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Natural products and enzymes from plant cell cultures

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Abstract

Plants represent an unlimited source of natural products. Many of the recently detected phytochemicals exhibit remarkable bioactivities, ranging from anticancer activity, phosphodiesterase inhibition to cytotoxicity against HIV-infected cells. Cultivated plant cells produce at their unorganized, dedifferentiated stage secondary metabolites, but in very different amounts in so far as new compounds are concerned. In fact, more than 140 novel natural products are presently known from plant cell cultures, which also include new metabolites formed by biotransformation. The biotransformation capacity of suspended cells is described and recent high yielding transformations, like the formation of arbutin by hydroquinone-transformation withRauwolfia cells are discussed. As an example of alkaloid production by cell suspensions, the pattern of monoterpenoid indole alkaloids of the Indian medicinal plantRauwolfia serpentina Benth. is described and the so far 30 identified compounds are divided into eight groups which are biosynthetically closely related. Some of the key biosynthetic reactions leading to theRauwolfia alkaloids are discussed and an overview of the enzymes involved in the formation of the alkaloid ajmaline and proteins catalyzing side reactions of the ajmaline pathway are given.

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References

  • Aimi N, Uchida N, Ohya N, Hosokawa H, Takayama H, Sakai Si, Mendoza LA, Polz L & Stöckigt J (1991) Novel indole alkaloids from cell suspension cultures ofAspidosperma quebracho blanco Schlecht. Tetrahedron Lett. 32: 4949–4952

    Google Scholar 

  • Akiu S, Suzuki Y, Fujinuma Y, Asahara T & Fukuda M (1988) Inhibitory effect of abutin on melanogenesis: Biochemical study in cultured B16 melanoma cells and effect on the UV-induced pigmentation in human skin. Proc. Jpn. Soc. Invest. Dermatol. 12: 138–139

    Google Scholar 

  • Alfermann AW & Reinhard E (1988) Biotransfomation of synthetic and natural compounds by plant cell cultures. In: Salomé M, Pais S, Marituna F & Novais JM (Eds) Plant Cell Biotechnol. (pp. 275–283) Springer, Berlin Heidelberg New York

    Google Scholar 

  • Amrhein N, Deus B, Gehrke P & Steinrücken HC (1980) The site of inhibition of the shikimate pathway by glyphosate. Plant Physiol. 66: 830–834

    Google Scholar 

  • Anet FAL, Chakravarti D, Robinson R & Schittler E (1954) Ajmalin I (pp 1242–1260). J. Am. Chem. Soc.

  • Carriere F, Gil G, Tapie P & Chagvardieff P (1989) Biotransformation of geraniol by photoautotrophic, photomixotrophic and heterotrophic plant cell suspensions. Phytochemistry 28: 1087–1090

    Google Scholar 

  • Chen Y, Bean MF, Chambers C, Francis T, Huddleston MJ, Offen P, Westley JW, Carté BK & Timermann BN (1991) Arrivacins, novel pseudoguaianolide esters with potent angiotensin II binding activity fromAmbrosia psilostachya. Tetrahedron 47: 4869–4878

    Google Scholar 

  • Cook JM, Le Quesne PW & Elderfield RC (1969) Alstonerine, a new indole alkaloid fromAlstonia muelleriana. Chem. Comm.: 1306–1307

  • Denis JN, Greene AE, Guenard D, Gueritte-Voegelein, Mangatal L & Potier P (1988) Highly efficient, practical approach to natural taxol. J. Am. Chem. Soc. 110: 5917–5919

    Google Scholar 

  • Ellis BE (1988) Natural products from plant tissue culture. Nat. Prod. Rep. 5: 581–612

    Google Scholar 

  • Endo Y, Ohta T & Nozoe S (1991) Flavelanone, a novel tetracyclic cyclopropane derivative from the brazilian plantCnidoscolus phyllacanthus. Tetrahedron Lett. 32: 5555–5558

    Google Scholar 

  • Endreß S, Suda S, Takayama H, Aimi N, Sakai Si & Stoöckigt J (1992) Isolation, identification and chemical synthesis of 6-hydroxyraumacline, a novel alkaloid from cultivatedRauwolfia serpentina cells. Planta Med. 58: 410–412

    Google Scholar 

  • Falkenstein E, Groth B, Mithoefer A & Weiler EW (1991) Methyljasmonate and α-linolenic acid are potent inducers of tendril coiling. Planta 185: 316–322

    Google Scholar 

  • Farmer EE & Ryan CA (1990) Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc. Natl. Acad. Sci. USA 87: 7713–7716

    Google Scholar 

  • Fleming PE, Mocek U & Floss HG (1993) Biosynthesis of taxoids, mode of formation of the taxol side chain. J. Am. Chem. Soc. 115: 805–807

    Google Scholar 

  • Fujita Y & Tabata M (1987) Secondary metabolites from plant cells-pharmaceutical applications and progress in commercial production. In: Green CE, Somers DA, Hackett WP & Biesboer DD (Eds) Plant Tissue and Cell Culture (pp 169–185) Liss, New York

    Google Scholar 

  • Fujita Y, Tabata M, Nishi A & Yamada Y (1982) New medium and production of secondary compounds with the two-staged culture method. In: Fujiwara (Ed) Proc. 5th Intl. Cong. Plant Tissue and Cell Culture (pp 399–400) Maruzen Co., Tokio

    Google Scholar 

  • Gundlach H, Mueller MJ, Kutchan TM & Zenk MH (1992) Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures. Proc. Natl. Acad. Sci. USA 89: 2389–2393

    Google Scholar 

  • Ikeda Y, Sugiura M, Fukaya C, Yokoyama K, Hashimoto Y, Kawanishi K & Moriyasu M (1991) Periandradulcins A, B and C: phosphodiesterase inhibitors fromPeriandra dulcis Mart. Chem. Pharm. Bull. 39: 566–571

    Google Scholar 

  • Inomata S, Yokoyama M, Seto S & Yanagi M (1991) High-level production of arbutin from hydroquinone in suspension cultures ofCatharanthus roseus plant cells. Appl. Microbiol. Biotechnol. 36: 315–319

    Google Scholar 

  • Kawaguchi K, Hirotani M & Furuya T (1989) Studies on plant tissue cultures part 58. Biotransformation of digitoxigenin by cell suspension cultures ofStrophanthus intermedius. Phytochemistry 28: 1093–1097

    Google Scholar 

  • Kesselring K (1985) Pflanzenzellkulturen (PZK) zur Auffindung neuer, therapeutischrelevanter Naturstoffe und deren Gewinnung durch Fermentationsprozesse. BMFT Bonn: 111–129

  • Koskinen A & Lounasmaa M (1983) In: Herz W, Grisebach H & Kirby GW (Eds) Progress in the Chemistry of Organic Natural Products, Vol 43 (pp 267–346). Springer, Vienna, New York

    Google Scholar 

  • Kutchan TM, Hampp N, Lottspeich F, Beyreuther K & Zenk MH (1988) The cDNA clone for strictosidine synthase fromRauwolfia serpentina. DNA sequence determination and expression inEscherichia coli. FEBS Lett. 237: 40–44

    Google Scholar 

  • Kutchan TM, Bock A & Dittrich H (1994) Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture. Phytochemistry 35: 353–360.

    Google Scholar 

  • Lutterbach R & Stöckigt J (1992) High yield formation of arbutin from hydrochinone by cell-suspension cultures ofRauwolfia serpentina. Helv. Chim. Acta 75: 2009–2011

    Google Scholar 

  • Majumdar SP, Potier P & Poisson J (1972) Structure of suaveoline, a new alkaloid fromRauwolfia suaveolens (Apocynaceae). Tetrahedron Lett. 16: 1563–1566

    Google Scholar 

  • mangatal L, Adeline MT, Guenard F, Gueritte-Voegelein & Potier P (1989) Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues. Tetrahedron 45: 4177–4190.

    Google Scholar 

  • Nagakura N, Rüffer M & Zenk MH (1979) The biosynthesis of monoterpenoid indole alkaloids from strictosidine. J.C.S. Perkin I: 2308–2312

    Google Scholar 

  • Nicolaou KC, Yang Z, Liu JJ, Ueno H, Nantermet PG, Guy RK, Claiborne CF, Renaud J, Couladouros EA, Paulvannan K & Sorensen EJ (1994) Total Synthesis of Taxol. Nature 367: 630–634

    Google Scholar 

  • Obitz P, Endreß S & Stöckigt J (1995) The enzymatic Biosynthesis of Raumacline. Phytochemistry in press.

  • Ohkuma H, Tsuno T, Konishi M, Naito T & Kawaguchi H (1991) Complete structures of brynins A and B. Chem. Pharm. Bull. 39: 942–944

    Google Scholar 

  • Pfitzner A & Stöckigt J (1983) Biogenetic link between sarpagine and ajmaline type alkaloids. Tetrahedron Lett. 24: 5197–5200

    Google Scholar 

  • Pfitzner A & Zenk MH (1982) Immobilization of strictosidine synthase fromCatharanthus cell cultures and preparative synthesis of strictosidine. Planta Med. 46: 10–14

    Google Scholar 

  • Polz L, Stöckigt J, Takayama H, Uchida N, Aimi N & Sakai Si (1990) The new indole alkaloids raumacline and N(b)-methylraumacline. Tetrahedron Lett. 31: 6693–6696

    Google Scholar 

  • Potier (1993) 5. Irseer Naturstofftage der DECHEMA e. V. 24–26 Febr.

  • Puhlmann J, Zenk MH & Wagner H (1991) Immunologically active polysaccharides ofArnica montana cell cultures. Phytochemistry 30: 1141–1145

    Google Scholar 

  • Rittershaus E, Ulrich J, Weiss A & Westphal K (1989) Large scale industrial fermentation of plant cells. Design, installation, and initial operation of a fermentation unit (75000 liters) for plant cell cultures. Biongineering 2: 28–34

    Google Scholar 

  • Ruyter CM, Akram M, Illahi I & Stöckigt J (1991) Investigation of the alkaloid content ofRauwolfia serpentina roots from regenerated plants. Planta Med. 57: 328–330

    Google Scholar 

  • Ruyter CM, Schübel H & Stöckigt J (1988) Novel glucoalkaloids fromRauwolfia Schnübel U & cell cultures-acetylrauglucine and related glucosides. Z. Naturforsch. 43c: 479–484

    Google Scholar 

  • Ruyter CM & Stöckigt J (1989) Neue Naturstoffe aus pflanzlichen Zell-und Gewebekulturen-eine Bestandsaufnahme. GIT Fachz. Lab. 33: 283–293

    Google Scholar 

  • Sahu BN (1987) Extraction ofRauwolfia alkaloids. In:Rauwolfia sepentina-Sarpagandha-Chemistry and Pharmacology. Vol 2 (pp 215–260). Today & Tomorrow's Printes and Publishers, New Delhi

    Google Scholar 

  • Schiel O, Martin B, Piehl GW, Nowak J, Hammer J, Sasse F, Schaer W, Lehmann J & Berlin J (1984) Some technological aspects on the production of cinnamoyl putrescines by cell suspension cultures ofNicotiana tabacum.Proc. IIIrd Eur. Congr. Biotechnology (pp 167–172). Verlag Chemie, Weinheim

    Google Scholar 

  • Schübel H, Ruyter CM & Stöckigt J (1989) Improved production of raucaffricine by cultivatedRauwolfia cells. Phytochemistry 28: 491–494

    Google Scholar 

  • Shiseido K (1936) Kougyo Kagaku Zasshi 39: 456 (in japanese)

    Google Scholar 

  • Stöckigt J & Lansing A (1992) Natürliche Wirkstoffe. Nachr. Chem Tech. Lab. 140(2): 162–165

    Google Scholar 

  • Stöckigt J, Pawelka KH, Tanahashi T, Danieli B & Hull WE (1983) Voafrine A and B the first dimeric indole alkaloid isolated from plant cell cultures. Helv. Chim. Acta 66: 2525–2533

    Google Scholar 

  • Stöckigt J, Pfitzner A & Firl J (1981) Indole alkaloids from cell suspension cultures ofRauwolfia serpentina Benth. Plant Cell Rep. 1: 36–39

    Google Scholar 

  • Strobel GA, Stierle A & Van Kujik (1992) Factors influencing thein vitro production of radiolabeled taxol by Pacific yew,Taxus brevifolia. Plant Sci. 84: 65–74

    Google Scholar 

  • Suzuki T, Yoshioka T, Tabata M & Fujita Y (1987) Potential ofDatura innoxia cell suspension cultures for glucosylating hydroquinone. Plant Cell Rep. 6: 275–278

    Google Scholar 

  • Tabata M, Ikeda F, Hiraoka M & Konoshima M (1976) Glucosylation of phenolic compounds byDatura innoxia suspension cultures. Phytochemistry 15: 1225–1229

    Google Scholar 

  • Tada M, Chiba K, Yamada H & Maruyama H (1991) Phloroglucinol derivatives as competitive inhibitors against thromboxane A2 and leukotriene D4 fromHypericum erectum. Phytochemistry 30: 2559–2562

    Google Scholar 

  • Takayama H, Kitajima M, Suda S, Aimi N, Sakai Si, Endreß S & Stöckigt J (1992) Structure and synthesis of a new indole alkaloid, 19(S)-hydroxy-Nb-methylraumacline, obtained by the biotransformation of Ajmaline in plant cell cultures ofRauwolfia serpentina Benth. Tetrahedron 48: 2627–2634

    Google Scholar 

  • Toyokawa S, Takeda T & Ogihara Y (1991) Isolation and characterization of a new abortifacient protein, karasurin, from root tubers ofTrichosanthes kirilowii Max. varjaponicum Kitam. Chem. Pharm. Bull. 39: 716–719

    Google Scholar 

  • Umetani Y, Kodakari E, Yamamura T, Tanaka S & Tabata M (1990) Glucosylation of salicylic acid by cell suspension cultures ofMallotus japonicus. Plant Cell Rep. 9: 325–327

    Google Scholar 

  • Ushiyama K (1991) Food and food additives. In: Komamine A, Misawa M & DiCosmo F (Eds) Plant Cell Culture in Japan (pp 92–113) CMC Co., Ltd

  • van Uden W, Pras N, Battermann S, Visser JF & Malingré TM (1992) The accumulation of coniferin and its isolation from high-producing cell suspension ofLinum flavum. 40th Annual Congress on Medicinal Plant Research. Planta Medica (pp A619). Georg Thieme Verlag, Stuttgart, New York

    Google Scholar 

  • Vollosovitch AG (1988) Some pecularities of alkaloid accumulation in tissue culture ofRauwolfia serpentina Benth. In: Paces V (Ed) 14th International Congress of Biochemistry, Vol 3 (pp 24–25). Academia Prague

    Google Scholar 

  • Wahl A, Guéritte-Voegelein F, Guénard D, Le Goff MT & Potier P (1992) Rearrangement reactions of taxanes: structural modifications of 10-deacetylbaccatin III. Tetahedron 48: 6965–6974

    Google Scholar 

  • Wani MC, Taylor HL, Wall ME, Coggon P & McPhail AT (1971) Plant antitumor agents VI: The isolation and structure of taxol, a novel antileucemic and antitumor agent fromTaxus brevifolia. J. Am. Chem. Soc. 93: 2325–2327

    Google Scholar 

  • Winkler JD & Subrahmanyam D (1992) Studies directed towards the synthesis of taxol: preparation of C-13 oxygenated taxane congeners. Tetrahedron 48: 7049–7056

    Google Scholar 

  • Yamamoto O & Yamada Y (1986) Production of reserpine and its optimization in culturedRauwolfia serpentina Benth. cells. Plant Cell Rep. 5: 50–53

    Google Scholar 

  • Yoshida T, Chou T, Matsuda M, Yasuhara T, Yazaki K, Hatano T, Nitta A & Okuda T (1991) Woodfordin-D and oenothein-A, trimeric hydrolizable tannins of macro-ring structure with antitumor activity. Chem. Pharm. Bull. 39: 1157–1162

    Google Scholar 

  • Zenk MH, El-Shagi H & Schulte U (1975) Anthrachinone production by cell suspension cultures ofMorinda citrifolia Planta Med. Suppl. 75: 79–101

    Google Scholar 

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Authors and Affiliations

  1. Lehrstuhl für Pharmazeutische Biologie, Institut für Pharmazie, Johannes Gutenberg-Universität, Staudinger Weg 5, 55099, Mainz, Germany

    J. Stöckigt, P. Obitz, H. Falkenhagen, R. Lutterbach & S. Endreß

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  1. J. Stöckigt
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  2. P. Obitz
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  3. H. Falkenhagen
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  4. R. Lutterbach
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  5. S. Endreß
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Stöckigt, J., Obitz, P., Falkenhagen, H. et al. Natural products and enzymes from plant cell cultures. Plant Cell Tiss Organ Cult 43, 97–109 (1995). https://doi.org/10.1007/BF00052163

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