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 X. Santarelli and D. 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

Citation Type

Citation Type

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… Expand
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… Expand
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. Expand
Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity
Biocatalytic preparation of acylated derivatives of silybin using several acyl donors (free fatty acids or their esters), catalyzed by immobilized Candida antarctica lipase B, was performed in… Expand
Direct acylation of flavonoid glycosides with phenolic acids catalysed by Candida antarctica lipase B (Novozym 435
Immobilised Candida antarctica lipase B (Novozym 435®) was used to acylate flavonoid glycosides, both purified and in fruit extracts, using carboxylic acids as acyl donors, in the presence of 4 A… Expand
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… Expand
Lipase-catalyzed acylation of naringin with palmitic acid in highly concentrated homogeneous solutions
Abstract Acylation reactions of naringin with palmitic acid were performed by a lipase after formation of highly concentrated homogeneous solutions. Their initial naringin concentration was 840–950… Expand
Biocatalytic synthesis and antitumor activities of novel silybin acylated derivatives with dicarboxylic acids.
TLDR
The synthesized esters retained the biological function of silybin and in some cases were more effective, indicating that target biotransformation may generate novel compounds with improved antitumor and antiangiogenic activities. Expand
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. Expand
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. Expand
...
1
2
3
4
...

References

SHOWING 1-10 OF 11 REFERENCES
Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments.
TLDR
The method described, which is the first allowing the direct synthesis of aromatic acid esters of flavonoid glucoside, can be applied to the acylation of other glucosides, including naringin, rutin, callistephin, and chrysanthemin. Expand
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.… Expand
Use of Mucor miehei lipase in the preparation of long chain 3-O-acylcatechins
Long chain 3-O-acylcatechins were prepared in high yield by alcoholysis with n-butanol of the corresponding pentaacylderivatives in the presence of lipase from Mucor miehei (immobilised, Lipozyme®… Expand
Modification of flavonoid using lipase in non-conventional media: effect of the water content.
TLDR
The enzymatic acylation of a flavonoid (naringin) was investigated in this work and the effect of the initial hydration level of the reaction medium components was pointed out for naringin palmitate synthesis. Expand
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… Expand
Effect of different biochemical parameters on the enzymatic synthesis of fructose oleate
Enzymatic synthesis of sugar ester was performed using an immobilized Candida antartica lipase, fructose and oleic acid methyl ester as substrates and 2-methyl 2-butanol as a solvent. The influence… Expand
Enzymatic synthesis of fatty acid ascorbyl esters
Abstract Lipase B from the yeast Candida antartica was used to catalyze the enzymatic synthesis of fatty acid ascorbyl esters, in 2-methyl-2-butanol as a solvent. The influence of water activity ( a… Expand
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. Expand
Lipase-catalyzed α-butylglucoside lactate synthesis in organic solvent for dermo-cosmetic application
Abstract α -Butylglucoside can be used as a vector for lactic acid: α -butylglucoside lactate synthesis can be achieved through transesterification catalyzed by immobilized Candida antarctica lipase.… Expand
Study of Citrus taitensis and radical scavenger activity of the flavonoids isolated
Abstract The GC-MS study of the head space volatiles of Citrus taitensis Risso revealed that the main component, constituting 60% of the oil, is linalool. Three N-containing compounds, benzyl… Expand
...
1
2
...