Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure

@article{Passicos2004RegioselectiveAO,
  title={Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure},
  author={Emilie Passicos and Xavier Santarelli and Denis Coulon},
  journal={Biotechnology Letters},
  year={2004},
  volume={26},
  pages={1073-1076}
}
A single-step acylation of rutin and naringin, catalyzed by immobilized Candida antarctica lipase B in 2-methyl-2-butanol, occurred preferentially on the primary hydroxyl group. Using palmitic methyl ester as acyl donor, the acylation rate of naringin was 10-fold higher than that of rutin. Under optimal conditions, i.e. a molar ratio acyl donor/naringin of 7:1 and 200 mbar, 92% naringin was acylated. 
View on Springer
ncbi.nlm.nih.gov
37 Citations
Highly Influential Citations
3
Background Citations
11
Methods Citations
4

37 Citations

Controllable Regioselective Acylation of Flavonoids Catalyzed by Lipase in Microreactors
A method for regioselective acylation of flavonoids (naringin and naringin dihydrochalcone) in a flow microreactor using Lipozyme TL IM from Thermomyces lanuginosus as the catalyst has been…
Controllable Regioselective Acylation of Rutin Catalyzed by Enzymes in Non-aqueous Solvents
An efficient route to synthesize 3′′- and 4′′′-vinyl rutin esters has been developed by enzyme-catalyzed regioselective acylation of rutin with divinyl dicarboxylates in organic media. Alkaline…
Enzymatic acylation of flavonoid glycosides by a carbohydrate esterase of family 16
TLDR
The results indicate that the acetyl esterase could be used for an easy modification of solubility and hydrophobicity of glycosylated compounds, including drugs and functional food additives.
Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity
TLDR
The antiproliferative effect of acylated sily bin derivatives on the growth of K562 human leukemia cells was estimated and compared with that of silybin.
Direct acylation of flavonoid glycosides with phenolic acids catalysed by Candida antarctica lipase B (Novozym 435
Enzymatic synthesis of flavonoid ester: elucidation of its kinetic mechanism and equilibrium thermodynamic behavior
In this study, flavonoid rutin was acylated with lauric acid in acetone catalyzed by an immobilized lipase from Candida antarctica. In addition to the reaction not being well studied, the…
Lipase-catalyzed acylation of naringin with palmitic acid in highly concentrated homogeneous solutions
Biocatalytic synthesis and antitumor activities of novel silybin acylated derivatives with dicarboxylic acids.
Lipase B from Candida antarctica — the wide applicable biocatalyst in obtaining pharmaceutical compounds
TLDR
It can be concluded, that CAL-B is an enzyme with a wide application in the biosynthesis of compounds with therapeutic activity, which could be also applied in the kinetic resolution of compounds being building blocks, derivates of drugs or conjugated forms.
Synthesis of naringin 6"-ricinoleate using immobilized lipase
TLDR
This work describes the reaction of naringin withCastor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica, and determined the chemical structure of naredin 6″-ricinoleate, which was determined using NMR analysis.
...
...

References

SHOWING 1-10 OF 11 REFERENCES
Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments.
Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media
Flavonoid fatty esters were prepared by acylation of flavonoids (rutin and naringin) by fatty acids (C8, C10, C12), catalyzed by immobilized lipase from Candida antarctica in various solvent systems.…
Use of Mucor miehei lipase in the preparation of long chain 3-O-acylcatechins
Modification of flavonoid using lipase in non-conventional media: effect of the water content.
A two-step efficient chemoenzymatic synthesis of flavonoid glycoside malonates.
A simple and high-yielding protocol for the malonylation of some flavonoid glycosides is described. The two-step synthesis is based on the regioselective enzymatic introduction of a benzylmalonyl…
Effect of different biochemical parameters on the enzymatic synthesis of fructose oleate
Enzymatic synthesis of fatty acid ascorbyl esters
Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters.
TLDR
This work demonstrates the feasibility of assembling complex flavonoid glycoside esters in just two steps by sequential use of commercially available glycosidases and lipases.
Lipase-catalyzed α-butylglucoside lactate synthesis in organic solvent for dermo-cosmetic application
Study of Citrus taitensis and radical scavenger activity of the flavonoids isolated
...
...