A composition for treating keratin material and methods thereof

Abstract

A COMPOSITION FOR TREATING KERATIN MATERIAL AND METHODS THEREOF The present disclosure provides a composition (A) comprising: a. oleanolic acid, its salts, solvates, or their mixtures thereof; b. ursolic acid, its salts, solvates, or their mixtures thereof; c. betulinic acid, its salts, solvates, or their mixtures thereof; and d. micromeric acid, its salts, solvates, or their mixtures thereof. The present disclosure further provides a rosemary extract and a composition (B). The present disclosure also provides a process for preparing the composition (A), the extract and methods thereof.

Description

A COMPOSITION FOR TREATING KERATIN MATERIAL AND METHODS THEREOFFIELD OF INVENTION

[0001] The present disclosure relates to a composition for treating keratin material, preferably skin. The present disclosure also relates to a process of obtaining the composition, a rosemary extract, and methods thereof.BACKGROUND OF INVENTION

[0002] In recent days, increasing pollution and deteriorating atmospheric conditions pose a significant challenge to skin. Hence, skin care needs a comprehensive approach to provide successful management of skin microbial community, maintain its cleanliness and manage its natural microbial fauna. Common skin issues seen are greasy skin, shiny skin, and acne.

[0003] Accordingly, there is an increased awareness of skin care. In today’s market, several products are available which claim for assured remedy for these issues. However, available chemical based synthetic formulations are not much appreciated by the consumers. Therefore, there has been a shift towards more eco- friendly bio-based skin care formulations. These formulations provide skin care benefits while maintaining a low environmental impact.

[0004] Hence, there is a need in the state of art to develop a composition with an optimized combination of natural components which can provide a wide range of skin benefits, especially for acne skin conditions.SUMMARY OF THE INVENTION

[0005] In an aspect of the present disclosure, there is provided a composition (A) comprising: a. oleanolic acid, its salts, solvates, or their mixtures thereof; b. ursolic acid, its salts, solvates, or their mixtures thereof; c. betulinic acid, its salts, solvates, or their mixtures thereof; and d. micromeric acid, its salts, solvates, or their mixtures thereof.

[0006] In another aspect of the present disclosure, there is provided a rosemary extract comprising: at least 30% by weight of ursolic acid, its salts, solvates, or their mixtures thereof; at least 10% by weight of oleanolic acid, its salts, solvates, or their mixtures thereof; at least 1% by weight of betulinic acid, its salts, solvates, or their mixtures thereof; and at least 5% by weight of micromeric acid, its salts, solvates, or their mixtures thereof.

[0007] In yet another aspect of the present disclosure, there is provided a process of preparing the composition (A) or the rosemary extract as disclosed herein, the process comprising: a. optionally grinding and sieving parts of Rosmarinus officinalis,' b. extracting parts of Rosmarinus officinalis with a first aprotic polar extractant to obtain a first filtrate and a first residue; c. optionally extracting the first residue with a second aprotic polar extractant to obtain a second filtrate and a second residue; d. concentrating the filtrate of step (b) and optionally step (c), to obtain a thick liquid mass; and e. precipitating the thick liquid mass using a prechilled aprotic polar solvent to obtain the composition (A) or the rosemary extract.

[0008] In one another aspect of the present disclosure, there is provided a composition (A) comprising a. oleanolic acid, its salts, solvates, or their mixtures thereof; b. ursolic acid, its salts, solvates, or their mixtures thereof; c, betulinic acid, its salts, solvates, or their mixtures thereof; and d. micromeric acid, its salts, solvates, or their mixtures thereof obtained by the process as disclosed herein.

[0009] In yet another aspect of the present disclosure, there is provided a composition (B) comprising: the composition (A) or the extract as disclosed herein in a physiologically acceptable medium optionally with at least one adjuvant.

[0010] In still another aspect of the present disclosure, there is provided a method of inhibiting growth of Cutibacterium acnes, the method comprising contacting Cutibacterium acnes with an effective amount of the composition (A) or the extract or the composition (B) as disclosed herein.

[0011] In more aspect of the present disclosure, there is provided a method of treating a keratin material, preferably skin, the method comprising applying the composition (A) or the extract or the composition (B) as disclosed herein, on thekeratin material, preferably skin. In some aspects, the method provides oil control and / or combats acne.

[0012] In another aspect of the present disclosure, there is provided a use of the composition (A), or the extract, or the composition (B) as disclosed herein, for treating a keratin material, preferably skin.

[0013] These and other features, aspects, and advantages of the present subject matter will be better understood with reference to the following description and appended claims. This summary is provided to introduce a selection of concepts in a simplified form. This summary is not intended to identify key features or essential features of the claimed subject matter, nor is it intended to be used to limit the scope of the claimed subject matter.DETAILED DESCRIPTION OF THE INVENTION

[0014] Those skilled in the art will be aware that the present disclosure is subject to variations and modifications other than those specifically described. It is to be understood that the present disclosure includes all such variations and modifications. The disclosure also includes all such steps, features, compositions, and compounds referred to or indicated in this specification, individually or collectively, and any and all combinations of any or more of such steps or features. Definitions

[0015] For convenience, before further description of the present disclosure, certain terms employed in the specification, and examples are delineated here. These definitions should be read in light of the remainder of the disclosure and understood as by a person of skill in the art. The terms used herein have the meanings recognized and known to those of skill in the art, however, for convenience and completeness, particular terms and their meanings are set forth below.

[0016] The articles “a”, “an” and “the” are used to refer to one or to more than one (i.e., to at least one) of the grammatical object of the article.

[0017] The terms “comprise” and “comprising” are used in the inclusive, open sense, meaning that additional elements may be included. It is not intended to be construed as “consists of only”.

[0018] The term "at least one" is used to mean one or more and thus includes individual components as well as mixtures / combinations.

[0019] Throughout this specification, unless the context requires otherwise the word “comprise”, and variations such as “comprises” and “comprising”, will be understood to imply the inclusion of a stated element or step or group of elements or steps but not the exclusion of any other element or step or group of element or steps.

[0020] The term “including” is used to mean “including but not limited to”, “including” and “including but not limited to” are used interchangeably.

[0021] The term “about” is used to mean an acceptable error range for the particular value as determined by one of ordinary skill in the art, which can depend in part on how the value is measured or determined, i.e., the limitations of the measurement system. For example, "about" can mean within 1 or more than 1 standard deviation, per the practice in the art. Where particular values are described in the present disclosure, unless otherwise stated the term "about" meaning within an acceptable error range for the particular value should be assumed.

[0022] The term “keratin material” refers in particular to skin, mucous membranes, fibers, eyelashes, and nails.

[0023] The term “skin” refers to the entire skin of the body, and more preferably the skin of the face, scalp, neckline, neck, arms, forearms, and back, and even more preferably, the skin of the face (especially the forehead, nose, cheeks, chin), neckline and neck.

[0024] The term “triterpenic acid” refers to phyto compounds, found in various plants. Triterpenic acids are a subclass of triterpenes and comprise six isoprene units. Triterpenic acids include but not limited to oleanolic acid, ursolic acid, betulinic acid, micromeric acid, glycyrrhetinic acid, boswellic acid and so on. For the purpose of the present disclosure, triterpenic acids refer to oleanolic acid, ursolic acid, betulinic acid and micromeric acid.

[0025] The term “salts” refers to an ionic compound formed by the neutralization reaction between an acid and a base. For the purpose of the present disclosure, the base may comprise an alkali metal (e.g. sodium or potassium) and alkali earth metal(e.g. calcium or magnesium) hydroxides, and organic bases, for example alkyl amines, arylalkyl amines and so on. For the purpose of present disclosure, the composition may comprise at least one of the disclosed compounds in the form of salt, such as one or more salts of oleanolic acid, and / or one or more salts of ursolic acid, and / or one or more salts of betulinic acid, and / or one or more salts of micromeric acid, preferably alkali metal salts, such as potassium salts. In a more preferred embodiment, the composition comprises one or more salts of oleanolic acid, one or more salts of ursolic acid, one or more salts of betulinic acid, and one or more salts of micromeric acid, preferably alkali metal salts, such as potassium salts.

[0026] The term “physiologically acceptable medium” refers to a medium, such as organic solvent or aqueous solvent optionally comprising components such as pH adjusters, buffers and / or nutrients, that are compatible with keratin materials, particularly skin, ensuring to maintain appropriate pH and other cosmetic benefits.

[0027] The term “solvates” refers to crystalline solids that contain stoichiometrically or non-stoichiometrically solvent molecules inside their crystal assembly. Solvents include but are not limited to water, alcohol, ether, nitriles or combination thereof. For the purpose of present disclosure, the composition may comprise at least one or more solvates of triterpenic acid selected from oleanolic acid, ursolic acid, betulinic acid, and micromeric acid.

[0028] The terms “aprotic polar extractant” and “aprotic polar solvent” independently refers to an extractant or a solvent which is polar in nature and does not have an acidic proton. These are devoid of hydroxyl and / or amine groups and, hence do not serve as proton donors in hydrogen bonding. For the purpose of the present disclosure, the process of preparing the composition involves the use of aprotic polar extractants / solvents independently selected from ethyl acetate, acetone, acetonitrile, and tetrahydrofuran.

[0029] The term “colony forming unit (CFU)” refers to a unit which defines the total number of viable microbial cells. In the controlled conditions these cells can multiply via binary fission.

[0030] The term “minimum bactericidal concentration (MBC)” refers to the lowest concentration of an anti-bacterial agent required to kill a particular bacteria or microbe. MBC is identified by determining the lowest concentration of antibacterial agent that reduces the viability of the initial bacterial inoculum by >99.9%.

[0031] The term “INCI” is an abbreviation of International Nomenclature of Cosmetic Ingredients, which is a system of names provided by the International Nomenclature Committee of the Personal Care Products Council to identify cosmetic or personal care ingredients.

[0032] All percentages, parts and ratios are based upon the total weight of the compositions of the present disclosure unless otherwise indicated. Ratios, concentrations, amounts, and other numerical data may be presented herein in a range format. It is to be understood that such range format is used merely for convenience and brevity and should be interpreted flexibly to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited. For example, a percentage range of 15 to 30% should be interpreted to include not only the explicitly recited limits of 15 to 30%, but also to include sub-ranges, such as 18 to 29%, 17 to 25%, and so forth, as well as individual amounts, including fractional amounts, within the specified ranges, such as 18.4 %, 22.2 %, and 24.75% for example.

[0033] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of the ordinary skill in the art to which this disclosure belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the disclosure, the preferred methods and materials are now described.

[0034] The present disclosure is not to be limited in scope by the specific embodiments described herein, which are intended for the purposes of exemplification only. Functionally equivalent products, compositions, and methods are clearly within the scope of the disclosure, as described herein.

[0035] As discussed in the background, use of skin care products is increasing day by day and there is always a need for an effective composition for skin treatment.Existing compositions have associated challenges to provide the acne-free skin along with skin compatible components. Hence, a skin care composition comprising natural ingredients is much desired. Accordingly, the present disclosure provides a composition (A) comprising oleanolic acid, its salts, solvates, or their mixtures thereof; ursolic acid, its salts, solvates, or their mixtures thereof; betulinic acid, its salts, solvates, or their mixtures thereof; and micromeric acid, its salts, solvates, or their mixtures thereof. The composition (A) comprises at least 60% by weight of these triterpenic acids. The specific weight ratio of said triterpenic acids in the composition is advantageous in terms of its anti-microbial activity, preferably anti-bacterial activity. Additionally, the present disclosure also provides a process of preparation of composition (A) and Rosmarinus officinalis extract, having a combination of oleanolic acid, ursolic acid, betulinic acid, and micromeric acid. The present disclosure also provides composition (B) comprising composition (A) o Rosmarinus officinalis extract in a physiologically acceptable medium with other adjuvants. The compositions or the extract of the present disclosure show biocidal and microbiostatic effects. The components of the composition function synergistically and exhibit selective inhibition against Cutibacterium acnes.

[0036] Accordingly, embodiments of the present disclosure include a composition (A) comprising at least 10% of oleanolic acid, at least 30% of ursolic acid, at least 1% of betulinic acid, and at least 5% of micromeric acid, process of preparation of the composition (A) or rosemary extract via extraction of Rosmarinus officinalis, a composition (B), a method of inhibiting growth of Cutibacterium acnes and a method of treating a keratin material, preferably skin. The disclosed embodiments of the present disclosure show, how an effective amount of the composition (A) or extract or composition (B) inhibits the growth of Cutibacterium acnes. Embodiments of the present disclosure further provide a composition (A) or extract or composition (B) which provides oil control and / or combats acne of the keratin material. Present disclosure further provides the use of disclosed composition (A) or the extract or the composition (B) for treating a keratin material, preferably skin.Composition (A)

[0037] Embodiments herein provide a composition (A) for treating a keratin material, preferably skin. The composition (A) of the present disclosure provides oil control and / or combats acne of the keratin material. The composition according to embodiments herein is a composition of an extract of Rosmarinus officinalis.

[0038] Embodiments herein provide a composition (A) comprising oleanolic acid, its salts, solvates, or their mixtures thereof; ursolic acid, its salts, solvates, or their mixtures thereof; betulinic acid, its salts, solvates, or their mixtures thereof; and micromeric acid, its salts, solvates, or their mixtures thereof.

[0039] The composition (A), according to embodiments herein, comprises at least 10% by weight of oleanolic acid, at least 30% by weight of ursolic acid, at least 1% by weight of betulinic acid and at least 5% by weight of micromeric acid.

[0040] The composition (A), according to the embodiments herein, comprises at least 60% by weight of triterpenic acids, their salts, solvates, or their mixtures thereof, selected from oleanolic acid, ursolic acid, betulinic acid, and micromeric acid. Preferably, the composition (A) comprises salts of triterpenic acids selected from salts of oleanolic acid, salts of ursolic acid, salts of betulinic acid, salts of micromeric acid, and their mixtures thereof.

[0041] The composition (A), according to embodiments herein, comprises oleanolic acid and micromeric acid in a weight ratio range of 1.2: 1 to 3 : 1, preferably in a range of 1.5: 1 to 2.5: 1.

[0042] In a preferred embodiment, the composition (A) comprises oleanolic acid and micromeric acid in a weight ratio range of 1.2: 1 to 3 : 1, preferably in a range of 1.5: 1 to 2.5: 1, and more preferably in a range of 1.8: 1 to 2.1 : 1.

[0043] The composition (A), according to embodiments herein, comprises oleanolic acid, ursolic acid, betulinic acid, and micromeric acid in a weight ratio range of 1.2:2:0.1 : l to 3:5:0.5: l.

[0044] In a preferred embodiment, the composition (A) comprises oleanolic acid, ursolic acid, betulinic acid, and micromeric acid in a weight ratio range of 2.1 : 4: 0.4: 1 to 1.8:3.5:0.34: 1 and more preferably in a range of 2.0: 3.8: 0.38: 1 to 1.85: 3.6: 0.34: 1.

[0045] The composition (A), according to embodiments herein, further comprises at least one component selected from polyphenols, carbohydrates, fat, proteins, water, or combinations thereof.

[0046] The composition (A), according to embodiments herein, exhibits antimicrobial activity, preferably anti-bacterial activity.

[0047] The composition (A) according to embodiments herein inhibits the growth of Cutibacterium acnes.

[0048] Embodiments herein also provide a composition (A) for treating a keratin material. Particularly, embodiments herein provide applying the composition on the keratin material for treating a keratin material, preferably skin. More preferably, the method provides oil control, and / or combats acne.Oleanolic acid

[0049] Embodiments herein provide a composition (A) comprising oleanolic acid.

[0050] The term “oleanolic acid” or “oleanic acid” refers to 3P-hydroxyolean-12- en-28-oic acid. The term oleanolic acid also refers to compound named as aS,6aR,6aS,6bR, aR, 105, YlaR, 14 / ?5)- l O-hy droxy -2,2,6a, 6b, 9,9,12a- heptamethyl-l,3,4,5,6,6a,7,8,8a,10,l l,12,13,14Z>-tetradecahydropicene-4a- carboxylic acid. Oleanolic acid is a pentacyclic triterpenoid which is widely distributed in plants.

[0051] The structure of oleanolic acid is shown in Formula (I).Formula (I)

[0052] In an embodiment, the composition (A) comprises oleanolic acid, its salts, solvates, or their mixtures thereof.

[0053] As examples of basic salts, mention may be made of alkali metal hydroxides such as sodium, potassium and lithium; alkaline-earth metal hydroxides such ascalcium and magnesium; hydroxides of other metals, such as aluminium and zinc; ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or tri-alkylamines; dicyclohexylamines; tributylamines; pyridine; N-methyl-N- ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2- hydroxyalkylamines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2- hydroxy-tert-butylamine, tris(hydroxymethyl)methylamine, N,N-dialkyl-N- (hydroxyalkyl)amines, such as N,N-dimethyl-N-(2-hydroxyethyl)amine; N- methyl-D-glucamine; and amino acids such as arginine and lysine.

[0054] In some embodiments, the composition (A) comprises oleanolic acid, its salt of inorganic bases or mixtures thereof. Examples of inorganic bases include but not limited to alkali metal hydroxides, alkaline earth metal hydroxides or combination thereof. In a preferred embodiment, the composition comprises oleanolic acid, its salt of inorganic bases or mixtures thereof, more preferably sodium or potassium salts.

[0055] In some embodiments, the composition (A) comprises oleanolic acid, or its solvate, their mixtures thereof. Examples of solvents for the formation of solvates include but not limited to water, alcohol, ether, or nitriles.

[0056] In a preferred embodiment, the composition (A) comprises oleanolic acid, its potassium salt or mixtures thereof.

[0057] In an embodiment, the composition (A) comprises at least 10% by weight of oleanolic acid, preferably in a range of 10 to 35% by weight, and more preferably in a range of 15 to 30% by weight.

[0058] In an embodiment, the composition (A) comprises at least 10% by weight of oleanolic acid, its salts, solvates or mixtures thereof, preferably in a range of 10 to 35% by weight, and more preferably in a range of 15 to 30% by weight.

[0059] In a preferred embodiment, the composition (A) comprises at least 10% by weight of oleanolic acid, preferably in a range of 10 to 35% by weight, more preferably in a range of 15 to 30% by weight, and most preferably in a range of 18 to 29% by weight.Ursolic acid

[0060] Embodiments herein provide a composition (A) comprising ursolic acid.

[0061] The term “ursolic acid” refers to 3P-hydroxyurs-12-en-28-oic acid or ( 1 S,2R, aS, 6aR, 6aS,6bR, 8aR, 1 OS, 12aR, 14bS)- 10-hy droxy- 1 ,2, 6a, 6b, 9,9, 12a- heptamethyl-2, 3, 4, 5,6,6a, 7,8,8a, 10,1 l , l 2, l 3, l4A-tetradecahydro- l7 / -picene-4a- carboxylic acid. This is a naturally occurring pentacyclic triterpenoid and is widely distributed in plants.

[0062] The structure of ursolic acid is shown in Formula (II).Formula (II)

[0063] In an embodiment, the composition (A) comprises ursolic acid, its salts, solvates, or their mixtures thereof.

[0064] In some embodiments, the composition (A) comprises ursolic acid, its salts or their mixtures thereof.

[0065] As examples of basic salts, mention may be made of alkali metal hydroxides such as sodium, potassium and lithium; alkaline-earth metal hydroxides such as calcium and magnesium; hydroxides of other metals, such as aluminium and zinc; ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or tri-alkylamines; dicyclohexylamines; tributylamines; pyridine; N-methyl-N- ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2- hydroxyalkylamines) such as mono-, bis- or tri s-(2-hy droxy ethyl)amine, 2- hy droxy -tert-butylamine, tris(hydroxymethyl)methylamine, N,N-dialkyl-N- (hydroxyalkyl)amines, such as N,N-dimethyl-N-(2-hydroxyethyl)amine; N- methyl-D-glucamine; and amino acids such as arginine and lysine.

[0066] In some embodiments, the composition (A) comprises ursolic acid, its salt of inorganic bases or mixtures thereof. Examples of inorganic bases include but not limited to alkali metal hydroxides, alkaline earth metal hydroxides or combination thereof. In a preferred embodiment, the composition comprises ursolic acid, its salt of inorganic bases or mixtures thereof, more preferably sodium or potassium salts.

[0067] In some embodiments, the composition (A) comprises ursolic acid, its solvate or their mixtures thereof. Examples of solvent for the formation of solvates include but not limited to water, alcohol, ether, or nitriles.

[0068] In preferred embodiment, the composition (A) comprises ursolic acid, its potassium salt or mixtures thereof.

[0069] In an embodiment, the composition (A) comprises at least 30% by weight of ursolic acid, preferably in a range of 30 to 60% by weight, and more preferably in a range of 35 to 55% by weight.

[0070] In an embodiment, the composition (A) comprises at least 30% by weight of ursolic acid, its salts, solvates or their mixtures thereof, preferably in a range of 30 to 60% by weight, and more preferably in a range of 35 to 55% by weight.

[0071] In a preferred embodiment the composition (A) comprises at least 30% by weight of ursolic acid, preferably in a range of 30 to 60% by weight, more preferably in a range of 35 to 55% by weight, and most preferably in a range of 36 to 54% by weight.Betulinic acid

[0072] Embodiments herein provide a composition (A) comprising betulinic acid.

[0073] The term “betulinic acid” refers to 3 P-hydroxylup-20(29)-en -28-oic acid or (\R, aS,5aR,5bR,1aR,9S,\ la / ?,l I / ri , l 3a / , l 3 / ri )-9-hydroxy-5a,5A,8,8, l la- pentamethyl- l -prop- 1 -en-2-yl- l ,2,3,4,5,6,7,7a,9, l 0, 1 1 , 1 1 / ?, l 2, 13, 13a, l 3A- hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid. This is a naturally occurring pentacyclic triterpenoid and widely distributed in plants.

[0074] The structure of betulinic acid is shown in Formula (III).Formula (III)

[0075] In an embodiment, the composition (A) comprises betulinic acid, its salts, solvates, or their mixtures thereof.

[0076] As examples of basic salts, mention may be made of alkali metal hydroxides such as sodium, potassium and lithium; alkaline-earth metal hydroxides such as calcium and magnesium; hydroxides of other metals, such as aluminium and zinc; ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or tri-alkylamines; dicyclohexylamines; tributylamines; pyridine; N-methyl-N- ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2- hydroxyalkylamines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2- hydroxy-tert-butylamine, tris(hydroxymethyl)methylamine, N,N-dialkyl-N- (hydroxyalkyl)amines, such as N,N-dimethyl-N-(2-hydroxyethyl)amine; N- methyl-D-glucamine; and amino acids such as arginine and lysine.

[0077] In some embodiments, the composition (A) comprises betulinic acid, its salt of inorganic bases or mixture thereof. Examples of inorganic bases include but not limited to alkali metal hydroxides, alkaline earth metal hydroxides or combination thereof. In a preferred embodiment, the composition (A) comprises betulinic acid, its salt of inorganic bases or mixture thereof, more preferably sodium or potassium salts.

[0078] In some embodiments, the composition (A) comprises betulinic acid, or its solvate, their mixtures thereof. Examples of solvent for the formation of solvates include but not limited to water, alcohol, ether, or nitriles.

[0079] In a preferred embodiment, the composition (A) comprises betulinic acid, its potassium salt or mixture thereof.

[0080] In an embodiment, the composition (A) comprises at least 1% by weight of betulinic acid, preferably in a range of 1 to 20% by weight, and more preferably in a range of 2 to 15% by weight.

[0081] In an embodiment, the composition (A) comprises at least 1% by weight of betulinic acid, its salts, solvates or their mixtures thereof, preferably in a range of 1 to 20% by weight, and more preferably in a range of 2 to 15% by weight.

[0082] In a preferred embodiment, the composition (A) comprises at least 1% by weight of betulinic acid, preferably in a range of 1 to 20% by weight, more preferably in a range of 2 to 15% by weight, and most preferably in a range of 3 to 6% by weight.Micromeric acid

[0083] Embodiments herein provide a composition (A) comprising micromeric acid.

[0084] The term “micromeric acid” refers to 3P-hydroxyurs-12,20(30)-dien-28-oic acid or lA,4a5',6a5',6Z>A,105',12aA,14Z>5)-10-hydroxy-l,6a,6Z>,9,9,12a-hexamethyl- 2-methylidene- 1 , 3 ,4, 5 ,6, 6a, 7, 8, 8a, 10, 11 , 12, 13 , 14Z>-tetradecahy dropicene-4a- carboxylic acid. This is a naturally occurring pentacyclic triterpenoid and widely distributed in plants.

[0085] The structure of micromeric acid is shown in Formula (IV)Formula (IV)

[0086] Preferably, the structure of micromeric acid is as shown in Formula (V)Formula (V)

[0087] In an embodiment, the composition (A) comprises, micromeric acid, its salts, solvates, or their mixtures thereof.

[0088] As examples of basic salts, mention may be made of alkali metal hydroxides such as sodium, potassium and lithium; alkaline-earth metal hydroxides such as calcium and magnesium; hydroxides of other metals, such as aluminium and zinc; ammonia and organic amines such as unsubstituted or hydroxy-substituted mono-, di- or tri-alkylamines; dicyclohexylamines; tributylamines; pyridine; N-methyl-N- ethylamine; diethylamine; triethylamine; mono-, bis- or tris-(2- hydroxyalkylamines) such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2- hydroxy-tert-butylamine, tris(hydroxymethyl)methylamine, N,N-dialkyl-N- (hydroxyalkyl)amines, such as N,N-dimethyl-N-(2-hydroxyethyl)amine; N- methyl-D-glucamine; and amino acids such as arginine and lysine.

[0089] In some embodiments, the composition (A) comprises micromeric acid, its salt of inorganic bases or mixtures thereof. Examples of inorganic bases include but not limited to alkali metal hydroxides, alkaline earth metal hydroxides or combination thereof. In a preferred embodiment, the composition comprises micromeric acid, its salt of inorganic bases or mixture thereof, more preferably sodium or potassium salts.

[0090] In some embodiments, the composition(A) comprises micromeric acid, its solvate, or their mixtures thereof. Examples of solvents include but not limited to water, alcohol, ether, nitriles or combination thereof.

[0091] In a preferred embodiment, the composition (A) comprises micromeric acid, its potassium salt or mixtures thereof.

[0092] In an embodiment, the composition (A) comprises at least 5% by weight of micromeric acid, preferably in a range of 5 to 22% by weight, and more preferably in a range of 7 to 20% by weight.

[0093] In an embodiment, the composition (A) comprises at least 5% by weight of micromeric acid, its salts, solvates or their mixtures thereof, preferably in a range of 5 to 22% by weight, and more preferably in a range of 7 to 20% by weight.

[0094] In a preferred embodiment, the composition (A) comprises at least 5% by weight of micromeric acid, preferably in a range of 5 to 22% by weight, more preferably in a range of 7 to 20% by weight, and most preferably in a range of 9 to 15% by weight.Other components

[0095] The composition (A), according to embodiments herein, may also include one or more other components, which may be notably chosen from polyphenols, carbohydrates, fat, proteins, water, or combinations thereof.

[0096] In an embodiment, the composition (A) further comprises at least one component selected from polyphenols, carbohydrates, fat, proteins, water, or combinations thereof.

[0097] In an embodiment, the composition (A) comprises polyphenols preferably less than 0.5% by weight.

[0098] In an embodiment, the composition (A) comprises other components preferably in a range of 10 to 45% by weight, and more preferably in a range of 15 to 40% by weight.

[0099] In an embodiment, the composition (A) comprises acetyl- 11-keto-beta boswelic acid or Boswelia serrata extract. In a particular embodiment the composition (A) comprises Boswelia serrata extract comprising acetyl- 11-keto- beta boswelic acid. In a preferred embodiment, the Boswelia serrata extract is rich in acetyl- 11-keto-beta boswelic acid.

[0100] It is understood that a person skilled in the art will take care to select the other components and / or the amount thereof such that the advantageous properties of the composition used according to the disclosure are not, adversely affected bythe envisaged addition. All such embodiments including the optional components are understood to be included within the scope of the present disclosure.Rosemary extract

[0101] Embodiments herein provide a rosemary extract comprising oleanolic acid, ursolic acid, betulinic acid, and micromeric acid.

[0102] In an embodiment, there is provided a rosemary extract comprising at least 30% by weight of ursolic acid; at least 10% by weight of oleanolic acid; at least 1% by weight of betulinic acid; and at least 5% by weight of micromeric acid.

[0103] In an embodiment, there is provided a rosemary extract comprising at least 30% by weight of ursolic acid, its salts, solvates, or their mixtures thereof; at least 10% by weight of oleanolic acid, its salts, solvates, or their mixtures thereof; at least 1% by weight of betulinic acid, its salts, solvates, or their mixtures thereof; and at least 5% by weight of micromeric acid, its salts, solvates, or their mixtures thereof.

[0104] In some embodiments, the rosemary extract comprises 30 to 60% by weight of ursolic acid; 10 to 35% by weight of oleanolic acid; 1 to 20% by weight of betulinic acid; and 5 to 22% by weight of micromeric acid.

[0105] In some embodiments, the rosemary extract comprises 35 to 55% by weight of ursolic acid; 15 to 30% by weight of oleanolic acid; 2 to 15% by weight of betulinic acid; and 7 to 20% by weight of micromeric acid.

[0106] In a preferred embodiment, the rosemary extract comprises 36 to 54% by weight of ursolic acid; 18 to 29% by weight of oleanolic acid; 3 to 6% by weight of betulinic acid; and 9 to 15% by weight of micromeric acid.

[0107] In a much preferred embodiment, the rosemary extract comprising 36 to 40% by weight of ursolic acid; 18 to 22% by weight of oleanolic acid; 3 to 4% by weight of betulinic acid; and 9 to 11% by weight of micromeric acid.

[0108] In an embodiment, the rosemary extract comprises oleanolic acid and micromeric acid in a weight ratio in a range of 1.2: 1 to 3 : 1, preferably in a range of 1.5: 1 to 2.5: 1, preferably in a range of 1.5 : 1 to 2.5 : 1 , and more preferably in a range of 1.6: 1 to 2.4: 1.

[0109] In an embodiment, the rosemary extract comprises oleanolic acid, ursolic acid, betulinic acid, and micromeric acid in a weight ratio in a range of 1.2:2:0.1 : 1 to 3:5:0.5: 1, preferably oleanolic acid, ursolic acid, betulinic acid, and micromeric acid are in a weight ratio in a range of 2.1 : 4: 0.4: 1 to 1.8: 3.5:0.34: 1.

[0110] In a preferred embodiment, the rosemary extract as disclosed herein, comprises oleanolic acid, ursolic acid, betulinic acid, and micromeric acid in a weight ratio in a range of 2.0: 3.8: 0.38:1 to 1.85: 3.6: 0.34: 1.[OHl] In an embodiment, the rosemary extract as disclosed herein, further comprises at least one component selected from polyphenols, carbohydrates, fat, proteins, water, or combinations thereof.

[0112] In an embodiment, the rosemary extract as disclosed herein, exhibits biocidal and microbiostatic effect.

[0113] In an embodiment, the rosemary extract as disclosed herein, is obtained by the process as disclosed herein.Process for obtaining composition (A) or the Rosemary extract

[0114] Embodiments herein provide a process of preparing the composition (A) or the rosemary extract as disclosed herein, the process comprises: step (a) of optionally grinding and sieving parts of Rosmarinus officinalis,' step (b) of extracting parts of Rosmarinus officinalis with a first aprotic polar extractant to obtain a first filtrate and a first residue; step (c) of optionally extracting the first residue with a second aprotic polar extractant to obtain a second filtrate and a second residue; step (d) of concentrating the filtrate of step (b) and optionally step (c), to obtain a thick liquid mass; and step (e) of precipitating the thick liquid mass using a pre-chilled aprotic polar solvent to obtain the composition.

[0115] The term “ Rosmarinus officinalis” refers to plant rosemary. It is an evergreen perennial aromatic shrub, native to the Mediterranean, northwestern Spain, Portugal, Sri Lanka and widely cultivated across the globe. Rosmarinus officinalis belongs to Rosmarinus genus, Lamiaaceae family and Officinalis species. In particular, the plant Rosemary of the present invention is of Sri Lankan origin.

[0116] Embodiments herein provide a process of preparing the composition (A) as disclosed herein or rosemary extract, wherein aerial parts of Rosmarinus officinalis such as stem, leaves and flowers, more preferably leaves of Rosmarinus officinalis are taken as a source for obtaining triterpenic acid rich composition as disclosed herein.

[0117] Embodiments herein provide a process of preparing the composition (A) or rosemary extract as disclosed herein, comprising step (a) of optionally grounding and sieving dried leaves of Rosmarinus officinalis. In another embodiment, the dried leaves of Rosmarinus officinalis comprising up to 5% moisture content are grounded and sieved.

[0118] In an embodiment, the grounded leaves of Rosmarinus officinalis are sieved through a sieve of mesh size in a range of 15 p to 500 p, preferably through a mesh size in a range of 50 p to 300 p and more preferably through a mesh size of 100 p.

[0119] In one embodiment, the leaves or the grounded leaves are subjected to an extraction process as described herein.

[0120] Embodiments herein provide a process of preparing the composition (A) or rosemary extract as disclosed herein, comprising step (b) of extracting parts of Rosmarinus officinalis with a first aprotic polar extractant to obtain a first filtrate and a first residue, and optionally step (c) of extracting the first residue with a second aprotic polar extractant to obtain a second filtrate and a second residue.

[0121] In another embodiment, the process comprises step (b) of extracting parts of Rosmarinus officinalis with a first aprotic polar extractant to obtain a first filtrate and a first residue, and step (c) of extracting the first residue with a second aprotic polar extractant to obtain a second filtrate and a second residue. In one another embodiment, the step (c) is repeated at least two times, preferably two to five times and more preferably is repeated thrice.

[0122] In an embodiment, the first and second aprotic polar extractant, are independently selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof, preferably selected from ethyl acetate, or acetone and more preferably is ethyl acetate.

[0123] In an embodiment, the extracting of step (b) and step (c) are independently carried out at a temperature in a range of 30 to 80°C, preferably in a range of 30 to 75°C, more preferably in a range of 55 to 72°C and better at a temperature of 70°C under a stirring speed of 300 rpm.

[0124] In an embodiment, the parts of Rosmarinus officinalis and the extractant of step (b) and step (c) are independently taken in a mass to volume ratio range of 1 :5 to 1 : 15, preferably in a mass to volume ratio range of 1 :8 to 1 : 13, and more preferably mass to volume ratio of 1 : 10.

[0125] Embodiments herein provide a process of preparing the composition (A) as disclosed herein or rosemary extract, comprising step (d) concentrating the filtrate of step (b) and optionally step (c), to obtain a thick liquid mass. In an embodiment, the filtrates of step (b) and step (c) are combined and concentrated to obtain the thick liquid mass.

[0126] In an embodiment, concentrating the filtrate is carried out by evaporation of the solvent under reduced pressure. In some embodiments, concentrating is carried out by reducing the volume of the filtrate upto at least its l / 5thof volume, preferably at least 1 / 10thof its volume, and more preferably upto 1 / 15thof volume.

[0127] Embodiment herein provides a process of preparing the composition (A) as disclosed herein or rosemary extract, comprising step (e) of precipitating the thick liquid mass using a pre-chilled aprotic polar solvent to obtain the composition (A) or rosemary extract.

[0128] In an embodiment, the aprotic polar solvent is selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof, preferably is selected from ethyl acetate or acetone, and more preferably is ethyl acetate.

[0129] In an embodiment, the pre-chilled aprotic polar solvent is at a temperature in a range of -20 to 10°C, preferably at a temperature of -15 to 10°C, and more preferably in a range of -10 to 0°C.

[0130] In a preferred embodiment, the step (e) of precipitating the thick liquid mass using a pre-chilled aprotic polar solvent is repeated at least twice and the precipitates are combined.

[0131] In a preferred embodiment, the step (e) of precipitating the thick liquid mass using a pre-chilled aprotic polar solvent is repeated thrice, the precipitates are combined and processed by washing and / or filtering to obtain the composition (A) or rosemary extract. In another embodiment, washing the precipitate is carried out to remove chlorophyll from the precipitate. In one another embodiment, filtering is carried out using Whatmann filter paper, preferably Whatmann filter paper no.l to obtain the composition (A) or rosemary extract.

[0132] In an embodiment, the process of preparing the composition (A) or rosemary extract comprises: step (a) of grinding and sieving parts of Rosmarinus officinalis^ step (b) of extracting grounded and sieved parts of Rosmarinus officinalis with a first aprotic polar extractant selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof, at a temperature of in a range of 30 to 80°C to obtain a first filtrate and a first residue; step (c) of extracting the first residue with a second aprotic polar extractant selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof, at a temperature of in a range of 30 to 80°C to obtain a second filtrate and a second residue; repeating step (c) at least two times; step (d) of concentrating the filtrate of step (b) and step (c), to obtain a thick liquid mass; and precipitating the thick liquid mass using a pre-chilled aprotic polar solvent selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof, to obtain the composition (A) or rosemary extract.

[0133] In an embodiment, the process of preparing the composition (A) or rosemary extract comprises the step of salification or solvate formation. In another embodiment, the composition (A) or rosemary extract obtained by the process as disclosed herein is further treated with a base or a solvent to obtain its salt or solvates thereof.

[0134] In an embodiment, the composition (A) obtained by the process as disclosed herein, comprises at least 60% by weight of triterpenic acids selected from oleanolic acid, its salts, solvates or their mixtures thereof; ursolic acid, its salts, solvates or their mixtures thereof; betulinic acid, its salts, solvates or their mixtures thereof; and micromeric acid, its salts, solvates or their mixtures thereof.

[0135] In one embodiment, the process of preparing the composition (A) includes mixing of triterpenic acids selected from oleanolic acid, ursolic acid, betulinic acid, and micromeric acid.

[0136] In some embodiments, the process of preparing the composition (A) includes mixing at least 10% by weight of oleanolic acid, at least 30% by weight of ursolic acid, at least 1% by weight of betulinic acid and at least 5% by weight micromeric acid, optionally in the presence of a solvent selected from ethanol, water, propylene glycol or combinations thereof.

[0137] In an embodiment, a composition (A) obtained by the process as disclosed herein comprises a. oleanolic acid, its salts, solvates, or their mixtures thereof; b. ursolic acid, its salts, solvates, or their mixtures thereof; c. betulinic acid, its salts, solvates, or their mixtures thereof; and d. micromeric acid, its salts, solvates, or their mixtures thereof.

[0138] In an embodiment, a composition (A) obtained by the process as disclosed herein further comprises at least one component selected from polyphenols, carbohydrates, fat, proteins, water, or combinations thereof.

[0139] In an embodiment, a composition (A) obtained by the process as disclosed herein comprises a. 30 to 60% by weight, and more preferably 35 to 55% by weight of oleanolic acid, its salts, solvates, or their mixtures thereof; b. 30 to 60% by weight, and more preferably 35 to 55% by weight of ursolic acid, its salts, solvates, or their mixtures thereof; c. 1 to 20% by weight, and more preferably 2 to 15% by weight of betulinic acid, its salts, solvates, or their mixtures thereof; and d. 5 to 22% by weight, and more preferably 7 to 20% by weight of micromeric acid, its salts, solvates, or their mixtures thereof.Composition (B)

[0140] Embodiments herein provide a composition (B) comprising the composition (A) or the extract as disclosed herein in a physiological acceptable medium optionally with at least one adjuvant.

[0141] Embodiments herein also provide a composition (B) comprising the composition (A) or the rosemary extract is present in an amount ranging from 0.001 to 30% by weight, preferably in a range of 0.01 to 20% by weight, more preferablyin a range of 0.05 to 10% by weight, better in a range of 0.1 to 8% by weight, better still in a range of 0.02 to 5% by weight and even better 0.05 to 1% by weight, relative to total weight of the composition.

[0142] It is understood that the concentration of rosemary extract in composition (B) is expressed as dry weight, meaning it only takes into account the weight of the solid components after complete water evaporation.

[0143] In an embodiment, the composition (B) comprises at least one adjuvants selected from surfactants, humectant, solvents, preservatives, pH adjusters, fragrances, or combinations thereof preferably selected from non-ionic surfactant, anionic surfactant, amphoteric surfactant, humectant, solvents, preservatives, pH adjusters, fragrances, or combinations thereof.

[0144] In an embodiment, the the composition (B) comprises acetyl- 11-keto-beta boswelic acid or Boswelia serrata extract. In a particular embodiment, the composition (B) comprises the Boswelia serrata extract comprising at least 10% by weight of acetyl- 11-keto-beta boswelic acid, preferably 10 to 100% by weight of acetyl- 11-keto-beta boswelic acid. In a preferred embodiment, the Boswelia serrata extract is rich in acetyl- 11-keto-beta boswelic acid.

[0145] win an embodiment, the composition (B) comprises surfactants selected from non-ionic surfactants, anionic surfactants, amphoteric surfactants, or combinations thereof. In another embodiment, the surfactant preferably include but not limited to alkyl polyglycoside, acyl glucamides, fatty amides, oxyalkylenated glycerol esters, amino acid surfactants, sulfonate surfactants, alkyl ether sulfates, alkyl sulfates, alkyl phosphates, alkyl ether phosphates, alkyl succinates, acyl taurates, (Cs-C2o)alkylbetaines, sulfobetaine, (C8-C20 alkyl)amido(C2-Cs alkyljbetaine, (C8-C20 alkyl)amido(C2-C8alkyl)sulfobetaine, (Cs-Ci4 acyl) amphoacetates, (Cs-Cu acyljamphoglycinates, or combinations thereof.

[0146] In an embodiment, the composition (B) comprises humectant preferably include but not limited to propylene glycol, glycerin, dipropylene glycol, other polyols, or combinations thereof.

[0147] In an embodiment, the composition (B) comprises pH adjusters which preferably include but not limited to ammonium hydroxide, alkali metal carbonates,alkali metal hydroxides such as sodium or potassium hydroxide, alkanolamines such as mono-, di- and triethanolamines and also their derivatives.

[0148] In an embodiment, the composition (B) comprises solvents which preferably include but not limited to water, ethanol or combinations thereof.

[0149] In an embodiment, the composition (B) comprises fragrances which preferably include but not limited to essential oils or mixture of essential oils.

[0150] In an embodiment, the composition (B) comprises preservatives which preferably include but not limited to phenoxy ethanol, caprylyl glycol, parabens, methyl isothiazolinone, benzisothiazolinone, methyl chloro isothiazolinone, benzyl alcohol, salicylic acid, sorbic acid, sodium benzoate, potassium sorbate, or combinations thereof.

[0151] In an embodiment, the composition (B) may further comprise other additives which include but not limited to niacinamide, salicylic acid, menthol, methyl diisopropyl propionamide, menthyl lactate, menthone glycerin acetal, menthyl lactate, ethyl menthane carboxamide, menthoxypropanediol, vitamin E, beta hydroxybutanoic acid, tropic acid, trethocanic acid, panthenol, glycolic acid, mandelic acid, malic acid, tartaric acid, lactobionic acid, gluconic acid or ester thereof, zinc gluconate, zinc sulfate, zinc salt of pyrrolidone carboxylic acid, vitamin B2, vitamin B6, vitamin C, ascorbyl tetraisopalmitate, sodium benzoate, essential oils, or combinations thereof.

[0152] Embodiments herein also provide a composition (B) for treating a keratin material. Particularly, embodiments herein provide applying the composition (B) on the keratin material for treating a keratin material, preferably skin. More preferably, the method provides oil control, and / or combats acne Method

[0153] Embodiments herein include a method of inhibiting growth of Cutibacterium acnes.

[0154] In an embodiment, the method of inhibiting growth of Cutibacterium acnes comprises contacting Cutibacterium acnes with an effective amount the composition (A) as disclosed herein.

[0155] In an embodiment, the method of inhibiting growth of Cutibacterium acnes is applicable to greasy skin and / or to shiny skin.

[0156] In an embodiment, the method of inhibiting growth of Cutibacterium acnes comprises contacting Cutibacterium acnes with an effective amount of the extract as disclosed herein.

[0157] In an embodiment, the method of inhibiting growth of Cutibacterium acnes comprises contacting Cutibacterium acnes with an effective amount of the composition (B) as disclosed herein.

[0158] Embodiments herein further include a method of treating a keratin material, preferably skin.

[0159] In an embodiment, the method comprises applying the composition (A) as disclosed herein on the keratin material, preferably skin.

[0160] In an embodiment, the method comprises applying the extract as disclosed herein on the keratin material, preferably skin

[0161] In an embodiment, the method comprises applying the composition (B) as disclosed herein on the keratin material, preferably skin.

[0162] The method, according to embodiments herein, comprises applying the composition (A) on a keratin surface on the skin. The method according to the present disclosure may include leaving the composition (A) on the keratin surface for a certain period of time after being applied onto the keratin surface and before rinsing off to enhance the desired skin benefits.

[0163] The method, according to embodiments herein, comprises applying the extract on a keratin surface on the skin. The method according to the present disclosure may include leaving the extract on the keratin surface for a certain period of time after being applied onto the keratin surface and before rinsing off to enhance the desired skin benefits.

[0164] The method, according to embodiments herein, comprises applying the composition (B) on a keratin surface on the skin. The method according to the present disclosure may include leaving the composition (B) on the keratin surface for a certain period of time after being applied onto the keratin surface and before rinsing off to enhance the desired skin benefits.

[0165] The method according to embodiments herein, provides oil control, shiny control and / or combats acne of the keratin material.Use

[0166] Embodiments herein provide use of the composition (A), the extract, or the composition (B) according to the present disclosure.

[0167] The composition (A), according to embodiments herein, may be used for treating a keratin material, preferably skin. In another embodiment, the composition(A) as disclosed herein is used to treat acne on skin, and / or to treat greasy skin and / or to treat shiny skin.

[0168] The extract, according to embodiments herein, may be used for treating a keratin material, preferably skin. In another embodiment, the extract as disclosed herein is used to treat acne on skin and / or to treat greasy skin and / or to treat shiny skin.

[0169] The composition (B), according to embodiments herein, may be used for treating a keratin material, preferably skin. In another embodiment, the composition(B) as disclosed herein is used to treat acne on skin, and / or to treat greasy skin and / or to treat shiny skin.

[0170] Although the present disclosure has been described in considerable detail with reference to certain embodiments and implementations thereof, other embodiments are possible to cover the modifications and variations of the present disclosure.Examples

[0171] The disclosure will now be illustrated with examples, which is intended to illustrate the working of disclosure and not intended to take restrictively to imply any limitations on the scope of the present disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood to one of ordinary skill in the art to which this disclosure belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice of the disclosed methods and compositions, the exemplary methods, devices, and materials are described herein. It is to be understood that thisdisclosure is not limited to particular methods, and experimental conditions described, as such methods and conditions may apply.

[0172] In the following examples, unless indicated otherwise, the percentages are indicated by weight of the total weight of the composition. The percentages are weight percentages by active ingredient, or active material.Example 1Composition

[0173] The composition according to the present invention is obtained by the extraction process as described below.

[0174] Composition Cl: The preparation of the composition includes the process of extraction of Rosmarinus officinalis. Rosmarinus officinalis used in the present process was of Sri Lankan origin. The aerial parts such as stem and leaves, preferably leaves of Rosmarinus officinalis were dried, preferably sun-dried, until the moisture content of the dried parts was found to be 1-3%. The dried parts of Rosmarinus officinalis were subjected to grinding using the IKA® Pilotina drymilling system. The grounded parts of Rosmarinus officinalis were sieved through 100 p mesh, and a coarse powder was obtained. 100 g of coarse powder of parts of Rosmarinus officinalis was taken with 100% ethyl acetate (first aprotic polar extractant) in a mass to volume ratio of 1 : 10 (m / v) and the extraction was carried out at 70°C at 300 rpm to obtain a first filtrate and a first residue. The first residue was further extracted at 70°C at 300 rpm with 100% ethyl acetate (second aprotic polar extractant) to obtain a second filtrate and a second residue. The second residue was further extracted with 100% ethyl acetate. The obtained filtrates from each step of extraction were combined, filtered by GFD® filter and the obtained filtrate was concentrated by evaporation of solvent using rotary evaporator under reduced pressure. The filtrate was concentrated upto 1 / 20thof volume to obtain a thick liquid mass. The obtained thick liquid mass was precipitated using pre-chilled (less than 5°C) ethyl acetate (aprotic polar solvent). Obtained precipitate was filtered using Whatmann no.l filter paper. After three consecutive precipitation steps, theprecipitates were combined, washed (redissolved) using pre-chilled ethyl acetate to remove traces of chlorophyll and filtered. The obtained resultant composition Cl was white coloured (5 g) solid powder.

[0175] Salification of composition Cl: Composition Cl (100g) was dissolved in ethanol (2L), under stirring at a temperature of 35-40°C at 300 rpm to obtain a transparent solution. To the solution, water (2L) was added and a hydroalcoholic solution was obtained. To the hydroalcoholic solution of the composition Cl an aqueous solution of KOH (6.8 g in 500 ml of water) was added at the rate of 3-4 ml / min to obtain a mixture. The mixture was then stirred for 2 hours and was filtered. The alcohol content in the obtained filtrate was concentrated by reducing under pressure in a rotary evaporator and the obtained product was lyophilized or spray dried and 40 - 50g of the salified composition (CS1) was obtained. Salified composition (CS1) showed solubility in a mixture of solvents comprising 3% (w / w) of propylene glycol and 97% (w / w) water.

[0176] The composition Cl obtained by said process (according to the present invention) comprised, 19.7% by weight of oleanolic acid; 36.8% by weight of ursolic acid; 3.5% by weight of betulinic acid; and 10% by weight of micromeric acid.

[0177] Along these triterpenic acids, composition Cl also comprised 1.8% by weight of proteins, 0.5% by weight of ash, 18.3% by weight of fats, 3.5% by weight of sugars, 0.25% by weight of polyphenols and water.

[0178] Comparative compositions CC1, CC2 and CC3 (outside of the invention) were obtained by the process as described below.

[0179] CC1: 100 g of grounded Rosmarinus officinalis leaves was extracted using 100% ethyl acetate and the extraction was carried out for three consecutive cycles under a stirring speed of 300 rpm at 70°C. Grounded Rosmarinus officinalis and ethyl acetate were taken in a mass to volume ratio range of 1 : 10. After three extraction cycles, the mixture was filtered using GFD filter, the filtrates were combined and was reduced under pressure using rotary evaporator. The obtained content was concentrated to afford 15-20 g of a dry green colored powder CC1.Similarly, CC2 and CC3 (outside of the invention) were also prepared by using 100% methanol and 100% ethanol as extractant respectively.

[0180] Composition (C3) comprising oleanolic acid, ursolic acid, betulinic acid and micromeric acid was prepared by mixing appropriate amounts of said acids as mentioned in Table 1. Similarly, comparative compositions CC4 and CC5 (outside of the invention) were also prepared using appropriate amounts of said acids as illustrated in Table 1.Table 1Example 2Anti-microbial studies

[0181] The anti-microbial potency of the compositions prepared in the Example 1 was analysed, in particular bactericidal activity of said composition against Cutibacterium acnes was determined.

[0182] For this purpose, Cutibacterium acnes ATCC 6919 were sub-cultured on Wilkins Chalgren Anaerobic Agar (WCA) and incubated at 37°C for 46-48 hoursin anaerobic condition (96 well format) in the Supplemented Brucella broth as the culture medium. The isolated colonies were suspended in sterile saline to prepare the bacterial suspension. The bacterial suspension was adjusted to ~1 x 108CFU / mL. All the samples were tested using dimethylsulfoxide (DMSO) as the solvent at 10 different concentrations ranging from 1024 pg / mL to 2 pg / mL. Vancomycin was used as the reference for this study at concentrations ranging from 32 pg / mL to 0.06 pg / mL. All the samples were studied in duplicates with visual growth inhibition as the end point (OD measured at 600 nm). Staphylococcus aureus ATCC 29213 was used as the quality control strain.

[0183] The controls used in the analysis were: a) growth medium without test sample and tester strain as broth control; b) growth medium and tester strain without test sample as culture control; c) growth medium with test sample as negative control; and d) solvent with tester strain as solvent control.

[0184] Minimum bactericidal concentration (MBC) were analysed by contacting 10 pl of each test composition with bacterial suspension on microtiter plate. These plates were further incubated at 37°C under anaerobic conditions. The visual growth inhibition was marked as the end point. The concentration of samples (test compositions) at which no growth exhibited was considered as MBC value. Obtained results are shown in Table 2 below.Table 2

[0185] These results revealed that the compositions according to the present invention showed effective bactericidal activity against Cutibacterium acnes ATCC 6919 with minimum MBC values. This could be attributed to the presence of optimal combination of oleanolic acid, ursolic acid, betulinic acid and micromeric acid in the composition. In contrast, the comparative compositions outside the invention were unable to control / inhibit growth of Cutibacterium acnes. Thus, thecompositions according to the invention were effective antimicrobial compositions for controlling acne and suitable to treat keratin material, preferably skin.ADVANTAGES OF THE PRESENT DISCLOSURE

[0186] The present disclosure provides a composition (A) comprising a combination of triterpenic acids such as oleanolic acid, ursolic acid, betulinic acid, and micromeric acid. The present disclosure provides an extract of Rosmarinus officinalis comprising said combination of triterpenic acids. The present disclosure further provides a composition (B) comprising the composition (A) or the extract. The present disclosure further also provides a process of preparing the composition(A). The composition (A), extract, and composition (B) comprises increased amount of triterpenic acids, which enables them as an anti-microbial composition for treating keratin material. The composition (A) or the extract or the composition(B) inhibits Cutibacterium acnes. which is an etiological agent for causing acne. The composition (A) or the extract or the composition (B) provides oil control, shiny control and / or combats acne, of the keratin material.

Claims

I / We claim:

1. A composition (A) comprising: a. oleanolic acid, its salts, solvates, or their mixtures thereof; b. ursolic acid, its salts, solvates, or their mixtures thereof; c. betulinic acid, its salts, solvates, or their mixtures thereof; and d. micromeric acid, its salts, solvates, or their mixtures thereof.

2. The composition (A) as claimed in claim 1, wherein the composition (A) comprises at least 10% by weight of oleanolic acid, preferably in a range of 10 to 35% by weight, and more preferably in a range of 15 to 30% by weight.

3. The composition (A) as claimed in claim 1, wherein the composition (A) comprises at least 30% by weight of ursolic acid, preferably in a range of 30 to 60% by weight, and more preferably in a range of 35 to 55% by weight.

4. The composition (A) as claimed in claim 1, wherein the composition (A) comprises at least 1% by weight of betulinic acid, preferably in a range of 1 to 20% by weight, and more preferably in a range of 2 to 15% by weight.

5. The composition (A) as claimed in claim 1, wherein the composition (A) comprises at least 5% by weight micromeric acid, preferably in a range of 5 to 22% by weight, and more preferably in a range of 7 to 20% by weight.

6. The composition (A) as claimed in any one of the preceding claims, wherein the oleanolic acid and micromeric acid are in a weight ratio range of 1.2: 1 to 3: 1, preferably in a range of 1.5: 1 to 2.5: 1.

7. The composition (A) as claimed in any one of the preceding claims, wherein the oleanolic acid, ursolic acid, betulinic acid, and micromeric acid are in a weight ratio range of 1.2:2:0.1 : 1 to 3:5:0.5: 1.

8. The composition (A) as claimed in any one of the preceding claims, wherein the composition is an extract of Rosmarinus officinalis.

9. The composition (A) as claimed in any one of the preceding claims, comprising at least 60% by weight of triterpenic acids selected from oleanolic acid, ursolic acid, betulinic acid, and micromeric acid.

10. The composition (A) as claimed in any one of the preceding claims, wherein the composition (A) further comprises at least one component selected from polyphenols, carbohydrates, fat, proteins, water, or combinations thereof.

11. The composition (A) as claimed in any one of the preceding claims, wherein the composition (A) exhibits anti-microbial activity, preferably anti-bacterial activity.

12. A rosemary extract, comprising: at least 30% by weight of ursolic acid, its salts, solvates, or their mixtures thereof; at least 10% by weight of oleanolic acid, its salts, solvates, or their mixtures thereof; at least 1% by weight of betulinic acid, its salts, solvates, or their mixtures thereof; and at least 5% by weight of micromeric acid, its salts, solvates, or their mixtures thereof.

13. The extract as claimed in claim 12, wherein the oleanolic acid and micromeric acid are in weight ratio range of 1.2: 1 to 3: 1, preferably in a range of 1.5: 1 to 2.5: 1.

14. The extract as claimed in claim 12, wherein the oleanolic acid, ursolic acid, betulinic acid, and micromeric acid are in a weight ratio range of 1.2:2:0.1 : 1 to 3:5:0.5: 1.

15. The extract as claimed in any one of the preceding claims, wherein the extract exhibits biocidal and microbiostatic effect.

16. A process of preparing the composition (A) or the rosemary extract as claimed in any one of the preceding claims the process comprising: a. optionally grinding and sieving parts of Rosmarinus officinalis,' b. extracting parts of Rosmarinus officinalis with a first aprotic polar extractant to obtain a first filtrate and a first residue; c. optionally extracting the first residue with a second aprotic polar extractant to obtain a second filtrate and a second residue;d. concentrating the filtrate of step (b) and optionally step (c), to obtain a thick liquid mass; and e. precipitating the thick liquid mass using a pre-chilled aprotic polar solvent to obtain the composition (A) or the rosemary extract.

17. The process as claimed in claim 16, wherein the step (c) is repeated at least two times.

18. The process as claimed in any one of the preceding claims 16 to 17, wherein the step (e) is repeated at least two times.

19. The process as claimed in any one of the preceding claims 16 to 18, wherein the sieving is carried out using a sieve of mesh size in a range of 15 p to 500 p.

20. The process as claimed in any one of the preceding claims 16 to 19, wherein the first and the second aprotic polar extractant are independently selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof.

21. The process as claimed in any one of the preceding claims 16 to 20, wherein the aprotic polar solvent is selected from ethyl acetate, acetone, acetonitrile, tetrahydrofuran, or combinations thereof.

22. The process as claimed in any one of the preceding claims 16 to 21, wherein the extracting is carried out at a temperature in a range of 30 to 80°C, preferably in a range of 30 to 75°C, and more preferably 55 to 72°C.

23. The process as claimed in any one of the preceding claims 16 to 22, wherein the parts of Rosmarinus officinalis and the extractant are taken in a mass to volume ratio range of 1 : 5 to 1 : 15.

24. The process as claimed in any one of the preceding claims 16 to 23, wherein the pre-chilled aprotic polar solvent is at a temperature in a range of -20 to 10°C.

25. The process as claimed in any one of the preceding claims 16 to 24, wherein the composition (A) or the extract is further processed to obtain its salts, solvates or their mixtures thereof.

26. A composition (A) as claimed in any one of claims 1 to 11 or a rosemary extract as claimed in any one of claims 12 to 15, obtained by the process as claimed in any one of the claims 16 to 25 .

27. A composition (B) comprising: the composition (A) or the extract as claimed in any one of the preceding claims 1 to 15 or 26, in a physiologically acceptable medium optionally with at least one adjuvant.

28. The composition (B) as claimed in claim 27, wherein the composition (A) or the extract is present in an amount ranging from 0.001 to 30% by weight, preferably in a range of 0.01 to 20% by weight, and more preferably in a range of 0.05 to 10% by weight, relative to total weight of composition (B).

29. The composition (B) as claimed in claim 27 or 28, wherein the at least one adjuvant is selected from surfactants, humectant, solvents, preservatives, pH adjusters, fragrances, or combinations thereof.

30. The composition (B) as claimed in claim 27, wherein the composition (B) comprises acetyl- 11-keto-beta boswelic acid or Boswelia serrata extract, preferably the Boswelia serrata extract comprising at least 10% by weight of acetyl- 11-keto-beta boswelic acid.

31. A method of inhibiting growth of Cutibacterium acnes. the method comprising: contacting Cutibacterium acnes with an effective amount of the composition(A) or the extract or the composition (B) as claimed in any one of the preceding claims.

32. A method of treating a keratin material, preferably skin, the method comprising applying the composition (A) or the extract or the composition(B) as claimed in any one of the preceding claims on the keratin material, preferably skin.

33. The method as claimed in claim 30, wherein the method provides oil control, shiny control and / or combats acne of the keratin material.

34. Use of the composition (A) or the extract or the composition (B) as claimed in any one of the preceding claims for treating a keratin material, preferably skin.

Images