title: Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus.
abstract: Catharanthus roseus cell suspension cultures converted exogenously supplied curcumin to a series of glucosides, none of which has been found in nature so far. The efficiency of glucosylation was dependent on culture stage of the cells and medium sucrose concentration. Methyl jasmonate and salicylic acid enhanced the glucoside formation only when they were added to the cultures prior to the addition of curcumin. The glucoside yield was 2.5 micromol/g fresh weight of the cells at an optimal culture condition. The water solubility of curcumin-4',4"-O-beta-D-digentiobioside was 0.65 mmol/ml, which was 20 million-fold higher than that of curcumin.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori 3-1, Mizuho-ku, Nagoya 467-8603, Japan.
authors.forename: Yasuhisa
authors.initials: Y
authors.lastname: Kaminaga
authors.forename: Akito
authors.initials: A
authors.lastname: Nagatsu
authors.forename: Takumi
authors.initials: T
authors.lastname: Akiyama
authors.forename: Naoki
authors.initials: N
authors.lastname: Sugimoto
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamazaki
authors.forename: Tamio
authors.initials: T
authors.lastname: Maitani
authors.forename: Hajime
authors.initials: H
authors.lastname: Mizukami
mesh_terms: D000085:Acetates / Q000494:pharmacology; D030008:Catharanthus / Q000166:cytology / Q000378:metabolism*; D002478:Cells, Cultured; D017077:Culture Media, Conditioned; D003474:Curcumin / Q000031:analogs & derivatives / Q000378:metabolism*; D003517:Cyclopentanes / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry; D005960:Glucosides / Q000096:biosynthesis* / Q000737:chemistry; D006031:Glycosylation; D006873:Hydroquinones / Q000737:chemistry; D047311:Luteolin; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D054883:Oxylipins; D020156:Salicylic Acid / Q000494:pharmacology; D012995:Solubility; D013395:Sucrose / Q000494:pharmacology; D013535:Suspensions; D014867:Water / Q000737:chemistry
chemical_list: D000085:Acetates; D017077:Culture Media, Conditioned; D003517:Cyclopentanes; D005419:Flavonoids; D005960:Glucosides; D006873:Hydroquinones; D054883:Oxylipins; D013535:Suspensions; D014867:Water; D013395:Sucrose; C072239:methyl jasmonate; D003474:Curcumin; D047311:Luteolin; D020156:Salicylic Acid; C031927:hydroquinone