Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
  • C09K15/34—Anti-oxidant compositions; Compositions inhibiting chemical change containing plant or animal materials of unknown composition
• • 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
  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
  • A61K8/9755—Gymnosperms [Coniferophyta]
  • A61K8/9767—Pinaceae [Pine family], e.g. pine or cedar
• • 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
  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
  • A61K8/9783—Angiosperms [Magnoliophyta]
  • A61K8/9789—Magnoliopsida [dicotyledons]
• • 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
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/08—Anti-ageing preparations
• • 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

Definitions

• the antioxidant used in removing the active oxygen is largely classified into synthetic antioxidants and natural antioxidants .
• the synthetic antioxidant includes, for example, BHA (butylated hydroxyanisole) , BHT (butylated hydroxytoluene) , etc.
• BHA butylated hydroxyanisole
• BHT butylated hydroxytoluene
• Korean Patent No. 10-0429406 discloses a method of preparing an antioxidant from pine needles, using methanol and ethylacetate as synthetic organic solvents.
• Korean Examined Patent Publication No. 1993-0005694 discloses a method of preparing an antioxidant from green tea leaves, comprising adding calcium carbonate to water to extract an extract, adsorbing an antioxidant using an adsorbing resin, and then separating the antioxidant using ethylacetate, methanol, acetone, etc., as synthetic organic solvents.
• Korean Patent No. 10-0341797 discloses a method of separating and purifying a natural antioxidant from safflower seeds, comprising separating an antioxidant using methanol, nucleic acid, ethylacetate, chloroform, etc., as synthetic organic solvents.
• Korean Patent No. 10-0109461 discloses a method of separating a natural antioxidant from sesame using methanol, ethylacetate, chloroform, etc., as synthetic organic solvents.
• Korean Patent No. 10- 0395464 discloses a method of extracting catechins from green leaves of green tea using dichloromethane, ethylacetate, acetone, etc., as synthetic organic solvents.
• Korean Patent No. 10-0439012 discloses a method of extracting an antioxidant from Korean raisins using methanol, ethylacetate, etc., as synthetic organic solvents.
• the present invention carried out by the present inventors aiming to avoid the above problems encountered in the prior art, provides an extraction method, which is advantageous because preparation processes are simplified and the environmental treatment cost is decreased due to the generation of a minimum amount of environment pollutants, by using a fermented alcohol solution as a natural solvent having low volatility and high antioxidant extraction capability to extract antioxidants from the bark of pine trees at high efficiency, and then by using an alcohol solution and/or natural animal or vegetable oil to efficiently remove nonpolar material such as pine resin from the extract and separate and concentrate the antioxidant.
• the antioxidant extract obtained from the bark of pine trees through extraction has high antioxidant activity and extraction yield.
• the extraction method of the present invention is suitable for use in highly price- competitive mass production of antioxidant from the bark of pine trees.
• an object of the present invention is to provide a method of extracting a natural antioxidant from the bark of pine trees, comprising extracting an antioxidant from the bark using a fermented alcohol solution as a natural solvent, and then efficiently removing nonpolar material such as pine resin from the bark extract using an alcohol solution or natural animal or vegetable oil.
• Another object of the present invention is to provide a method of efficiently extracting a natural antioxidant, in which conditions including the concentration of ethanol in the alcohol solution, the amount of alcohol solution used, the extraction temperature, etc., are predetermined to increase the antioxidant activity and extraction efficiency of the antioxidant extract, and also, conditions including the amount of solvent when using the alcohol solution or animal or vegetable oil, the extraction temperature, and filtration and concentration techniques are predetermined to efficiently remove the nonpolar material from the extract.
• a further object of the present invention is to provide a natural antioxidant extract obtained by the above extracting method, and in particular, an extract usable as a material and an additive for food, cosmetics, medicine and feed.
• the present invention pertains to a method of extracting an antioxidant from the bark of pine trees, comprising pre- treating the bark of pine trees, pulverizing the bark of pine trees, extracting an extract using an alcohol solution, concentrating or drying the extract, extracting a nonpolar material using an alcohol solution and/or animal or vegetable oil, and drying an antioxidant.
• the term 'pine tree' is defined as a plant belonging to the pine family, and includes, for example, Pinus densiflora Sieb & Zucc, Pinus thumbergii Parlatore, Pinus densiflora Sieb. & Zucc. for.
• the term 'bark of pine trees' means the external layer that may be taken from the trunk and branches but not the leaves or roots of a plant belonging to the pine family.
• the pre-treated bark may be pulverized to 5-100 meshes to increase solvent extraction efficiency.
• 'alcohol solution' or 'fermented alcohol solution' used throughout the process of the present invention is defined as a fluid consisting mainly of ethanol, obtained by fermenting a material containing starch or a material containing sugar.
• the alcohol solution used in the extraction of the bark of pine trees includes 1.0-95% ethanol, and preferably, 30-95% ethanol.
• the alcohol solution used in the extraction of the nonpolar material includes 10-95% ethanol, and preferably, 40-95% ethanol.
• the natural animal or vegetable oil used in the extraction of the nonpolar material includes, for example, soybean oil, corn oil, canola oil, rice bran oil, sesame oil, perilla oil, safflower oil, sunflower oil, cottonseed oil, peanut oil, olive oil, palm oil, coconut oil, mixed edible oil, refined oil, shortening, red pepper seed oil, beef tallow, or lard. Below, each process of the method of the present invention is specifically described. However, these processes do not limit the technical scope of the present invention.
• Pre-Treatment Of Bark From the bark of pine trees, external impurities and the outermost black weathered bark portion are removed, and only a red bark portion is separated for use in the subsequent pulverizing process.
• Pulverizing Of Bark The separated bark is pulverized into particle or powder using a homogenizer and pulverizer, and then employed in the subsequent extraction process. Preferably, the bark is pulverized to 5-100 meshes.
• the pulverized bark powder is added with a fermented alcohol solution serving as a natural solvent, to first extract an antioxidant.
• the alcohol solution includes 1.0-95% ethanol, and preferably, 30- 95% ethanol.
• the bark and the alcohol solution are mixed at a weight ratio from 1:3 to 1:50, and preferably, at a weight ratio from 1:4 to 1:20, to extract the antioxidant.
• the extraction process is conducted at a temperature ranging from -20 to 90 ° C, and preferably, from 10 to 70°C, for a time from 5 min to 3 days, and preferably, from 30 min to 24 hr, by allowing the mixture to stand, intermittently mixing it, or continuously mixing it, to extract the antioxidant. 4.
• a filtration aid includes, for example, diatomaceous earth, china clay, bentonite, acid earth, talc, pearlite, activated carbon, etc.
• the alcohol solution is added to the bark filter cake in an amount 1-20 times, and preferably, 3-15 times, greater than the amount of the filter cake, so that the antioxidant remaining in the bark filter cake is further extracted once or twice.
• the extracts thus filtered are combined, after which ethanol and water are removed using a known vacuum concentration technique.
• the extract liquid is concentrated so that the concentrated extract liquid has 1.0-30% solid content, and preferably, 3.0-15% solid content.
• the concentrated extract liquid may be used unchanged, or be dried using a known drying technique, for example, freeze drying, vacuum drying, hot air drying or spray drying, and then pulverized into powder, which is then used for the subsequent separation of a nonpolar material .
• Separation Of Nonpolar Material Using Alcohol Solution And/Or Natural Animal or Vegetable Oil Any one of the following two processes is selectively applied to separate the nonpolar material, such as pine resin, from the concentrated extract liquid or dried extract powder, thus concentrating an antioxidant .
• the alcohol solution for use in the separation of a nonpolar material includes 10-95% ethanol, and preferably, 40-95% ethanol.
• the concentrated extract liquid or extract powder and the alcohol solution are mixed at a weight ratio of 1:1-1:30, and preferably, 1:3-1:15, followed by separating the nonpolar material and concentrating the antioxidant.
• the extraction process is carried out at a temperature ranging from -20 to 90 ° C, and preferably, from 0 to 70°C, for a time ranging from 5 min to 24 hr, and preferably from 30 min to 10 hr, by allowing the mixture to stand, intermittently mixing it, or continuously mixing it, to separate the nonpolar material.
• the antioxidant and the alcohol solution containing the nonpolar material may be separated using a known filtration or centrifugation technique.
• the natural animal or vegetable oil is selected from the group consisting of soybean oil, corn oil, canola oil, rice bran oil, sesame oil, perilla oil, safflower seed oil, sunflower oil, cottonseed oil, peanut oil, olive oil, palm oil, coconut oil, mixed edible oil, refined oil, shortening, red pepper seed oil, beef tallow, lard, and mixtures thereof.
• the concentrated extract liquid or extract powder and the natural oil are mixed at a weight ratio of 1:0.5-1:20, and preferably, 1:1-1:10, thus separating the nonpolar material using the oil layer and concentrating the antioxidant.
• the extraction process is carried out at a temperature ranging from 0 to 120 ° C, and preferably, from 20 to
• the concentrated antioxidant extract and the natural oil containing the nonpolar material may be separated from each other using a known filtration or centrifugation technique.
• the extraction process for the separation of the nonpolar material is carried out at a temperature ranging from -20 to 90 ° C, and preferably, from 10 to 80 ° C, for a time ranging from 30 min to 24 hr, and preferably, from 1.0 to 10 hr, by allowing the mixture to stand, intermittently mixing it, or continuously mixing it.
• the concentrated antioxidant extract without the nonpolar material is prepared into concentrated liquid or solid powder using known concentration, drying and pulverizing techniques.
• the present invention provides an environmentally friendly preparation method having high workability, which is characterized by extracting the antioxidant from the bark of pine trees using a fermented alcohol solution as a natural solvent having stable physicochemical properties, and then separating the nonpolar material, such as pine resin, from the extract using a fermented alcohol solution as a natural solvent having stable physicochemical properties, and then separating the nonpolar material, such as pine resin, from the extract using a fermented alcohol solution as a natural solvent having stable physicochemical properties, and then separating the nonpolar material, such as pine resin, from the extract using a
• the preparation method of the present invention can enable the antioxidant to be produced at an extraction yield 2.6-21 times higher than conventional methods.
• the antioxidant activity of the extract obtained using the present invention is higher than that of antioxidants prepared by conventional methods . This is believed to be because the conventional method includes a plurality of complicated processes, during which a large amount of antioxidant may be lost, and also, because the extraction separating process of a nonpolar material having low efficiency is applied.
• the antioxidant extract obtained by the present invention has antioxidant activity 2.6-45 times higher than that obtained by conventional methods .
• Example 1 with the exception of using alcohol containing 95% ethanol in the extraction and filtration of Example 1. Finally, 12.3 g of red-brownish antioxidant powder were obtained.
• An antioxidant was prepared in the same manner as in Example 1, with the exception of using an alcohol solution containing 30% ethanol in the extraction and filtration of
• Example 1 Finally, 13.5 g of red-brownish antioxidant powder were obtained.
• the nonpolar material was extracted in a shaken water tank at a constant 5 ° C for 5 hr to remove it, and then filtered.
• the filter cake containing the concentrated' antioxidant was dried at 50 ° C for 3 hr, and then pulverized, finally obtaining 15.7 g of red-brownish antioxidant powder.
• the nonpolar material was extracted in a shaken water tank at a constant 5 ° C for 5 hr to remove it, and then filtered.
• the filter cake containing the concentrated antioxidant was dried at 50 ° C for 3 hr, and then pulverized, finally obtaining 13.5 g of red-brownish antioxidant powder.
• the extract from the bark of pine trees was prepared as follows.
• the bark of pine trees used in the extraction As the bark of pine trees used in the extraction,
• the dehydrated ethylacetate layer was concentrated in a vacuum, to remove 80% ethylacetate.
• the concentrated ethylacetate layer was added with 200 ml of chloroform to form a precipitate, which was then separated using a filter.
• the precipitate was washed with 50 ml of chloroform, and then dried at 40 ° C, finally obtaining 0.21 g of antioxidant powder.
• the extract from the pine tree bark was prepared as follows.
• the methanol solution was
• the filtered methanol extracts were combined, and concentrated to 330 ml using a vacuum concentrator.
• the concentrated extract liquid was added with 330 ml of methanol, and then with 660 ml of heptane, after which the nonpolar material was removed in a mixed shaken water tank at 30 ° C for 2 hr. This procedure was further performed twice using heptane, removing the nonpolar material.
• the methanol extract was added with 300 ml of diethylether, and the nonpolar material was removed in a mixed shaken water tank at 30 ° C for 2 hr.
• the antioxidant prepared by the present invention exhibited antioxidant activity on DPPH radicals, that was superior to materials prepared by conventional methods, and also, had antioxidant activity about 1.1-1.7 higher than Trolox. Further, although the antioxidant prepared by the present invention had superoxide antioxidant activity similar to the sample of U.S. Patent No. 4,698,360, it had activity about 1.7 times higher than the sample of Korean Patent No. 10- 0212974. In particular, the antioxidant of the present invention manifested superoxide scavenging activity about 1.7- 2.2 times higher than BHA, and about 27-35 times higher than Trolox. Thus, as is apparent from Table 3, the antioxidant prepared according to the present invention has both extraction yield and antioxidant activity much higher than those prepared using conventional methods .
• the antioxidant prepared according to the present invention can have both high antioxidant activity and an economical preparation process .
• the present invention provides a method of extracting an antioxidant from the bark of pine trees using a natural solvent and an antioxidant prepared thereby.
• a natural fermented alcohol solution and a natural animal or vegetable oil suitable for use in food may be used, thus solving various problems caused by conventionally using a variety of synthetic organic solvents, for example, danger of fire due to the use of the highly volatile solvent, worker safety, disposal cost of waste, re- treatment cost of the solvent, limited applicability of the
• the preparation method of the present invention is simple and safe, and generates less environmental pollutants.
• the prepared antioxidant extract may be directly used in food, and a natural antioxidant having excellent activity and price competitive power and preparation processes thereof may be provided.
• the extract of the present invention may be used as an additive or material for cosmetics, medicine or feed.
• the bark of pine trees obtainable using byproducts of wood industries and fields and mountains in Korea are utilized, to prepare a natural antioxidant having high activity, which may be then inexpensively supplied. Accordingly, the method of the present invention is advantageous because forest by-products in Korea may be recycled, and the value of pine trees and the income of forest farms in Korea may be increased.
• various health foods, processed foods and medicines may be developed using the antioxidant of the present invention, developing food industries and improving the health of people and the quality of life. Additionally, through the export of the antioxidant of the present invention, international imports and exports may be further balanced.

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• 2005
  • 2005-02-28 KR KR1020050016421A patent/KR100659945B1/ko active IP Right Grant
  • 2005-06-14 WO PCT/KR2005/001802 patent/WO2006090953A1/en active Application Filing

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