High production of β-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum

Kwon, S. and Shimoda, K. and Hamada, H. and Ishihara, K. and Masuoka, N. and Hamada, H. (2008) High production of β-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum. Acta Biologica Hungarica, 59 (3). pp. 347-355. ISSN 0236-5383

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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 of Nicotiana tabacum glycosylated β-thujaplicin to two glucosides, 4-isopropyltropolone 2- O -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 of N. tabacum in sodium alginate gel much improved the yield of the products; the glycosylation of β-thujaplicin with immobilized 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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