WO2012073051A1 - Extraction and formation of inclusion complexes of propolis active components with hydroxypropyl - beta - cyclodextrin - Google Patents

Extraction and formation of inclusion complexes of propolis active components with hydroxypropyl - beta - cyclodextrin Download PDF

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Publication number
WO2012073051A1
WO2012073051A1 PCT/GR2011/000054 GR2011000054W WO2012073051A1 WO 2012073051 A1 WO2012073051 A1 WO 2012073051A1 GR 2011000054 W GR2011000054 W GR 2011000054W WO 2012073051 A1 WO2012073051 A1 WO 2012073051A1
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extraction
cyclodextrin
hydroxypropyl
propolis
components
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PCT/GR2011/000054
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French (fr)
Inventor
Ioannis Mourtzinos
Nikolaos Koutsianas
Panagiota Dragani
Anna Patera
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Apivita Sa
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Priority to EP11797026.9A priority Critical patent/EP2646041A1/en
Publication of WO2012073051A1 publication Critical patent/WO2012073051A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/987—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of species other than mammals or birds
    • A61K8/988—Honey; Royal jelly, Propolis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof
    • A23L21/20—Products from apiculture, e.g. royal jelly or pollen; Substitutes therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/63—Arthropods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/738—Cyclodextrins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/63—Arthropods
    • A61K35/64—Insects, e.g. bees, wasps or fleas
    • A61K35/644—Beeswax; Propolis; Royal jelly; Honey

Definitions

  • the present invention relates to a new extraction method for propolis which provides new possibilities for incorporation of propolis' active components in cosmetic products, foodstuffs and medicaments.
  • the extraction is performed with glycerol/water mixtures, wherein in the aqueous phase of the extraction medium hydroxypropyl-P-cyclodextrin is added as inclusion media.
  • hydroxypropyl-P-cyclodextrin is added as inclusion media.
  • inclusion complexes during extraction increases the solubility of propolis active components in the extraction medium, providing at the same time a stable extract, since the entrapped components are protected against oxidation and decomposition.
  • radical neutralization capacity total polyphenol content
  • total flavonoid content total flavonoid content
  • Propolis is a resinous material produced by honey bees. It is sticky at room temperature and becomes more solid upon freezing. It has an antimicrobial and antioxidative action and is used in the preparation of foodstuffs and cosmetics. Its composition varies depending on the geographical location and the collection season, thus its formulation is difficult. It contains on average 50% resins, 30% waxes, 10% flavourings, 5% pollen and 5% other components.
  • the active components of propolis are polyphenols, terpenes, steroids, as well as sugars and aminoacids.
  • the main polyphenols are flavonoids and phenolic acids. Due to complexity of propolis, the extracts thereof usually do not have specific specifications in respect to one or more components.
  • the extraction of propolis has usually low yield.
  • wetting with the extraction solvent for large time periods is effected or higher extraction temperatures are employed. Higher temperatures and long time periods lead to decomposition of labile propolis components, and deterioration of the final extract.
  • inclusion complexes with cyclodextrins provides advantages, such as increase in water solubility, protection against oxidation and protection against decomposition by heat or light.
  • the formation of inclusion complexes is an encapsulation technique and is applied on individual simple molecules. In the new invention, complex formation is effected for the first time on propolis components during extraction, combining the advantages of the inclusion complexes with the extraction, thereby increasing the efficiency of the latter.
  • Aim of the present invention is the extraction of propolis by a new method, wherein the propolis components form inclusion complexes during extraction. Complex formation increases the extraction efficiency and at the same time provides a stable final extract. The above is achieved by the addition of hydroxypropyl-p-cyclodextrin in the extraction solvent system.
  • the procedure begins with a reduction in the size of the propolis particles.
  • the propolis particles are then dispersed in the solvent system.
  • the extraction solvent consists of water and glycerol at a specific glycerol/water ratio 0/100 to 70/30.
  • hydroxypropyl-P-cyclodextrin has been previously dissolved at a proportion of 10% to 30%.
  • the inclusion agent increases the extraction efficiency, increasing the solubility of the active components. Dissolution is effected by entrapment of the propolis components in the cyclodextrin cavity.
  • the final extract is titrated in respect of active propolis components, such as total polyphenols and total flavonoids,
  • the method is independent of pH.
  • the pH of the extraction solvent system needs not to be specified by the use of a buffer solution, which would otherwise require the use of further chemicals,
  • the extract is considered effective for use in products with antioxidative capacity, since the radical quenching capacity is measured during extraction and determines the final point of extraction,
  • the ingredients of the extract are protected against oxidation or against decomposition by light or high temperatures.
  • Propolis having a specific particle size is dispersed in an extraction solvent consisting of water-glycerol at a ratio of 50/50.
  • an extraction solvent consisting of water-glycerol at a ratio of 50/50.
  • hydroxypropyl- ⁇ -cyclodextrin has been previously dissolved at a proportion of 11 ,25%.
  • the final point of extraction is determined by the values of the parameters given in table 1. After extraction completion, propolis is filtered to remove the insoluble components.
  • Propolis having a specific particle size is dispersed in an extraction solvent consisting of water-glycerol at a ratio of 75/25.
  • an extraction solvent consisting of water-glycerol at a ratio of 75/25.
  • hydroxypropyl- ⁇ -cyclodextrin has been previously dissolved at a proportion of 22,5%.
  • the final point of extraction is determined by the values of the parameters given in table 1. After extraction completion, propolis is filtered to remove the insoluble components.
  • the product obtained by the described method may be used in enriching foodstuffs, in the preparation of nutrition supplements, face and body cosmetic products, and medicaments.

Abstract

The extraction of propolis is effected at room temperature, without the use of ultrasound or microwaves, by adding hydroxypropyl-β-cyclodextrin in the extraction solvent system. The solubility of the active components is increased by the formation of inclusion complexes during extraction and this leads to an increase in the extraction efficiency. The final extract is more stable and at the same time it has certain specifications as regards antioxidative capacity, total polyphenol content and total flavonoid content. The extract may be used in enriching foodstuffs, in the preparation of nutrition supplements, face and body cosmetic products, and medicaments.

Description

EXTRACTION AND FORMATION OF INCLUSION COMPLEXES OF PROPOLIS ACTIVE COMPONENTS WITH HYDROXYPROPYL - BETA - CYCLODEXTRIN
The present invention relates to a new extraction method for propolis which provides new possibilities for incorporation of propolis' active components in cosmetic products, foodstuffs and medicaments. In particular, the extraction is performed with glycerol/water mixtures, wherein in the aqueous phase of the extraction medium hydroxypropyl-P-cyclodextrin is added as inclusion media. The formation of inclusion complexes during extraction increases the solubility of propolis active components in the extraction medium, providing at the same time a stable extract, since the entrapped components are protected against oxidation and decomposition. During extraction and on specific time periods samples are obtained and the following parameters are measured: radical neutralization capacity, total polyphenol content and total flavonoid content. The extraction is completed when these parameters have specific values.
Propolis is a resinous material produced by honey bees. It is sticky at room temperature and becomes more solid upon freezing. It has an antimicrobial and antioxidative action and is used in the preparation of foodstuffs and cosmetics. Its composition varies depending on the geographical location and the collection season, thus its formulation is difficult. It contains on average 50% resins, 30% waxes, 10% flavourings, 5% pollen and 5% other components. The active components of propolis are polyphenols, terpenes, steroids, as well as sugars and aminoacids. The main polyphenols are flavonoids and phenolic acids. Due to complexity of propolis, the extracts thereof usually do not have specific specifications in respect to one or more components.
The extraction of propolis has usually low yield. In order to increase the extraction efficiency, wetting with the extraction solvent for large time periods is effected or higher extraction temperatures are employed. Higher temperatures and long time periods lead to decomposition of labile propolis components, and deterioration of the final extract.
Other extraction techniques comprise the use of ultrasound or microwaves, which requires specialized equipment, thereby leading to an increase in the extraction cost. Furthermore, energy is transferred to the propolis molecules, which may promote oxidation and in general decomposition of the active components. l The solvents commonly employed in the extraction are various alcohols, such as methanol, ethanol, butylene glycol, and propylene glycol. Methanol is an effective solvent for propolis active components however is very toxic and may be used only for research purposes. Glycols are solvents compatible to cosmetic systems; however they have been recently implicated in skin irritation.
As it is known from the literature, formation of inclusion complexes with cyclodextrins provides advantages, such as increase in water solubility, protection against oxidation and protection against decomposition by heat or light. The complexity of the propolis composition, the low solubility of its components in water and the presence of labile components, make the formation of inclusion complexes an ideal technique for increasing the extraction efficiency. The formation of inclusion complexes is an encapsulation technique and is applied on individual simple molecules. In the new invention, complex formation is effected for the first time on propolis components during extraction, combining the advantages of the inclusion complexes with the extraction, thereby increasing the efficiency of the latter.
Aim of the present invention is the extraction of propolis by a new method, wherein the propolis components form inclusion complexes during extraction. Complex formation increases the extraction efficiency and at the same time provides a stable final extract. The above is achieved by the addition of hydroxypropyl-p-cyclodextrin in the extraction solvent system.
The procedure begins with a reduction in the size of the propolis particles. The propolis particles are then dispersed in the solvent system. The extraction solvent consists of water and glycerol at a specific glycerol/water ratio 0/100 to 70/30. In the aqueous phase hydroxypropyl-P-cyclodextrin has been previously dissolved at a proportion of 10% to 30%. During extraction the following parameters are measured:
- antioxidative capacity by measuring the quenching of 2,2-diphenyl-l- picrylhydrazyl radical (DPPH)
- Total polyphenol content by Folin-Ciocalteau method,
- Total flavonoids.
The final point of extraction is determined by the values of the above measurable parameters and the extraction is completed when these parameters obtain specific values. After extraction completion, propolis is filtered to remove the insoluble components. Advantages and novel elements of the method are the following:
- the procedure of the inclusion complex formation, between hydroxypropyl-β- cyclodextrin and the active components of propolis, is effected during extraction in a vessel,
- the inclusion agent increases the extraction efficiency, increasing the solubility of the active components. Dissolution is effected by entrapment of the propolis components in the cyclodextrin cavity.
- only safe and edible components are used during extraction,
- it is the only method of propolis extraction in which a selective increase in the extraction efficiency is achieved since the cyclodextrin employed has a cavity of specific size and allows the entrapment of components such as polyphenols which comprise a phenyl ring in their molecule,
- it is a simpler, high-efficiency extraction method, which avoids the energy- consuming use of high temperatures, ultrasound or microwaves,
- the final extract is titrated in respect of active propolis components, such as total polyphenols and total flavonoids,
- the method is independent of pH. The pH of the extraction solvent system needs not to be specified by the use of a buffer solution, which would otherwise require the use of further chemicals,
- the extract is considered effective for use in products with antioxidative capacity, since the radical quenching capacity is measured during extraction and determines the final point of extraction,
- the extract is inherently stable without addition of further preservatives. This is due to the pH value (pH = 4), the high content of diols or triols, and the antimicrobial activity of propolis,
- the quality of the final extract, determined by the measured parameters, is independent of the type of propolis,
- the ingredients of the extract are protected against oxidation or against decomposition by light or high temperatures.
The following examples are given for better understanding of the present invention. Example 1
Propolis having a specific particle size is dispersed in an extraction solvent consisting of water-glycerol at a ratio of 50/50. In the aqueous phase, hydroxypropyl- β-cyclodextrin has been previously dissolved at a proportion of 11 ,25%.
The final point of extraction is determined by the values of the parameters given in table 1. After extraction completion, propolis is filtered to remove the insoluble components.
Table 1
Figure imgf000005_0001
Example 2
Propolis having a specific particle size is dispersed in an extraction solvent consisting of water-glycerol at a ratio of 75/25. In the aqueous phase, hydroxypropyl- β-cyclodextrin has been previously dissolved at a proportion of 22,5%.
The final point of extraction is determined by the values of the parameters given in table 1. After extraction completion, propolis is filtered to remove the insoluble components.
Table 1
Figure imgf000005_0002
The product obtained by the described method may be used in enriching foodstuffs, in the preparation of nutrition supplements, face and body cosmetic products, and medicaments.

Claims

1. Method for extracting propolis, characterized in that it comprises the complexation of the extractable components by hydroxypropyl-P-cyclodextrin, as inclusion media, during extraction. In the first stage of the method, the size of the propolis particles is reduced by a device for cutting edible hard materials. The second stage of the method comprises the dispersion of the propolis particles in a water/glycerol mixture, in the aqueous phase of which hydroxypropyl-p-cyclodextrin has been dissolved. This mixture is the extraction solvent. During extraction, the following parameters are measured: antioxidative capacity by measuring the quenching of 2,2-diphenyl-l-picrylhydrazyl radical (DPPH), total polyphenol content by Folin- Ciocalteau method, and total flavonoid content. The final point of the extraction is the point where the three parameters obtain the following values: > 3.5 ± 0.5 (Trolox equivalent), > 880 ± 20 (mg 1 gallic acid) and > 0.28 ± 0.02 (mM querqetin), respectively. After extraction completion, filtration is effected to remove the solids and to obtain a clear extract.
2. Method according to claim 1, wherein in the aqueous phase of the extraction solvent, hydroxypropyl-P-cyclodextrin is added, as inclusion agent, at a proportion of 10 to 30%.
3. Method according to claims 1 and 2, wherein the extraction efficiency is increased selectively since hydroxypropyl-P-cyclodextrin is used which increases the solubility of specific molecules, such as polyphenols, and thus aids in the extraction of these components.
4. Product obtained by the extraction method of claims 1 to 3, exhibiting the following specifications: antioxidative capacity, total polyphenol content, and total flavonoid content with values > 3.5 ± 0.5 (Trolox equivalent), > 880 ± 20 (mg l gallic acid) and > 0.28 ± 0.02 (mM querqetin), respectively.
5. Product obtained by the extraction method of claims 1 to 3, the components of which have formed an inclusion complex with hydroxypropyl-P-cyclodextrin.
6. The product obtained according to claims 1 to 3 and having the features of claims 4 and 5 is used in enriching foodstuffs, in the preparation of nutrition supplements, face and body cosmetic products, and medicaments.
PCT/GR2011/000054 2010-12-01 2011-11-30 Extraction and formation of inclusion complexes of propolis active components with hydroxypropyl - beta - cyclodextrin WO2012073051A1 (en)

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WO2022045371A1 (en) * 2020-08-31 2022-03-03 合同会社レビアスファーマ Composition and manufacturing method for said composition, method for improving fat-soluble component absorbability, method for improving fat-soluble component extraction efficiency, and fat-soluble component

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GR1009175B (en) * 2016-06-13 2017-12-18 Apivita Καλλυντικα Διαιτητικα Φαρμακα Ανωνυμη Εμπορικη Και Βιοτεχνικη Εταιρεια Combination of nannochloropsis gaditana-and-propolis extracts acting as drastic components in skin-care cosmetic formulas

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Publication number Priority date Publication date Assignee Title
WO2014163513A1 (en) 2013-04-05 2014-10-09 Manuka Health New Zealand Limited Therapeutic compositions and uses thereof
JP2016516751A (en) * 2013-04-05 2016-06-09 マヌカ ヘルス ニュージーランド リミテッド Therapeutic compositions and uses thereof
EP2983681A4 (en) * 2013-04-05 2017-01-04 Manuka Health New Zealand Limited Therapeutic compositions and uses thereof
US10420804B2 (en) 2013-04-05 2019-09-24 Manuka Health New Zeland Limited Therapeutic compositions and uses thereof
WO2022045371A1 (en) * 2020-08-31 2022-03-03 合同会社レビアスファーマ Composition and manufacturing method for said composition, method for improving fat-soluble component absorbability, method for improving fat-soluble component extraction efficiency, and fat-soluble component

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