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Long chain glycolipids useful to avoid perishing or microbial contamination of materials

a technology of microbial contamination and long chain glycolipids, which is applied in the direction of antibacterial agents, biocides, hair cosmetics, etc., can solve the problems of reducing the shelf life or useful life of such products or goods, affecting the taste of products, and limited preservative effects in both duration and effect duration, so as to reduce the growth of microbial contaminants, reduce the ph value, and the effect of cost-effectiveness

Inactive Publication Date: 2014-06-26
IMD NATURAL SOLUTIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent relates to the use of certain glycolipid compounds with preservative or antimicrobial properties. The invention includes new compounds of the glycolipid class and methods of using them. The technical effect of this invention involves providing new compounds with preservative or antimicrobial properties that can be used in various applications such as in cosmetics and personal care products.

Problems solved by technology

Bacteria and other microbial organisms cause food and beverage products, cosmetic and home care products as well as other products to go bad, thereby reducing the shelf life or useful life of such products or goods.
Other food preservatives such as salt, sugar and vinegar have been used for generations and while relatively safe to use, their preservative effect is limited in both duration of effect and the types of food and beverages for which they can be used.
In addition, at higher levels, preservatives such as salt and vinegar can affect the taste of the product.
However, these materials often may not be tolerated or, e.g. in the case of formaldehyde, may even be toxic and even carcinogenic, or they may cause allergies or food intolerance.
Also smoke is often used for preserving meat products, with the undesirable side effect of formation of polycyclic aromatic hydrocarbons which have carcinogenic properties.
Other materials and also other types of beverages are susceptible to spoilage by microorganisms.
Also, packaged waters are susceptible to contamination by molds.
Furthermore, product packaging, solubility of the preservative and its antimicrobial susceptibility profile will influence preserving efficacy and, consequently, the shelf life of the products.
Also weak acid preservation systems, however, have limitations:
In addition, the other process techniques for low acid beverages (i.e., pH 4.6) have limitations.
To that end, those processing techniques may not eliminate the potential for spoilage.
Other chemical preservatives can likewise cause adverse side effects when consumed.
In addition, many preservatives, such as sodium benzoate, proprionates, aromatic benzenes, organic acids, propylene glycol and glycerol, for example, when used at levels sufficient for antimicrobial effects, impart an unpleasant taste on the beverage or food, masking or altering to some degree the taste expected by the consumer.
Weak acids can impart throat or mouth burn when used at high levels.
Although there are certain shelf-stable beverages where this attribute may be acceptable, this sensory perception is often considered negative.
Similarly, polyphosphates used in weak acid preservation systems can have some limitations.
The emollient solvents used as preservatives in cosmetics do not usually produce skin reactions, and in addition, render the skin smooth and silky.
Nevertheless the reported difficulties in the production teach the limitation of industrial usage as being relative low yields, high fermentation costs and difficult isolation procedures within industrial processes.
As commonly understood in the art, the definitions of the terms “preserve”, “preservative,” and “preservation” do not provide a standard time period for how long the matter to be preserved is kept from spoilage, decomposition, or discoloration.
Without a stated time period, it can be difficult or impossible to infer the time period required for a composition to act as a “preservative”.
In summary, many preservatives and preservation methods have undesirable side effects, such as toxicity, allergenicity, carcinogenicity, occasionally formation of resistance, and / or often are not accepted by the consumers in a time where natural preservation is preferred over preservation with synthetic or other products having a negative health image.

Method used

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  • Long chain glycolipids useful to avoid perishing or microbial contamination of materials
  • Long chain glycolipids useful to avoid perishing or microbial contamination of materials
  • Long chain glycolipids useful to avoid perishing or microbial contamination of materials

Examples

Experimental program
Comparison scheme
Effect test

example 1

Cultivation

A) Media:

[0510]1) SDB (Sabouraud Dextrose Broth, Ref. 238230, Difco™ Lawrence, Kans., USA, containing 0.5% Peptic Digest of Animal Tissue, 0.5% Pancreatic Digest of Casein, 2.0% Dextrose, pH 5.6.[0511]2) YMG (Yeast-Malt-Glucose) medium: D-glucose 0.4% (Merck, Darmstadt, Germany, Ref. K25252846 831), malt extract 1% (Carl Roth, Karlsruhe, Germany, Ref. X976.2), yeast extract 0.4% (Merck, Darmstadt, Germany, Ref. 1.11926.1000), pH 6.3.[0512]3) PDB (Potato Dextrose Broth): 2.0% D-glucose, 0.4% mashed potatoes (Pfanni, Hamburg, Germany).[0513]4) Cornmeal medium (CM): 2.0% corn meal (Neuform, Zarrentin, Germany), 1.0% D-glucose.[0514]5) GM1 (Glucose-Yeast medium 1): 2.0% D-glucose, 0.5% yeast extract.[0515]6) GM2 (Glucose-Yeast medium 2): 2.0% D-glucose, 0.1% yeast extract.[0516]7) Malt medium 1: 2.0% malt extract, 0.5% yeast extract.[0517]8) Malt medium 2: 2.0% malt extract without yeast extract.[0518]9) Apple juice medium: 10% apple juice (common commercial product: clear ju...

example 2

Structural Characterisation

Compound No. [1]

[0542]The molecular structure was elucidated by thorough interpretation of high resolution mass spectrometric data and 1D and 2D NMR spectra. The structural characterisation follows the general methodology which is known to the person skilled in the art and described in more detail in the scientific literature (examples: Nishida et al., J. Antibiot. 1991, 44, 541; Nishida et al, Chem. Pharm. Bull. 1991, 39, 3044).

[0543]The numbering of the atoms is shown in FIG. 1.

[0544]Chemical Formula: C49H88O21

[0545]Exact Mass: 1012.5818 Da

[0546]Molecular Weight: 1013.2104 Da

[0547]HR-ESIMS: found m / z 1013.5874; calculated m / z 1013.5891 for [M+H]+

[0548]NMR spectra were obtained in CD3OD at 293 K on a Bruker DRX spectrometer operating at 500 MHz proton frequency. The residual solvent peak was used as internal reference (δH=3.30; δC=49.0). The assigned NMR data are summarized in Tables 5-14.

TABLE 5NMR data for Compound No. [1]aglycon moietycarbohydrate moi...

example 3

HPLC-UV-MS-ELSD Analysis

A General Methods

a) “Standard Method”

[0549]LC-MS / UVELSD analyses were performed using an Agilent HP1100 (Agilent, Waldbronn, Germany) liquid chromatograph coupled with a LCT mass spectrometer (Waters Corporation, Milford, Mass., USA) in the positive and negative electrospray ionization (ESI) mode and a Sedex 75 Evaporative Light Scattering Detector (Sedere, Alfortville Cedex, France). A Waters symmetry column (Waters Symmetry® (Trademark by Waters) C18, 3.5 μm, 2.1 mm×150 mm, Waters GmbH, Eschborn, Germany) was used as stationary phase with a flow rate of 0.4 ml / min at 40° C. Mobile phase A: 0.1% formic acid in water, mobile phase B: 0.1% formic acid in acetonitrile; gradient: 0-1 min. 98% A, from 1-21 min. to 100% B, from 21-27 min 100% B. The UVN is spectra were recorded between 200-500 nm, the LC-MS (Liquid Chromatography-Mass Spectrometry coupling) spectra were recorded in the range of molecular weights between 160 and 1.600 Da.

b) “Adapted Method”

[0550]LC...

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Abstract

The invention relates to the use of, and methods of use employing, certain glycolipid compounds as defined in detail below and having preservative or antimicrobial properties, novel compounds of the glycolipid class, and related invention embodiments.The compounds have the formula Iwherein m is 3 to 5, n is 2 to 5, o is 0 or 1 and p is 3 to 17, with the proviso that the sum m+n+o+p is not less than 14; andR is a carbohydrate moiety bound via one of its carbon atoms to the binding oxygen,and / or a physiologically, especially pharmaceutically or nutraceutically or cosmetically, acceptable salt thereof, or an ester thereof,as such or in the form of a composition,where the compound may be present in open chain form and / or in the form of a lactone (FIG. 1).

Description

SUMMARY OF THE INVENTION[0001]The invention relates to the use of, and methods of use employing, certain glycolipid compounds as defined in detail below and having preservative or antimicrobial properties, novel compounds of the glycolipid class, and related invention embodiments.[0002]These and related invention embodiments are described below and in the claims which are incorporated into the specification by reference.BACKGROUND OF THE INVENTION[0003]Bacteria and other microbial organisms cause food and beverage products, cosmetic and home care products as well as other products to go bad, thereby reducing the shelf life or useful life of such products or goods. Thus, numerous efforts have been made to reduce the deleterious effects of microbial contaminants in food and beverage products, cosmetics, dressing material and other materials, e.g. medical devices such as implants.[0004]Other food preservatives such as salt, sugar and vinegar have been used for generations and while rel...

Claims

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Application Information

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IPC IPC(8): A01N43/16A61Q5/02A23L2/44C07H15/04A61K8/33A01N63/30
CPCA01N43/16A23L2/44C07H15/04A61Q5/02A61K8/33A01N43/14C12P19/44A23B4/20A23B5/14A23B7/154A23B9/26A61K8/365A61K8/37A61Q17/005A01N63/30A61K8/9728A61P31/04A61P31/10
Inventor STADLERBITZER, JENSKOPCKE, BARBELREINHARDT, KATHRINMOLDENHAUER, JANA
Owner IMD NATURAL SOLUTIONS GMBH
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