Abstract
Secondary metabolites contribute to plant fitness by interacting with the ecosystems, and thus play a major role in the survival of the plant in its environment. Besides the importance for the plant itself, several secondary metabolites are commercially available as fine chemicals, such as drugs, dyes, flavors, fragrances, and insecticides. Due to their extensive biological activities, plant secondary metabolites have been used for centuries in traditional medicine. Alkaloids are an important group of secondary metabolites, of which colchicine is a useful agent in the treatment of acute attacks of gout. Apart from inhibiting the assembly of microtubules, the major biological effects of colchicine include leukocyte diapedesis, lysosomal degranulation, and inhibition of proliferation of fibroblasts as well as collagen transport to the extracellular space. In this way it relieves the pain associated with acute gout, decreases interleukin-l production in patients with primary biliary cirrhosis, and is used in the prevention or treatment of amyloidosis, scleroderma, and chronic cutaneous leukocytoclastic vasculitis. Colchicine prevents recurrences of acute pericarditis in adults and children. Colchicine is sold under different brand/trade names in different countries as a medicine for gout. The increased demand for colchicine has stimulated great interest in known plant sources of colchicine, new sources, and the route by which the alkaloid could be synthesized. Colchicine and related compounds have been found in several genera such as Colchicum, Merendera, Androcymbium, Gloriosa, and Littonia. Plant secondary products are vulnerable to fluctuations in value, depending on the effects of climate, pests, and diseases on the producing crops, or political changes in the producing countries. This has raised interest in developing biotechnological processes for the industrial production of such fine chemicals. However, very few reports are available on biotechnological approaches toward the biological production of such an important alkaloid. The evolving commercial importance of colchicine in recent years is sure to pave ways to extensive study by plant biotechnologists leading to exciting opportunities to engineer colchicine metabolism in plants.
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References
Pichersky E, Gang D R (2000) Trends Plant Sci 5:439–445
De Luca V, St-Pierre B (2000) Trends Plant Sci 5:168–173
Kossel A (1891) Arch Physiol 181–186
Czapek F (1921) Spezielle Biochemie, Biochemie der Pflanzen, vol. 3, G. Fischer, Jena, p 369
Bourgaud F, Gravot A, Milesi S, Gontier E (2001) Plant Sci 161:839–851
Harborne JB (ed) (1978) Biochemical Aspects of Plant and Animal Coevolution: Proceedings of the Phytochemical Society of Europe, Vol 15. Academic Press, London
Li J, Ou-Lee TM, Raba R, Amundson RG, Last RL (1993) Plant Cell 5:171–179
Torssell KBG (1997) Chemical ecology. In: Torssell KBG (e.d) Natural Product Chemistry, A Mechanistic Biosynthetic and Ecological Approach. Swedish Pharmaceutical Press, Stockholm, pp 42–79
Harborne JB (1999) Classes and functions of secondary products. In: Walton NJ, Brown DE (eds) Chemicals from Plant, Perspectives on Secondary Plant Products. Imperial College Press, London, pp 1–25
Verpoorte R, van der Heijden R, Memelink J (2000) Transgenic Res 9:323–343
Verpoorte R (2000) J Pharm Pharmacol 52:253–262
Verpoorte R, van der Heijden R and Memelink J (1998) Plant biotechnology and the production of alkaloids. Prospects of metabolic engineering. In: GA Cordell (ed) The Alkaloids, Vol. 50. Academic Press, San Diego, pp 453–508
Verpoorte R, van der Heijden R, ten hoopen HJG, Memelink J (1999) Biotech Lett 21:467–479
Facchini PJ (2001) Annu Rev Plant Physiol Plant Mol Biol 52:29–66
Wink M (1999) Plant secondary metabolites: biochemistry, function and biotechnology. In: Wink M (ed) Biochemistry of Plant Secondary Metabolism (Annual Plant Reviews), Vol. 2. Sheffield Academic Press, Sheffield, pp 1–16
Rueffer M, Zenk MH (1998) FEBS Lett 438:111–113
Budavari S (ed) (1989) The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals. Merck, Rahway, NJ, pp 386–387
Reynolds JEF (ed) (1993) Martindale, the Extra Pharmacopoeia, 30th edn. The Pharmaceutical Pres, London, pp 335–337
Chapman OL, Smith HG (1961) J Am Chem Soc 83:3914–3916
Chapman OL, Smith HG, King RW (1963) J Am Chem Soc 85:803–812
Loudon JD, Speakman JC (1950) Research 3:583–584
Murray SS, Kramlinger KG, McMichan JC (1983) Mayo Clin Proc 58:528–532
Stern N, Kupferschmidt H, Meier-Abt PJ (1997) Schweiz Rundsch Med Prax 86:952–956
Davies HO, Hyland RH, Morgan CD (1988) Can Med Assoc J 138:335–336
Caplan YH, Orloff KG, Thompson BC (1980) J Anal Toxicol 4:153–155
Jäger AK, Schottländer B, Smitt UW, Nyman U (1993) Plant Cell Rep 12:517–520
Stapczynski JS, Rothstin RJ, Gaye WA (1981) Ann Emerg Med 10:364
Watt JM, Breyer-Brandwijk MG (1962) The Medicinal and Poisonous Plants of Southern and Eastern Africa. Edinburgh and Livingstone, London
Medical Economics (1995) Physician’s Desk Reference. Medical Economics Data Production, Montvale, NJ
Darwin C (1875) Insectivorous Plants. John Murray, London
Eigsti OJ, Dustin P Jr (1955) Colchicine in Agriculture, Medicine, Biology and Chemistry. Iowa State College Press, Ames, Iowa
Pernice B (1889) Silicia Med 265–279
Cook J, Loudon J (1951) Colchicine. In: Holmes and Mankse (ed) Alkaloids. Academic Press, New York, pp 261–325
Ludford RJ (1936) Arch Exp Zelforsch Mikr Anat 18:411–441
Famaey JP (1988) Clin Exp Rheumatol 6:305–317
Insel PA (1996) Analgesic-antipyretic and anti inflammatory agents and drugs employed in the treatment of gout: colchicine. In: Goodman LS, Limbird LE, Milinoff PB, Ruddon RW, Goodman Gilman A (eds) Goodman and Gilman’s: The Pharmacological Basis of Therapeutics, 9th edn. Mc Graw-Hill, pp 614–658
Schiffmann E (1982) Annu Rev Physiol 44:553–568
Greenberg MS (2000) Drugs used for connective-tissue disorders and oral mucosal diseases. In: Ciancio SG (ed) ADA Guide to Dental Therapeutics. ADA Publishing, Chicago, pp 438–453
Kovacs P, Csaba G (2006) Cell Biochem Funct 24:419–429
Sullivan TP, King LE, Boyd AS (1998) J Am Acad Dermatol 39:993–999
Yu YS, Youn DH (1987) Korean J Ophthalmol 1:59–71
Chang DM, Baptiste P, Schur PH (1990) J Rheumatol 17:1148–1157
O’Brien JM Jr, Wewers MD, Moore SA, Allen JN (1995) J Immunol 154:4113–4122
Zemer D, Livneh A, Langevitz P (1992) Ann Intern Med 116:426
Rosenbaum M, Rosner I (1995) Clin Exp Rheumatol 13:126
Callen JP (1985) J Am Acad Dermatol 13:193–200
Rodriguez de la Serna A, Guindo Soldevila J, Marti Claramunt V, Bayes de Luna A (1987) Lancet 26:1517
Spodick DH (1991) Circulation 83:1830–1831
Millaire A, de Groote P, Decoulx E, Goullard L, Ducloux G (1994) Eur Heart J 15:120–124
Brucato A, Cimaz R, Balla E (2000) Pediatr Cardiol 21:395–396
Voet D, Voet JG (1990) Biochemistry. John Wiley and Sons, New York, pp 758–762
Katzung BG (ed) (1995) Basic and Clinical Pharmacology. Apleton and Lange, Norwalk, pp 536–559
Laster L, Seegmiller TE, Stetten D, Liddle LV (1957) J Clin Invest 36:908
Seegmiller JE, Howell RR, Malawista SE (1962) J Clin Invest 41:1399
Singer CJ (1996) A Short History of Scientific Ideas. Barnes and Noble Books, New York
Buskila D, Zaks N, Neumann L, Livneh A, Greenberg S, Pras M, Langevitz P (1997) Clin Exp Rheumatol 15:355–360
Gökel Y, Canataro˘glu A, Satar S, Köseo˘glu Z (2000) Turk J Med Sci 30:401–403
Levy M, Spino M, Read S (1991) Pharmacotherapy 11:196–211
Guttadauria M, Diamond H, Kaplan D (1977) J Rheumatol 4:272–276
Wallace SL (1980) Colchicine. In: Kelley WN, Harris ED, Ruddy S, Sledge CB (eds) Textbook of Rheumatology. Saunders, Philadelphia, pp 878–884
Folpini A, Furfori P (1995) J Toxicol Clin Toxicol 33:71–77
Ruah CB, Stram JR, Chasin WD (1988) Arch Otolaryngol Head Neck Surg 114:671–675
Katz J, Langevitz P, Shemer J (1994) J Am Acad Dermatol 31:459–461
Andreu JM, Perez-Ramirez B, Gorbunoff MJ, Ayala D, Timasheff SN (1998) Biochemistry 37:8356 – 8368
Berg U, Bladh H, Mpampos K (2004) Org Biomol Chem 2:2125–2130
Barnabás B, Pfahler PL, Kovács G (1991) Theor Appl Genet 81:675–678
Mathias R, Röbbelen G (1991) Plant Breed 106:82–84
Alemanno L, Guiderdoni E (1994) Plant Cell Rep 13:432–436
Barcelo P, Cabrera A, Hagle C, Lörz H (1994) Theor Appl Genet 87:741–745
Saisingtong S, Schmid JE, Stamp P, Büter B (1996) Theor Appl Genet 92:1017–1023
Fühner H, Rehbein M (1915) Arch Exp Path Pharmak 79:1–18
Rossbach MJ (1876) Arch Ges Physiol 12:308–325
Carr GD, King RM, Powell AM, Robinson H (1999) Am J Bot 86:1003–1013
Hill RN, Spragg RG, Wedel MK, Moser KM (1975) Ann Intern Med 83:523–524
Hobson CH, Rankin AP (1986) Anaesth Intens Care 14:453–455
Kontos HA (1962) N Engl J Med 266:238
Mouren P, Tatossian A, Poiso Y, Giudicelli S, Jouglard J, Dufour H, Poyen D (1969) Presse Med 77:14:505–508
Favarel-Garrigues JC, Bony D, Poisot D (1975) Concours Med 97:5183–5197
Bismuth C, Gaultier M, Conso F (1977) Nouv Presse Med 6:1625–1629
Kuncl RW (1987) N Engl J Med 316:1562–1568
Boruchow IB (1966) Cancer 19:541–543
Heaney D, Derghazarian CB, Pineo GF (1976) Am J Med Sci 271:233–238
Rangam CM, Bhagwat RR (1960) Indian J Med Res 48:549–557
Wang D, Greenbaum AL, Harkness RD (1963) Biochem J 86:62–64
Ben-Chetrit E, Levy M (1998) Semin Arthritis Rheum 28:48–59
The Drug Monitor (2007) Ed:Nasir Anaizi, http://www.thedrugmonitor.com/colchicines
Webb DI (1968) N Engl J Med 279:845–850
Pelletier PS, Caventou J (1820) J Ann Chim Phy 14:69–83
Zeisel S (1888) Monatsch Chem 9:1–30
Houde A (1884) C R Acad Sci Paris 98:1442
Séris L (1947) La Rev Sci Fas 88:489–493
Corrodi H, Hardegger E (1955) Helv Chem Acta 38:2030–2033
Oberlin ML (1857) Ann Chim Phys 50:108–114
Windaus A (1924) Ann Chem 439:59–75
Cohen A, Cook JW, Roe EMF (1940) J Chem Soc 1940:194–197
Tarbell DS, Frank HR, Fanta PE (1946) J Am Chem Soc 68:502–506
Rapport H, Williams AR, Cisney M (1951) J Am Chem Soc 73:1414–1421
Cook JW, Jacj J, Loudon JD, Buchanan GL, MacMillan J (1951) J Chem Soc 1951:1397–1403
Koo J (1953) J Am Chem Soc 75:720–723
Dewar MJS (1945) Nature 155:50–51, 141–142, 479
Doering W von E, Knox LH (1951) J Am Chem Soc 73:828–838
Rapport H, Williams AR (1951) J Am Chem Soc 76:1896–1897
Rapport H, Williams AR, Campion JE, Pack D (1954) J Am Chem Soc 76:3693–3698
Walasek EJ, Kelesey FE, Geiling EMK (1952) Science 116:225–227
Battersby AR, Reynolds JJ (1960) Proc Chem Soc 1960:346–347
Leete E, Nemeth PE (1961) J Am Chem Soc 83:2192–2194
Battersby AR (1965) Angew Chem 4:79–80
Battersby AR, Binks R, Yeowell DA (1964) Proc Chem Soc 1964:86
Battersby AR, Binks R, Reynolds JJ, Yeowell DA (1964) J Chem Soc 1964:4257–4268
Battersby AR, Herbert RB (1964) Proc Chem Soc 1964:260
Leete E (1963) J Am Chem Soc 85:3666–3669
Leete E, Nemeth PE (1960) J Am Chem Soc 82:6055–6057
Hill RD, Unrau AM (1965) Can J Chem 43:709–711
Leete E (1965) Tetrahedron Lett 1965:333–336
Kuhn R (1993) Molekulare Asymmetrie. In: Fredenberg K (ed) Stereochemie. Franz Deutike, Leipzig-Wien pp 803
Eliel EL, Wilen SH (1994) Stereochemistry of Organic Compounds. John Wiley and Sons, New York, pp 1119–1122
Wildman WC (1959) Colchicine and related compounds. In: Manske RHF (ed) The Alkaloids VI. Academic Press, New York, pp 247
Šantavý F (1956) Oesterr Botan Z 103:300–311
Šantavý F, Zajíček DV, Něměcková A (1957) Collection Czech Chem Commun 22:1482–1488
Šantavý F, Coufalík E (1951) Collect Czech Chem C 16:198–203
Linsmaier EM, Skoog F (1965) Physiol Plant 18:100
Hunault G (1979) Rev Cytol Biol Végét-Bot 2:103
Hayashi T, Yoshida K, Sano K (1988) Phytochem 27:1371–1374
Murashige T, Skoog F (1962) Physiol Plant 15:473–497
Yoshida K, Hayashi T, Sano K (1988) Phytochem 27:1375–1378
Finnie JF, Van Staden J (1989) Plant Cell Tissue Organ Cult 19:151–158
Finnie JF, Van Staden J (1994) Gloriosa superba L (Flame Lily): microproapgation and in vitro production of colchicine. In: Bajaj YPS (ed) Biotechnology in Agriculture and Forestry, Vol. 26 Medicinal and Aromatic Plants VI. Springer–-Verlag, Berlin, Heidelberg, New York, pp 146–166
Ghosh B, Mukherjee M, Jha TB, Jha S (2002) Biotechnol Lett 24:231–234
Ghosh S, Ghosh B, Jha S (2006) Biotechnol Lett 28:497–503
Sivakumar G, Krishnamurthy KV, Hahn EJ, Paek KY (2004) J Hort Sci Biot 79:602–605
Perrot E (1936) Compt Rend 202:1088–1089; Chem Abstr 30:3946
Hrbek J, Šantavý F (1962) Collect Czech Chem C 27:255–267
Moza BK, Potešilová H, Šantavý F (1962) Planta Med 10:152–159
Šantavý F (1957) Collect Czech Chem C 22:652–653
Bellet P (1952) Ann Pharm Franç 10:81–88
Hamidi A, Fahmy MA (1960) J Chem UAR 3:279
Weizmann A (1952) Bull Res Council Israel Sect D 2:21–26
Yusupov MK, Sadykov AS (1964) Zh Obsch Khim 34:1672–1676
Salo VM (1963) Aptech Delo 12:40–43
Podoselov BD (1963) Glasnik Hem Drustva Beograd 28:461–463
Kaul JL, Moza BK, Šantavý F, Vrublovský (1964) Collect Czech Chem C 29:1689–1701
Fell KR, Ramsden D (1966) J Pharm Pharmacol 18:126S–132S
Beer AA, Karapetyan SA, Kolesnikov AI, Snegirev DP (1949) Dokl Akad Nauk SSSR 67:883–884
Salo VM (1961) Aptech Delo 10:28–32
Bryan JT, Lauter WM (1951) J Am Pharm Assoc 40:253
Lang B, Maturova M, Reichstein T, Šantavý F (1959) Planta Med 7:298–309
Burden E, Grindley DN, Prowse GA (1955) J Pharm Pharmacol 7:1063–1071
Mehra PN, Khoshoo TN (1951) J Pharm Pharmacol 3:486–496
Sadykov AS, Yusupov MK (1960) Dokl Akad Nauk Uz SSSR 1960:34–36
Sadykov AS, Yusupov MK (1962) Sci Rep Tashkent Univ 203:15–21
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Ghosh, S., Jha, S. (2008). Colchicine – an Overview for Plant Biotechnologists. In: Ramawat, K., Merillon, J. (eds) Bioactive Molecules and Medicinal Plants. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-74603-4_11
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