Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments.

  title={Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments.},
  author={Nobuyoshi Nakajima and Kohji Ishihara and Toshiyuki Itoh and Tsutomu Furuya and Hiroki Hamada},
  journal={Journal of bioscience and bioengineering},
  volume={87 1},

Enzyme-catalyzed Acylation of Plant Polyphenols for Interpretation of Their Functions

The one-step acylation of plant polyphenols, naringin and rutin, to the corresponding cinnamate esters was achieved by a lipase-catalyzed regioselective transesterification in a dry organic solvent.

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

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

Novel enzymatic approach to the synthesis of flavonoid glycosides and their esters.

This work demonstrates the feasibility of assembling complex flavonoid glycoside esters in just two steps by sequential use of commercially available glycosidases and lipases.

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

Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues

Most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, but they showed significantly better 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes.

Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases

Naringin, one of the citrus flavonoids and known as a natural antioxidant, has limited bioavailability owing to its low stability and solubility. However, naringin esters formed via acylation have

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

Lipase-catalyzed synthesis of arbutin cinnamate in an organic solvent and application of transesterification to stabilize plant pigments.

High resolution NMR and FAB-MS 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.

Enzyme‐Mediated Regioselective Acylations of Flavonoid Disaccharide Monoglycosides

Flavonoid disaccharide monoglycosides have been acylated by the catalytic action of the protease subtilisin in anhydrous pyridine. The effects of the nature of the sugars and of the interglycosidic

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

Lipase-Catalyzed Transesterification of Aryl-Substituted Alkanols in an Organic Solvent

It is proposed that a lipase from Pseudomonas cepacia can form a complex easily with each enantiomer, although the complex with the (S)-enantiomer is abortive.

Effects of Substrate Structure on Lipase-Catalyzed Transesterification of .OMEGA.-Substituted 1-Alkanols in Organic Solvents.

It is proposed that a lipase form Pseudomonas cepacia has a domain to attract an aromatic moiety of a substrate to investigate Lipase-catalyzed transesterifications of ω-phenyl-1-alkanols with vinyl acetate in organic solvents.

Chemo‐enzymatic Synthesis of 6″‐O‐(3‐Arylprop‐2‐enoyl) Derivatives of the Flavonol Glucoside Isoquercitrin

A chemo-enzymatic approach to some 6″-O-(3-arylprop-2-enoyl) derivatives of the flavonol glucoside isoquercitrin (2a) was explored to overcome the inability to directly introduce these acyl moieties

Enzyme-catalyzed processes in organic solvents.

Lipases can catalyze several other processes in organic media including esterification, aminolysis, acyl exchange, thiotransesterification, and oximolysis; some of these reactions proceed to an appreciable extent only in nonaqueous solvents.

Radical scavenging by flavonoid antioxidants.

The data do not conclusively prove that the biological function of flavonoids might be the scavenging of radicals, but the very high rate constants of formation and the relative stability of some of the aroxyl radicals, are in support of such a hypothesis.