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Kind code of ref document: Ref legal event code: Country of ref document: Date of ref document: Year of fee payment: The present invention relates to new water-soluble yellow colorant preparations derived dihydrochalcones, process for their preparation, and their uses, including food, pharmaceutical, or cosmetic.

The food and cosmetics industry has little solution for highly water-soluble yellow pigments. The most commonly used pigments are usually tartrazine E and curcumin E Tartrazine result of a chemical synthesis and has a certain allergenic. She is currently banned in Austria and Norway. Curcumin is, for its part, poorly water-soluble. Phloridzine is a natural polyphenol specific to apples, whose enzymatic oxidation has already been the subject of published work Raa and Overeem, Oszmianski and Lee, Ridgway et al,without however this work has resulted neither isolation nor to the elucidation of the chemical structure of the pigment formed.

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In addition, phloridzine is also known for its antioxidant activity Miller et al. One of the main objects of the present invention is to provide a novel compound usable as a dietary water-soluble yellow dye, and having the advantage: The invention also aims to provide compounds alkylated derivatives of the aforementioned compounds, maintaining a coloring ability menthr whose water-solubility is, where appropriate, modified with respect to that of the compound above-mentioned dye.

The invention also aims siop provide above-mentioned compounds for the preparation of drugs for radical scavenging activities antioxidant.

The invention relates to the compounds of the following formula I: The invention relates more particularly to the compounds defined above, of formula I- a follows: The invention more particularly relates to the compounds defined above, the formula I- b following: The invention relates more particularly to further compounds of formula Ia-1 and Ib-1 corresponding respectively to compounds Ia and Ib of the formulas defined above, wherein R 1 is H, and R 2 represents a glucose.

Alternatively, the used PPO is xe enzymatic extract of fungal or bacterial origin, such as described in Oszmianski and Lee, The invention also relates to a method as described above, characterized in that purification of the compounds of formula I- a or I- b, is performed by high performance liquid chromatography, preferably reverse phase, or by methods comprising filtration steps, centrifugation, and low pressure frontal chromatography.

The invention also relates to any alimentary composition characterized in that it comprises at least one compound of formula I- a or I- b above, or a composition as defined above.

The invention also relates to the use of at least one compound of formula I- a or I- b above, preferably of formula I-b, or a composition as defined above, as a colorant yellow to orange, particularly in the context of the food or feed. The invention also relates to any pharmaceutical or nutraceutical composition characterized in that it comprises at least one compound of formula Ia or I b above, preferably of formula Ia, or a composition as defined above, if appropriate in association with a pharmaceutically acceptable carrier.

The invention more particularly relates to any pharmaceutical composition as defined above, characterized in that it is presented in a form administrable by oral route, particularly in the form of oral suspension or tablets or capsules.

The invention also relates to the use of at least one compound of formula Ia or I b above, preferably of formula Ia, or a composition as defined above for the preparation of a medicament for antioxidant and radical-scavenging activity, in particular for the prevention or treatment of oxidative stress and diseases related to oxidative stress, including intervening in reducing the risk of developing cardiovascular disease and cancer. The invention also relates to any cosmetic composition characterized in that it comprises at least one compound of formula Ia or I b above, preferably of formula Ia, or a composition as defined above.


Advantageously, the above cosmetic compositions in the form of creams, or gels. The invention also relates to any method of cosmetic treatment, characterized in that it comprises applying to the skin of an individual to an aforementioned cosmetic composition. The invention will be also illustrated by the detection and structural characterization of compounds of formula I- a-1 that is 3- 4,5,4 ‘, 6′-tetrahydroxy-2’-glucosyl-biphenyl yl -propionic acid which is a precursor of the dye of formula I- b The term POP will be used to describe the coloring preparation containing the compounds of Formula Ib-1 and Ia-1, preferably of formula Ib As had been observed by Oszmianski and Leethe enzymatic oxidation of phlorizin has a lag time before the appearance of the color corresponding to yellow product of formula I- b The enzymatic oxidation of phloridzine seems to be virtually sequentially.

Oxidation of phloridzin first form the 3-hydroxy-phlorizin limiting step which is rapidly consumed to form the compound I- a This is then oxidized back again to form the product I-b-1 slower. It seems that the product I-b-1 thus has a lower affinity for catecholase activity of PPO extract as 3-hydroxyphloridzine. From this observation several technical solutions can produce a more or less rich in preparing dyes of the formula compounds I-b-1, or its direct precursor of formula I- a It can be obtained in a biotechnological reaction medium, controlling the enzymatic oxidation of phloridzin catalysed by the polyphenol oxidase activity PPOas it occurs naturally in the production of apple juice: The plant parenchyma, for example apple pulp is crushed in a medium allowing to avoid oxidation acid pH, cold, ascorbic acid.

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The solid particles of size greater than 50 microns are then removed by sieving to obtain a homogeneous suspension. It is then subjected to a tangential micro-filtration membrane 0. Finally, the recovered retentate is washed with a buffer without ascorbic acid, and then centrifuged. The pellet is dispersed in a minimum buffer.

An excerpt from phloridzine confronted with this excerpt from OPP. The cresolase activity, allows 3-hydroxyphloridzine training.

Chemical formula exhibits strong structural originality by the presence of a carboxylic acid functional group giving the molecule a strongly hydrophilic character. This is easily esterifiable by various chemical groups to give new structures more or less water-soluble, or can bring new features without affecting the coloring properties.

Unlike the main food soluble yellow dye currently used – tartrazine E – which is the result of chemical synthesis, the dye in question has been derived from phloridzin by an enzymatic method and corresponds to a portion of the natural color of a juice Apple. Instead POP dye is freely soluble in water logP negative. While the POP dye is readily washable with water.

Furthermore, colorimetric measurements with a Minolta spectrophotometer shows that the compound of formula I-b-1, the major component of the dye POP: The yellow pigment, referred to as POP ie Product Oxidation of Phloridzine is produced by enzymatic oxidation of phlorizin, a naturally occurring phenolic compound in apple and specific of this fruit.

The enzyme responsible is polyphenoloxidase, also naturally present in the potato but in a cellular compartment plastid different from phloridzin and other phenolic substrates vacuoles. Obtaining proper of the colorant preparation POP can be achieved in two ways: The detailed protocol is described below. For example the OPP method of extraction from plant pulp was applied to the apple pulp as indicated below: The cresolase activity apple PPO was extracted with 4 kg of apple Idared, placed in 20 L of water containing ascorbic acid 20 mM, 3.

Compote obtained by fine milling was then sieved, micro-filtered, rinsed and then centrifuged and taken up in 50 mL of water. Thus cresolase activity of the enzyme may be recovered from apples commercial from cold roomwithout special precautions at the pH adjustment. The oxidation was conducted in a volume of 1.


The assembly thus set allows the system to remain saturated with air. The solution was clarified by centrifugation and then lyophilized.


Injections 3 injections of 3 ml of the solution were carried out or 3 x 60 mg of lyophilizate. The volumes of 3 collections were gathered. The residual aqueous fraction was frozen, lyophilized and weighed. Structural analysis was performed on the dye molecule and its colorless intermediate purified. Confirmation de la conversion en esters: Confirmation of the conversion to esters: The conversion efficiencies were calculated based on the chromatograms at nm by taking the ratio of the areas of the peak of the ester to that of the peak of the compound of formula I-b-1 concentration in the same conditions see Table I.

Chromatographic Retention time, pseudo-molecular ions and conversion efficiencies of the compound of formula Ib-1 and its ester derivatives. It is therefore easily possible to convert the dye compound in other less soluble pigments for other applications cosmetics The antioxidant capacity of the molecule of formula I- a-1 colorless precursor and I- b-1 yellow pigment was determined on these molecules purified according to a protocol similar to that described in paragraph D.

Two methods of measuring antioxidant capacity in vitro were used: For comparison or to the expression of results, the antioxidant capacity following compounds were also measured: The given in brackets correspond to standard deviation. The expression values of antioxidant capacity Trolox equivalent TEAC showed very good consistency of results between the two methods.

The molecule of formula I-b-1 yellow pigment showed a weak antioxidant capacity.

This is the same as that of the phlorizin itself very low compared to other apple polyphenols such as – – epicatechin. However, the molecule of formula 1 a-1 colorless precursor showed significant antioxidant capacity 10 times that of its precursor phloridzin which however remains slightly lower than that of other standards such as the – – epicatechin, vitamin C or Trolox. Color measurements Minolta Chroma were also performed in this pH range.

Detailed results of the colorimetric parameters are reported below. Dye coloring of the parameters with respect to distilled water reference were measured in solution in a buffer of M c Ilvaine citrate-phosphate at various pH 2. Chromatographiee with the calibration plate Minolta No.

The coordinates of dye measured against distilled water are summarized in Table IV. Il faut remarquer cependant une grande constance de la teinte entre pH 2. However, note a great consistency of color between pH 2. An increase in pH also to accentuate the color saturation simultaneously with the color change. Comparable calorimetric study was carried out at pH 3 for varying concentrations Table V.

In the same way as when the change in pH, the brightness of the dye solutions decreases only very slightly as a function of concentration. The color remains in the yellow regardless of the concentration with a slight decrease in green shades with increasing concentration. L -1 The color saturation is well correlated with the concentration of dye to the concentration of 20 mg.

L -1, the detector saturates, the absorbance of the solution reaching from 3 to nm Figure 5 Figure 5. This correlation allows to assert that a 1 mg L -1 of dye in solution at pH 3 is equivalent to a gain of about 2 saturation points. The UV-visible spectrum is relatively stable at pH between 3 and 5 corresponding to the majority of the food. For higher pH, the color becomes orange while it becomes pale yellow with a slight green tinge to a pH below 3.

Finally, the color of the dye solution is at least as stable if not greater than tartrazine. For concentrations as high the resulting color is black with orange highlights.