Lipase-catalyzed synthesis of arbutin cinnamate in an organic solvent and application of transesterification to stabilize plant pigments.
Arbutin cinnamate was synthesized from arbutin (4-hydroxyphenyl beta-D-glucopyranoside) and vinyl cinnamate by regioselective transesterification with a bacterial lipase in acetonitrile. The product was identified by NMR and FAB-MS analyses. These spectra showed that one ester bond was formed between the primary alcohol moiety of the D-glucose of arbutin and the carboxyl residue of cinnamic acid. Furthermore, plant pigments such as isoquercitrin (quercetin 3-O-beta-D-glucopyranoside) and callistephin (pelargonidin 3-O-beta-D-glucopyranoside) were also converted to their corresponding cinnamate esters in the same manner.
Nakajima
N
N
Department of Nutritional Science, Okayama Prefectural University, Japan.
Ishihara
K
K
Matsumura
S
S
Hamada
H
H
Nakamura
K
K
Furuya
T
T
D000097:Acetonitriles / Q000737:chemistry; D000107:Acetylation; D001104:Arbutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism*; D002241:Carbohydrates / Q000138:chemical synthesis; D002855:Chromatography, Thin Layer; D002934:Cinnamates / Q000138:chemical synthesis*; D004355:Drug Stability; D004952:Esters / Q000138:chemical synthesis; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010860:Pigments, Biological / Q000737:chemistry*; D010944:Plants / Q000737:chemistry; D012997:Solvents; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000097:Acetonitriles; D001426:Bacterial Proteins; D002241:Carbohydrates; D002934:Cinnamates; D004952:Esters; D010860:Pigments, Biological; D012997:Solvents; D001104:Arbutin; D008049:Lipase; C032159:acetonitrile