Tsutomu Furuya

Flavonoids and phenylethanoids from hairy root cultures of Scutellaria baicalensis

We successfully established hairy root cultures of Scutellaria baicalensis by direct inoculation on sterile seedlings with Agrobacterium rhizogenes pRil5834 harbouring pBI121. Transformation was proved by direct detection of the inserted T-DNA by the polymerase chain reaction. To determine the optimal medium for growth of hairy roots, the effects of five basal media were investigated; growth was best in B5 liquid medium. A new flavone glucoside, 5,7,2′,6′-tetrahydroxyflavone 2′-O-β-d-glucopyranoside 15 known flavonoids and five known phenylethanoids were isolated from the hairy root cultures of S. baicalensis for the first time. Their structures were elucidated by various spectroscopic methods.

Phytoremediation of bisphenol A by cultured suspension cells of Eucalyptus perriniana-regioselective hydroxylation and glycosylation

On biotransformation of bisphenol A by cultured suspension cells of Eucalyptus perriniana, three new biotransformation products, 2,2-bis(4-β-d-glucopyranosyloxyphenyl)propane, 2-(4-β-d-glucopyranosyloxy-3-hydroxyphenyl)-2-(4-β-d-glucopyranosyloxyphenyl)propane and 2-(4-β-d-glucopyranosyloxy-3-hydroxyphenyl)-2-(3-β-d-glucopyranosyloxy-4-hydroxyphenyl)propane were isolated after three days incubation. Cultured suspension cells of E. perriniana are capable of regioselective hydroxylation and glycosylation of bisphenol A.

Hydroxylation of benzylic and allylic sites by plant cultured suspension cells

Abstract A novel transformation of α-substituted benzylcyanides by hydroxylation of benzyl sites using cultured cells of cotton, Gossypium hirsutum, producing alkano- or benzophenones via presumably α-cyanohydrin is demonstrated. Also regioselective hydroxylation of 4 S -(−)-perillyl alcohol and 3 S -(−)-citronellol by cultured suspension cells of Catharanthus roseus is reported.

Biotransformation of β-thujaplicin by cultured cells of Eucalyptus perriniana

Abstract Four new biotransformation products, 4-isopropyltropolone 2-O-β- d -glucoside, 4-isopropyltropolone 2-O-β- d -gentiobioside, 6-isopropyltropolone 2-O-β- d -glucoside and 6-isopropyltropolone 2-O- d -gentiobioside, were isolated from cell suspension culture of Eucalyptus perriniana following administration of β-thujaplicin. The chemical structures of all products were determined by 1 H and 13 C NMR and MS spectroscopy. It was also observed that the production ratio of biotransformation products was higher in iron-deficient medium than in the medium containing iron ion.

Preparation of a new pepper : chemoenzymatic synthesis of capsaicin oligosaccharide and 8-nordihydrocapsaicin oligosaccharide

Capsaicin and 8-nordihydrocapsaicin were readily converted into the corresponding monoglucosides (capsaicin β-d-glucopyranoside and 8-nordihydrocapsaicin β-d-glucopyranoside) with tetraacetyl-α-d-glucose fluoride (TAGF) in the presence of BF3·OEt2. Furthermore, capsaicin oligosaccharides and 8-nordihydrocapsaicin oligosaccharides were synthesized from their monoglucosides by a cyclodextrin glucanotransferase (CGTase)-catalyzed glycosylation for the preparation of higher water-soluble capsaicinoids.

A chemoenzymatic synthesis of aromatic carboxylic acid vinyl esters

Abstract The practical synthesis of vinyl p-coumarate (vinyl 4-hydroxycinnamate) and vinyl ferulate (vinyl 4-hydroxy-3-methoxycinnamate) was accomplished via a transesterification to the corresponding aromatic acid using vinyl acetate and a catalytic amount of PdCl2, followed by the lipase-catalyzed regioselective alcoholysis in EtOH.

Highly selective transformation by plant catalysts

Abstract This review outlines the recent progress in the biotransformation of foreign substrate by plant cultured suspension cells. The reaction types and stereochemistry involved in the biotransformations are described.

Biotransformation of artemisinic acid by cultured cells of Artemisia annua

Abstract Three new biotransformation products, artemisinic acid β- d -glucopyranosyl ester, 9-β-hydroxyartemisinic acid β- d -glucopyranosyl ester and 3-β-hydroxyartemisinic acid β- d -glucopyranosyl ester, were isolated from a cell culture of Artemisia annua following the administration of artemisinic acid.

Biotransformation of Paclitaxel by Cell Suspension Cultures of Eucalyptus Perriniana

Abstract Incubation of Eucalyptus perriniana cells in medium containing paclitaxel lead to the isolation of three taxoid derivatives which were identified by 1H NMR and MS spectrometry data as baccatin III, 10-deacetylbaccatin III and 2-debenzoyltaxol. No transformation occurs in medium without Eucalyptus cells.

Biotransformation of p-aminobenzoic acid by cultured cells of Eucalyptus perriniana.

Abstract Two new biotransformation products, p -aminobenzoyl β - d -glucopyranoside and p -( N - β - d -glucopyranosylamino) benzoyl β - d -glucopyranoside, were isolated from cell suspension culture of Eucalyptus perriniana following administration of p -aminobenzoic acid. The chemical structures of these products were determined by 1 H and 13 C NMR and MS spectra.