Acta Biologica Hungarica

, Volume 59, Issue 3, pp 347–355 | Cite as

High Production of β-Thujaplicin Glycosides by Immobilized Plant Cells of Nicotiana Tabacum

  • S. Kwon
  • K. Shimoda
  • H. Hamada
  • K. Ishihara
  • N. Masuoka
  • H. HamadaEmail author


β-Thujaplicin (hinokitiol) is a tropolone derivative present in the heartwood of cupressaceous plants and is used as a medicine, a food additive, and a preservative, and in cosmetics as hair tonic. The cultured plant cells o. Nicotiana tabacum glycosylated β-thujaplicin to two glucosides, 4-isopropyltropolone 2-0-β-D-glucoside (6%) and 6-isopropyltropolone 2-O-β-D-glucoside (12%), and two gentiobiosides, 4-isopropyltropolone 2-O-β-D-gentiobioside (2%) and 6-isopropyltropolone 2-O-β-D-gentiobioside (5%) after 48 h incubation. The use of immobilized cells o. N. tabacum in sodium alginate gel much improved the yield of the products; the glycosylation of β-thujaplicin with immobilize. N. tabacum gave the glycoside products, 4-isopropyltropolone 2-O-β-D-glucoside (11%), 4-isopropyltropolone 2-O-β-D-gentiobioside (6%), 6-isopropyltropolone 2-O-β-D-glucoside (20%), and 6-isopropyltropolone 2-O-β-D-gentiobioside (10%). On the other hand, 4-isopropyltropolone 2-O-β-D-glucoside (14%), 4-isopropyltropolone 2-O-β-D-gentiobioside (7%), 6-isopropyltropolone 2-O-β-D-glucoside (33%), and 6-isopropyltropolone 2-O-β-D-gentiobioside (13%) were obtained through the biotransformation with immobilized cells in the medium without iron ions. In comparison with the case of bioconversion in the normal medium containing iron ions, removal of iron ions improved the yields of products.


Glycosylation β-thujaplicin β-glucoside β-gentiobiosid Nicotiana tabacum immobilized cells 


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  1. 1.
    Suga, T., Hirata, T. (1990) Biotransformation of exogenous substrates by plant cell cultures. Phytochemistry 29, 2393–2406.CrossRefGoogle Scholar
  2. 2.
    Voutquenne, L., Guinot, P., Froissard, C., Thoison, O., Litaudon, M., Lavaud, C. (2005) Haemolytic acylated triterpenoid saponins fro. Harpullia austro-caledonica. Phytochemistry 66, 825–835.CrossRefGoogle Scholar
  3. 3.
    Eskander, J., Lavaud, C., Pouny, I., Soliman, H. S. M., Abdel-Khalik, S. M., Mahmoud, I. I. (2006) Saponins from the seeds o. Mimusops laurifolia. Phytochemistry 67, 1793–1799.CrossRefGoogle Scholar
  4. 4.
    Melek, F. R., Miyase, T., Ghaly, N. S., Nabil, M. (2007) Triterpenoid saponins with N-acetyl sugar from the bark o. Albizia procera. Phytochemistry 68, 1261–1266.CrossRefGoogle Scholar
  5. 5.
    Shao, B., Guo, H., Cui, Y., Ye, M., Han, J., Guo, D. (2007) Steroidal saponins fro. Smilax china and their anti-inflammatory activities. Phytochemistry 68, 623–630.CrossRefGoogle Scholar
  6. 6.
    Vincken, J. P., Heng, L., Groot, A., Gruppen, H. (2007) Saponins, classification and occurrence in the plant kingdom. Phytochemistry 68, 275–297.CrossRefGoogle Scholar
  7. 7.
    Moyer, B. G., Gustine, D. L. (1987) Esterification of 3-nitropropanoic acid to glucose by suspension cultures o. Coronilla varia. Phytochemistry 26, 139–140.CrossRefGoogle Scholar
  8. 8.
    Furuya, T., Ushiyama, M., Ashida, Y., Yoshikawa, T., Orihara, Y. (1988) Biotransformation of pheny-lacetic acid and 2-phenyl-propionic acid in suspension culture o. Coffea arabica. Phytochemistry 27, 803–807.CrossRefGoogle Scholar
  9. 9.
    Tabata, M., Umetani, Y., Ooya, M., Tanaka, S. (1988) Glucosylation of phenolic compounds by plant cell cultures. Phytochemistry 27, 809–813.CrossRefGoogle Scholar
  10. 10.
    Upmeier, B., Thomzik, J. E., Barz, W. (1988) Nicotinic acid-JV-glucoside in heterotrophic parsley cell suspension cultures. Phytochemistry 27, 3489–3493.CrossRefGoogle Scholar
  11. 11.
    Furuya, T., Ushiyama, M., Ashida, Y., Yoshikawa, T. (1989) Biotransformation of 2-phenylpropionic acid in root culture o. Panax ginseng. Phytochemistry 28, 483–487.CrossRefGoogle Scholar
  12. 12.
    Ushiyama, M., Asada, T., Yoshikawa, T., Furuya, T. (1989) Biotransformation of aromatic carboxylic acids by root cultur. of Panax ginseng. Phytochemistry 28, 1859–1869.CrossRefGoogle Scholar
  13. 13.
    Lewinson, E., Berman, E., Mazur, Y., Gressel, J. (1996) Glucosylation of exogenous flavanones by grapefrui. (Citrus paradisi) cell cultures. Phytochemistry 25, 2531–2535.CrossRefGoogle Scholar
  14. 14.
    Inamori, Y., Nishiguchi, K., Matsuo, N., Tsujibo, H., Baba, K., Ishida, N. (1991) Phytogrowth-inhibitory activities of tropolone and hinokitiol. Chem. Pharm. Bull. 39, 2378–2381.CrossRefGoogle Scholar
  15. 15.
    Inamori, Y., Shinohara, S., Tsujibo, H., Okabe, T., Morita, Y., Sakagami, Y., Kumeda, Y., Ishida, N. (1999) Antimicrobial activity and metalloprotease inhibition of hinokitiol-related compounds, the constituents o. Thujopsis dolabrata S. and Z. hondai Mak. Biol. Pharm. Bull. 22, 990–993.CrossRefGoogle Scholar
  16. 16.
    Inamori, Y., Sakagami, Y., Morita, Y., Shibata, M., Sugiura, M., Kumeda, Y., Okabe, T., Tsujibo, H., Ishida, N. (2000) Antifungal activity of hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities. Biol. Pharm. Bull. 23, 995–997.CrossRefGoogle Scholar
  17. 17.
    Miyamoto, D., Endo, N., Oku, N., Arima, Y., Suzuki, T., Suzuki, Y. (1998) Beta-thujaplicin zinc chelate induces apoptosis in mouse high metastatic melanoma B16BL6 cells. Biol. Pharm. Bull. 21, 1258–1262.CrossRefGoogle Scholar

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© Akadémiai Kiadó, Budapest 2008

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Authors and Affiliations

  • S. Kwon
    • 1
  • K. Shimoda
    • 2
  • H. Hamada
    • 3
  • K. Ishihara
    • 4
  • N. Masuoka
    • 4
  • H. Hamada
    • 4
    Email author
  1. 1.Department of Applied Science, Faculty of ScienceOkayama University of ScienceOkayamaJapan
  2. 2.Department of Pharmacology and TherapeuticsFaculty of Medicine, Oita UniversityOitaJapan
  3. 3.National Institute of Fitness and Sports in KanoyaKagoshimaJapan
  4. 4.Department of Life Science, Faculty of ScienceOkayama University of ScienceOkayamaJapan

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