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Progress in Chemistry 2010, Vol. 22 Issue (11): 2147-2155 Previous Articles   Next Articles

• Review •

Structural Modification Methods of 5,4′-hydroxyl-containing Flavonoid Glycoside and Aglycone Molecules

He Fang   LI Ruixia  Wu Da-cheng*   

  1. (Institute of Textile of Sichuan University, Chengdu 610065, China)
  • Received: Revised: Online: Published:
  • Contact: Wu Dacheng E-mail:wudacheng@scu.edu.cn
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Multi-hydroxyl flavonoids (glycoside and their aglycones) are known to exhibit a variety of physiochemical properties and biological activities. But they are characterized by a low bioavailability and stability in vivo plus nonspecific action in pharmacology. Owing to their importance in pharmaceutics, food and cosmetics, the purpose of this work is an overview of valuable findings concerning hemisynthesis of multi-hydroxyl flavonol (e.g. rutin, quercetin) and dihydroflavone (e.g. Naringenin, Naringin) involving three types of substitutions (Ar-O-substitution, Ar (C)-substitution and glycoside-O-substitution catalyzed by enzymes). And wherein, the comparative analysis was made on the protection approaches for phenolic hydroxyls following by particular discussion for C-substitution by applying a Mannich-type reaction (including effects of substrate, monomer and systematic pH). The results indicate that a reasonable selection of the protection methods for hydroxyl groups and bioactive groups of monomers is critical to obtain desired products combining stability and target-specific bioactivity via selective hemisynthesis. Furthermore, O-substituted reactions for multi-hydroxyl flavonols and dihydroflavone exhibit comparably stronger reactivity than C-substitution but with poor regioselectivity once substitution occurs. In addition, their reactions with long alkyl-chain monomers (C≥12) in general belong to a monosubstitution, and the resultant hydrophobic substitution products, as a class of bisurfactants, exert a broad prospect for research and application.

Contents
1 Introduction
2 Characteristics of structural modification for flavonoids
2.1 Non-protection of phenolic hydroxyls
2.2 Protection and deprotection of phenolic hydroxyls
3 O-substituted flavonoid derivatives
3.1 Mono-O-substitution
3.2 Multi-O-substitution
4 C-substituted flavonoid derivatives
4.1 Effect of reactive substrate and monomer
4.2 Effect of systematic pH
5 Flavonoid glycoside-O-substituted derivatives
6 Conclusion and prospects

Key words: rutin, quercetin, naringenin, flavonol, dihydroflavone, structural modification, Mannich

CLC Number: 

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