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

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.

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Correspondence to H. Hamada.

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Kwon, S., Shimoda, K., Hamada, H. et al. High Production of β-Thujaplicin Glycosides by Immobilized Plant Cells of Nicotiana Tabacum. BIOLOGIA FUTURA 59, 347–355 (2008). https://doi.org/10.1556/ABiol.59.2008.3.8

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Keywords

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