Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus.
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.
Kaminaga
Yasuhisa
Y
Graduate School of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori 3-1, Mizuho-ku, Nagoya 467-8603, Japan.
Nagatsu
Akito
A
Akiyama
Takumi
T
Sugimoto
Naoki
N
Yamazaki
Takeshi
T
Maitani
Tamio
T
Mizukami
Hajime
H
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
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