Flavonoid Inclusion Compound Production via Rhamnose Cleavage

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Solution Overview

Problem

Existing methods for producing flavonoid inclusion compounds and compositions of flavonoid glycosides are not efficient in improving solubility, leading to insufficient water solubility of flavonoids, particularly those with a rhamnoside structure.

Innovation Solution

A method involving the cleavage of rhamnose from sparingly soluble flavonoids using an enzyme with rhamnosidase activity in the presence of cyclodextrin, followed by glycosidation with a glycosyltransferase, to produce flavonoid inclusion compounds with enhanced water solubility, specifically targeting isoquercitrin, hesperetin-7-glucoside, and naringenin-7-glucoside.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a sparingly soluble flavonoid with a rhamnoside structure is used directly, then the physiological effects and bioavailability are limited, but the water solubility is insufficient for use in foods, beverages, medicaments, or cosmetics

Engineering Contradiction:
ImprovebioavailabilityVSAvoidwater solubility
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The invention extracts and removes the rhamnose moiety from the rhamnoside structure of flavonoids using enzymatic hydrolysis with beta-glucosidase or other rhamnosidases, converting sparingly soluble flavonoid rhamnosides into more water-soluble aglycones or glucose conjugates that can be effectively used in aqueous formulations

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the chemical structure parameter of flavonoids by cleaving the rhamnoside bond, thereby transforming the solubility parameter from sparingly soluble to highly water-soluble, enabling effective use in foods, beverages, medicaments, and cosmetics

Inventive Principle:
Principle #35Parameter changes

2Productivity

If existing methods for producing flavonoid inclusion compounds are used, then the production process is complex and inefficient, but the water solubility improvement is insufficient

Engineering Contradiction:
Improveproduction efficiencyVSAvoidwater solubility
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The invention merges the hydrolysis reaction and inclusion compound formation into a single integrated process where cyclodextrin is present during the enzymatic cleavage of rhamnose, allowing simultaneous production of water-soluble flavonoid derivatives and their inclusion compounds, thereby simplifying the production process and improving both efficiency and solubility

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention uses cyclodextrin as an intermediary substance that facilitates both the hydrolysis reaction and the formation of water-soluble inclusion compounds, acting as a mediator that enhances water solubility while streamlining the production process

Inventive Principle:
Principle #24Intermediary (Mediator)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The method achieves high solubility of flavonoids in water, improving their bioavailability and physiological effects, and can be applied to foodstuffs, medicaments, and cosmetics, enhancing their functionality and stability.

Implementation Method 1

treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having a rhamnosidase activity to cleave a rhamnose

Methodology Applied
Scientific EffectEnzymatic hydrolysis: Hydrolysis

Implementation Method 2

in the presence of a cyclodextrin to cleave a rhamnose... producing a water-soluble flavonoid and a cyclodextrin

Methodology Applied
Scientific EffectInclusion complexation: Absorption (physical)

Data Source

PatentUS10676496B2Method for producing flavonoid inclusion compound
Publication Date: 2020.06.09 TAIYO KAGAKU CO LTD
  • US10676496B2 patent drawing
  • US10676496B2 patent drawing
  • US10676496B2 patent drawing

AI summary

A method for producing a flavonoid inclusion compound, including a cleaving step including treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having a rhamnosidase activity in the presence of a cyclodextrin to cleave a rhamnose. According to the production method of the present invention, a flavonoid inclusion compound and a composition of flavonoid glycosides having excellent solubility in water can be efficiently produced, so that the compound and composition can be suitably utilized in the fields of medicaments, foodstuff, health foods, foods for specified health use, cosmetics, and the like.