Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives

a technology of activation and phenolics, applied in the field of preparation of phenolics derivatives, can solve the problems of difficult to reach concentration and stability, difficult to achieve concentration and stability, and difficult to achieve oxidation resistant forms of phenolics, so as to prevent carcinogenesis, reduce allergic reactions, and potent immunosuppressive effects

Inactive Publication Date: 2009-09-17
LIBRAGEN SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0035]Rosmarinic acid was first shown to reduce allergic reactions in mice using the mouse ear-passive cutaneous anaphylaxis reaction (MAKINO T, FURATA Y, WAKUSHIMA H, FUJII H, SAITO K, KANO Y (2003) Anti-allergic effect of Perilla frutescens and its active constituents. Phytother Res 17(3): 240-3). One study showed that rosmarinic acid inhibited IL-2 promoter activation of T cells in a large-scale screening of plant extracts (WON J, HUR Y G, HUR E M, PARK S H, KANG M A, CHOI Y, PARK C, LEE K H, YUN Y (2003), Rosmarinic acid inhibits TCR-induced T cell activation and proliferation in a Lck-dependent manner. Eur J Immunol 33(4): 870-9). Another study showed that rosmarinic acid, by inhibiting both the activation and proliferation of T cells, had potent immunosuppressive effects when combined with rapamycin, an anti-rejection drug (YUN S Y, HUR Y G

Problems solved by technology

Since these formulations must also satisfy the constraints associated with their final usage, the compromise between acceptability, concentration and stability is often difficult to reach.
More water soluble and/or oxidation resistant forms of phenolics such as the glycosides are not always available in nature and may demand, when they exist, complex procedures of extraction and purification from the plant material.
As phenolic compounds have several free hydroxyl groups, attempts for chemical modifications of phenolic compounds lead to unselective reactions, generating a panel of different molecules.
Nevertheless, this approach is impaired by the very high cost of t

Method used

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  • Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives
  • Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives
  • Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Glucosylated Taxifolin; Solubility in Water of Highly Purified Glucosylated Taxifolin and Stability of the Glucosylated Derivative Molecule at Temperatures Ranging from 4° C. to 45° C.

[0441]The conditions that were carried out for the synthesis of glucosylated Taxifolin are as follows (amounts for 1 liter of reaction medium):

IngredientOriginAmountConcentrationSolution of Taxifolin atTaxifolin: SIGMA T 4512100mlTaxifolin: 9 g / L90 g / L in pure DMSODMSORiedel de Haën 60153250mlTotal DMSO:350 ml / LSodium acetate bufferAcetic acid:40mlSodium acetate:500 mM pH 5.2Prolabo 20104.29820 mMSodium hydroxide:Riedel de Haën 6203Sucrose at 500 g / LProlabo 27478.296300ml150 g / L(1,462 M)0.439 MWaterDeionizedQsp 1.00L#Calcium chloride,Merck 1.02382.050010mg10 mg / Ldihydrate(can also be introduced inthe reaction medium in theform of a solution at 2 g / L;the dose is then 5 ml / L)DextransucrasePurified from L. mesenteroides170ml3.1 U / mlpreparation (18 U / ml)NRRL B-512F culture broth

[0442]The react...

example 2

Influence of the DMSO Concentration on the Efficiency of the Synthesis of Taxifolin Glucoside

[0469]Taxifolin glucoside enzymatic synthesis was carried out as described in Example 1 with the following exceptions:

[0470]enzyme concentration was 1 U / ml

[0471]DMSO concentration was 35%, 25%, 15% or 5%.

[0472]After 22 hours of incubation, relative Taxifolin glucoside concentrations in the four reaction medium are reported in the following table.

DMSO, %3525155Taxifolin glucoside10013316117(relative concentration), %

[0473]The optimal DMSO concentration for the synthesis of Taxifolin glucoside appears to be at a value significantly lower than 30% and close to 15%.

example 3

Activation of Taxifolin Glucoside by Human Skin Micro-Flora

[0474]Cutaneous flora was separately collected from 5 donors. The forearms and forehead of each donor were scraped with a cotton-wool swab saturated with NaCl solution (v=5 mL, 8 g / l). After each scraping, the swab was divided into the remaining NaCl solution and squeezed to deliver the sampled material. After two cycles of scraping / squeezing on both forearms and three on the forehead, the obtained trouble preparation was filtered (40 μm) to eliminate squama and finally centrifuged (4° C., 5000 g, 15 min). The microbial pellets were resuspended in a NaCl solution (v=1 mL, 8 g / l) and characterized by OD at 600 nm.

[0475]The five microbial samples were mixed to form the final microbial suspension used for the test. Microbial cells were cultivated using the Hickey-Tresner culture medium (yeast extract at 1.0 g / L, meat extract at 1.0 g / L, casein peptone at 2.0 g / L, starch at 10.0 g / L, cobalt chloride hexahydrate at 20 mg / l; pH=6)...

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Abstract

The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5). These O-α-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhythmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application.

Description

FIELD OF THE INVENTION[0001]The present invention relates to the preparation of phenolics derivatives, pharmaceutic and cosmetic compositions comprising such phenolics derivatives, and their use for the beauty of the skin and for treating diseases.BACKGROUND OF THE INVENTIONPhenolic Compounds and their Properties[0002]Phenolic compounds (also called phenolics), or polyphenols, constitute one of the most numerous and widely-distributed groups of substances in the plant kingdom, with more than 8,000 phenolic structures currently known. Polyphenols are products of the secondary metabolism of plants. The expression “phenolic compounds” embraces a considerable range of substances that possess an aromatic ring bearing one or more hydroxyl substituents. Most of the major classes of plant polyphenol are listed in Table 1, according to the number of carbon atoms of the basic skeleton. The structure of natural polyphenols varies from simple molecules, such as phenolic acids, to highly polymer...

Claims

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Application Information

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IPC IPC(8): A61K31/7048C12P19/60C07H17/06A61P35/00
CPCC12P17/02C12P19/02C07H15/203C12P19/60C07H15/26C07H17/075C12P19/44C07H15/24A61K8/602A61K31/7034A61Q19/00A61P17/00A61P29/00A61P31/04A61P35/00A61P37/02A61P37/08A61P9/00C07H17/00C12N1/20A61K8/73A61Q19/02
Inventor AURIOL, DANIELNALIN, RENAUDROBE, PATRICKLEFEVRE, FABRICE
Owner LIBRAGEN SA
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