Stabilization of vitamin C

Details Stabilization of vitamin C Stabilization of vitamin C

2000-02-15

2001-05-22

Krass, Frederick (Department: 1614)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

C514S027000, C514S474000, C424S401000, C424S439000, C424S440000, C424S195110

Reexamination Certificate

active

06235721

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an enriched natural anti-oxidative blend from
Emblica officinalis
fruit in the form of an amorphous powder, and, more particularly to a stable composition of Vitamin C or its derivatives, which has advantageous antioxidant and free radical captodative properties, and cosmetic, pharmaceutical and nutritional use compositions thereof.
2. Description of the Prior Art
As it is well known, L-ascorbic acid (vitamin C) is a naturally-occurring compound found in many fruits and vegetables. L-ascorbic acid functions in many biological processes such as collagen synthesis, anti-oxidation, intestinal absorption of iron and metabolism of some amino acids. An essential function of L-ascorbic acid in these processes is to act as a cofactor for the hydroxylation of proline and lysine residues in collagen, a major protein component of the body. L-ascorbic acid also increases the transcription rate of procollagen genes and stabilizes procollagen mRNA. Its well-known ability to cure scurvy, for example, may be also due to the stimulation of collagen synthesis in connective tissues.
While ascorbic acid possesses many indispensable biological properties, it has several disadvantages. For example, it is susceptible to air oxidation and sensitive to heat, and is unstable in aqueous solution, even under neutral pH and at room temperature. To solve these problems, the art has stabilized ascorbic acid by complexation with cyclodextrin, zeolites or liposomes. Another approach consists of stabilizing ascorbic acid by derivatization of its ene-diol function at the 2-position, for example, as L-ascorbic acid 2-phosphate or L-ascorbic acid 2-sulfate. The ascorbic acid 2-phosphate derivative does show some biological activity, however, ascorbic acid 2-sulfate is no longer an effective biological agent.
The provision of a stable ester at the 2-position of ascorbic acid also has been proposed. Monoalkyl esters having 1 to 18 carbon atoms, fluoroalkyl esters having 2 to 7 carbons and from 4 to 15 atoms of fluorine, and substituted benzoyl or cinnamate esters have been prepared for this purpose.
It is important to note that ascorbic acid can react with metal ions, such as iron and copper to yield active oxygen species and may act as a dangerous prooxidant [B. Halliwell,
Free Radical Research
, 25, 439-54 (1996)].
SUMMARY OF THE INVENTION
Accordingly, an object of this invention is to provide a natural antioxidant composition or blend having enriched antioxidant and free radical captodative properties, a process for obtaining such blends, and cosmetic, pharmaceutical and nutritional use formulations thereof, particularly for protection of skin against the damaging effects of the sun.
A particular object of this invention is to provide blends of such natural antioxidant composition, and ascorbic acid or derivatives thereof which are substantially more stable over extended periods of storage than for ascorbic acid itself.
These and other objects and features of the invention will be made apparent from the following more detailed description.
It has now been found, surprisingly, that the anti-oxidative fraction of
Emblica officinalis
, a member of small genus of Emblica trees, which are native to India, Sri Lanka, Malaysia and China, is much more stable under self-oxidation than L-ascorbic acid itself and some of its derivatives described in the literature. S. Ghosal et al, Indian J. of Chem. 35B, Sept. 1996, pages 941-948. Moreover, it has been found, unexpectedly, that the compounds according to this invention have much better anti-oxidative properties against reactive oxygen species and can stabilize and prolong the anti-oxidative properties of ascorbic acid.
The major advantage of the anti-oxidative product of this invention is its enhanced stability in an aqueous environment when compared with ascorbic acid or even magnesium ascorbyl phosphate. The product of this invention also contains low to medium molecular weight tannoids which augments its resultant anti-oxidant properties.
In addition to its anti-oxidative activity, the product herein can be formulated to provide significant protection against UV-induced erythema, particularly, by at least 50% when compared with a placebo formulation.
The anti-oxidant product of the invention (referred to hereinafter as “CAPROS”) is isolated in stable form from the fruit of
Emblica officinalis plant
using a very dilute aqueous or alcoholic water salt solution, e.g. a 0.1 to 5% (w/w), preferably 1 to 2%, of a sodium chloride, potassium chloride, calcium chloride or magnesium chloride solution, which prevents degradation of the anti-oxidant compounds therein by enzymes present in the fruits of the
Emblica officinalis plant
. Alternately, the antioxidant product is isolated using buffer solution, e.g. 0.1 to 5% (w/w), preferably 1 to 2%, of sodium citrate/citric acid, sodium acetate/acetic acid, sodium phosphate/phosphoric acid, instead of aqueous or alcoholic water salt solution.
The antioxidant composition of the invention provides advantageous cosmetic, pharmaceutical and nutritional compositions, generally at a use level of the invention compositions of from about a 0.05 to about 10% by weight.
The anti-oxidant composition of this invention contains, by weight, Em-A and B (gallic/ellagic acid derivatives of 2-keto-glucono-&dgr;-lactone) (35-55%), Punigluconin (2,3-di-O-galloyl-4,6-(S)-hexahydroxy-diphenoylgluconic acid) (4-15%), Pedunculagin (2,3,4,6-bis-(S)-hexahydroxydiphenoyl-D-glucose) (10-20%); Rutin (flavanol-3-)glycoside (5-15%); low to medium molecular weight gallo-ellagi tannoids (10-30%); gallic acid (0-5%) and ellagic acid (0-5%).
As a feature of the invention there is provided herein synergistically stabilized ascorbic acid or derivatives thereof by blending ascorbic acid with the anti-oxidant composition of the invention. The stability of such ascorbic acid-antioxidant formulations approach 100% as the antioxidant content is increased to 75% by weight of the formulation. More particularly, this blend is devoid of pro-oxidant activity, whereas Vitamin C or its derivatives have pro-oxidant properties
DETAILED DESCRIPTION OF THE INVENTION
Small tannoids of the gallo-ellagi tannins class couple with reductones like 2-keto-gluconolactone (and equivalents) to produce Emblicanin-A and Emblicanin-B, and other related tannoids of low molecular weight, which act as potent antioxidative and free radical captodative agents. The free radical chain-breaking process takes place more efficiently by CAPROS than the combination of ascorbic acid and vitamin E. In the presence of Rutin, a synergistic antioxidative-radical captodative effect was observed for the constituents in CAPROS.
A simple and efficient method of extracting, concentrating and preserving CAPROS, present in the fresh fruits of
Emblica officinalis
(Hindi, Amia), is described hereinafter.
This CAPROS extraction, concentration and preservation process results in the destruction of the native hydrolytic enzymes, e.g. glycosidases, present in the fresh fruits of Amia. The destruction of the glycosidic enzymes is achieved herein by heating the fresh fruit pulp in water containing, for example, 1 % NaCl (w/w), for 1 hour on a steam bath at 70°±5° C. The mixture is then filtered, refrigerated for 3 days, and spray-dried or, alternatively, vacuum dried. The presence of NaCl in the extraction medium prevent hyrolysis by the glycosidic enzymes in the plant, and, also, to protect the product from microbial infestation.
Several varieties of Amia, collected from certain regions in India, and at a predetermined time of harvesting, contain a relative abundance of Emblicanin-A and B, and their equivalents, and these compounds are isolated during the process of the invention. The CAPROS product obtained thereby can be used directly as a potent antioxidative and free radical captodative agent, or enriched further by subsequent chromatography.
The increased concentration of these agents in the composition of the i

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