WO2015195060A1 - Substance naturelle en forme de poudre contenant des composés phytochimiques en concentration élevée pouvant être trouvés dans des fruits et légumes et son procédé de préparation - Google Patents

Substance naturelle en forme de poudre contenant des composés phytochimiques en concentration élevée pouvant être trouvés dans des fruits et légumes et son procédé de préparation Download PDF

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Publication number
WO2015195060A1
WO2015195060A1 PCT/TR2015/000249 TR2015000249W WO2015195060A1 WO 2015195060 A1 WO2015195060 A1 WO 2015195060A1 TR 2015000249 W TR2015000249 W TR 2015000249W WO 2015195060 A1 WO2015195060 A1 WO 2015195060A1
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phytochemicals
fruits
vegetables
found
membrane
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PCT/TR2015/000249
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English (en)
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Ercan Durmus
İlhami CELIK
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Ercan Durmus
Celik İlhami
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Publication of WO2015195060A1 publication Critical patent/WO2015195060A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • 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
    • A61K35/57—Birds; Materials from birds, e.g. eggs, feathers, egg white, egg yolk or endothelium corneum gigeriae galli

Definitions

  • the invention is related to a natural powder material and its preparation method that can be use d as raw, semi-processed and processed materials in many areas such as health, food and cosmetics industries, and obtained in intact form of phytochemicals from fruits and vegetables while preserving natural structure and activity of phytochemicals, and containing high concentrations of the phytochemicals.
  • Phytochemicals act as a natural defence system in plants and also give colour, aroma and taste to the fruit and vegetable.
  • bioactive phytochemicals found abundantly in fruits are ellagic acid having anti-carcinogenic effect, antioxidants such as flavonoic acid and flavonoids, anthocyanins, quercetin, kaempferol, myricetin polyphenols, resveratrol, carotenoids and vitamin C.
  • antioxidants such as flavonoic acid and flavonoids, anthocyanins, quercetin, kaempferol, myricetin polyphenols, resveratrol, carotenoids and vitamin C.
  • polyphenols including anthocyanins are known as antiinflammatory, antiviral antioxidant agents.
  • Alkaloids, polyphenols, flavonoids and anthocyanins those are abundant especially in the grape and berry species, and pomegranate are the phytochemicals, which the effects and action mechanism well understood phytochemicals.
  • ROS reactive oxygen species
  • Phytochemicals are also increase consistency and aroma of the food, improves the colour.
  • Polyphenols are a phytochemical group found in plants having more than one phenolic group. The plant synthesizes these substances against to the ecological and physiological constraints such as disease agents, insect attack, ultraviolet light exposure and injury.
  • Basic chemical property of phenolic compounds is having an aromatic ring containing one or more hydroxyl groups. By concerning the number of phenolic units in the molecule, the polyphenols are divided into two basic groups as simple and polyphenols. Plant origin phenolic compounds can be classified into simple phenols, coumarins, lignins, lignans, condensed and hydrolysable tannins, phenolic acids and flavonoids.
  • Tannins are polyphenols of bitter plants and shrinking (astringent) molecules that bind to proteins and precipitate or shrink them.
  • the antiinflammatory effect of tannins is helpful in the control of all inflammatory symptoms. With their astringent effect, prevent the wound from infection by creating a protective layer on it. Tannins contribute to the healing of wounds in the mouth.
  • phenols that can be reduced to some sugar and phenolic acids are called as hydrolysable tannins, and are divided into two groups called as gallotanens and ellagitanens.
  • Ellagitanens have a high molecular weight and water-soluble phenolic substances, have the ability of precipitating proteins and alkaloids.
  • ester bond are hydrolyzed and hexadihidroxyphenic acid is spontaneously transformed into water-soluble ellagic acid.
  • Ellagitanens are transferred into the body through consumption of dark fruits such as raspberries and blackberries.
  • Ellagic acid is found naturally in many plants as a free molecule and glycosides of ellagitanen.
  • Ellagic acid is low soluble in water, however well soluble in methanol and dimethyl sulfoxide. Preventive health effects of the ellagic acid have not be explained yet, in detail.
  • Ant carcinogenic effect is attributed to prevention binding of carcinogens to DNA, inhibition of carcinogenic activation, stimulation detoxification of the carcinogens, formation of complex molecules with reactive carcinogens.
  • Ant carcinogenic effects of ellagic acid is considered to start in intestines by inhibiting absorption of carcinogens through intestinal wall via stimulating Phase II enzymes, which are called as detoxification enzymes, in the liver.
  • ellagic acid is also reported (Hurley, 1998) to blockade tumor cell development via preventing activity of Topoisomerase I and II enzymes, which play significant roles in DNA replication and therefore in cell growth and differentiation.
  • ellagic acid has the highest ant carcinogenic activity.
  • anti carcinogenic activity of ellagic acid was 80-300 times higher than those of the others. Because that ellagic acid is also an antioxidant, it can prevent the onset of cancer by inactivating free oxygen radicals and reactive metabolites of carcinogens.
  • Ellagic acid is a strong antioxidant preventing this process. Unlike other phenolic acids, ellagic acid exerts its anti carcinogenic effect when taken orally with food, in addition to receiving through injection route.
  • Flavonoids are water-soluble, containing 15 carbon atoms and are the most commonly available polyphenolic compounds in plant tissue. Flavones, flavonols, iso-flavonols, anthocyanins, anthocyanidins, proanthocyanidins and catechins are members of the flavonoid family. All flavonoids are derived from aromatic amino acids such as phenylalanine and tyrosine, and have three rings. Structural differences between different flavonoid molecules arise from the type and extent of hydroxylation, prenilation, alkalinisation, glycosylation reactions changing the basic molecule.
  • Phenolic acids are also antioxidant molecules, such as polyphenols and flavonoids, and blockade the mechanisms that lead to degenerative diseases. Oxygen in the body transforms into reactive oxygen species (ROS) under certain conditions, that these oxygen species cause to atherosclerosis, cardiac ischemia (insufficient blood supply to cardiac muscle), ageing, diabetes, and suppression of immune system, the diseases associated with nerve damage, cancer and other chronic diseases. Antioxidants also have great importance in prevention and treatment of reactive radical mediated diseases because that they hunt and eliminate dangerous oxygen species. Phenolic acids are another phenolic molecule family, present mostly in ester, glycoside or amide forms but not found in free form in the plant kingdom. Differences between phenolic acids arise from the placement and number of hydroxyl groups on the aromatic rings.
  • Phenolic acids have basic structures and these are hydroxybenzoic and hydroxycinnamic acids. Hydroxycinnamic acid derivatives contain ferulic, caffeic, p-coumaric and synapic acids. Derivatives of the hydroxybenzoic acid are gallic, vanillic, syringic and protocathechuic acids. Another large group of the phenolic compounds is phenolic compounds found in the plant cell walls. Two important groups of phenolic compounds found in the plant cell wall are hydroxycinnamic acids and lignins. These compounds protect plant cells from infection, injury and ultraviolet light during plant growth.
  • Phenolic compounds give specific bitter taste and colour of the fruits and vegetables. Some phenolic compounds have a role in the formation of the bitter taste. Phenolic compounds are important in many ways as they are as a food ingredient; functions in public health, effects in taste and the odour, participation in colour formation and change, antimicrobial and anti oxidative effects, causing inhibition of enzymatic activity, being purity control criteria in various foods. In addition, the well-known effects of the phenolic compounds, positive effects on human health are also evidenced by the results of a number of researches. Phenolic compounds are antioxidant compounds with the ability of free radical binding capabilities. Antioxidant molecules are the compounds inactivating free radicals, that causing cardiovascular disease, cancer and geriatric problems by attacking to DNA, cells and the immune system.
  • anthocyanin which is abundant phytochemical group in fruits and vegetables, is derived from the Greek words “anthos” (flower), “kyanos” (blue). These substances are water-soluble natural substances providing a wide range of colours ranging from blue to red colours to root, body and fruits of many fruits and root vegetables. Fruit and vegetable juices contain high amounts of anthocyanins. Chemically, anthocyanins are glycosides of "antocyanidin” molecule. Therefore, if the chemical bond attaching the molecule to glycoside molecule is separated by partial hydrolysis, the remaining structure is antocyanidin molecule which is also called as "aglycone". The part of the molecule bonding to aglycone with glycoside bond is one of the different sugar molecules.
  • esterified form of anthocyanidins with sugars is anthocyanins.
  • anthocyanins Approximately about 20 different antocyanidins are known. Six of them are common in the fruits, vegetables and their products. These anthocyanins are pelargonidine, cyanidine, pheonidine, delphinidine, petunidine and malvidine. The most common anthocyanine in the nature is "cyanidin 3- glycoside". Colour of many anthocyanins varies depending on the pH, at higher pH values the colour disappears. Therefore, they can also be used as a pH indicator. Anthocyanins are the purple-red at low pH, whereas at high pH values they gain a green-blue colour.
  • anthocyanins are light red color at acid milieu, purple in neutral environment, blue-green-violet at low alkaline milieu and blue at high alkaline milieu.
  • Anthocyanins have a strong using potential as food colouring agents because of their high quality colour rendering properties and high quality products. Water-solubility properties of anthocyanins facilitate their participation into the aqueous food systems. Because that anthocyanins have a very powerful antioxidant (antiradical) capacity, they are also supplemented in order to increase oxidative stability of the foods in addition to the food colouring.
  • antioxidant antioxidant
  • cyanidin and cyanidin 3-glucoside are known to have strong ant oxidative activity in various systems, even in some systems, their ant oxidative capacity higher than a- tocopherol (vitamin E).
  • Anthocyanins used as food colouring, nutraceuticals and pharmaceuticals are mostly derived from vegetable sources and waste materials. The average daily intake of anthocyanins was calculated as 180-215 mg and the amount is higher than those of the flavonoids, such as such as flavonole.
  • flavonoids such as such as flavonole.
  • anthocyanins are also antioxidants.
  • anthocyanins These functions are associated with ant carcinogenic and anti-inflammatory properties of anthocyanins.
  • Methods to be applied in the extraction and preparation of consumable products rich in the bioactive phytochemicals found in fruits and vegetables are mainly depend on the extraction purposes and structure of phytochemical.
  • the factors that affect the structure and stability of these molecules should be well known.
  • the extraction or enrichment method should be a method preserving the molecules as possible as close to their natural state.
  • the factors such as preservation of bioactivity of extracted materials, maximal pigment yield when used as food additive, staining strength and stability are quite crucial.
  • the extraction and purification processes should not be too complicated, time-consuming and expensive.
  • anthocyanins are stable in neutral or alkaline solutions, acidic solutions are often preferred in the extraction process.
  • the traditional and most common method used in the extraction of anthocyanins is extracting plant material in a solution containing small amounts of mineral acid and an alcohol having a low boiling point (ethyl or methyl alcohols) extraction.
  • Methanol is widely used in the extraction, due to its toxic effects; acidic ethanol might also be used, although the extraction capacity is weaker than that of the methanol, concentrating the product more difficult because of higher boiling point, in the preparation of food-based preparations.
  • the main solvents used for extraction are weak alcohol solution prepared with mineral acids. Hydrochloric acid assists to maintain the pH at ⁇ ower levels, the use of mineral acids can lead to loss of anthocyanins pigments and may alter the complex natural structure of anthocyanin pigments. Therefore, the researchers have proposed the use of very weak acid solutions instead of strong acid solutions.
  • neutral solvents (60% methanol, acetone/methanol/water mixtures, n-buthanole, cold acetone or boiled water) are preferred in starting pigment extraction in order to extract anthocyanins, in close form to the natural state of the pigment molecule.
  • weak organic acids mostly formic acid, acetic acid, citric acid and tartaric acid is also suitable.
  • alcohol-containing solution may be concentrated at low temperature and then, if necessary to product can be purified and concentrated with techniques such as column or paper chromatography.
  • patent documents US2007014912, US8609152, US20100040758 and US7208181 application numbers have been reached.
  • there are many scientific studies based on dissolving in alcohols and their derivatives Direct use of the concentrated product obtained with the previous methods as food additive, pigment, nutraceutical, pharmaceutical or cosmetics additive is not possible, without application of further enrichment and purification processes. Because that methanol used in the extraction solution is toxic and should be completely removed from the product before use.
  • ethyl and methyl alcohol solutions with an acid pH are used is used as the extraction liquid in the traditional methods to extract bioactive phytochemicais found in vegetables and fruits.
  • the treatment with mineral acids can disrupt the natural structure of the pigment molecule, which is having a complex structure and can cause substantial loss of activity in the subsequent concentration step. This can result in reduction, significant loss or completely destruction of biological activity of the expected benefits of the phytochemicais.
  • the obtained product cannot be used without removal of acid and alcohols; it also creates economical problems in addition to cause negative results for human health.
  • the invention is related to a natural powder material and its preparation method, that can be use d as raw, semi-processed and processed materials in many areas such as health, food and cosmetics industries, and obtained in intact form of phytochemicais from fruits and vegetables while maintaining the natural structure of phytochemicals, and containing phytochemicals at high concentrations.
  • a new and different product in the powder form has been developed by using eggshell membrane and semi-processed product of fruit and vegetable origins. Because that the product has high amounts of beneficial phytochemicals, it is suitable in use alone or in combination with other ingredients in health and care products, mainly in food colouring and cosmetics industries.
  • Many chemical methods are applied to obtain the plant phenolic compounds traditionally used in many industrial fields. Most of these methods aimed to the low scale production of the phytochemicals that will be used in the analysis procedure in the scientific work. Most of the chemicals produced with these methods are decomposed structurally and their activity decreases. On the other hand, structural deteriorations and activity losses occur in the phenolic compounds derived from fruit and vegetables the effect of environmental conditions over time.
  • the phytochemicals are purified as bound to bio adsorbent with organic origin, they maintain their activities for longer period.
  • the pH of extraction solution containing ethyl alcohol at low concentration adjusted to optimal level for best dissolution of the phytochemicals with weak organic acid, in most cases, intermediate product prepared by cleavage of fruits and vegetables does not need to this process. Either sedimentation or column systems is used, the remaining liquid fraction can be directly used as human food following the pH is adjusted to the natural level.
  • Eggshell membranes are composed of 70% of organic matter, 10% of the inorganic material and 20% water. The membranes contain 16% nitrogen, 2% saccharides and 1.35-1.4% lipids. The ratio of neutral lipids to complex lipids 86:14. Sixty three % of complex lipids is sphingomyelin and 12% is phosphatidylcholine.
  • Shell membrane structure is in the form of fibrous structure, forming a complex mesh nodes or random networks. Fibrous membrane proteins arranged so as to provide semi-permeable properties to the membrane. Eggshell membrane contain high amounts of arginine, glutamic acid, methionine, histidine, cysteine, and proline amino acids. It also contains hydroxy proline, hydroxylysine and the amino acid desmosine.
  • Eggshell membrane proteins are water-insoluble in the native form. However, a water-soluble eggshell membrane protein can be prepared from the hydrolyzed shell membrane. Adsorption capacity of eggshell is proportionally related to the particle size, and the particles become smaller, metal ion and dye retention capacity increases due to increase of surface area of the particles.
  • Eggshell membrane surfaces there are proton binding or proton providing functional groups such as functional groups such as amine, amide and carboxyl groups, depending on the pH environment. These groups are positively charged domains, which mainly form -NH3 + , -CO-, N + H2- groups, when exposed to acidic environments.
  • Eggshell membranes are two separate sheets as outer and iner layer, located beneath the eggshell. Eggshell membrane is a by-product formed because of both consumption and hatchery operations. Because of emerging in large quantities throughout the world, it is a major concern for the storage of waste in some countries, re-evaluation of the waste might help to the reduction of environmental pollution as well as economic benefits will positively contributes.
  • Bio adsorbent product prepared from eggshell membrane selectively binds to textile dyes, metal ions such as iron (Fe + 3), copper (Cu + 2), zinc (Zn + 2), cadmium (Cd + 2 ), cobalt (Co + 2 ), silver (Ag + ) platinum (Pt + 2 ), gold (Au + 3 ), nickel (Ni + 2 ), chromium (Cr + 3 ) ions and actinides in wastewater and descent to the bottom.
  • metal ions such as iron (Fe + 3), copper (Cu + 2), zinc (Zn + 2), cadmium (Cd + 2 ), cobalt (Co + 2 ), silver (Ag + ) platinum (Pt + 2 ), gold (Au + 3 ), nickel (Ni + 2 ), chromium (Cr + 3 ) ions and actinides in wastewater and descent to the bottom.
  • Eggshell membrane can be obtained in large amounts as a by-product of the egg industry. Therefore, extensively have been studied on the use of eggshell membrane as bio sorbent in the purification of textile dyes from wastewater from the textile industry, separation of heavy metals from industrial wastewater.
  • the shell membrane largely constituted of type I collagen; there is no inconvenience in consumption as human food.
  • Eggshell membrane Adsorptive capacity of eggshell membrane is directly proportional to the particle size and the smaller the particles, the higher metal ion and dye retention capacities are achieved.
  • Eggshell membrane has either proton binding or proton releasing functional groups such as amine, amide and carboxyl, in aqueous media depending on pH.
  • the shell membrane powder has a wide surface area (about 21 m2/g) efficiency, which is preferential feature adsorption process.
  • the temperature effect in the adsorption is very definite, in order not to loss in the activity of both membrane particles and phytochemicals, the temperature should be maintained about at 45°C during purification process.
  • Agitation speed of the eggshell membrane particles has a profound impact on the determination of adsorption capacity of the membrane particles. For example, 400 rpm gave good results for chemical dyes.
  • the amount, molecular surface characteristics, the optimal pH level and agiatation speed parameters should be determined previously.
  • the invention is related to a natural powder material and its preparation method, that can be use d as raw, semi-processed and processed materials in many areas such as health, food and cosmetics industries, and obtained in intact form of phytochemicals from fruits and vegetables while maintaining the natural structure of phytochemicals, and containing high concentrations of the phytochemicals.
  • the method of obtaining the natural powder material consists of the following steps;
  • the egg shell is demineralised. For each 250 mg of eggshell 5 ml of 20% acetic acid is used. Partial demineralization is accomplished by rinsing the membranes in the acetic acid solution at +4°C. When dissolution is completed, shell membranes are separated. The separated membrane pieces are washed 3 times with deionised water and dried overnight in a vacuum oven at 50°C under 300 mbar vacuum. The obtained product is stored in the freezer until use. 1.3.
  • Preparation of eggshell membrane for adsorption The dried membrane fragments are ground into a powder constituted of particles sized between 1 - 1000 ⁇ / ⁇ . Because that adsorption capacity is is directly correlated with particle size, the membrane powder is sieved and classified according to the particle size as; 5-25 pm, 25- 50 pm, 50-100 pm, 100-250 pm, 250-500 pm and 500- 1000 pm. Before regular use, the optimum membrane particle size for different phytochemicals is determined.
  • the mixture is left to rest for at least 24 hours at 4°C.
  • the residue at the bottom is dried overnight at 50°C under at least 300 mbar vacuum.
  • the obtained product is milled and sieved through the sieves having appropriate pore size for particle classification, packed and stored in a cool place until use.
  • Preparing phytochemicals in column system In this method, the column is filled with a specially prepared eggshell membrane powder comprising particles with suitable size and prepared by the method described above. For this purpose, pre-determined particle size and the optimal duration are preferred for maximum retention of phytochemicals. Large chunks in the fruit or vegetable juices, which are prepared by mechanical disintegration, are separated through filtration and 96% ethyl alcohol (v / v) is added to the filtrate at a maximum of 1 : 3. The pH of the mixture adjusted to optimum adsorption level for the types, acidity or alkalinity of phytochemicals which is determined in the analysis and will be purified, with organic acid or sodium bicarbonate.
  • This mixture is passed through column in a predetermined suitable time and rate for specified phytochemicals.
  • Column material taken out after the process and dried overnight at least under 300 mbar vacuum at maximum 50°C under vacuum, and milled, sieved through sieves with pores of suitable size, packaged and stored in a cool place until use.

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Abstract

L'invention concerne une substance naturelle en poudre et son procédé de préparation qui peut être utilisée en tant que matière première, matière semi-traitée et traitée dans de nombreux domaines tels que les industries de la santé, alimentaires et cosmétiques, et obtenue à partir d'une forme intacte de composés phytochimiques provenant de fruits et de légumes tout en maintenant la structure naturelle desdits composés phytochimiques, et contenant des concentrations élevées desdits composés phytochimiques.
PCT/TR2015/000249 2014-06-19 2015-06-04 Substance naturelle en forme de poudre contenant des composés phytochimiques en concentration élevée pouvant être trouvés dans des fruits et légumes et son procédé de préparation WO2015195060A1 (fr)

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TR2014/07135 2014-06-19
TR201407135 2014-06-19

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Citations (10)

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JP2004189688A (ja) * 2002-12-13 2004-07-08 Yukio Hasebe 育毛・発毛促進剤
US20040180025A1 (en) * 2003-03-12 2004-09-16 New Life Resources, Llc Therapeutic, nutraceutical and cosmetic applications for eggshell membrane and processed eggshell membrane preparations
US20070014912A1 (en) 2005-05-13 2007-01-18 Giuseppe Mazza Extraction of phytochemicals
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JP2010046006A (ja) * 2008-08-21 2010-03-04 Yukio Hasebe 卵殻膜粉末を含有する飲料
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US7208181B1 (en) 2002-06-12 2007-04-24 The United States Of America, As Represented By The Secretary Of Agriculture Isolation of polyphenolic compounds from fruits or vegetables utilizing sub-critical water extraction
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JP2010046006A (ja) * 2008-08-21 2010-03-04 Yukio Hasebe 卵殻膜粉末を含有する飲料
JP2013040115A (ja) * 2011-08-12 2013-02-28 Pharma Foods International Co Ltd リジルオキシダーゼ活性を有する卵殻膜粉末
US20130216521A1 (en) * 2012-02-03 2013-08-22 Melinda Fernyhough Culver Dietary supplement for enhancing animal health
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