The Plant Cell Culture Library

Nicotiana suaveolens
Cell Line ID NS-05192
Media Type B88
Lowest Tolerable USDA Zone 8a
Drought Tolerance Averag
Availability Medium
Order Solanales
Family Solanaceae
Genus Nicotiana
Antifungal Genus Level ➡ 59 citations
Anthelmintic Genus Level ➡ 2 citations
Insecticidal Genus Level ➡ 128 citations
Anticancer Genus Level ➡ 1 citations
Common Names Australian tobacco
Plant Habit Herb Annual
Plant Habitat Warm Temperate
Culture Start Material Shoot
Native Range Southeast Australia
Plant Supplier Botanical Garden Chelsea Physic Garden
Antifungal Citations
  1. Gu, Q. et al., Mol. Gen. Genet., 1992, 234, 89- 96 (FST)
  2. Burden, R.S. et al., Phytochemistry, 1975, 14, 221- 223 (Nicotiana glutinosa constit) [https://doi.org/10.1016/0031-9422(75)85043-6]
  3. Murai, A. et al., Bull. Chem. Soc. Jpn., 1980, 53, 1045- 1048 (ir, ms, pmr, cmr, abs config,synth, uv) [https://doi.org/10.1246/bcsj.53.1045]
  4. Kawase, Y. et al., Bull. Chem. Soc. Jpn., 1980, 53, 1049- 1056 (synth) [https://doi.org/10.1246/bcsj.53.1057]
  5. Fuchs, A. et al., Phytochemistry, 1983, 22, 1197- 1199 (Nicotiana glutinosa constit) [https://doi.org/10.1016/0031-9422(83)80221-0]
  6. Banerjee, A.K., J. Sci. Ind. Res., 1996, 55, 915- 930 (synth)
  7. Banerjee, A.K. et al., Stud. Nat. Prod. Chem., 2006, 33, 193- 237 (synth, activity, rev) [https://doi.org/10.1016/S1572-5995(06)80028-1]
  8. Aldrich Library of 13C and 1H FT-NMR Spectra, 1992, 1, 263A (nmr)
  9. Ruzicka, L. et al., Helv. Chim. Acta, 1942, 25, 621- 630 (Sclareol, struct, bibl)
  10. Bigley, D.B. et al., JCS, 1960, 4613- 4627 (synth, stereochem)
  11. Almqvist, S. et al., Acta Chem. Scand., Ser. B, 1975, 29, 695- 702 (cmr)
  12. Bohlmann, F. et al., Phytochemistry, 1980, 19, 71- 74 (Gnaphalium undulatum constit) [https://doi.org/10.1016/0031-9422(80)85015-1]
  13. Uchio, Y. et al., Tet. Lett., 1980, 21, 3775- 3778 (Aster spathuliflorus fucosides) [https://doi.org/10.1016/0040-4039(80)80175-4]
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  15. Stierle, D.B. et al., Phytochemistry, 1988, 27, 517 (13-Episclareol) [https://doi.org/10.1016/0031-9422(88)83132-7]
  16. Banthorpe, D.V. et al., Phytochemistry, 1990, 29, 2145 (biosynth, bibl) [https://doi.org/10.1016/0031-9422(90)83025-V]
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  18. Martres, P. et al., Tet. Lett., 1993, 34, 629 (synth) [https://doi.org/10.1016/S0040-4039(00)61637-4]
  19. Barrero, A.F. et al., Tetrahedron, 1993, 49, 10405 (synth) [https://doi.org/10.1016/S0040-4020(01)80567-6]
  20. Torrenegra, R. et al., Phytochemistry, 1994, 35, 195 (ent-Sclareol) [https://doi.org/10.1016/S0031-9422(00)90533-8]
  21. Ulubelen, A. et al., Phytochemistry, 1994, 36, 971 (Sclareol, pmr, cmr) [https://doi.org/10.1016/S0031-9422(00)90474-6]
  22. Chinou, L. et al., Planta Med., 1994, 60, 34- 36 (13-Episclareol, isol, activity) [https://doi.org/10.1055/s-2006-959403]
  23. Nagashima, F. et al., Phytochemistry, 1997, 45, 353 (13-Episclareol, cmr, cryst struct) [https://doi.org/10.1016/S0031-9422(96)00821-7]
  24. Topçu, G. et al., Phytochemistry, 1999, 50, 1195- 1199 (Sclareol, activity) [https://doi.org/10.1016/S0031-9422(98)00675-X]
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  27. Jassbi, A.R. et al., Z. Naturforsch., C, 2002, 57, 1016- 1021 (14,15-Epoxysclareol) [https://doi.org/10.1515/znc-2002-11-1211]
  28. Lee, S.O. et al., J. Nat. Prod., 2005, 68, 1471- 1474 (fucoside) [https://doi.org/10.1021/np058044e]
  29. Arture Silva-Filho, F. et al., J. Braz. Chem. Soc., 2007, 7, 1374- 1378 (Egletes viscosa constit)
  30. Socolsky, C. et al., J. Nat. Prod., 2007, 70, 1837- 1845 (Gleichenia quadripartita glucoside) [https://doi.org/10.1021/np070119m]
  31. Ono, M. et al., Chem. Pharm. Bull., 2008, 56, 1621- 1624 (Viteagnusin C) [https://doi.org/10.1248/cpb.56.1621]
  32. Schalk, M. et al., JACS, 2012, 134, 18900- 18903 (biosynth) [https://doi.org/10.1021/ja307404u]
  33. Kulkarni, R.R. et al., J. Nat. Prod., 2013, 76, 1836- 1841 (Leucas stelligera constit) [https://doi.org/10.1021/np400002p]
  34. The Good Scents Company, http://www.thegoodscentscompany.com/search.html (Sclareol,use)
  35. Bukhari, S.T.K. et al., JCS(C), 1969, 1073- 1079 (Rishitin, stereochem)
  36. Ishizaka, N. et al., Plant Cell Physiol., 1969, 10, 183- 192 (activity)
  37. Masamune, AT. et al., Bull. Chem. Soc. Jpn., 1977, 50, 1201- 1205, 1206 - 1216 (Rishitin,isol, struct, synth) [https://doi.org/10.1246/bcsj.50.1201]
  38. Stoessl, A. et al., Can. J. Chem., 1983, 61, 1766- 1770 (biosynth) [https://doi.org/10.1139/v83-302]
  39. Kodama, H. et al., Phytochemistry, 1984, 23, 690- 692 (sophoroside) [https://doi.org/10.1016/S0031-9422(00)80412-4]
  40. Kodama, H. et al., Agric. Biol. Chem., 1985, 49, 1527- 1528 (sophoroside, activity)
  41. Kodama, H. et al., Agric. Biol. Chem., 1985, 49, 2537- 2541 (rhamnosylglucosylglucoside)
  42. Brindle, P.A. et al., Phytochemistry, 1985, 24, 1219- 1222 (biosynth) [https://doi.org/10.1016/S0031-9422(00)81105-X]
  43. Alphey, T.J.W. et al., Rev. Nematol., 1988, 11, 399- 404 (activity)
  44. Banerjee, A.K. et al., Tetrahedron, 1993, 49, 4761- 4788 (synth, rev) [https://doi.org/10.1016/S0040-4020(01)80397-5]
  45. Chen, J. et al., Tet. Lett., 1997, 38, 1889- 1892 (synth) [https://doi.org/10.1016/S0040-4039(97)00228-1]
  46. Engstrom, K. et al., Potato Res., 1999, 42, 43- 50 (activity)
  47. Coxon, D.T. et al., Tet. Lett., 1974, 15, 2921- 2924 (Solavetivone) [https://doi.org/10.1016/S0040-4039(01)91781-2]
  48. Anderson, R.C. et al., Chem. Comm., 1977, 27- 28 (tobacco constit, abs config) [https://doi.org/10.1039/c39770000027]
  49. Yamada, K. et al., Chem. Comm., 1977, 554- 555 (synth, stereochem) [https://doi.org/10.1039/C39770000554]
  50. Stoessl, A. et al., Can. J. Chem., 1978, 56, 645- 653 (biosynth) [https://doi.org/10.1139/v78-106]
  51. Fujimori, T. et al., Phytochemistry, 1979, 18, 2032 (Solavetivone, tobacco constit) [https://doi.org/10.1016/S0031-9422(00)82732-6]
  52. Murai, A. et al., Bull. Chem. Soc. Jpn., 1984, 57, 2276- 2281 (synth) [https://doi.org/10.1246/bcsj.57.2276]
  53. Murai, A. et al., Bull. Chem. Soc. Jpn., 1984, 57, 2282- 2285 (synth) [https://doi.org/10.1246/bcsj.57.2282]
  54. Murai, A. et al., Chem. Lett., 1986, 771- 772 (Oxysolavetivone) [https://doi.org/10.1246/cl.1986.771]
  55. Iwata, C. et al., Chem. Pharm. Bull., 1987, 35, 544- 552 (synth) [https://doi.org/10.1248/cpb.35.544]
  56. Hwu, J.R. et al., JOC, 1992, 57, 922- 928 (synth, abs config, bibl) [https://doi.org/10.1021/jo00029a025]
  57. Takemoto, Y. et al., Tetrahedron, 1997, 53, 603- 616 (synth) [https://doi.org/10.1016/S0040-4020(96)01006-X]
  58. Engstrom, K. et al., Potato Res., 1999, 42, 43- 50 (Solavetivone, activity)
  59. Fu, J.-J. et al., Chem. Pharm. Bull., 2010, 58, 1263- 1266 (Argutosin D)
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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.
[top⬆]
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]
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  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]
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  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]
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  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]
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  105. Aislaitner, G. et al., Med. Sci. Res., 1992, 20, 897- 899 ((-)-(S)-form, metab)
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Anticancer Citations
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Inquiries regarding the purchase of Plant cell lines or other PCCL services can be directed to Michael Daley mpdaley@umass.edu

Acknowledgements

The establishment of the PCCL has been sponsored by National Science Foundation (NSF/DBI-156 1572), United States Department of Agriculture Massachusetts Experiment Station Award (MAS00496), the Science and Technology fund from the President's office of the University of Massachusetts, and the 2016 UMass Amherst Armstrong Fund for Science.

National Science FoundationCenter for Agriculture, Food and the Environment

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