Preserving the properties of vegetable oils

The combination of echinacea and pomegranate extracts with triglycerides of fatty acids addresses the challenges of inflammation and microbial growth in denture care by inhibiting triglyceride oxidation and providing anti-inflammatory effects, enhancing the care and protection of dentures and the oral cavity.

WO2025084941A1PCT designated stage expired Publication Date: 2025-04-24OBSHCHESTVO S OGRANICHENNOJ OTVETSTVENNOSTYU SPLAT GLOBAL
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Patent Information

Application Number
PCT/RU2023/000307
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-10-16
Publication Date
2025-04-24

AI Technical Summary

Technical Problem

Existing solutions for caring for dentures and the oral cavity often fail to effectively address inflammation, microbial growth, and wound healing, while also being environmentally friendly.

Method used

A composition combining echinacea and pomegranate extracts with triglycerides of fatty acids, which demonstrates synergistic antioxidant and anti-inflammatory properties, inhibiting the oxidation of fatty acid triglycerides in vegetable oils.

Benefits of technology

The combination of echinacea and pomegranate extracts significantly inhibits the oxidation of triglycerides, providing anti-inflammatory effects and promoting wound healing, thus enhancing the care and protection of dentures and the oral cavity.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention relates to a composition for lowering the peroxide value of a vegetable oil, containing echinacea extract and pomegranate extract.
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Description

[0001] PRESERVATION OF PROPERTIES OF VEGETABLE OILS

[0002] The invention relates to the field of means for caring for teeth, the oral cavity or dentures, in particular, to a combination of pomegranate and echinacea extracts, demonstrating pronounced synergism in the ability to inhibit the oxidation processes of fatty acid triglycerides in vegetable oils.

[0003] AREA OF TECHNOLOGY

[0004] A large number of people use dentures every day. According to statistics, the proportion of elderly patients forced to use dentures was 58% in Canada, 41% in Finland and 46% in the United Kingdom (Bilhan et al., 2012). Adentia affects various aspects: economic, social, physical and psychological, significantly worsening the quality of life. Not all patients forced to resort to prosthetics can afford fixed dentures both because of the high cost and because of health issues. Wearing removable dentures is associated with a number of fears and inconveniences for the consumer: concern about possible shifts of the denture and subsequent problems with pronunciation, chewing, the likelihood of food getting under the denture. The use of creams and gels for fixation allows the consumer to be confident in the condition of the denture. According to analysts, there is a trend towards developing not only functional dental products, but also products with improved properties.The market for dental products, including dentures, has grown in European countries [Mintel, 2022 UK oral Care Market report]. Consumers pay more attention to the content of natural ingredients in the composition of the product, eco-friendly packaging, and the ability of the product to cope not only with the main function, but also to provide additional care and protection [Mintel, The future of oral 2022].

[0005] The use of removable dentures is an economical solution that helps patients restore aesthetic and chewing functions, as well as solve problems with pronunciation that arise when teeth are lost and the jaw is deformed. However, it can entail a number of complications and affect oral health. One of the most common problems was the loss of retention of the denture. Loose fit led to viral microorganisms getting under the plate, which contributed to the development of gum inflammation or the formation of caries on healthy teeth. Many patients also spoke about a long period of adaptation to the denture, during which various wounds, traumatic ulcers and inflammations at the junction of healthy skin and the denture part, dental stomatitis occurred. Allergic reactions to resins in the composition of denture materials were observed.Thus, a modern denture cream should not only reliably fix, but also, if possible, combine the following functions: help cope with irritation and inflammation, have an antimicrobial effect, preventing the development of pathogenic microorganisms under the denture, moisturize the mucous membrane and promote wound healing. It is important for consumers not only to fix the denture, but also to protect themselves from possible complications associated with its use. One solution may be a composition using plant extracts and triglycerides of fatty acids, which will provide not only an anti-inflammatory effect, but will also promote wound healing and fight microorganisms that can cause oral diseases.

[0006] Denture stomatitis is a term used by dentists to describe pain and inflammation of the oral mucosa associated with wearing dentures. It can occur under both full and partial removable dentures on both jaws, but is more common on the upper jaw. It manifests itself as focal inflammation, point hyperemia and ulcers, as well as inflammation of entire areas. The prevalence of denture stomatitis reaches 65% in certain groups of patients (Budtz-Jorgensen, 1981). The causes of the disease are varied and may be related to the design of the denture, individual reactions of the body to the materials for prosthetics and improper hygiene of the denture.For example, when using materials with low thermal conductivity, the so-called “greenhouse effect” may occur, when the temperature under the denture plate is a fraction of a degree higher than in the oral cavity, which promotes the proliferation of bacterial and fungal microflora with subsequent development of the inflammatory process. The roughness of the denture materials, the discrepancy with the anatomical relief of the oral cavity can lead to microscopic traumatic damage to the mucous membrane and cause inflammation, and the ingress of microorganisms into the wounds can contribute to the development of infections. A number of researchers believe that the main cause of stomatitis is insufficient oral hygiene. With improper care, a favorable environment for the vital activity of bacteria is formed under the removable denture: moisture and food debris accumulate. Bacteria are able to penetrate into the plate material, and their number only increases as the period of use of the denture increases.At the same time, there is active growth of Candida albicans, the causative agent of candidiasis.

[0007] Thus, one of the priority areas in companies developing products for denture and oral care is the introduction of new components into formulations that effectively deal with inflammation, prevent the proliferation of harmful microorganisms and are environmentally friendly.

[0008] BACKGROUND OF THE INVENTION Several patent documents and commercial products implement various combinations of pomegranate extract, fatty acids, and echinacea extract. Document CH703109A1 (published 2011-11-15) describes a composition containing triglycerides of fatty acids for use in an adhesive cream for dentures. Fatty acids are planned to be used to maintain the structure of the composition. The authors did not consider the possibility of adding plant extracts to the composition, in particular pomegranate and echinacea extracts. Also, the authors do not consider other possible effects of the product, except for fixation of dentures.

[0009] Document CN1745744A (published 2006-03-15) discusses a composition with an extract of purple coneflower for oral care, aimed at the prevention and treatment of pain, inflammation of the gums, hemorrhages and ulcers in the oral cavity. The composition is planned to be used in the composition of toothpastes, thus the field of application is different. In addition, this document did not consider the interaction of the echinacea extract with fatty acid triglycerides or pomegranate.

[0010] Document US9968101B2 (published 2014-08-28) describes antimicrobial botanical compositions suitable for topical application to wounds, burns and pressure ulcers and potentially containing pomegranate oil and echinacea extract. In this composition, echinacea extract is used as antimicrobial and antiviral agents. However, the scope of application of the invention differs from this one. The authors also consider the use of echinacea extract as one of the possible options, but the authors provided a composition without it as an experimental sample of the composition, therefore, experimental confirmation of the operability of the product with pomegranate and echinacea was not obtained or provided by the authors.

[0011] Document KR101904684 (published 2017-06-08) describes variants of cosmetic compositions based on fatty acid triglycerides, where it is proposed to use pomegranate extract as an inhibitor of matrix metalloproteinase. It is proposed to use purple echinacea extract as a stimulator of glycosaminoglycan synthesis or as an anti-inflammatory component. The authors plan to use the composition in an emulsion for the skin, which does not correspond to the scope of application of this invention.

[0012] Document US9192635 (published 2015-11-24) describes a composition containing pomegranate extract and discusses its antioxidant properties. The authors described the ability of polyphenols included in the extract to bind peroxides, preventing oxidation. The composition is aimed at healing damaged mucosal tissue by inactivating toxic compounds in the target area. The authors did not consider the properties of pomegranate associated with the ability to provide anti-inflammatory effects. In addition, the use of the composition for denture care is not considered, which indicates a different field of application.

[0013] In document W02016106313A1 (published 2016-06-30), the authors propose an oral composition that can soothe irritated mucous membranes, stimulate saliva secretion and freshen breath. It is also planned to use it for the prevention of periodontitis and the treatment of gingivitis. It discusses the use of echinacea extract as a soothing and antiseptic agent, but does not discuss the use of pomegranate extract or triglycerides. In addition, the scope of application of the composition is different; the authors do not plan to use it as a cream for dentures.

[0014] Thus, when developing products for denture and oral care, there is a need to introduce new components into the formulations that effectively cope with inflammation, prevent the proliferation of harmful microorganisms and are environmentally friendly. One such solution is a cream composition using biogenic components such as triglycerides and plant extracts. This document examines the compositions of pomegranate and echinacea extracts, as well as fatty acid triglycerides from vegetable oils.

[0015] ESSENCE OF THE INVENTION

[0016] In a first aspect, the invention relates to a composition for reducing the peroxide value of vegetable oil, containing an echinacea extract and a pomegranate extract.

[0017] In an embodiment of the invention, the content of echinacea extract is from about 0.01 to about 1% by weight.

[0018] In an embodiment of the invention, the content of echinacea extract is about 0.05% by weight.

[0019] In an embodiment of the invention, the content of pomegranate extract is from about 0.01 to about 1% by weight.

[0020] In an embodiment of the invention, the content of pomegranate extract is about 0.05% by weight.

[0021] In an embodiment of the invention, the weight ratio of echinacea extract and pomegranate extract is approximately 1:1.

[0022] In an embodiment of the invention, the echinacea extract is hydroglycerin.

[0023] In one embodiment of the invention, the pomegranate extract is aqueous-glycerin.

[0024] In an embodiment of the invention, the composition additionally contains a solubilizer.

[0025] In an embodiment of the invention, the solubilizer is polysorbate 80.

[0026] In a second aspect, the invention relates to a vegetable oil composition comprising the composition of the invention.

[0027] In a third aspect, the invention relates to the use of a composition according to the invention for reducing the peroxide value of a vegetable oil. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Fig. 1 shows data on the peroxide value of the studied compositions 1-7.

[0029] DETAILED DESCRIPTION OF THE INVENTION

[0030] Punica granatum, commonly known as pomegranate, is considered useful for maintaining oral health. Pomegranate extract is obtained from the peel and pulp of the fruit. Due to the substances it contains, pomegranate extract has numerous beneficial properties that are widely used in cosmetics, medicine and oral hygiene. In vivo and in vitro studies have demonstrated pomegranate's anti-inflammatory, antioxidant and antimicrobial properties. Polyphenols, tannins, ellagic acid and anthocyanins contained in the plant are powerful antioxidants. Pomegranate peel exhibits antibacterial and astringent activity, and helps strengthen gums. Pomegranate extract also contains catechins and anthocyanins, which can have anti-inflammatory effects. Punica granatum has been shown to have anti-inflammatory activity, which has been attributed to its immunoregulatory activity against macrophages and lymphocytes (Gracious Ross et al., 2001).Several studies have shown that pomegranate extract helps treat periodontitis. Testing for antimicrobial activity against bacteria and yeasts showed that pomegranate was able to inhibit the growth of Staphylococcus aureus and some Candida species (Kote et al., 2011). Pomegranate extract significantly reduced the growth rate of Streptococcus mutans, sanguis, and lactobacilli colonies, the main microorganisms in dental plaque.

[0031] Echinacea is used worldwide as a supplement to strengthen the immune system, prevent and treat colds, and has phagocytic activity. The extract contains lipophilic compounds such as alkamides and polyacetylenes, chicory and caffeic acids, water-soluble polysaccharides, and a large number of flavonoids. Polyacetylenes isolated from Echinacea are capable of exerting anti-inflammatory activity (Safarabadi et al., 2017), and its polysaccharides promote the activation of T-lymphocytes and increased phagocytosis, which in turn helps fight various infections, including those in the oral cavity. Echinacea has been officially approved as a wound healing agent and an agent for combating pathogens such as Streptococcus mutans. The plant extract is also able to inhibit the growth of Staphylococcus Aureus, Staphylococcus epidermis, and E. coli.Also, according to some studies, the components of the echinacea extract are capable of destroying the cell walls of fungi, which makes it effective in the fight against mycosis and candidiasis. This is a type of gram-positive bacteria found in the oral cavity and is one of the main causes of caries due to the release of lactic acid. The synergy of chicory, coffee and rosmarinic acids and a mixture of alkamides from purple echinacea showed a significant antioxidant effect (Dalby-Brown et al., 2005). Chlorhexidine solution is often used to disinfect the oral cavity in dentistry and medicine, but scientists from Iran have shown that echinacea solution is also effective, but does not cause a number of side effects, such as xerostomia, increased dryness of the mucous membrane, unpleasant taste and burning after use.

[0032] Fatty acid triglycerides are organic molecules that are products of esterification of carboxylic acids and the trihydric alcohol glycerol. They consist of glycerol and three acid radicals with an unbranched structure and an even number of carbon atoms; the acid residues can be either saturated or unsaturated. Triglycerides obtained from olive oil are rich in oleic acid, palm oil - palmitic and oleic, and flaxseed - linoleic and linolenic. Fats are viscous liquids or solids, they are hydrophobic and practically insoluble in water, but dissolve well in organic solvents. Triglycerides from vegetable oils are used in medicinal, care and decorative cosmetics as emollients - moisturizing substances that saturate and soften the skin. Also, fatty acid esters can serve as a base in which the remaining functional components included in the composition will be placed.In addition, a properly selected composition of fatty acid residues can promote the transport function of triglycerides: the delivery of biologically active substances through the lipid barrier of the skin.

[0033] The introduction of fatty acid triglycerides into formulations was previously a problem, since polyunsaturated fatty acids are unstable and easily oxidized by atmospheric oxygen. When oxidized, they not only lose their properties, but also acquire an unpleasant taste and odor, which prevents their use in compositions. The depth and speed of oxidation processes depend on the amount of glycerides and the degree of unsaturation of acids. Oxidation occurs at the CH2 group located next to the double bond, the oxidation rate increases significantly if the CH2 group is located between two double bonds. The rate of oxidation can be affected by the intensity of interaction with oxygen and temperature. Due to the interaction of fats with atmospheric oxygen, there is an accumulation of decay products that can worsen the rheological properties of the composition. When saturated fatty acids are oxidized, saturated hydroperoxides are formed, and when unsaturated acids are oxidized, unsaturated hydroperoxides are formed.Peroxide compounds are unstable. They decompose under the influence of various agents to form secondary, more stable compounds - hydroxy acids, epoxides, aldehydes, ketones. There are so-called oxidation inhibitors - substances that prevent or delay the oxidation of fats. Tocopherols, which are part of pomegranate, can be such natural antioxidants. In addition, polyphenols, anthocyanins and acids from pomegranate extract have a powerful antioxidant effect and have long been used in the food industry as a preservative. Chicory and chlorogenic acids contained in echinacea extract are phenolic compounds and also have good antioxidant activity (Molaveisi et al., 2021). Due to this, the plant extracts included in the composition described in this document will prevent the oxidation of fatty acid triglycerides.

[0034] However, the inclusion of pomegranate and echinacea extracts in formulations may be associated with a number of problems due to their strong oxidation. Chicory and chlorogenic acids, as well as various caffeic acid derivatives, which are part of the echinacea extract and are responsible for its antioxidant properties, have low stability. They have been shown to be susceptible to enzymatic degradation and oxidation in aqueous environments (Molaveisi et al., 2021).

[0035] Ellagic acid, which is abundant in pomegranate extract, is unstable over a wide range of pH values. Ellagic acid is hydrolyzed to hexahydroxydiphenic acid, which results in color change of the extract (Panichayupakaranant et al., 2010). This makes it unsuitable for use in any aqueous solution. Galloylglucose, punicalin, gallic acid, and other phenolic compounds found in pomegranate extract are also unstable in solutions (Yepes-molina et al., 2021).

[0036] The authors unexpectedly discovered that the combination of pomegranate and echinacea extracts has a strong synergistic effect, expressed in a significant increase in their antioxidant properties, due to which they prevent the oxidation of fatty acid triglycerides. In addition, the combination of the two extracts inhibits the oxidation of each of them, which makes it possible to obtain a stable product. Thus, the invention relates to a composition for reducing the peroxide value of vegetable oil, containing echinacea extract and pomegranate extract.

[0037] The content of the echinacea extract may be from about 0.01 to about 1% by weight, such as about 0.01, about 0.02, about 0.03, about 0.04, about 0.05, about 0.06, about 0.07, about 0.08, about 0.09 or about 1% by weight, including from about 0.01 to about 0.02% by weight and similar ranges therebetween, where the term "about" refers to ±10% of the value. A content of about 0.05% by weight is preferred.

[0038] The content of the echinacea extract may be from 0.01 to 1% by weight, such as 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09 or 1% by weight, including from 0.01 to 0.02% by weight and similar ranges between the indicated values. A content of 0.05% by weight is preferred.

[0039] The content of the pomegranate extract may be from about 0.01 to about 1% by weight, such as about 0.01, about 0.02, about 0.03, about 0.04, about 0.05, about 0.06, about 0.07, about 0.08, about 0.09 or about 1% by weight, including from about 0.01 to about 0.02% by weight and similar ranges therebetween, where the term "about" refers to ±10% of the value. A content of about 0.05% by weight is preferred.

[0040] The content of the pomegranate extract may be from 0.01 to 1% by weight, such as 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09 or 1% by weight, including from 0.01 to 0.02% by weight and similar ranges between the indicated values. A content of 0.05% by weight is preferred.

[0041] In addition, a preferred weight ratio of the echinacea extract to the pomegranate extract may be about 1:1, where the term "about" refers to ±10% of the value. A weight ratio of 1:1 is preferred.

[0042] Echinacea extract may be hydroglycerin.

[0043] The pomegranate extract may be water-glycerin. and the composition may additionally contain a solubilizer. Such a solubilizer may be polysorbate 80.

[0044] The invention also relates to a vegetable oil composition containing a composition for reducing the peroxide value according to the invention, containing an echinacea extract and a pomegranate extract.

[0045] The invention also relates to the use of a composition according to the invention, containing an extract of echinacea and an extract of pomegranate, for reducing the peroxide value of vegetable oil.

[0046] IMPLEMENTATION OF THE INVENTION

[0047] Example 1.

[0048] Rancidity of vegetable oils was assessed using the method of determining the peroxide value in accordance with GOST R 51487-99.

[0049] The method is based on the reaction of the interaction of oxidation products of vegetable oils (peroxides and hydroperoxides) with potassium iodide in a solution of acetic acid and isooctane or chloroform, followed by quantitative determination of the released iodine with a solution of sodium thiosulfate using the titrimetric method.

[0050] The peroxide value is taken as the amount of such substances in the sample, expressed in mmol of active oxygen per 1 kg of fat, which, under the conditions of determination, oxidize potassium iodide.

[0051] Olive oil was used as a source of triglycerides; echinacea and pomegranate extracts were used in the form of aqueous-glycerol (AG) extracts, where the % of extracted substances was from 10 to 25% by weight. Polysorbate-80 (Tween 80) was chosen as a solubilizer.

[0052] The studied compositions and the experimental results are presented in Table 1 and Fig. 1.

[0053] Table 1. Peroxide value of compositions.

[0054] As can be seen from Table 1 and Fig. 1, the combination of pomegranate (0.05% wt.) and echinacea (0.05% wt.) (composition 4) has a pronounced synergistic effect on the ability to prevent premature oxidation of triglycerides in vegetable oil, which is expressed in a decrease in the peroxide value compared to the negative control (composition 1) and compared to the addition of single extracts (compositions 2 and 3). However, the authors unexpectedly discovered that with an increase in the concentration of extracts (up to 0.25% wt., composition 7), there is no inhibition of the triglyceride oxidation process, which may indicate a limited antioxidant potential of the extracts. It is possible that the extracts also contain oxidants in addition to antioxidants, which can additionally lead to oxidation of vegetable oils with an increase in the concentration of the studied extracts.

[0055] Thus, the authors demonstrated that the combination of pomegranate and echinacea extracts demonstrates pronounced synergism in the ability to inhibit the oxidation of fatty acid triglycerides in vegetable oils, which is a very useful property for maintaining the effectiveness and technical characteristics of the product. The authors also identified the concentrations at which the effectiveness of the combination is demonstrated.

[0056] LIST OF REFERENCES

[0057] 1) Bilhan, N., Erdogan, O., Ergin, S., Celik, M., Ates, G., & Geckili, O. (2012). Complication rates and patient satisfaction with removable dentures. The Journal of Advanced Prosthodontics, 4(2), 109. https: / / doi.Org / 10.4047 / jap.2012.4.2.109

[0058] 2) Budtz-Jorgensen, E. (1981). Oral mucosal lesions associated with the wearing of removable dentures. Journal of Oral Pathology and Medicine, 10(2), 65-80. https: / / doi.Org / 10.llll / j.1600-0714.1981.tb01251.x

[0059] 3) Dalby-Brown , L. , Barsett , H. , Landbo , A.-KR , Meyer , AS , & Molgaard , P. (2005). Synergistic Antioxidative Effects of Alkamides, Caffeic Acid Derivatives, and Polysaccharide Fractions from Echinacea purpurea on In Vitro Oxidation of Human Low-Density Lipoproteins. Journal of Agricultural and Food Chemistry, 55(24), 9413-9423. https: / / doi.org / 10.1021 / jf0502395

[0060] 4) Gracious Ross , R. , Selvasubramanian , S. , & Jayasundar , S. (2001). Preliminary studies on immunomodulatory activity of Punica granatum in rabbits. Journal of Ethnopharmacology, 78(1), 85-87. https: / / doi.org / 10.1016 / S0378-8741(01)00287-2

[0061] 5) Cote, S., Cote, S., & Nagesh, L. (2011). Effect of pomegranate juice on dental plaque microorganisms (streptococci and lactobacilli). Ancient Science of Life, 57(2). 6) Researcher, M., Shahidi Noghabi, M., Parastouei, K., & Taheri, RA (2021).

[0062] Fate of nano-phytosomes containing bioactive compounds of Echinacea extract in an acidic food beverage. Food Structure, 27, 100177. https: / / doi.org / 10.1016 / j .foostr.2021.100177

[0063] 7) Panichayupakaranant, P., Itsuriya, A., & Sirikatitham, A. (2010). Preparation method and stability of ellagic acid-rich pomegranate fruit peel extract. Pharmaceutical Biology, 48(2). https: / / doi.org / 10.3109 / 13880200903078503

[0064] 8) Safarabadi, M., Ghaznavi-Rad, E., Pakniyat, A., Rezaie, K., & Jadidi, A.

[0065] (2017). Comparing the effect of echinacea and chlorhexidine mouthwash on the microbial flora of intubated patients admitted to the intensive care unit. Iranian Journal of Nursing and Midwifery Research, 22(6), 481. https: / / doi.org / 10.4103 / ijnmr.IJNMR_92_l 6

[0066] 9) Yepes-molina, L., Hernandez, J. A., & Carvajal, M. (2021).

[0067] Nanoencapsulation of pomegranate extract to increase stability and potential dermatological protection. Pharmaceutics, 18(2). https: / / doi.org / 10.3390 / pharmaceuticsl3020271

Claims

CLAUSE OF INVENTION 1. A composition for reducing the peroxide value of vegetable oil, containing echinacea extract and pomegranate extract.

2. The composition according to claim 1, wherein the content of the echinacea extract is from about 0.01 to about 1% by weight.

3. The composition according to claim 2, in which the content of echinacea extract is about 0.05% by weight.

4. The composition according to claim 1, wherein the content of pomegranate extract is from about 0.01 to about 1% by weight.

5. The composition according to claim 4, in which the content of pomegranate extract is about 0.05% by weight.

6. The composition according to claim 1, wherein the weight ratio of the echinacea extract and the pomegranate extract is approximately 1:

1.

7. The composition according to claim 1, wherein the echinacea extract is hydroglycerin.

8. The composition according to claim 1, wherein the pomegranate extract is aqueous-glycerin.

9. The composition according to claim 1, additionally containing a solubilizer.

10. The composition of claim 9, wherein the solubilizer is polysorbate 80.

11. A vegetable oil composition comprising a composition according to any one of claims 1-10.

12. Use of a composition according to any of paragraphs 1-10 for reducing the peroxide value of vegetable oil.

Citation Information

Patent Citations

  • Process for reduction of peroxide compounds in animal / vegetable oils and fatty substances

    RU2008333C1

  • Formulations for treating upper airway disorders

    RU2580643C2

  • Botanical antimicrobial compositions

    US9968101B2

  • Oral compositions containing botanical extracts

    WO2009045952A1

  • Compositions useful in the prevention and / or treatment of osteoarticular inflammation and pain and cartilage damage

    WO2018002144A1