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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
Article

Abstract

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.

Keywords

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

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© Akadémiai Kiadó, Budapest 2008

This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.

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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