scholar 

  167. Leete, E.: The biogenesis of nicotine. Chem. and Ind. 537 (1955).

    Google Scholar 

  168. Leete, E.: The biogenesis of nicotine and anabasine. J. Amer. Chem. Soc. 78, 3520 (1956).

    CAS  Google Scholar 

  169. Leete, E.: The biogenesis of nicotine. V. New precursors of the pyrrolidine ring. J. Amer. Chem. Soc. 80, 2162 (1958).

    CAS  Google Scholar 

  170. Leete, E.: Biosynthesis of the Nicotiana alkaloids. XI. Investigation of tautomerism in N-methyl-Δ1-pyrrolinium chloride and its incorporation into nicotine. J. Amer. Chem. Soc. 89, 7081 (1967).

    CAS  Google Scholar 

  171. Leete, E.: Biosynthesis of the Nicotiana alkaloids. XIV. The incorporation of Δ1-piperideine-6-14C into the piperidine ring of anabasine. J. Amer. Chem. Soc. 91, 1697 (1969).

    CAS  Google Scholar 

  172. Leete, E.: Biomimetic synthesis of nicotine. J. Chem. Soc. Chem. Commun. 1091 (1972).

    Google Scholar 

  173. Leete, E.: Biosynthesis and metabolism of the tobacco alkaloids. Proceedings of the First Philip Morris Science Symposium, 1973.

    Google Scholar 

  174. Leete, E.: Biosynthesis of anatabine and anabasine in Nicotiana glutinosa. J. Chem. Soc. Chem. Commun. 9 (1975).

    Google Scholar 

  175. Leete, E., and V. M. Bell: The biogenesis of the Nicotiana alkaloids. VIII. The metabolism of nicotine in N. tabacum. J. Amer. Chem. Soc. 81, 4358 (1959).

    CAS  Google Scholar 

  176. Leete, E., and M. R. Chedekel: The aberrant formation of (—)-N-methylanabasine from N-methyl-Δ1piperideinium chloride in Nicotiana tabacum and N. glauca. Phytochem. 11, 2751 (1972).

    CAS  Google Scholar 

  177. Leete, E., and M. R. Chedekel: Metabolism of nicotine in Nicotiana glauca. Phytochem. 13, 1853 (1974).

    CAS  Google Scholar 

  178. Leete, E., M. R. Chedekel, and G. B. Bodem: Synthesis of myosmine and nor-nicotine using an acyl carbanion equivalent as an intermediate. J. Organ. Chem. 37, 4465 (1972).

    CAS  Google Scholar 

  179. Leete, E., E. G. Gros, and T. J. Gilbertson: The biosynthesis of anabasine. Origin of the nitrogen of the piperidine ring. J. Amer. Chem. Soc. 86, 3907 (1964).

    CAS  Google Scholar 

  180. Biosynthesis of the pyrrolidine ring of nicotine — feeding experiments with 15 N-labelled ornithine-2-14C. Tetrahedron Letters 587 (1964).

    Google Scholar 

  181. Leete, E., and Y.-Y. Liu: Metabolism of [2-3H]-and [6-3H]-nicotinic acid in intact Nicotiana tabacum plants. Phytochem. 12, 593 (1973).

    CAS  Google Scholar 

  182. Lloyd, R. A., C. W. Miller, D. L. Roberts, J. A. Giles, J. P. Dickerson, N. H. Nelson, C. E. Rix, and P. H. Ayers: Flue-cured tobacco flavor. I. Essence and essential oil components. Tob. Sci. 20, 43 (1976).

    Google Scholar 

  183. Lupukás, R., A. A. Arojan, J. Kupovář, und K. Bupláha: Zur Konfiguration stickstoffhaltiger Verbindungen XV. Bestimmung der absoluten Konfiguration von Anabasin und Anatabin. Coll. Czech. Chem. Commun. 27, 751 (1962).

    Google Scholar 

  184. Manske, R. H. F., and L. Marion: The alkaloids of Lycopodium species. I. Lyco-podium complanatum L. Can. J. Res. B. 20, 87 (194

    CAS  Google Scholar 

  185. Manske, R. H. F., and L. Marion: Alkaloids of Lycopodium species. VII. Lycopodium lucidulum. Can. J. Res. B. 24, 57 (1946).

    CAS  Google Scholar 

  186. Marion, L.: The occurrence of L-nicotine in Asclepias syriaca. Can. J. Res. B. 17, 21 (1939).

    Google Scholar 

  187. Marion, L.: The alkaloids of Sedum acre. Can. J. Res. B. 23, 165 (1945).

    Google Scholar 

  188. Marion, L., and R. H. F. Manske: Alkaloids of Lycopodium species. IV. Lycopodium tristachyum Pursh. Can. J. Res. B. 22, 1 (1944).

    Google Scholar 

  189. Marion, L., and R. H. F. Manske: Alkaloids of Lycopodium species. VI. Lycopodium clavatum. Can. J. Res. B 22, 137 (1944).

    Google Scholar 

  190. Marion, L., and R. H. F. Manske: Alkaloids of Lycopodium species. VIII. Lycopodium sabinaefolium. Can. J. Res. B 24, 63 (1946).

    CAS  Google Scholar 

  191. Marion, J. P., F. Müggler-Chavan, R. Viani, J. Bricout, D. Reymond, et R. H. Egli: Sur la composition de l’arôme de cacao. Helv. Chim. Acta 50, 1509 (1967).

    CAS  Google Scholar 

  192. Mckennis, H., E. R. Bowman, L. D. Quin, and R. C. Denney: Structure of dibromoticonine, a bromination product of nicotine. J. Chem. Soc. Perkin I, 2046 (1973).

    Google Scholar 

  193. Milborrow, B. V.: Biosynthesis of abscisic acid by a cell-free system. Phytochem. 13, 131 (1974).

    CAS  Google Scholar 

  194. Milborrow, B. V.: The stereochemistry of cyclization in abscisic acid. Phytochem. 14, 123 (1975).

    CAS  Google Scholar 

  195. Mizusaki, S., Y. Tanabe, M. Noguchi, and E. Tamaki: Phytochemical studies on tobacco alkaloids. XIV. The occurrence and properties of putrescine N-methyltrans-ferase in tobacco roots. Plant Cell Physiol. 12, 633 (1971).

    CAS  Google Scholar 

  196. Mizusaki, S., Y. Tanabe, M. Noguchi, and E. Tamaki: N-Methylputrescine oxidase from tobacco roots. Phytochem. 11, 2757 (1972).

    CAS  Google Scholar 

  197. Mori, K.: Synthesis of the optically active dehydrovomifoliol. A synthetic proof of the absolute configuration of (+)-abscisic acid. Tetrahedron Letters 2635 (1973).

    Google Scholar 

  198. Mousseron-Canet, M., J.-P. Dalle, et J.-C. Mani: Photooxydation sensibilisée de composes apparentes aux carotenoides. Analogie avec la structure des carotenoides oxygenes, alleniques et autres. Tetrahedron Letters 6037 (1968).

    Google Scholar 

  199. Mundy, B. P., and B. R. Larsen: A new approach to pyrrolidine and piperidine alkaloids. Synthetic Commun. 2, 197 (1972).

    CAS  Google Scholar 

  200. Mundy, B. P., B. R. Larsen, L. F. Mckenzie, and G. Braden: A convenient synthesis of myosmine. J. Organ. Chem. 37, 1635 (1972).

    CAS  Google Scholar 

  201. Nathan, R. A., and A. H. Adelman: Photosensitized generation of singlet molecular oxygen with near-infrared radiation. Chem. Commun. 674 (1974).

    Google Scholar 

  202. Neurath, G., und M. Dünger: Isolierung schwach basischer Heteroaromaten aus dem Tabakrauch. Beitr. Tabakforsch. 5, 1 (1969).

    CAS  Google Scholar 

  203. Neurath, G., A. Krull, B. Pirmann, und K. Wandrey: Untersuchung der flüchtigen Basen des Tabaks, II. Beitr. Tabakforsch. 3, 571 (1966).

    CAS  Google Scholar 

  204. Newell, J. A., M. E. Mason, and R. S. Matlock: Precursors of typical and atypical roasted peanut flavour. J. Agric. Food Chem. 15, 767 (1967).

    CAS  Google Scholar 

  205. Noga, E.: Über die Alkaloide im Tabakextrakt. Fachl. Mitt. Österr. Tabak-Regie I (1914).

    Google Scholar 

  206. Ohloff, G.: Classification and genesis of food flavours. Flavour Industry 501 (1972).

    Google Scholar 

  207. Ohloff, G., D. Rautenstrauch, und K. H. Schulte-Elte: Modellreaktionen zur Biosynthese von Verbindungen der Damascon-Reihe und ihre präparative Anwendung. Helv. Chim. Acta 56, 1503 (1973).

    CAS  Google Scholar 

  208. Onishi, I., H. Tomita, and T. Fukuzumi: Essential oils of tobacco leaves. IV. Neutral fraction. Bull. Agr. Chem. Soc. Japan 20, 61 (1956).

    CAS  Google Scholar 

  209. Oreykov, A., und G. Menshikov: Über die Alkaloide von Anabasis aphylla L. (I. Mitteilung.) Chem. Ber. 64, 266 (1931).

    Google Scholar 

  210. Pack, A. B.: The curing and quality of flue-cured tobacco: the effect of certain cultural and curing practices on the plastid pigment and carbohydrate contents. N. C. State College, Ph. D. Thesis 1950 (unpublished), from WEYBREW, J. A., Tob. Sci. 1, 1 (1957).

    Google Scholar 

  211. Paris, R. R., et P. Frigot: Étude par Chromatographie et par electrophorèse des alcaloïdes de diverse Crassulacceés indigènes; caractérisation de la nicotine chez le Sempervivum araenoideum. C. R. Acad. Sci. 248, 1849 (1959).

    CAS  Google Scholar 

  212. Pelletier, S. W., S. Lajsic, Y. Ohtsuka, and Z. Djarmati: Naturally occurring terpenes. Synthesis of (+)-and (±)-14,15-bisnor-8α-hydroxylabd-11(E)-en-13-one, (+)-drimane-8, 11-diol, and (-)-drimenol. J. Organ. Chem. 40, 1607 (1975).

    CAS  Google Scholar 

  213. Pictet, A., und G. Court: Über einige neue Pflanzenalkaloide. Chem. Ber. 40, 3771 (1907).

    Google Scholar 

  214. Pictet, A., und P. Crépieux: Über Phenyl-und Pyridylpyrrole und die Constitution des Nicotins. Chem. Ber. 28, 1904 (1895).

    CAS  Google Scholar 

  215. Pictet, A., und A. Rotschy: Über neue Alkaloide des Tabaks. Chem. Ber. 34, 696 (1901).

    CAS  Google Scholar 

  216. Pinner, A: Über Nicotin. (I. Mitteilung.) Arch. Pharmaz. 231, 378 (1893).

    Google Scholar 

  217. Pinner, A: Über Nikotin (Metanicotin). VIL Mitteilung. Chem. Ber. 27, 1053 (1894).

    Google Scholar 

  218. Pinner, A., und RÖWER: Über Nicotin. Die Konstitution des Alkaloids. Chem. Ber. 26, 292 (1893).

    Google Scholar 

  219. Poindexter, E. H., and R. D. Carpenter: The isolation of harmane and norharmane from tobacco and cigarette smoke. Phytochem. 1, 215 (1962).

    CAS  Google Scholar 

  220. Posselt, W., und L. Reimann: Chemische Untersuchung des Tabaks und Darstellung eines eigentümlichen wirksamen Prinzips dieser Pflanze. Geigers Mag. Pharmac. 24, 138 (1828).

    Google Scholar 

  221. Quan, P. M., T. K. B. Karns, and L. D. Quin: Total synthesis of dl-anatabine. Chem. and Ind. 1553 (1964).

    Google Scholar 

  222. Ramamurthy, V., and R. S. H. Liu: Photochemistry of dehydro-β-ionone and related compounds. Tetrahedron Letters 441 (1973).

    Google Scholar 

  223. Rayburn, C. H., W. R. Harlan, and H. R. Hanmer: Rearrangement of nicotine oxide. J. Amer. Chem. Soc. 72, 1721 (1950).

    CAS  Google Scholar 

  224. Reid, W. W.: The action of inhibitors on the incorporation of [2-14C]-mevalonate into the triterpenes and sterols of Nicotiana tabacum. Biochem. J. 100, 13P (1966).

    Google Scholar 

  225. Reid, W. W.: The phytochemistry of the genus Nicotiana. Ann. du Tabac S.E.I.T.A. 2, 145 (1974).

    Google Scholar 

  226. Ribas-Scmuparqués, I, y Y. A. Nodar Blanco: Alcaloides de las Papilionaceas XXXIX. Configuration absoluta de adenocarpina, santiaquina, ammodendrina, anabasina, anatabina y de sus metil-derivados. Configuraciôn absoluta parcial del a,β’-dipiperi-dilo. Soc. Espan. Fis. Quim. 57, 781 (1961).

    Google Scholar 

  227. Richardson, B., J. R. Baur, R. S. Halliwell, and R. Langston: Sterol metabolism in normal and tobacco mosaic virus infected tobacco plants. Steroids 11, 231 (1968).

    CAS  Google Scholar 

  228. Richardson, S. H., and S. C. Rittenberg: Bacterial oxidation of nicotine. IV. Isolation and identification of 2,6-dihydroxy-N-methylmyosmine. J. Biol. Chem. 236, 959 (1961).

    CAS  Google Scholar 

  229. Bacterial oxidation of nicotine. V. Identification of 2,6-dihydroxypseudooxy-nicotine as the third oxidative product. J. Biol. Chem. 236, 964 (1961).

    Google Scholar 

  230. Roberts, D. L.: Tobacco. U.S. Patent 3, 217, 717; November 16, 1965.

    Google Scholar 

  231. Roberts, D. L.: The structure of a new sesquiterpene isolated from tobacco. Phytochem. 11, 2077 (1972).

    CAS  Google Scholar 

  232. Roberts, D. L., R. A. Heckman, B. P. Hege, and S. A. Bellin: Synthesis of (R,S)-abscisic acid. J. Organ. Chem. 33, 3566 (1968).

    CAS  Google Scholar 

  233. Roberts, D. L., C. W. Miller, and R. A. Lloyd, Jr.: Tobacco carotenoids. 27th Tobacco Chemist’s Research Conference, Winston-Salem, N. C, October 3–5, 1973.

    Google Scholar 

  234. Roberts, D. L., and W. A. Rohde: Isolation and identification of flavour components of Burley tobacco. Tob. Sci. 16, 107 (1972).

    CAS  Google Scholar 

  235. Roberts, D. L., and R. L. Rowland: Macrocyclic diterpenes. a-and β-4,8,13-duvatriene-l,3-diols from tobacco. J. Organ. Chem. 27, 3989 (1962).

    CAS  Google Scholar 

  236. Roberts, D. L., and J. N. Schumacher: Tobacco. U. S. Patent No. 3, 217, 716. November 16, 1965.

    Google Scholar 

  237. Rowland, R. L.: Flue-cured tobacco. IL Neophytadiene. J. Amer. Chem. Soc. 79, 5007 (1957).

    CAS  Google Scholar 

  238. Rowland, R. L.: Flue-cured tobacco. III. Solanachromene and α-tocopherol. J. Amer. Chem. Soc. 80, 6130 (1958).

    Google Scholar 

  239. Rowland, R. L., and J. A. Giles: Flue-cured tobacco. V. Polyisoprenoid compounds. Tob. Sci. 4, 29 (1960).

    CAS  Google Scholar 

  240. Rowland, R. L., and P. H. Latimer: Flue-cured tobacco. IV. Isolation of solanesyl esters. Tob. Sci. 3, 1 (1959).

    CAS  Google Scholar 

  241. Rowland, R. L., P. H. Latimer, and J. A. Giles: Flue-cured tobacco. I. Isolation of solanesol, an unsaturated alcohol. J. Amer. Chem. Soc. 78, 4680 (1956).

    CAS  Google Scholar 

  242. Rowland, R. L., and D. L. Roberts: Macrocyclic diterpenes isolated from tobacco, α-and β-4,8,13-Duvatriene-l,5-diols. J. Organ. Chem. 28, 1165 (1963).

    CAS  Google Scholar 

  243. Rowland, R. L., A. Rodgman, J. N. Schumacher, D. L. Roberts, L. C. Cook, and W. E. Walker, Jr.: Macrocyclic diterpene hydroxyethers from tobacco and cigarette smoke. J. Organ. Chem. 29, 16 (1964).

    CAS  Google Scholar 

  244. Rüegg, R., U. Gloor, A. Langemann, M. Kofler, C. Von Planta, G. Ryser, and O. Isler: Total synthesis of solanesol. Helv. Chim. Acta 43, 1745 (1960).

    Google Scholar 

  245. Sabetay, S., L. Trabaud, and H. F. Emmanuel: Constituents of the concrete oil of tobacco leaves (Nicotiana tabacum). Comp. rend. 213, 321 (1941).

    CAS  Google Scholar 

  246. Sanderson, G. W., H. Co, and J. G. Gonzalez: Biochemistry of tea fermentation: the role of carotenes in black tea aroma formation. J. Food Sci. 36, 231 (1971).

    CAS  Google Scholar 

  247. Schenk, H. R., H. Gutmann, O. Jeger, und L. Ruzicka: Zur Kenntnis der Diterpene, XLII. Über eine neue, ergiebige Partialsynthese des Ambreinolides. Helv. Chim. Acta 35, 817 (1952).

    Google Scholar 

  248. Schmeltz, L, R. L. Miller, and R. L. Stedman: Gas Chromatographic study of the steam-volatile fatty acids of various tobaccos. J. Gas Chromatog. 1, 27 (1963).

    CAS  Google Scholar 

  249. Schmeltz, I., R. L. Stedman, and R. L. Miller: Composition studies on tobacco. XVI. Steam-volatile acids. J. Assoc. Offic. Agr. Chemists 46, 779 (1963).

    CAS  Google Scholar 

  250. Schulte-Elte, K. H., M. Gadola, und G. Ohloff: Oxydative Umsetzungen in der Damascon-Reihe. 1ΔgO2-und SeO2-Oxydation von β-Damascenon. Helv. Chim. Acta 56, 2028 (1973).

    CAS  Google Scholar 

  251. Schulte-Elte, K. H., B. L. Müller, und G. Ohloff: Die farbstoffsensibilisierte Photo-Oxygenierung von β-Damascol. Ein einfaches Verfahren zur Darstellung von β-Damascenon. Helv. Chim. Acta 54, 1899 (1971).

    CAS  Google Scholar 

  252. Schumacher, J. N., and R. A. Heckman: On the natural occurrence and relative configurations of the tetrahydroactinidiolide isomers. Phytochem. 10, 421 (1971).

    CAS  Google Scholar 

  253. Schumacher, J. N., and L. Vestal: Isolation and identification of some components of Turkish tobacco. Tob. Sci. 18, 43 (1974).

    CAS  Google Scholar 

  254. Supchütte, H. R., W. Maier, and K. Mothes: Methylputrescine as possible precursor of nicotine in Nicotiana rustica. Acta Biochem. Polon. 13, 401 (1966).

    Google Scholar 

  255. Schwieter, U., W. Arnold, W. E. Oberhänsli, N. Rigassi, und W. Vetter: Synthese in der Carotinoid-Reihe. Ein Beitrag zur Chromsäure-Oxydation von Polyenen. Helv. Chim. Acta 54, 2447 (1971).

    CAS  Google Scholar 

  256. Scott, T. A., and J. P. Glynn: The incorporation of [2,3,7-14C]-nicotinic acid into nicotine by Nicotiana tabacum. Phytochem. 6, 505 (1967).

    CAS  Google Scholar 

  257. Shigematsu, H., S. Shibata, T. Kurata, H. Kato, and M. Fujimaki: 5-Acetyl-2,3-dihydro-1 H-pyrrolizines and 5,6,7,8-tetrahydroindolizin-8-ones, odor constituents formed on heating L-proline with D-glucose. J. Agric. Food Chem. 23, 233 (1975).

    CAS  Google Scholar 

  258. Skorianetz, W., und G. Ohloff: Säurekatalysierte Umlagerung von trans-5,6-Di-hydroxy-5,6-dihydro-β-jonon. Helv. Chim. Acta 56, 2025 (1973).

    CAS  Google Scholar 

  259. Über vinyloge English-Zimmerman-Spaltungen in der Iononreihe. Helv. Chim. Acta 58, 771 (1975).

    Google Scholar 

  260. Skraup, ZD. H., und A. Cobenzl: Über α-und β-Naphthochinolin. Monatsh. Chem. 4, 459 (1883).

    Google Scholar 

  261. Smith, C. R.: Occurrence of anabasine in Nicotiana glauca R. Grah. (Solanaceae). J. Amer. Chem. Soc. 57, 959 (1935).

    CAS  Google Scholar 

  262. Smith, H. H., and C. R. Smith: Alkaloids in certain species and interspecific hybrids of Nicotiana. J. Agr. Res. 65, 347 (1942).

    CAS  Google Scholar 

  263. Solt, M. L., R. F. Dawson, and D. R. Christman: Biosynthesis of anabasine and of nicotine by excised root cultures of Nicotiana glauca. Plant. Physiol. 35, 887 (1960).

    CAS  Google Scholar 

  264. Springer, J. P., J. Clardy, R. H. Cox, H. G. Cutler, and R. J. Cole: The structure of a new type of plant growth inhibitor extracted from immature tobacco leaves. Tetrahedron Letters 2737 (1975).

    Google Scholar 

  265. Suppäth, E., und S. Biniecki: Tobacco Alkaloids. XVI. Af-Methylpyrrolidin, ein neues Tabak-Alkaloid und zur Konstitution des Iso-Nicoteins. Chem. Ber. 72, 1809 (1939).

    Google Scholar 

  266. Suppäth, E., und H. Bretschneider: Eine neue Synthese des Nicotins und einige Bemerkungen zu den Arbeiten NAGAIS über Ephedrine. Chem. Ber. 61, 327 (1928).

    Google Scholar 

  267. Suppäth, E., und F. Kesztler: L-Anatabin, ein neues Tabakalkaloid. (XL Mitteilung über Tabakbasen.) Chem. Ber. 70, 239 (1937).

    Google Scholar 

  268. Suppäth, E., und F. Kesztler: Über das Vorkommen von d,l-Nornicotin, d,l-Anatabin und l-Anabasin im Tabak. (XII. Mitteilung über Tabakalkaloide.) Chem. Ber. 70, 704 (1937).

    Google Scholar 

  269. Suppäth, E., und F. Kesztler: Über neue Basen des Tabaks. (XIII. Mitteilung über Tabakalkaloide.) Chem. Ber. 70, 2450 (1937).

    Google Scholar 

  270. Suppäth, E., und L. Mamoli: Synthese des Myosmins (VI. Mitteilung über Tabakbasen) und Bemerkungen zu einer Notiz von T. Reynolds und R. Robinson. Chem. Ber. 69, 757 (1936).

    Google Scholar 

  271. Suppäth, E., und L. Mamoli: Eine neue Synthese des d,l-Anabasins. (VII. Mitteilung über Tabakalkaloide.) Chem. Ber. 69, 1082 (1936).

    Google Scholar 

  272. Suppäth, E., J. P. Wibaut, und F. Kesztler: Über das N-Methylmyosmin. Chem. Ber. 71, 100 (1938).

    Google Scholar 

  273. Späth, E., und E. Zajic: Über neue Tabakalkaloide (VIII. Mitteilung über Tabakbasen) und Bemerkungen zur Kenntnis des Rhoeadins, des l-Peganins und des Ammoresinols. Chem. Ber. 69, 2448 (1936).

    Google Scholar 

  274. Steadman, J. R., and L. Sequeira: Abscisic acid in tobacco plants. Plant Physiol. 45, 691 (1970).

    CAS  Google Scholar 

  275. Stevens, K. L., R. Lundin, and D. L. Davis: Acid catalyzed rearrangement of β-ionone epoxide. Tetrahedron 31, 2749 (1975).

    CAS  Google Scholar 

  276. Stevens, M. A.: Relationship between polyene-carotene content and volatile compound composition of tomatoes. J. Amer. Soc. Horticult. Sci. 95, 461 (1970).

    CAS  Google Scholar 

  277. Stevenson, J., F. W. Hemming, and R. A. Morton: The intracellular distribution of solanesol and plastoquinone in green leaves of the tobacco plant. Biochem. J. 88, 52 (1963).

    CAS  Google Scholar 

  278. Stoll, M., et M. Hinder: Odeur et constitution VIII. Recherches sur quelques produits de dégradation du sclaréol. Helv. Chim. Acta 36, 1984 (1953).

    CAS  Google Scholar 

  279. Strain, H. H.: Leaf xanthophylls. Carnagie Inst. Wash., Publ. No. 490 (1938).

    Google Scholar 

  280. Strain, H. H.: Leaf xanthophylls. J. Amer. Chem. Soc. 70, 1672 (1948).

    CAS  Google Scholar 

  281. VAN Tamelen, E. E., and R. M. Coates: Biogenetic-type synthesis of (±)-farnesiferol A and (±)-farnesiferol C. Chem. Commun. 413 (1966).

    Google Scholar 

  282. VAN Tamelen, E. E., A. Storni, E. J. Hessler, and M. Schwartz: The biogenetically patterned in vitro oxidation-cyclization of farnesyl acetate. J. Amer. Chem. Soc. 85, 3295 (1963).

    Google Scholar 

  283. Tanemura, M., T. Suzuki, T. Kato, and Y. Kitahara: Synthesis of levantenolides from acyclic progenitor. Tetrahedron Letters 1463 (1970).

    Google Scholar 

  284. Thesing, J., und A. Müller: Synthese des Nicotellins. Angew. Chem. 68, 577 (1956).

    CAS  Google Scholar 

  285. Tso, T. C, and R. N. Jeffrey: Biochemical studies on tobacco alkaloids. I. The fate of labeled tobacco alkaloids supplied to Nicotiana plants. Arch. Biochem. Bio-phys. 80, 46 (1959).

    CAS  Google Scholar 

  286. Wada, E.: Microbial degradation of nornicotine. Arch. Biochem. Biophys. 64, 244 (1956).

    CAS  Google Scholar 

  287. Wada, E.: Microbial degradation of the tobacco alkaloids and some related compounds. Arch. Biochem. Biophys. 72, 145 (1957).

    CAS  Google Scholar 

  288. Wada, E., T. Kisaki, and K. Saito: Autooxidation of nicotine. Arch. Biochem. Biophys. 79, 124 (1959).

    CAS  Google Scholar 

  289. Wada, E., and K. Yamasaki: Degradation of nicotine by soil bacteria. J. Amer. Chem. Soc. 76, 155 (1954).

    CAS  Google Scholar 

  290. Wahl, R.: Über das Vorkommen von Metanikotin in natürlich nikotinfreien Tabaksorten. Tabak-Forsch. Sonderheft 36 (1953).

    Google Scholar 

  291. Wahlberg, I., K. Karlsson, D. J. Austin, N. Junker, J. Roeraade, C. R. Enzell, and W. H. Johnson: TO be published.

    Google Scholar 

  292. Wahlberg, I., K. Karlsson, and C. R. Enzell: To be published.

    Google Scholar 

  293. Wahlberg, I., K. Karlsson, T. Nishida, K.-P. Cheng, and C. R. Enzell: TO be published.

    Google Scholar 

  294. Warfield, A. H., W. D. Galloway, and A. G. Kallianos: Some new alkaloids from Burley tobacco. Phytochem. 11, 3371 (1972).

    CAS  Google Scholar 

  295. Von Wartburg, B. R., H. R. Wolf, und O. Jeger: Photochemische Reaktionen. Neuartige Photoreaktionen des (±)-trans-β-Ionon-Epoxids. Helv. Chim. Acta 56, 1948 (1973).

    Google Scholar 

  296. Von Wartburg, B. R., H. R. Wolf, und O. Jeger: Photochemische Reaktionen. Notiz zur Photoreaktivität ausgewählter ungesättigter Ketoalkohole der Iononreihe. Helv. Chim. Acta 56, 1956 (1973).

    Google Scholar 

  297. Weil, L., and J. Mäher: Photodynamic action of méthylène blue on nicotine and its derivatives. Arch. Biochem. 29, 241, (1950).

    Google Scholar 

  298. Weiss, G., M. Koreeda, and K. Nakanishi: Stereochemistry of theaspirone and the blumenols. Chem. Commun. 565 (1973).

    Google Scholar 

  299. Wenusch, A.: Über das Auftreten von Nicotyrin im Tabak. Biochem. Z. 275, 361 (1935).

    CAS  Google Scholar 

  300. Wenusch, A., und R. Supchöller: Beitrag zur Kenntnis der Zusammensetzung des Tabakrauches. Fachl. Mitt. österr. Tabak-Regie 2 (1933).

    Google Scholar 

  301. Whitfield, D. M., and K. S. Rowan: Changes in the chlorophylls and caro-tenoids of leaves of Nicotiana tabacum during senescence. Phytochem. 13, 77 (1974).

    CAS  Google Scholar 

  302. Witkop, B.: Infrared diagnosis of the hydrochlorides of organic bases. II. Structure of myosmine. J. Amer. Chem. Soc. 76, 5597 (1954).

    CAS  Google Scholar 

  303. Woollen, B. H., W. J. Irvine, P. W. Brown, and D. H. Jones: A thin-layer chro-matographic method for tobacco lipid analysis. Tob. Sci. 16, 101 (1972).

    Google Scholar 

  304. Wright, Jr., H. E., W. W. Burton, and R. C. Berry Jr.: Carotenoids and related colorless polyenes of aged Burley tobacco. Arch. Biochem. Biophys. 82, 107 (1959).

    CAS  Google Scholar 

  305. Yang, K. S., R. K. Gholson, and G. R. Waller: Studies on nicotine biosynthesis. J. Amer. Chem. Soc. 87, 4184 (1965).

    CAS  Google Scholar 

  306. Yasumatsu, N., and S. Akaike: Studies on the volatile bases in tobacco. Part 1. Volatile amines in cured leaves and tobacco plant. Nippon Nogeikagaku Kaishi 39, 347 (1965).

    CAS  Google Scholar 

  307. Zane, A.: 4,8,13-Duvatriene-l-ol-3-one and 11-isopropyl-4,8-dimethyl-3,7,12-penta-decatriene-2,14-dione isomers from Nicotiana tabacum. Phytochem. 12, 731 (1973).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemical Research Department, Swedish Tobacco Company, Stockhohn, Sweden

    C. R. Enzell, I. Wahlberg & A. J. Aasen

Authors
  1. C. R. Enzell
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. Wahlberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. J. Aasen
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Tallahassee, Fla., USA

    W. Herz

  2. Freiburg i. Br., Deutschland

    H. Grisebach

  3. Glasgow, Scotland

    G. W. Kirby

Rights and permissions

Reprints and permissions

Copyright information

© 1977 Springer-Verlag/Wien

About this chapter

Cite this chapter

Enzell, C.R., Wahlberg, I., Aasen, A.J. (1977). Isoprenoids and Alkaloids of Tobacco. In: Herz, W., Grisebach, H., Kirby, G.W. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 34. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8476-9_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8476-9_1

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8478-3

  • Online ISBN: 978-3-7091-8476-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation