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Cyclodextrins as a useful tool for bioconversions in plant cell biotechnology

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Abstract

The application of cyclodextrins as precursor solubilizers in biotechnological processes, in which plant cells are involved, is new. In this paper the possibilities for cyclodextrin facilitated bioconversions by freely suspended and/or immobilized plant cells or plant enzymes are demonstrated. After complexation with β-cyclodextrin, the phenolic steroid 17β-estradiol could be ortho-hydroxylated into a catechol, mainly 4-hydroxyestradiol, by a phenoloxidase from in vitro grown cells of Mucuna pruriens. By complexation with β-cyclodextrin the solubility of the steroid increased from almost insoluble to 660 μM. In addition, by complexation with β-cyclodextrin, a solution of 3 mM coniferyl alcohol could be fed to cell cultures of Podophyllum hexandrum in order to enhance the accumulation of podophyllotoxin. Finally, the glucosylation of podophyllotoxin by cell cultures derived from Linum flavum was investigated. Four cyclodextrins: β-cyclodextrin, γ-cyclodextrin, hydroxypropyl-β-cyclodextrin and dimethyl-β-cyclodextrin were used to improve the solubility of podophyllotoxin. Dimethyl-β-cyclodextrin met our needs the best and the solubility of podophyllotoxin could be enhanced from 0.15 to 1.92 mM. Podophyllotoxin-β-d-glucoside was formed at a rate of 0.51 mmol l-1 suspension per day by the L. flavum cells growing in the presence of 1.35 mM podophyllotoxin, complexed with dimethyl-β-cyclodextrin.

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Abbreviations

DW:

dry weight

E2:

17β-estradiol

FW:

fresh weight

PCV:

packed cell volume

References

  • Berlin J, Wray V, Mollenschott C & Sasse F (1986) Formation of β-peltatin-A-methylether and coniferin by root cultures of Linum flavum. J. Nat. Prod. 49: 435–439

    Google Scholar 

  • Berlin J, Bedorf N, Mollenschott C, Wray V, Sasse F & Höfle G (1988) On the podophyllotoxins of root cultures of Linum flavum. Planta Med. 54: 204–206

    Google Scholar 

  • Duchêne D & Wouessidjewe D (1990a) Physicochemical characteristics and pharmaceutical uses of cyclodextrin derivatives, Part I. Pharm. Technol. 14 (6): 26–34

    Google Scholar 

  • Duchêne D & Wouessidjewe D (1990b) Physicochemical characteristics and pharmaceutical uses of cyclodextrin derivatives, Part II. Pharm. Technol. 14 (8): 22–30

    Google Scholar 

  • Hesselink PGM, Van Vliet S, De Vries H & Witholt B (1989) Optimization of Mycobacterium steroid side chain cleavage in the presence of cyclodextrins. Enzyme Microbiol. Technol. 11: 398–404

    Google Scholar 

  • Higuchi T & Connors K (1965) Phase solubility techniques. Adv. Anal. Chem. Industr. 4: 117–212

    Google Scholar 

  • Hirayama F & Uekama K (1987) Methods of investigating and preparing inclusion compounds. In: Duchêne D (Ed) Cyclodextrins and Their Industrial Uses (pp 131–172). Editions de Santé, Paris

    Google Scholar 

  • Hösel W (1981) Glycosylation and glycosidases. In: Conn EE, Stumpf PK (Ed) The Biochemistry of Plants, Vol 7 (pp 725–753). Academic Press, New York

    Google Scholar 

  • Jackson DE & Dewick PM (1984) Biosynthesis of Podophyllum lignans — II. Interconversions of aryltetralin lignans in Podophyllum hexandrum. Phytochemistry 23: 1037–1042

    Google Scholar 

  • Le Bas G & Rysanek N (1987) Structural aspects of cyclodextrins. In: Duchêne D (Ed) Cyclodextrins and Their Industrial Uses (pp 105–130). Editions de Santé, Paris

    Google Scholar 

  • Luckner M (1986) In: Secondary Metabolism in Microorganisms, Plants and Animals, 2nd edition. Springer-Verlag, Heidelberg/New York/Tokyo

    Google Scholar 

  • Mayer AM (1987) Polyphenol oxidases in plants — recent progress. Phytochemistry 26: 11–20

    Google Scholar 

  • Müller BW & Brauns U (1986) Hydroxypropyl-β-cyclodextrin derivatives: influence of average degree of substitution on complexing ability and surface activity. J. Pharm. Sci. 75 (6): 571–572

    Google Scholar 

  • Pras N (1989) Biotechnological production of catechols: bioconversion spectrum and related kinetic aspects of entrapped cells of Mucuna pruriens L. Pharm. Weekbl. Sci. ed. 11: 30–31

    Google Scholar 

  • Pras N (1992) Bioconversion of naturally occurring precursors and related synthetic compounds using plant cell cultures: a review. J. Biotechnol. 26: 29–62

    Google Scholar 

  • Pras N, Wichers HJ, Bruins AP & Malingré ThM (1988) Bioconversion of para-substituted monophenolic compounds into corresponding catechols by alginate-entrapped cells of Mucuna pruriens. Plant Cell Tiss. Org. Cult. 13: 15–26

    Google Scholar 

  • Pras N, Hesselink PGM, Guikema WM & Malingré ThM (1989) Further kinetic characterization of alginate-entrapped cells of Mucuna pruriens L. Biotechnol. Bioeng. 33: 1461–1468

    Google Scholar 

  • Saenger W (1984) Structural aspects of cyclodextrins and their inclusion complexes. In: Atwood JL, Davies JED & MacNicol DD (Eds) Inclusion Compounds (pp 231–259). Academic Press, London

    Google Scholar 

  • Sébille B (1987) Cyclodextrin derivatives. In: Duchêne D (Ed) Cyclodextrins and Their Industrial Uses (pp 353–392). Editions de Santé, Paris

    Google Scholar 

  • Sicard PJ & Saniez MH (1987) Biosynthesis of cycloglucosyl-transferase and obtention of its enzymatic reaction products. In: Duchêne D (Ed) Cyclodextrins and Their Industrial Uses (pp 77–103). Editions de Santé, Paris

    Google Scholar 

  • Szejtli J & Pagington J (1989) Solubility isotherms. Cyclodextrin News 3: 77–79

    Google Scholar 

  • Uekama K, Narisawa S, Hirayama F & Otagiri M (1983) Improvement of dissolution and absorption characteristics of benzodiazepines by cyclodextrin complexation. Int. J. Pharm. 16: 327–338

    Google Scholar 

  • Uekama K & Irie T (1987) Pharmaceutical applications of methylated cyclodextrin derivatives. In: Duchêne D (Ed) Cyclodextrins and Their Industrial Uses (pp 395–439). Editions de Santé, Paris

    Google Scholar 

  • Van Uden W, Pras N, Visser JF & Malingré ThM (1989) Detection and identification of podophyllotoxin produced by cell cultures derived from Podophyllum hexandrum Royle. Plant Cell Rep. 8: 165–168

    Google Scholar 

  • Van Uden W, Pras N, Vossebeld EM, Mol JNM & Malingré ThM (1990a) Production of 5-methoxypodophyllotoxin in cell suspension cultures of Linum flavum L. Plant Cell Tiss. Org. Cult. 20: 81–87

    Google Scholar 

  • Van Uden W, Pras N & Malingré ThM (1990b) On the improvement of the podophyllotoxin production by phenylpropanoid precursor feeding to cell cultures of Podophyllum hexandrum Royle. Plant Cell Tiss. Org. Cult. 23: 217–224

    Google Scholar 

  • Van Uden W, Pras N, Batterman S, Visser JF & Malingré ThM (1991a) The accumulation and isolation of coniferin from a high-producing cell suspension of Linum flavum L. Planta 183: 25–30

    Google Scholar 

  • Van Uden W, Pras N, Homan B & Malingré ThM (1991b) Improvement of the production of 5-methoxypodophyllotoxin using a new selected root culture of Linum flavum L. Plant Cell Tiss. Org. Cult. 27: 115–121

    Google Scholar 

  • Van Uden W, Homan B, Woerdenbag HJ, Pras N & Malingré ThM, Wichers HJ & Harkes M (1992) Isolation, purification, and cytotoxicity of 5-methoxypodophyllotoxin, a lignan from a root culture of Linum flavum. J. Nat. Prod. 55: 102–110

    Google Scholar 

  • Van Uden W, Oeij H, Woerdenbag HJ & Pras N (1993) Glucosylation of cyclodextrin-complexed podophyllotoxin by cell cultures of Linum flavum L. Plant Cell Tiss. Org. Cult. (in press)

  • Wichers HJ, Harkes MP & Arroo RJ (1990) Occurrence of 5-methoxypodophyllotoxin in plants, cell cultures and regenerated plants of Linum flavum. Plant Cell Tiss. Org. Cult. 23: 93–100

    Google Scholar 

  • Wichers HJ, Versluis-De Haan GG, Marsman JW & Harkes MP (1991) Podophyllotoxins in plants and cell cultures of Linum flavum. Phytochemistry 30: 3601–3604

    Google Scholar 

  • Woerdenbag HJ, Pras N, Frijlink HW, Lerk CF & Malingré ThM (1990a) Cyclodextrin-facilitated bioconversion of 17β-estradiol by a phenoloxidase from Mucuna pruriens cell cultures. Phytochemistry 29: 1551–1554

    Google Scholar 

  • Woerdenbag HJ, Van Uden W, Frijlink HW, Lerk CF, Pras N & Malingré ThM (1990b) Increased podophyllotoxin production in Podophyllum hexandrum cell suspension cultures after feeding coniferyl alcohol as a β-cyclodextrin complex. Plant Cell Rep. 9: 97–100

    Google Scholar 

  • Yamamoto M, Yoshida A, Hirayama F & Uekama K (1989) Some physicochemical properties of branched β-cyclodextrins and their inclusion characteristics. Int. J. Pharm. 49: 163–171

    Google Scholar 

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van Uden, W., Woerdenbag, H.J. & Pras, N. Cyclodextrins as a useful tool for bioconversions in plant cell biotechnology. Plant Cell Tiss Organ Cult 38, 103–113 (1994). https://doi.org/10.1007/BF00033867

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