The University of Massachusetts Amherst

The Plant Cell Culture Library

Nicotiana tabacum
Cell Line ID NT-12392
Media Type M72
Availability Low
Order Solanales
Family Solanaceae
Genus Nicotiana
Antifungal Species Level ➡ 1 citations
Anthelmintic Species Level ➡ 2 citations
Insecticidal Species Level ➡ 128 citations
Anticancer Species Level
Culture Initiation Site DSM
Plant Habit Herb Annual/biennial
Plant Habitat Warm Temperate
Native Range Summer: Northeast Argentina, Bolivia
Plant Supplier Inst/LMU Munich
Antifungal Citations
  1. Gu, Q. et al., Mol. Gen. Genet., 1992, 234, 89- 96 (FST)
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Anthelmintic Citations
  1. Nouri F, Nourollahi-Fard SR, Foroodi HR, Sharifi H. In vitro anthelmintic effect of Tobacco (Nicotiana tabacum) extract on parasitic nematode, Marshallagia marshalli. J Parasit Dis. 2016 Sep;40(3):643-7. [https://doi.org/10.1007/s12639-014-0550-3.] Epub 2014 Sep 5. PubMed PMID: 27605759; PubMed Central PMCID: PMC4996163.
  2. Iqbal Z, Lateef M, Jabbar A, Ghayur MN, Gilani AH. In vitro and In vivo anthelmintic activity of Nicotiana tabacum L. leaves against gastrointestinal nematodes of sheep. Phytother Res. 2006 Jan;20(1):46-8. PubMed PMID: 16397920.
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Insecticidal Citations
  1. Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 768B (ir)
  2. Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 1537B (ir)
  3. Aldrich Library of 13C and 1H FT-NMR Spectra, 1992, 3, 294B (nmr)
  4. Karrer, P. et al., Helv. Chim. Acta, 1925, 8, 364 (abs config) [https://doi.org/10.1002/hlca.19250080157]
  5. Swan, M.L. et al., JACS, 1949, 71, 1341 (uv) [https://doi.org/10.1021/ja01172a057]
  6. Witkop, B., JACS, 1954, 76, 5597 (ir) [https://doi.org/10.1021/ja01651a003]
  7. Hellmann, H. et al., Annalen, 1964, 672, 97 (synth)
  8. Duffield, A.M. et al., JACS, 1965, 87, 2926 (ms) [https://doi.org/10.1021/ja01091a024]
  9. Breuer, E. et al., Tet. Lett., 1969, 3595 (synth) [https://doi.org/10.1016/S0040-4039(01)88462-8]
  10. Kim, H.S. et al., Acta Cryst. B, 1971, 27, 1123 (cryst struct, salicylate) [https://doi.org/10.1107/S0567740871003637]
  11. Crain, W.O. et al., JACS, 1971, 93, 990 (cmr)
  12. Phillipson, J.D. et al., Phytochemistry, 1975, 14, 2683 (oxide) [https://doi.org/10.1016/0031-9422(75)85250-2]
  13. Hutchinson, C.R. et al., JACS, 1976, 98, 6006 (biosynth) [https://doi.org/10.1021/ja00435a038]
  14. Whidby, J.F. et al., JOC, 1976, 41, 1585 (pmr, config) [https://doi.org/10.1021/jo00871a022]
  15. Enzell, C.R. et al., Fortschr. Chem. Org. Naturst., 1977, 34, 44 (rev)
  16. Wigle, I.D. et al., Chem. Comm., 1982, 662 (biosynth) [https://doi.org/10.1039/c39820000662]
  17. Banerjee, A. et al., Life Sci. Adv., 1982, 1, 327 (rev, pharmacol)
  18. Schievelbein, H., Pharmacol. Ther., 1982, 18, 233 (rev, metab) [https://doi.org/10.1016/0163-7258(82)90068-7]
  19. Aceto, M.D. et al., CRC Handb. Stereoisomers: Drugs Psychopharmacol., 1984, 67 (rev)
  20. Seeman, J.I., Heterocycles, 1984, 22, 165 (rev) [https://doi.org/10.3987/R-1984-01-0165]
  21. Slaven, R.W., J. Het. Chem., 1984, 21, 1329 (cmr, pmr)
  22. Domino, E.F., Psychopharmacol. Bull., 1986, 22, 870 (rev, pharmacol)
  23. Brunner, H. et al., Arch. Pharm. (Weinheim, Ger.), 1988, 321, 73 (synth, ir, pmr)
  24. Mahboobi, S. et al., Arch. Pharm. (Weinheim, Ger.), 1988, 321, 175 (synth, ir, pmr)
  25. Kyerematen, G.A. et al., Drug Metab. Dispos., 1988, 16, 125 (pharmacol)
  26. Pesticide Manual, 9th edn., 1991, 8900
  27. Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A298
  28. Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1393
  29. Levin, E.D. et al., Med. Chem. Res., 1993, 2, 509, 522 (revs, pharmacol)
  30. Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion, (Gorrod, J.W., ed.), Chapman and Hall, 1993 (book)
  31. Schmidt, B. et al., Synthesis, 1998, 42- 44 (S-N-oxide) [https://doi.org/10.1055/s-1998-1997]
  32. Djuric, V.J. et al., Physiol. Behav., 1999, 67, 533- 537 (pharmacol) [https://doi.org/10.1016/S0031-9384(99)00091-8]
  33. Girard, S. et al., Tet. Lett., 2000, 41, 9245- 9249 (R-form, synth) [https://doi.org/10.1016/S0040-4039(00)01675-0]
  34. Felpin, F.-X. et al., JOC, 2001, 66, 6305- 6312 (synth) [https://doi.org/10.1021/jo010386b]
  35. Welter, C. et al., Org. Biomol. Chem., 2005, 3, 3266- 3268 (synth) [https://doi.org/10.1039/b508634e]
  36. Wagner, F.F. et al., Tetrahedron, 2007, 63, 8065- 8082 (rev, synth) [https://doi.org/10.1016/j.tet.2007.04.100]
  37. Clayton, P.M. et al., Chirality, 2013, 25, 288- 293 (ecd, uv)
  38. Apsunde, T.D. et al., Synthesis, 2013, 45, 2120- 2124 (synth, ir, pmr, cmr)
  39. Guo, C. et al., JACS, 2015, 137, 90- 93 (S-form, synth, pmr, cmr) [https://doi.org/10.1021/ja511422q]
  40. Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NDN000, NDR000, NDS500, NDR500
  41. Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 1537D (ir)
  42. Aldrich Library of 13C and 1H FT-NMR Spectra, 1992, 3, 295A (nmr)
  43. Orechoff, A. et al., Ber., 1931, 64, 266- 274; 1932, 65, 232 - 234 (isol)
  44. Späth, E. et al., Ber., 1937, 70, 70- 72 (resoln)
  45. Otroshchenko, O.S., J. Gen. Chem. USSR (Engl. Transl.), 1954, 24, 1847- 1849 (N-Ac,synth)
  46. Linnell, R.H., JACS, 1954, 76, 1391- 1393 (uv) [https://doi.org/10.1021/ja01634a077]
  47. Buchel, K.H., Chem. Ber., 1962, 95, 2438- 2443 ((±)-N-Me, synth)
  48. Lukeš, R. et al., Coll. Czech. Chem. Comm., 1962, 27, 751- 756 (config)
  49. Talipov, S.T., J. Anal. Chem. USSR (Engl. Transl.), 1963, 18, 161- 164 (N-Ac, use)
  50. Duffield, A.M. et al., JACS, 1965, 87, 2926- 2932 (ms) [https://doi.org/10.1021/ja01091a024]
  51. Zharekeev, V.Kh. et al., Chem. Nat. Compd. (Engl. Transl.), 1971, 7, 524 (R-form, isol) [https://doi.org/10.1007/BF00564776]
  52. Aslanov, Kh.A. et al., Chem. Nat. Compd. (Engl. Transl.), 1972, 8, 319- 321 (isol, manuf) [https://doi.org/10.1007/BF00563739]
  53. Testa, B. et al., Mol. Pharmacol., 1973, 9, 10- 16 (cd)
  54. Fitch, W.L. et al., JOC, 1974, 39, 2974- 2979 (S-form, S-N-Me, isol) [https://doi.org/10.1021/jo00934a008]
  55. Leete, E., Chem. Comm., 1975, 9- 10 (biosynth) [https://doi.org/10.1039/c39750000009]
  56. Nehme, M. et al., An. Quim., 1977, 73, 307- 308 (Tetrahydroanabasine)
  57. Alberici, G.F. et al., Tet. Lett., 1983, 24, 1937- 1940 (synth, (±)-N-Me) [https://doi.org/10.1016/S0040-4039(00)81810-9]
  58. Strunz, G.M. et al., Alkaloids (Academic Press), 1985, 26, 89- 183 (rev)
  59. Walton, N.J. et al., Plant Cell Rep., 1988, 7, 115- 118 (biosynth) [https://doi.org/10.1007/BF00270118]
  60. Pfrengle, W. et al., JOC, 1989, 54, 4261- 4263 (S-form, synth) [https://doi.org/10.1021/jo00279a001]
  61. Pesticide Manual, 9th edn., 1991, No. 380 (Anabasine)
  62. Hattori, K. et al., Tetrahedron, 1993, 49, 1749- 1760 (S-form, synth) [https://doi.org/10.1016/S0040-4020(01)80532-9]
  63. Plaquevent, J.C. et al., Bull. Soc. Chim. Fr., 1996, 133, 369- 380 ((±)-N-Me, synth, pmr, cmr)
  64. Wanner, M.J. et al., JOC, 1996, 61, 5581- 5586 (Tetrahydroanabasine, biosynth, bibl) [https://doi.org/10.1021/jo9602130]
  65. Wanner, M.J. et al., Pure Appl. Chem., 1996, 68, 2051- 2056 (Tetrahydroanabasine) [https://doi.org/10.1351/pac199668112051]
  66. Deo, N.M. et al., Tet. Lett., 1996, 37, 1137- 1140 (synth) [https://doi.org/10.1016/0040-4039(96)00002-0]
  67. Yang, C.-M. et al., Can. J. Chem., 1997, 75, 616- 620 (synth, ir, pmr, cmr, ms) [https://doi.org/10.1139/v97-073]
  68. US Pat., 1998, 5 741 802, ( Univ. Florida) (S-N-Me, synth, pmr, activity)
  69. Leclerq, S. et al., J. Chem. Ecol., 2001, 27, 945- 952 (isol, abs config) [https://doi.org/10.1023/A:1010335003297]
  70. Felpin, F.-X. et al., JOC, 2001, 66, 6305- 6312 (S-form, S-N-Me, synth, pmr, cmr) [https://doi.org/10.1021/jo010386b]
  71. Bartholomeusz, T.A. et al., J. Photochem., 2005, 66, 1890- 1897 (R-form, S-form, N-Me,metab) [https://doi.org/10.1016/j.phytochem.2005.07.012]
  72. Castro, A. et al., Heterocycles, 2007, 71, 2699- 2708 (synth) [https://doi.org/10.3987/COM-07-11171]
  73. Hong, S.P. et al., Nihon Shinzobyo Gakkai, 2007, 50, 351- 362 (activity)
  74. Spangenberg, T. et al., Org. Lett., 2009, 11, 261- 264 (S-form, synth, ir, pmr, cmr) [https://doi.org/10.1021/ol802314g]
  75. Giera, D.S. et al., Synthesis, 2009, 3797- 3802 (S-form, synth)
  76. Yang, Y. et al., Tet. Lett., 2011, 52, 1549- 1552 (synth) [https://doi.org/10.1016/j.tetlet.2011.01.090]
  77. Saloranta, T. et al., Tet. Lett., 2011, 52, 4619- 4621 (synth, pmr, cmr) [https://doi.org/10.1016/j.tetlet.2011.06.093]
  78. Guo, C. et al., JACS, 2015, 137, 90- 93 (S-form, synth, pmr, cmr) [https://doi.org/10.1021/ja511422q]
  79. Sax's Dangerous Properties of Industrial Materials, 10th edn., J. Wiley, 2000, AON875
  80. Späth, E. et al., Ber., 1935, 68, 1388- 1393, 1667-1670 (isol)
  81. Swain, M.L. et al., JACS, 1949, 71, 1342- 1345 (uv)
  82. Erdtman, H. et al., Acta Chem. Scand., 1963, 17, 1717- 1726 (synth) [https://doi.org/10.3891/acta.chem.scand.17-1717]
  83. Duffield, A.M. et al., JACS, 1965, 87, 2926- 2932 (ms) [https://doi.org/10.1021/ja01091a024]
  84. Leete, E. et al., JOC, 1972, 37, 4465- 4466 (synth) [https://doi.org/10.1021/jo00799a038]
  85. Bolt, A.J.N., Phytochemistry, 1972, 11, 2341- 2343 (N-Hexanoylnornicotine, N-Octanoylnornicotine, isol) [https://doi.org/10.1016/S0031-9422(00)88406-X]
  86. Warfield, A.H. et al., Phytochemistry, 1972, 11, 3371- 3378 (N-Acetylnornicotine, N-Formylnornicotine, synth) [https://doi.org/10.1016/S0031-9422(00)86411-0]
  87. Seeman, J.I., Synthesis, 1977, 498- 500 (synth, nmr, ms) [https://doi.org/10.1055/s-1977-24463]
  88. Hecht, S.S. et al., JOC, 1978, 43, 72- 76 (N'-nitroso, synth, bibl) [https://doi.org/10.1021/jo00395a017]
  89. Nakane, M. et al., JOC, 1978, 43, 3922- 3931 (synth) [https://doi.org/10.1021/jo00414a027]
  90. Heck, R.F., Acc. Chem. Res., 1979, 12, 146- 151 (synth) [https://doi.org/10.1021/ar50136a006]
  91. Miyano, M. et al., Agric. Biol. Chem., 1979, 43, 2205- 2206 (N-Isopropylnornicotine)
  92. Siddiqui, I.R. et al., Carbohydr. Res., 1981, 98, 57- 63 (fructosyl) [https://doi.org/10.1016/S0008-6215(00)87141-4]
  93. Leete, E., Phytochemistry, 1981, 20, 1037- 1040 (N-Isopropylnornicotine) [https://doi.org/10.1016/0031-9422(81)83023-3]
  94. Jacob, P., JOC, 1982, 47, 4165- 4167 (synth, resoln) [https://doi.org/10.1021/jo00142a032]
  95. Castonguay, A. et al., Methods Enzymol., 1982, 84, 641- 650 (N'-nitroso, rev) [https://doi.org/10.1016/0076-6879(82)84051-2]
  96. Luanratana, O. et al., Phytochemistry, 1982, 21, 449- 452 (N-Acetylnornicotine, N-Formylnornicotine) [https://doi.org/10.1016/S0031-9422(00)95286-5]
  97. Langhals, E. et al., Annalen, 1983, 330- 333 (synth)
  98. Seeman, J.I. et al., JOC, 1985, 50, 5419- 5421 (synth) [https://doi.org/10.1021/jo00225a094]
  99. Zador, E. et al., Plant Physiol., 1986, 82, 479- 484 (N-(3-Hydroxy-12-methyltridecanoyl), isol,biosynth) [https://doi.org/10.1104/pp.82.2.479]
  100. Severson, R.F. et al., ACS Symp. Ser., 1988, 380, 335- 362 (Nicotiana repanda constits,activity)
  101. Mahboobi, S. et al., Arch. Pharm. (Weinheim, Ger.), 1988, 321, 175- 177 (synth)
  102. Kuno, H. et al., Agric. Biol. Chem., 1989, 53, 535- 536 (N-(3-Hydroxy-12-methyltridecanoyl),synth)
  103. Braumann, T. et al., Phytochemistry, 1990, 29, 3693- 3694 (N-Ethylnornicotine) [https://doi.org/10.1016/0031-9422(90)85311-3]
  104. Pesticide Manual, 9th edn., 1991, No. 9050
  105. Aislaitner, G. et al., Med. Sci. Res., 1992, 20, 897- 899 ((-)-(S)-form, metab)
  106. Deo, N.M. et al., Tet. Lett., 1996, 37, 1137- 1140 (synth) [https://doi.org/10.1016/0040-4039(96)00002-0]
  107. Girard, S. et al., Tet. Lett., 2000, 41, 9245- 9250 (R-form, synth) [https://doi.org/10.1016/S0040-4039(00)01675-0]
  108. Isomura, S. et al., JOC, 2001, 66, 4115- 4121 (R-form, S-form, synth, pmr, cmr) [https://doi.org/10.1021/jo001442w]
  109. Felpin, F.-X. et al., JOC, 2001, 66, 6305- 6312 (S-form, synth) [https://doi.org/10.1021/jo010386b]
  110. Prokopczyk, B. et al., Chem. Res. Toxicol., 2002, 15, 677- 685 (N'-nitroso, toxicol) [https://doi.org/10.1021/tx0101088]
  111. Baxendale, I.R. et al., JCS Perkin 1, 2002, 143- 154 (synth)
  112. Moir, D. et al., Chem. Res. Toxicol., 2008, 21, 494- 502 (N'-nitroso, toxicol) [https://doi.org/10.1021/tx700275p]
  113. Huang, K. et al., JOC, 2008, 73, 4017- 4026 (N-Et, synth) [https://doi.org/10.1021/jo800204n]
  114. Spangenberg, T. et al., Org. Lett., 2009, 11, 261- 264 (N-formyl, synth) [https://doi.org/10.1021/ol802314g]
  115. Mitch, C.H. et al., J. Med. Chem., 2011, 54, 8000- 8012 ((±)-form, resoln) [https://doi.org/10.1021/jm200789r]
  116. Clayton, P.M. et al., Chirality, 2013, 25, 288- 293 (ecd, uv)
  117. Qian, X. et al., Org. Lett., 2014, 16, 5228- 5231 ((S)-form, synth) [https://doi.org/10.1021/ol502693r]
  118. IARC Monogr. (Web), http://monographs.iarc.fr/
  119. Sax's Dangerous Properties of Industrial Materials, 11th edn., J. Wiley, 2004, NNR500, NNS500
  120. Späth, E. et al., Ber., 1937, 70, 2450 (Nicotyrine)
  121. Swain, M.L. et al., JACS, 1949, 71, 1341 (Nicotyrine) [https://doi.org/10.1021/ja01172a057]
  122. Ryang, H. et al., Chem. Comm., 1972, 594- 595 (synth) [https://doi.org/10.1039/c39720000594]
  123. Shibagaki, M. et al., Agric. Biol. Chem., 1988, 52, 2651 (synth)
  124. Mullen, G.B. et al., JOC, 1989, 54, 2476 (synth, ir, pmr, bibl) [https://doi.org/10.1021/jo00271a052]
  125. Savoia, D. et al., JOC, 1991, 56, 1822 (synth, ir, pmr, ms) [https://doi.org/10.1021/jo00005a030]
  126. Noland, W.E. et al., Acta Cryst. C, 2003, 59, o263- o267 (cryst struct)
  127. Wei, X. et al., Synth. Commun., 2003, 33, 3305- 3315 (Nicotyrine, synth)
  128. Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NDX300, PQB500
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