KR101332803B1 - Method for Preparing Supercritical Fluid Extract of Cinnamomum verum and Its Use - Google Patents
Method for Preparing Supercritical Fluid Extract of Cinnamomum verum and Its Use Download PDFInfo
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- KR101332803B1 KR101332803B1 KR1020120012156A KR20120012156A KR101332803B1 KR 101332803 B1 KR101332803 B1 KR 101332803B1 KR 1020120012156 A KR1020120012156 A KR 1020120012156A KR 20120012156 A KR20120012156 A KR 20120012156A KR 101332803 B1 KR101332803 B1 KR 101332803B1
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- South Korea
- Prior art keywords
- cinnamon
- supercritical
- extract
- present
- extraction
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- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
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Abstract
본 발명은 계피 초임계 추출물의 제조방법 및 계피 초임계 박 추출물의 제조방법을 제공한다. 본 발명의 방법에 의해 제조된 계피 초임계 추출물은 현저한 항균 활성을 나타내며, 계피 초임계 박 추출물은 매우 우수한 자유 라디칼 소거활성을 나타낸다. 따라서, 본 발명의 추출물은 항균제 또는 항산화제의 활성성분으로 개발될 수 있다. The present invention provides a method for preparing a cinnamon supercritical extract and a method for preparing a cinnamon supercritical gourd extract. The cinnamon supercritical extract prepared by the method of the present invention exhibits significant antimicrobial activity, and the cinnamon supercritical gourd extract exhibits very good free radical scavenging activity. Therefore, the extract of the present invention can be developed as an active ingredient of an antimicrobial or antioxidant.
Description
본 발명은 계피 초임계 추출물의 제조방법 및 이의 용도에 관한 것이다.
The present invention relates to a method of preparing a cinnamon supercritical extract and its use.
최근 생활수준이 향상됨에 따라 천연식품에 대한 소비자들의 선호 경향이 높아지고 식용 가능한 식물들에 대한 새로운 식품학적 가치가 인정되면서 천연물 유래의 활성물질 탐색에 연구가 집중되고 있으며, 이러한 천연 식물 자원을 대상으로 항균, 항산화, 항암을 비롯한 성인병 예방 및 면역증강 등에 대한 연구가 활발히 진행되고 있다(5, 16, 18, 19). 산소는 호흡을 하는 생물인 인체 내에서 꼭 필요한 원소이지만 외부적인 자극이나, 에너지 대사 과정 중에 발생하는 과산화물, 산화질소, 하이드록실, 퍼록실, 알콕실, 하이드로퍼록실 라디칼과 같은 활성산소종(Reactive oxyzen species)은 미토콘드리아와 같은 세포 내 기관의 정상적인 대사 및 세포질 내 일부 효소들에 의하여 자연적으로 생성되며, 세포 내에 적당량이 존재할 경우 여러 가지 세포반응을 조절하는 인자가 된다. 하지만 과량의 활성산소종은 DNA 분절과 단백질의 불활성화 및 세포 생체막의 구성성분인 불포화 지방산을 공격하여 생체기능을 저하시킴으로써 노화를 유발 할 뿐만 아니라 류마티스성 관절염, 당뇨병, 심장병, 동맥경화, 암 등과 같은 여러 질환의 원인으로 잘 알려져 있다(12, 23). 생체 내에는 활성산소로부터 세포를 보호하기 위한 방어 시스템이 있지만(7), 현대인들은 환경오염, 스트레스, 식습관으로 활성산소에 노출되어 있다. BHT(butylated hydroxytoluene), BHA(butylated hydroxyanisole), PG(proply gallate), TVHQ(tertiary butyihydroquinone), 아스코르빈산, 토코페롤류, β-카로틴등은 활성산소를 차단하는 항산화제로서 사용되고 있지만(1), BHT와 BHA는 지질변화 및 발암독성 때문에 사용이 제한되어 있기 때문에 인체에 부작용이 없는 천연식물 추출물이 간접적으로 생체 내 항산화 방어시스템을 증가시키거나 직접적으로 ROS를 소거시키는 효과가 있다면 그 추출물은 다양한 질병을 예방하기 위한 기능성 소재로 사용 될 수 있을 것이다(10).With the recent increase in living standards, consumers' preferences for natural foods have increased and new food values for edible plants have been recognized. Research has been focused on the search for active substances derived from natural products. Research on the prevention of adult diseases, including antimicrobial, antioxidant, and anticancer and immune enhancement is actively being conducted (5, 16, 18, 19). Oxygen is an essential element in the body that is a breathing organism, but it is reactive oxygen species such as peroxides, nitric oxides, hydroxyls, peroxyls, alkoxyl and hydroperoxyl radicals that occur during external stimulation or energy metabolism. Oxyzen species are naturally produced by the normal metabolism of organelles such as mitochondria and some enzymes in the cytoplasm and, when present in the cell, are factors that regulate various cellular responses. Excessive reactive oxygen species, however, cause aging by deactivating DNA fragments and proteins and attacking unsaturated fatty acids, which are components of cellular membranes, to degrade bodily function, as well as rheumatoid arthritis, diabetes, heart disease, arteriosclerosis, and cancer. It is well known as the cause of several such diseases (12, 23). In vivo, there are defense systems to protect cells from free radicals (7), but modern people are exposed to free radicals due to environmental pollution, stress, and eating habits. Butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), proply gallate (PG), tertiary butyihydroquinone (TVHQ), ascorbic acid, tocopherols, and β-carotene are used as antioxidants to block free radicals (1), Because BHT and BHA are limited in their use due to lipid changes and carcinogenic toxicity, natural plant extracts that have no side effects on the human body indirectly increase antioxidant defense systems in vivo or directly eliminate ROS. It can be used as a functional material to prevent (10).
또한 전 세계적으로 합성 식품첨가물에 대한 안정성과 사용 규정들이 다시 검토되면서 식품의 위생관념이 철저해지고 있는 추세이다. 그러나 지구 온난화 및 실내온도 상승 등 환경뿐만 아니라 외식의 확대와 학교급식의 의무화 등과 같은 단체급식의 확대로 식중독 발생이 지속적으로 증가 하고 있는 추세이다(3). 국내 식중독 발생 현황은 2008년 354건, 7,453명으로 100만명당 153.8명에 이른다(13). 식중독의 원인체는 Escherichia coli, Salmonella sp, Staphylococcus aureus, Vibrio parahaemolyticcus 등이 주요 세균성 식중독의 원인체이며, 식중독원인체가 불명확한 것을 제외한 전체 식중독의 95%가 식품위해미생물에 의한 식중독이 차지하고 있다. 이러한 식중독 원인 미생물이나 부패 미생물을 제어하여 식품을 안전하게 저장하기 위한 수단으로 아질산염, 소르브산, 메타중아황산나트륨, 염소제 등 다양한 합성 보존료가 장기간 사용되어왔다(2). 하지만 소비자들의 건강 지향적 욕구 증가와 안정성에 대한 의식 고조로 천연항균물질에 대한 선호 인식이 높아지고 있다. In addition, as the safety and use regulations for synthetic food additives are re-examined around the world, food hygiene is becoming more thorough. However, food poisoning continues to increase due to the expansion of eating out and the mandatory provision of school meals, as well as the environment such as global warming and room temperature rise (3). The number of domestic food poisoning cases was 354 cases in 2008, 7,453, or 153.8 cases per million (13). The cause of food poisoning is Escherichia coli , Salmonella sp , Staphylococcus Aureus and Vibrio parahaemolyticcus are the major causes of bacterial food poisoning. 95% of the food poisonings are caused by food hazard microorganisms, except for the unknown cause of food poisoning. Various synthetic preservatives such as nitrite, sorbic acid, sodium metabisulfite, and chlorine agents have been used for a long time as a means to control food poisoning microorganisms or decaying microorganisms and to store food safely (2). However, increasing awareness of health-oriented needs and heightened awareness of stability has led to increased awareness of natural antibiotics.
계피(Cinnamomum verum)는 중국 남부 및 북 베트남에서 주로 많이 생산된다. 모양은 반관상, 반통상 또는 한쪽으로 말려 들어가 있는 관상의 껍질인데, 대부분 조각 형태로, 크기는 다양하다. 바깥 면은 짙은 적갈색이고 내면은 평탄하나 역시 적갈색이고 파절이 용이하다. 특이한 향이 있고 맛은 처음에 약간 달고 매우며 나중에는 점액성을 띄고 떫다. 성분은 시남 알데하이드가 주성분이며, 그 외에도 시나밀 아세테이트, 페닐프로필아세테이트, 계피산, 살리실알데하이드 등이 있으며, 디테르페노이드류로는 신제일라놀이 존재한다. 그 외에도 정유(essential oil)로서 캠펜, 시네올, 유제놀 등이 있다. 계피는 다양한 효능과 향이 있어 한방 및 민간요법에서 널리 사용되어 왔으며, 차, 음료 또는 한약의 재료로 오랫동안 사용되고 있다. 알려진 약리작용으로는 혈압강화, 말초혈관 확장, 혈액순환이 있고, 한방에서는 감기, 진통에 사용되고 있다(25, 26, 27). Cinnamomum verum ) is mainly produced in southern China and northern Vietnam. The shape is semi-tubular, semi-traditional or curled tubular shell, mostly in the form of pieces, varying in size. The outer side is dark reddish brown and the inner side is flat but also reddish brown and easy to fracture. It has an unusual aroma, tastes a bit sweet at first, and very viscous afterwards. The main ingredient is cinnamic aldehyde, and in addition, cinnamil acetate, phenylpropyl acetate, cinnamic acid, salicyaldehyde, etc., and diterpenoids include cinnaylol. Other essential oils include camphor, cineol and eugenol. Cinnamon has been widely used in herbal and folk medicine because of its various effects and scents, and has been used for a long time as a material for tea, drinks, or herbal medicine. Known pharmacological actions include strengthening blood pressure, peripheral blood vessel expansion, and blood circulation, and are used for colds and pain in oriental medicine (25, 26, 27).
이처럼 질병의 치료와 예방을 위해 천연물로부터 유용성 성분을 분리하는 많은 연구방법이 제시되어 왔다. 그러나 대부분의 천연유효성분은 그 구조가 매우 복잡하고 정교할 뿐만 아니라 불안정하여 이들을 효율적으로 추출하는데 어려움이 있다. 현재 식물 내 유효성분을 추출하기 위한 방법으로는 특정 용매에 대한 구성물의 용해도 차이를 이용하는 용매 추출법이 널리 쓰이고 있지만, 이는 높은 온도를 장시간 사용해야 함으로써 발생하는 유용성분의 변성이나 파괴가 야기되고, 사용된 용매의 일부가 유용성분에 잔존할 가능성이 있어 이용에 제한적이다(17). 따라서 위의 단점을 보완하기 위한 추출법으로써 초임계 유체를 이용한 초임계 추출법이 주목 받고 있다. 초임계 추출공법은 저온에서 조작할 수 있어 천연물과 같이 열에 약한 물질의 추출에 유용하며, 임계점 이상의 압력과 온도를 설정해 줌으로써 액상의 용해력과 기상의 확산계수가 높고 점도가 낮기 때문에 빠른 추출과 상 분리가 가능하다. 최근의 초임계 유체 추출기술에는 이산화탄소가 가장 널리 이용되고 있는데, 이는 이산화탄소의 낮은 임계 온도와 압력으로 온화한 조건에서 추출을 수행할 수 있으며, 독성, 가연성, 추출대상물질과의 반응성 및 부식성이 없고 고순도의 이산화탄소를 쉽게 구할 수 있기 때문이다. 그리고 온도에 민감한 물질을 변성이나 분해 없이 분리할 수 있어서 식품이나 의약품 등 인체에 직접 적용되는 제품의 생산에 매우 유용하나, 아직 추출법에 따른 유용성분의 추출과 관련된 체계적인 연구는 없다. 또한 추출하고 남은 부산물(박)은 폐기하는 실정이므로 이에 대한 활용방안도 고려해 보아야 한다.
As such, many research methods have been proposed for separating useful components from natural products for the treatment and prevention of diseases. However, most of the natural active ingredients are difficult to extract them efficiently because their structure is very complicated and sophisticated as well as unstable. Currently, a solvent extraction method using a difference in the solubility of constituents in a specific solvent is widely used as a method for extracting the active ingredient in a plant, but this causes the denaturation or destruction of useful components caused by using a high temperature for a long time. Some of the solvent may remain in the useful component and is limited in use (17). Therefore, a supercritical extraction method using a supercritical fluid is attracting attention as an extraction method to compensate for the above disadvantages. The supercritical extraction method can be operated at low temperature, which is useful for the extraction of heat-sensitive substances such as natural products, and by setting the pressure and temperature above the critical point, it can be quickly extracted and phase separated because of its high solvent dissolution and gas phase diffusion coefficient and low viscosity. Is possible. Recently, carbon dioxide is the most widely used supercritical fluid extraction technology, which can perform extraction under mild conditions with low critical temperature and pressure of carbon dioxide, and is nontoxic, flammable, reactive with extractables, non-corrosive and high purity. This is because carbon dioxide is easily available. In addition, it is very useful for the production of products directly applied to the human body such as food or medicine because it can separate the temperature-sensitive substances without denaturation or decomposition, but there is no systematic study related to the extraction of useful components by the extraction method. In addition, the remaining by-products (bakes) are to be discarded, so the utilization method should be considered.
본 명세서 전체에 걸쳐 다수의 논문 및 특허문헌이 참조되고 그 인용이 표시되어 있다. 인용된 논문 및 특허문헌의 개시 내용은 그 전체로서 본 명세서에 참조로 삽입되어 본 발명이 속하는 기술 분야의 수준 및 본 발명의 내용이 보다 명확하게 설명된다.
Numerous papers and patent documents are referenced and cited throughout this specification. The disclosures of the cited papers and patent documents are incorporated herein by reference in their entirety to better understand the state of the art to which the present invention pertains and the content of the present invention.
본 발명자들은 계피로부터 유용성분을 분리할 수 있는 보다 효율적인 방법을 개발하고자 노력하였다. 그 결과, 본 발명자들은 초임계유체를 이용한 초임계 추출법을 계피에 적용한 계피 초임계 추출방법을 개발하였고, 이 방법을 통해 제조된 계피 초임계 추출물이 항균 활성을 가지며, 계피 초임계 추출물의 부산물로부터 수득한 계피 초임계 박 추출물이 항산화 활성을 갖는다는 것을 확인함으로써, 본 발명을 완성하게 되었다. The present inventors have sought to develop a more efficient way to separate useful components from cinnamon. As a result, the present inventors have developed a cinnamon supercritical extraction method applying supercritical extraction method using cinnamon to the cinnamon, the cinnamon supercritical extract prepared through this method has antibacterial activity, and by-products of cinnamon supercritical extract By confirming that the obtained cinnamon supercritical gourd extract has antioxidant activity, the present invention was completed.
따라서, 본 발명의 목적은 계피 초임계 추출물의 제조방법을 제공하는데 있다. Accordingly, it is an object of the present invention to provide a method for preparing a cinnamon supercritical extract.
본 발명의 다른 목적은 계피 초임계 추출물을 포함하는 항균용 조성물을 제공하는데 있다. Another object of the present invention to provide an antimicrobial composition comprising a cinnamon supercritical extract.
본 발명의 또 다른 목적은 계피 초임계 박 추출물의 제조방법을 제공하는데 있다. Still another object of the present invention is to provide a method of preparing cinnamon supercritical gourd extract.
본 발명의 또 다른 목적은 계피 초임계 박 추출물을 포함하는 항산화용 조성물을 제공하는데 있다.
Another object of the present invention to provide an antioxidant composition comprising a cinnamon supercritical gourd extract.
본 발명의 다른 목적 및 이점은 하기의 발명의 상세한 설명 및 청구범위에 의해 보다 명확하게 된다.
Other objects and advantages of the present invention will become apparent from the following detailed description and claims.
본 발명의 일 양태에 따르면, 본 발명은 다음 단계를 포함하는 계피 초임계 추출물의 제조방법을 제공한다: (a) 계피를 파쇄하는 단계; (b) 상기 단계 (a)에서 얻어진 계피 파쇄물을 초임계 추출용기에 넣고, 초임계유체 및 보조 용매를 계피 파쇄물에 접촉하도록 상기 추출용기에 흘려주어 초임계 추출을 행하는 단계; 및 (c) 상기 단계 (b)에서 얻어지는 초임계 추출물에서 초임계유체 및 보조용매를 제거하여 계피 초임계 추출물을 얻는 단계. According to one aspect of the present invention, the present invention provides a method for preparing a cinnamon supercritical extract, comprising the following steps: (a) crushing cinnamon; (b) putting the cinnamon crushed product obtained in step (a) into a supercritical extraction container, and performing supercritical extraction by flowing a supercritical fluid and an auxiliary solvent into the extraction container so as to contact the cinnamon crushed product; And (c) removing the supercritical fluid and the cosolvent from the supercritical extract obtained in step (b) to obtain a cinnamon supercritical extract.
본 발명자들은 계피로부터 유용성분을 분리할 수 있는 보다 효율적인 방법을 개발하고자 노력하였다. 그 결과, 본 발명자들은 초임계유체를 이용한 초임계 추출법을 계피에 적용한 계피 초임계 추출방법을 개발하였고, 이 방법을 통해 제조된 계피 초임계 추출물이 항균 활성을 가지며, 계피 초임계 추출물의 부산물로부터 수득한 계피 초임계 박 추출물이 항산화 활성을 갖는다는 것을 확인함으로써, 본 발명을 완성하게 되었다. The present inventors have sought to develop a more efficient way to separate useful components from cinnamon. As a result, the present inventors have developed a cinnamon supercritical extraction method applying supercritical extraction method using cinnamon to the cinnamon, the cinnamon supercritical extract prepared through this method has antibacterial activity, and by-products of cinnamon supercritical extract By confirming that the obtained cinnamon supercritical gourd extract has antioxidant activity, the present invention was completed.
본 발명은 기본적으로 초임계유체 추출 과정을 따른다. 초임계 추출의 원재료인 계피(Cinnamomum verum)를 적합한 크기의 입자 분말 형태가 되도록 파쇄하여 사용한다. 본 발명의 방법에서 사용할 수 있는 초임계 추출용기는 온도와 압력이 조절될 수 있으며, 추출원료와 초임계 유체가 접촉하도록 구성된 용기이면 특별히 한정되지 않는다. The present invention basically follows the supercritical fluid extraction process. Cinnamomum verum , a raw material for supercritical extraction, is crushed to form a powder of suitable size. The supercritical extraction container which can be used in the method of the present invention can be controlled in temperature and pressure, and is not particularly limited as long as the container is configured to contact the extraction raw material and the supercritical fluid.
본 발명에서 이용되는 초임계유체는 당업계에서 통상적으로 이용되는 다양한 초임계유체를 포함하며, 바람직하게는 물 또는 이산화탄소를 사용한다. The supercritical fluid used in the present invention includes various supercritical fluids conventionally used in the art, and preferably water or carbon dioxide is used.
상기 초임계유체와 함께 사용되는 보조용매는 당업계에서 통상적으로 이용되는 극성 용매를 포함하며, 바람직하게는 알코올, 물, 에틸렌 글라이콜, 폴리에틸렌글라이콜, 프로필렌카보네이트, 포름산, 아세트산, 아세토니트릴, 클로로디프루오로메탄 또는 이의 혼합물로 구성된 군으로부터 선택되며, 보다 바람직하게는 메탄올, 에탄올, 프로판올, 1-헥사놀, 2-메톡시에탄올 및 그의 조합으로 구성된 군으로부터 선택되는 알코올이고, 보다 더 바람직하게는 메탄올 또는 에탄올이며, 가장 바람직하게는 에탄올이다. Cosolvents used with the supercritical fluid include polar solvents commonly used in the art, preferably alcohol, water, ethylene glycol, polyethylene glycol, propylene carbonate, formic acid, acetic acid, acetonitrile , Chlorodifluoromethane or a mixture thereof, more preferably an alcohol selected from the group consisting of methanol, ethanol, propanol, 1-hexanol, 2-methoxyethanol and combinations thereof, and even more Preferably methanol or ethanol, most preferably ethanol.
본 발명의 바람직한 구현 예에 따르면, 상기 단계 (b)의 초임계 추출에서의 압력은 100-500 bar, 보다 바람직하게는 200-400 bar, 가장 바람직하게는 300-400 bar이다. According to a preferred embodiment of the present invention, the pressure in the supercritical extraction of step (b) is 100-500 bar, more preferably 200-400 bar, most preferably 300-400 bar.
본 발명의 다른 바람직한 구현 예에 따르면, 상기 단계 (b)의 초임계 추출에서의 온도는 10-100℃, 보다 바람직하게는 30℃-70℃, 보다 더 바람직하게는 30-50℃이고, 가장 바람직하게는 30-40℃이다. According to another preferred embodiment of the invention, the temperature in the supercritical extraction of step (b) is 10-100 ° C., more preferably 30 ° C.-70 ° C., even more preferably 30-50 ° C., most Preferably it is 30-40 degreeC.
본 발명의 또 다른 바람직한 구현 예에 따르면, 상기 단계 (b)의 초임계 추출에서의 초임계 유체 및 보조용매의 유속은 10-100 g/분, 보다 바람직하게는 30-70 g/분, 가장 바람직하게는 40-50 g/분이다. According to another preferred embodiment of the invention, the flow rate of the supercritical fluid and the cosolvent in the supercritical extraction of step (b) is 10-100 g / min, more preferably 30-70 g / min, most Preferably 40-50 g / min.
본 발명의 또 다른 바람직한 구현 예에 따르면, 본 발명의 방법에 의해 제조된 계피 초임계 추출물은 시남알데하이드를 포함한다. 본 발명의 계피 초임계 추출물에 포함되는 시남알데하이드의 양은 바람직하게는 50-500 mg/g, 보다 바람직하게는 100-400 mg/g, 보다 더 바람직하게는 200-400 mg/g, 가장 바람직하게는 300-400 mg/g을 포함한다. According to another preferred embodiment of the present invention, the cinnamon supercritical extract prepared by the method of the present invention comprises sinamaldehyde. The amount of cinnaaldehyde contained in the cinnamon supercritical extract of the present invention is preferably 50-500 mg / g, more preferably 100-400 mg / g, even more preferably 200-400 mg / g, most preferably Contains 300-400 mg / g.
본 발명의 다른 일 양태에 따르면, 본 발명은 상기 본 발명의 방법에 의해 제조된 계피 초임계 추출물을 유효성분으로 포함하는 항균용 조성물을 제공한다. According to another aspect of the present invention, the present invention provides an antimicrobial composition comprising the cinnamon supercritical extract prepared by the method of the present invention as an active ingredient.
본 발명의 바람직한 구현 예에 따르면, 본 발명의 계피 초임계 추출물은 식중독 유발하는 원인균에 대해 항균활성을 나타낸다. According to a preferred embodiment of the present invention, the cinnamon supercritical extract of the present invention exhibits antimicrobial activity against the causative agent causing food poisoning.
상기 식중독 균은 대장균(Escherichia coli), 바실러스 세레우스(Bacillus cereus), 황색포도상구균(Staphylococcus aureus), 리스테리아모노사이토제네스(Listeria monocytogenes), 스트렙토코커스 뮤탄스(Streptococcus mutans), 살모넬라 티피뮤리움(Salmonella typhimurium), 녹농균(Pseudomonas aeruginosa), 또는 장염비브리오(Vibrio parahaemolyticus)을 포함하나, 이에 한정되지 않는다. The food poisoning bacterium is Escherichia coli ), Bacillus cereus , Staphylococcus aureus ), Listeria monocytogenes ( Listeria) monocytogenes ), Streptococcus mutans), Salmonella typhimurium (Salmonella typhimurium ), Pseudomonas aeruginosa ), or Vibrio parahaemolyticus .
본 발명의 상기 항균용 조성물은 항균용 약제학적 조성물로 제조될 수 있다. 즉, 본 발명의 항균용 약제학적 조성물은 (a) 상술한 본 발명의 계피 초임계 추출물의 약제학적 유효량; 및 (b) 약제학적으로 허용되는 담체를 포함하는 약제학적 조성물이다. 본 명세서에서 용어 “약제학적 유효량”은 상술한 계피 초임계 추출물의 항균 효능 또는 활성을 달성하는 데 충분한 양을 의미한다. The antimicrobial composition of the present invention may be prepared as an antimicrobial pharmaceutical composition. That is, the antimicrobial pharmaceutical composition of the present invention comprises (a) a pharmaceutically effective amount of the cinnamon supercritical extract of the present invention; And (b) a pharmaceutically acceptable carrier. As used herein, the term “pharmaceutically effective amount” means an amount sufficient to achieve the antimicrobial efficacy or activity of the cinnamon supercritical extract described above.
본 발명의 조성물이 약제학적 조성물로 제조되는 경우, 본 발명의 약제학적 조성물은 약제학적으로 허용되는 담체를 포함한다. 본 발명의 약제학적 조성물에 포함되는 약제학적으로 허용되는 담체는 제제시에 통상적으로 이용되는 것으로서, 락토스, 덱스트로스, 수크로스, 솔비톨, 만니톨, 전분, 아카시아 고무, 인산 칼슘, 알기네이트, 젤라틴, 규산 칼슘, 미세결정성 셀룰로스, 폴리비닐피롤리돈, 셀룰로스, 물, 시럽, 메틸 셀룰로스, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 활석, 스테아르산 마그네슘 및 미네랄 오일 등을 포함하나, 이에 한정되는 것은 아니다. 본 발명의 약제학적 조성물은 상기 성분들 이외에 윤활제, 습윤제, 감미제, 향미제, 유화제, 현탁제, 보존제 등을 추가로 포함할 수 있다. 적합한 약제학적으로 허용되는 담체 및 제제는 Remington's Pharmaceutical Sciences (19th ed., 1995)에 상세히 기재되어 있다.When the composition of the present invention is manufactured from a pharmaceutical composition, the pharmaceutical composition of the present invention includes a pharmaceutically acceptable carrier. Pharmaceutically acceptable carriers included in the pharmaceutical compositions of the present invention are those commonly used in the preparation, such as lactose, dextrose, sucrose, sorbitol, mannitol, starch, acacia rubber, calcium phosphate, alginate, gelatin, Calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl cellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil, and the like It doesn't happen. In addition to the above components, the pharmaceutical composition of the present invention may further include a lubricant, a humectant, a sweetener, a flavoring agent, an emulsifier, a suspending agent, a preservative, and the like. Suitable pharmaceutically acceptable carriers and formulations are described in detail in Remington ' s Pharmaceutical Sciences (19th ed., 1995).
본 발명의 약제학적 조성물은 경구 또는 비경구 투여할 수 있으며, 바람직하게는 경구 투여 방식으로 적용된다.The pharmaceutical composition of the present invention can be administered orally or parenterally, and is preferably administered orally.
본 발명의 약제학적 조성물의 적합한 투여량은 제제화 방법, 투여 방식, 환자의 연령, 체중, 성, 병적 상태, 음식, 투여 시간, 투여 경로, 배설 속도 및 반응 감응성과 같은 요인들에 의해 다양하게 처방될 수 있다. 본 발명의 약제학적 조성물의 일반적인 투여량은 성인 기준으로 0.001-100 ㎎/kg 범위 내이다. The appropriate dosage of the pharmaceutical composition of the present invention may vary depending on factors such as the formulation method, administration method, age, body weight, sex, pathological condition, food, administration time, administration route, excretion rate, . Typical dosages of the pharmaceutical compositions of the invention are in the range of 0.001-100 mg / kg on an adult basis.
본 발명의 약제학적 조성물은 당해 발명이 속하는 기술분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있는 방법에 따라, 약제학적으로 허용되는 담체 및/또는 부형제를 이용하여 제제화함으로써 단위 용량 형태로 제조되거나 또는 다용량 용기 내에 내입시켜 제조될 수 있다. 이때 제형은 오일 또는 수성 매질중의 용액, 현탁액, 시럽제 또는 유화액 형태이거나 엑스제, 산제, 분말제, 과립제, 정제 또는 캅셀제 형태일 수도 있으며, 분산제 또는 안정화제를 추가적으로 포함할 수 있다. The pharmaceutical compositions of the present invention may be prepared in unit dose form by formulating with a pharmaceutically acceptable carrier and / or excipient according to methods which can be easily carried out by those skilled in the art. Or may be prepared by incorporation into a multi-dose container. The formulation may be in the form of solutions, suspensions, syrups or emulsions in oils or aqueous media, or in the form of extracts, powders, powders, granules, tablets or capsules, and may further comprise dispersants or stabilizers.
본 발명의 다른 양태에 따르면, 본 발명은 다음 단계를 포함하는 계피 초임계 박 추출물의 제조방법을 제공한다: (a) 계피를 파쇄하는 단계; (b) 상기 단계 (a)에서 얻어진 계피 파쇄물을 초임계 추출용기에 넣고, 초임계유체 및 보조 용매를 계피 파쇄물에 접촉하도록 상기 추출용기에 흘려주어 초임계 추출을 행하는 단계; (c) 상기 단계 (b)의 초임계 추출을 행하고 난 후의 계피 파쇄물의 잔여물을 얻는 단계; 및 (d) 상기 단계 (c)의 계피 파쇄물의 잔여물에 추출 용매를 가하여 추출하는 단계. According to another aspect of the present invention, the present invention provides a method of preparing a cinnamon supercritical gourd extract, comprising the following steps: (a) crushing cinnamon; (b) putting the cinnamon crushed product obtained in step (a) into a supercritical extraction container, and performing supercritical extraction by flowing a supercritical fluid and an auxiliary solvent into the extraction container so as to contact the cinnamon crushed product; (c) obtaining a residue of cinnamon crush after the supercritical extraction of step (b); And (d) extracting by adding an extraction solvent to the residue of the cinnamon crush of step (c).
본 명세서에서 사용되는 용어 “계피 초임계 박 추출물”은 계피로부터 초임계 추출물을 추출하고 남은 계피 부산물에 대하여 추가 용매 추출 단계를 거쳐 수득한 추출물을 의미한다. As used herein, the term “cinnamon supercritical gourd extract” refers to an extract obtained by extracting the supercritical extract from cinnamon and performing a further solvent extraction step on the remaining cinnamon by-products.
본 발명의 명세서에서 계피 초임계 박 추출물 제조방법에서 상기 계피 초임계 추출물 제조방법과 공통된 내용은 본 명세서의 과도한 복잡성을 피하기 위해서 그 기재를 생략한다. In the description of the present invention, the method common to the cinnamon supercritical extract manufacturing method in the cinnamon supercritical gourd extract manufacturing method is omitted in order to avoid excessive complexity of the present specification.
본 발명의 바람직한 구현 예에 따르면, 본 발명의 계피 초임계 박 추출물은 계피로부터 초임계 추출 후 남은 부산물에 추출 용매를 가하여 수득할 수 있다. 상기 추출 용매는 당업계에서 통상적으로 이용되는 어떠한 추출 용매도 포함한다. According to a preferred embodiment of the present invention, the cinnamon supercritical gourd extract of the present invention can be obtained by adding an extraction solvent to the by-products remaining after supercritical extraction from cinnamon. The extraction solvent includes any extraction solvent commonly used in the art.
바람직하게는 물, 탄소수 1-4개의 무수 또는 함수 저급 알코올, 아세톤, 에틸아세테이트, 부틸아세테이트, 클로로포름, 헥산, 디에틸에테르 또는 1,3-부틸렌 글리콜이다. Preferably it is water, anhydrous or hydrous lower alcohol of 1-4 carbon atoms, acetone, ethyl acetate, butyl acetate, chloroform, hexane, diethyl ether or 1,3-butylene glycol.
본 발명의 다른 일 양태에 따르면, 본 발명은 상기 계피 초임계 박 추출물의 제조방법에 의해 제조된 계피 초임계 박 추출물을 유효성분으로 포함하는 항산화용 기능성 식품 조성물을 제공한다. According to another aspect of the present invention, the present invention provides a functional food composition for antioxidant comprising the cinnamon supercritical gourd extract prepared by the method of preparing the cinnamon supercritical gourd extract as an active ingredient.
본 발명의 다른 일 양태에 따르면, 본 발명은 상기 계피 초임계 박 추출물의 제조방법에 의해 제조된 계피 초임계 박 추출물을 유효성분으로 포함하는 항산화용 화장품 조성물을 제공한다. According to another aspect of the present invention, the present invention provides a cosmetic composition for antioxidant comprising the cinnamon supercritical gourd extract prepared by the method of preparing the cinnamon supercritical gourd extract as an active ingredient.
본 발명의 계피 초임계 박 추출물은 우수한 DPPH 자유 라디칼 및 ABTS 자유 라디칼 소거활성을 가진다. Cinnamon supercritical gourd extract of the present invention has excellent DPPH free radicals and ABTS free radical scavenging activity.
본 발명의 조성물이 기능성 식품 조성물로 제공되는 경우 (ⅰ) 계피 초임계 박 추출물의 식품학적 유효량; 및 (ⅱ) 식품학적으로 허용되는 담체를 포함하는 식품 조성물이다. 본 발명의 조성물이 식품 조성물로 제조되는 경우, 유효성분으로서 계피 초임계 박 추출물뿐만 아니라, 식품 제조 시에 통상적으로 첨가되는 성분을 포함하며, 예를 들어, 단백질, 탄수화물, 지방, 영양소, 조미제 및 향미제를 포함한다. 상술한 탄수화물의 예는 모노사카라이드, 예를 들어, 포도당, 과당 등; 디사카라이드, 예를 들어 말토스, 슈크로스, 올리고당 등; 및 폴리사카라이드, 예를 들어 덱스트린, 사이클로덱스트린 등과 같은 통상적인 당 및 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 향미제로서 천연 향미제 [타우마틴, 스테비아 추출물 (예를 들어 레바우디오시드 A, 글리시르히진 등]) 및 합성 향미제(사카린, 아스파르탐 등)를 사용할 수 있다. 예컨대, 본 발명의 식품 조성물이 드링크제로 제조되는 경우에는 본 발명의 계피 초임계 박 추출물 이외에 구연산, 액상과당, 설탕, 포도당, 초산, 사과산, 과즙, 두충 추출액, 대추 추출액, 감초 추출액 등을 추가로 포함시킬 수 있다. (Iii) a food-effective amount of cinnamon supercritical gourd extract, when the composition of the present invention is provided as a functional food composition; And (ii) a pharmaceutically acceptable carrier. When the composition of the present invention is prepared as a food composition, it contains not only cinnamon supercritical gourd extract as an active ingredient, but also components commonly added during food preparation, and include, for example, proteins, carbohydrates, fats, nutrients, and seasonings. And flavoring agents. Examples of the above-mentioned carbohydrates are monosaccharides such as glucose, fructose, and the like; Disaccharides such as maltose, sucrose, oligosaccharides and the like; And polysaccharides such as dextrin, cyclodextrin and the like, and sugar alcohols such as xylitol, sorbitol and erythritol. Natural flavorings such as tau martin and stevia extract (e.g., rebaudioside A and glycyrrhizin) and synthetic flavorings (saccharine, aspartame, etc.) can be used as flavorings. For example, when the food composition of the present invention is prepared with a drink, in addition to the cinnamon supercritical gourd extract of the present invention, citric acid, liquid fructose, sugar, glucose, acetic acid, malic acid, fruit juice, tofu extract, jujube extract, licorice extract, etc. Can be included.
본 발명의 조성물이 화장품 조성물로 제공되는 경우 상기 계피 초임계 박 추출물 이외에 화장품 조성물에 통상적으로 이용되는 성분들을 포함하며, 예컨대 항산화제, 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제, 그리고 담체를 포함한다. When the composition of the present invention is provided as a cosmetic composition, in addition to the cinnamon supercritical gourd extract, it contains ingredients conventionally used in cosmetic compositions, such as conventional supplements such as antioxidants, stabilizers, solubilizers, vitamins, pigments and flavorings. And carriers.
본 발명의 화장품 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클렌징, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 유연 화장수 (스킨), 영양 화장수 (밀크로션), 영양 크림, 맛사지 크림, 에센스, 아이 크림, 클렌징 크림, 클렌징 포옴, 클렌징 워터, 팩, 스프레이 또는 파우더의 제형으로 제조될 수 있다. Cosmetic compositions of the present invention may be prepared in any formulation conventionally prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing , Oils, powder foundations, emulsion foundations, wax foundations and sprays, and the like, but are not limited thereto. More specifically, it may be prepared in the form of a flexible lotion (skin), nourishing lotion (milk lotion), nourishing cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder. .
본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다. When the formulation of the present invention is a paste, cream or gel, an animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component .
본 발명의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다. In the case where the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. Especially, in the case of a spray, a mixture of chlorofluorohydrocarbons, propane / Propane or dimethyl ether.
본 발명의 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌 글리콜, 1,3-부틸글리콜오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다. When the formulation of the present invention is a solution or emulsion, a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소 결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다. When the formulation of the present invention is a suspension, a liquid diluent such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, and microcrystals are used as carrier components. Soluble cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.
본 발명의 제형이 계면-활성제 함유 클렌징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올 에테르설페이트, 설포숙신산 모노에스테르, 이세티오네이트, 이미다졸리늄 유도체, 메틸타우레이트, 사르코시네이트, 지방산 아미드 에테르 설페이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세리드, 지방산 디에탄올아미드, 식물성 유, 라놀린유도체 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다.
When the formulation of the present invention is a surfactant-containing cleansing, the carrier component is an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, an isethionate, an imidazolinium derivative, a methyltaurate, a sarcosinate, a fatty acid amide. Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
본 발명의 특징 및 이점을 요약하면 다음과 같다:The features and advantages of the present invention are summarized as follows:
(ⅰ) 본 발명은 계피 초임계 추출물의 제조방법을 제공한다. (Iii) The present invention provides a method for preparing a cinnamon supercritical extract.
(ⅱ) 본 발명의 계피 초임계 추출물은 항균 활성을 가지며, 특히 식중독 유발균에 대해 항균활성이 우수하다. (Ii) The cinnamon supercritical extract of the present invention has antimicrobial activity, and particularly excellent antimicrobial activity against food poisoning causing bacteria.
(ⅲ) 본 발명은 계피 초임계 박 추출물의 제조방법을 제공한다.(Iii) The present invention provides a method for preparing cinnamon supercritical gourd extract.
(ⅳ) 본 발명의 계피 초임계 박 추출물은 우수한 자유 라디칼 소거활성을 나타낸다.
(Iii) The cinnamon supercritical gourd extract of the present invention shows excellent free radical scavenging activity.
도 1은 계피 초임계 추출물의 GC/MS 분석을 통해 확인한 (E)-시남알데하이드의 화학구조를 나타낸 그림이다. 1 is a diagram showing the chemical structure of (E) -cinnamaldehyde confirmed through GC / MS analysis of cinnamon supercritical extract.
이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 의해 제한되지 않는다는 것은 당업계에서 통상의 지식을 가진 자에 있어서 자명할 것이다.
Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for describing the present invention in more detail and that the scope of the present invention is not limited by these embodiments in accordance with the gist of the present invention .
실시예Example
재료 및 방법Materials and methods
계피 메탄올 추출물 제조Cinnamon Methanol Extract Manufacturer
본 실험에서 사용한 계피(Cinnamomum verum)는 대구시 약령시장에서 건조 상태의 것을 구입하여 분쇄한 후, 무게의 10 배량(w/v)의 80％ 메탄올을 가하여 24 hr 정치하여 총 3 회 반복 추출하였다. 추출액은 여과지(Whatman No. 3, Whatman International Ltd., Maidstone, England)로 여과한 다음 회전진공농축기(UT-1000, EYELA, Tokyo, Japan)로 55℃에서 농축한 후 동결 건조하여 메탄올 추출물로 사용하였다. Cinnamomum used in this experiment verum ) was dried and pulverized at the Yangnyeong market in Daegu, and then extracted 10 times (w / v) of 80% methanol for 24 hr and extracted three times. The extract was filtered using filter paper (Whatman No. 3, Whatman International Ltd., Maidstone, England), concentrated using a rotary vacuum concentrator (UT-1000, EYELA, Tokyo, Japan) at 55 ° C, and freeze-dried to be used as a methanol extract. It was.
계피 cinnamon 초임계Supercritical 추출물( extract( SFESFE OilOil )의 제조Manufacturing
초임계 추출에는 초임계 추출 장치 Waters AD-RC 08(Waters CO., Milford, MA, USA)를 사용하였다. 시료를 추출 용기에 300 g을 넣어 이산화탄소(CO2)유속 : 보조용매유속 = 47.5 g/분 : 2.5 g/분으로 하여 총 유속(이산화탄소유속 + 보조용매유속)은 50 g/분의 속도로 흘려주었고, 보조용매로는 HPLC급 에틸 알코올(JT Baker Co., Phillipsburg, NJ, USA)를 사용하였다. 추출 온도는 35℃, 추출 시간은 120분으로 고정하였으며, 압력을 200, 300, 400 bar로 하여 압력이 다른 3가지 조건에서 추출하였다. 회수된 추출물을 40℃에서 회전진공농축기(EYELA Co., Tokyo, Japan)를 이용하여 농축한 후 실험에 사용하였다. A supercritical extraction device, Waters AD-RC 08 (Waters CO., Milford, MA, USA) was used for supercritical extraction. 300 g of the sample was placed in the extraction vessel and the carbon dioxide (CO 2 ) flow rate: co-solvent flow rate = 47.5 g / min: 2.5 g / min, and the total flow rate (carbon dioxide flow rate + co-solvent flow rate) was flowed at a rate of 50 g / min. HPLC grade ethyl alcohol (JT Baker Co., Phillipsburg, NJ, USA) was used as a cosolvent. The extraction temperature was fixed at 35 ° C. and the extraction time was 120 minutes. The pressures were 200, 300, and 400 bar, and extracted under three different conditions. The recovered extract was concentrated at 40 ° C. using a rotary vacuum concentrator (EYELA Co., Tokyo, Japan) and used for experiments.
계피 cinnamon 초임계Supercritical 박 메탄올 추출물( Gourd methanol extract ( SFMSFM ) 제조) Produce
초임계 추출을 하고 남은 계피의 부산물인 계피 박을 무게의 10배(w/v)의 메탄올(80％)을 가하여 24 시간 정치하여 3회 반복하여 회수된 추출물을 여과하여 회전진공농축기로 55℃에서 감압 농축한 후 동결 건조하여 사용하였다. After the supercritical extraction, the remaining cinnamon by-product of cinnamon was added 10 times (w / v) of methanol (80%) and left for 24 hours. The extract was recovered three times and filtered. Concentrated under reduced pressure at and then lyophilized.
추출 수율Extraction yield
추출 조건별 추출 수율은 추출 전 시료 건조물의 중량에 대비 각 추출 방법에 의해 생성된 추출 용액을 회전진공농축기로 감압 농축하여 나온 추출물 무게에 대한 백분율로 나타내었다.The extraction yield for each extraction condition was expressed as a percentage of the weight of the extract obtained by concentrating the extraction solution produced by each extraction method under reduced pressure with a rotary vacuum concentrator, relative to the weight of the sample before extraction.
추출수율(％, w/w) = 추출물건조무게 / 시료건조무게 X 100 Extraction yield (%, w / w) = extract dry weight / sample dry weight X 100
GCGC /Of MSMS 를 이용한 성분 분석Component Analysis
계피 초임계 추출물을 에탄올에 희석한 후 0.45 μM 멤브레인 필터로 여과하여 분석 시료로 사용하였다. 실험에 사용한 GC/MS 시스템은 HP 190915-433 모델(Paloalto, California, USA)이며 컬럼은 HP-5MS (30 m X 0.25 mm, 0.25 μM)를 사용하였고 검출기로는 MS를 이용하였다. ESI 모드에서 70 eV의 에너지로 이온화하였으며 TIC의 SCAN 모드에서 검출이온 질량범위 35-350으로 설정하여 각 질량스펙트럼 중에서 가장 강도가 강한 메인 조각 이온을 중심으로 라이브러리를 검색하여 물질 확인 분석을 하였다. 주입기 온도는 260℃, 검출기 온도는 280℃이며 캐리어 가스는 헬륨을 사용하여 유속을 1 mL/분으로 사용하였다. 오븐 온도는 최초 50℃에서 5분 동안 유지한 후 4℃/분 속도로 200℃까지 상승시킨 후, 200℃에서 20℃/분 속도로 280℃까지 온도를 상승시킨 후 20분간 유지하였다. 라이브러리를 통해 검색된 메인 피크인 계피의 주요 성분인 시남알데하이드는 50, 500, 1000 ppm의 농도로 제조한 후 정량 분석에 이용하였다. Cinnamon supercritical extract was diluted in ethanol and filtered through 0.45 μM membrane filter to use as analytical sample. The GC / MS system used in the experiment was HP 190915-433 model (Paloalto, California, USA) and the column was HP-5MS (30 m × 0.25 mm, 0.25 μM) and MS was used as a detector. In the ESI mode, it was ionized with energy of 70 eV and the detection ion mass range was set to 35-350 in the SCAN mode of TIC, and the library was searched for the strongest main fragment ions among the mass spectra. The injector temperature was 260 ° C., the detector temperature was 280 ° C. and the carrier gas used helium at a flow rate of 1 mL / min. The oven temperature was first maintained at 50 ° C. for 5 minutes, then raised to 200 ° C. at 4 ° C./min, and then increased to 200 ° C. at 200 ° C./min at 280 ° C. for 20 minutes. Cinnamic aldehyde, the main component of cinnamon, the main peak retrieved through the library, was prepared at a concentration of 50, 500, and 1000 ppm and used for quantitative analysis.
DPPHDPPH (α-α- (α-α- 디페닐Diphenyl -β--β- 피크릴히드라질Picrylhydrazil ) ) 라디칼Radical 소거 활성 Scavenging activity
시료의 자유 라디칼 소거 활성은 안정한 라디칼인 DPPH(α-α-디페닐-β-피크릴히드라질)에 대한 환원력을 측정한 것으로 99％ 메탄올에 각 시료를 녹여 농도별로 희석한 희석액 160 μL와 메탄올에 녹인 0.15 mM DPPH 용액 40 μL를 가하여 실온에 30분 방치한 후 517 nm에서 흡광도를 측정하였다. 각 시료 추출물의 자유 라디칼 소거활성은 시료를 첨가하지 않은 대조구의 흡광도를 1/2로 환원시키는데 필요한 시료의 농도인 RC50값으로 나타내었다. 이때 활성비교를 위하여 BHA를 사용하였다. The free radical scavenging activity of the samples was measured by reducing the radicals of DPPH (α-α-diphenyl-β-picrylhydrazyl), which is 160 μL of diluent diluted with each concentration in 99% methanol and methanol. 40 μL of the dissolved 0.15 mM DPPH solution was added thereto, and the mixture was left at room temperature for 30 minutes and absorbance was measured at 517 nm. The free radical scavenging activity of each sample extract was expressed as a value of RC 50 , which is the concentration of the sample required to reduce the absorbance of the control group without the sample to 1/2. BHA was used for activity comparison.
ABTSABTS 라디칼Radical 소거 활성 Scavenging activity
7 mM 2,2'-아지노-비스(3-에틸벤지아졸린-6-술폰산)(ABTS, Sigma Chemical Co., St. Louis, MO, USA)와 2.45 mM 과황산 칼륨을 최종 농도로 혼합하여 실온인 암소에서 24시간 동안 방치하여 ABTS+·을 형성시킨 후 96-웰에 734 nm에서 흡광도 값이 0.70(±0.02)이 되게 PBS(pH 4)로 희석하였다. 희석된 용액 180 μL에 샘플 20 μL를 가하여 정확히 1분 동안 방치한 후 흡광도를 측정하였다. 각 시료 추출물과 단일 물질의 자유 라디칼 소거 활성은 시료를 첨가하지 않은 대조구의 흡광도를 1/2로 환원시키는데 필요한 시료의 농도인 RC50값으로 나타내었다.7 mM 2,2'-azino-bis (3-ethylbenziazolin-6-sulfonic acid) (ABTS, Sigma Chemical Co., St. Louis, MO, USA) and 2.45 mM potassium persulfate were mixed to final concentration After standing for 24 hours in the dark at room temperature to form ABTS +. The 96-well was diluted with PBS (pH 4) to the absorbance value of 0.70 (± 0.02) at 734 nm. 20 μL of the sample was added to 180 μL of the diluted solution, and the absorbance was measured after standing for exactly 1 minute. The free radical scavenging activity of each sample extract and a single substance was expressed by the RC 50 value, which is the concentration of the sample required to reduce the absorbance of the control without the sample to 1/2.
사용 균주 및 배지Strains and Mediums Used
본 실험에서 사용한 대장균(Escherichia coli ) O157:H7의 표준균주인 ATCC 4388, 바실러스 세레우스(Bacillus cereus)의 표준균주인 ATCC 12573은 미국균주보존센터로부터, 황색포도상구균(Staphylococcus aureus)의 표준균주인 KCTC 1621, 리스테리아모노사이토제네스(Listeriamonocytogenes)의 표준균주인 KCTC 3710은 한국생명공학연구원 생물자원센터로부터, 스트렙토코커스 뮤탄스(Streptococcus mutans)의 표준균주인 KCCM 40105, 살모넬라 티피뮤리움(Salmonella typhimurium)의 표준균주인 KCCM 11862, 녹농균(Pseudomonas aeruginosa )의 표준균주인 KCCM 1132, 장염비브리오(Vibrio parahaemolyticus)의 표준균주인 KCCM 11965을 한국미생물보전센터로부터 분양 받아 각각의 균들을 TSB(tryptic soy broth, Difco, Detroit, USA)에 1백금이 접종하여 37℃에서 24시간 진탕하여 3회 계대 배양 후 성장 최적조건에서 배양 시켰다. 또한, 생균수 측정을 위한 배지는 TSA(tryptic soy agar, Difco)를, 세균을 희석하기 위한 희석수로는 멸균 증류수를 사용하였다. Escherichia coli used in this experiment coli ) O157: H7 standard strain ATCC 4388, Bacillus cereus standard strain ATCC 12573 from the US Center for Conservation, Staphylococcus from aureus) strains of KCTC 1621, Listeria monocytogenes strains of KCTC 3710 the Korea Research Institute of Bioscience and Biotechnology Biological Resource Center of jeneseu (Listeriamonocytogenes) of Streptococcus mutans (standard strain KCCM 40105, Salmonella typhimurium of Streptococcus mutans) Salmonella typhimurium ) standard strain KCCM 11862, Pseudomonas aeruginosa ) standard strain KCCM 1132, Vibrio KCCM 11965, a standard strain of parahaemolyticus , was distributed from the Korea Center for Microbiological Conservation, and each bacterium was inoculated with platinum to TSB (tryptic soy broth, Difco, Detroit, USA) and shaken for 24 hours at 37 ° C for three passages. Cultured at optimum growth conditions. In addition, TSA (tryptic soy agar, Difco) was used as a medium for measuring the number of viable cells, and sterile distilled water was used as dilution water for diluting bacteria.
항균활성 측정Antimicrobial Activity
추출물의 항균력 검색은 원판확산법(15)을 이용하여 실시하였다. 균주를 100 mL TSB에 접종하고 37℃에서 진탕하면서 24시간 배양하여 활성화시키고 3일 계대 배양 후 분광광도계(UNIKON922, Kontron, Milan, Italy)를 이용하여 560 nm에서 O.D값이 0.2가 되게 하여 균수를 1 X 107 cfu/mL로 사용하였다. 고체배지에 멸균된 자유 스프레더로 균을 고르게 펼친 후, 8 mm 종이 디스크(지름 8 mm, Adantec co., Tokyo, Japan)를 올려놓은 다음 추출물을 최종 농도가 0.5, 2.5, 5 mg/디스크가 되도록 DMSO에 용해시키고, 50 를 주입하여 완전히 흡수시킨 후 37℃ 배양기에서 24시간 배양시켜 종이 디스크 주위의 억제대(inhibition zone, mm)의 직경을 측정하였다. Antimicrobial activity search of the extract was carried out using the disc diffusion method (15). The strain was inoculated in 100 mL TSB and incubated for 24 hours with shaking at 37 ° C. After 3 days of passage, the OD value was 0.2 at 560 nm using a spectrophotometer (UNIKON922, Kontron, Milan, Italy). 1 X 10 7 cfu / mL was used. Spread the bacteria evenly with a sterile free spreader in a solid medium, put an 8 mm paper disc (8 mm diameter, Adantec co., Tokyo, Japan) and place the extract at a final concentration of 0.5, 2.5 or 5 mg / disk. After dissolving in DMSO, 50 were completely absorbed, and then incubated in a 37 ° C. incubator for 24 hours, the diameter of the inhibition zone (mm) around the paper disc was measured.
실험 결과Experiment result
계피 메탄올 추출물과 계피 Cinnamon Methanol Extract and Cinnamon 초임계Supercritical 추출물의 수율 Yield of Extract
하기 표 1에서 나타낸 것과 같이, 계피 메탄올 추출물의 수율은 19.93％이었다. 계피의 초임계 추출 수율의 최적의 조건을 검토하기 위하여 35℃ 에서 200, 300, 400 bar의 압력 조건에서 초임계 추출을 실시한 결과, 계피 초임계 추출물(SFE)과 계피 초임계 박 메탄올 추출물(SFE)의 수율은 용매 추출물에 비해 다소 낮은 추출 수율(초임계 추출물(SFE)은 4.73-7.56％, 계피 초임계 박 메탄올 추출물(SFM)은 7.83-10％)을 보였으나, SFE 및 SFE에서 압력이 높아질수록 수율이 증가하는 경향을 보였다. As shown in Table 1 below, the yield of cinnamon methanol extract was 19.93%. In order to examine the optimum conditions for the yield of supercritical extraction of cinnamon, supercritical extraction was carried out at 35, 200, 300 and 400 bar under pressure conditions. ) Yield was slightly lower than that of solvent extract (4.73-7.56% for supercritical extract (SFE), 7.83-10% for supercritical gourd methanol extract (SFM) of cinnamon), but the pressure in SFE and SFE The yield tended to increase as it increased.
a80 ％ 메탄올: 계피(Cinnamomum verum )의 메탄올 추출물 a 80% methanol: cinnamomum The methanol extract of verum)
bSFE: 계피 초임계 추출물(supercritical fluid extracts) b SFE: supercritical fluid extracts
cSFM: 계피 초임계 박 메탄올 추출물(Methanol extract of SFE Marc)
c SFM: Cinnamon Supercritical Pak Methanol Extract of SFE Marc
GCGC /Of MSMS 를 이용한 Using 시남알데하이드Sinamaldehyde 함량 분석 Content analysis
각 조건별 계피 초임계 추출물을 GC/MS를 이용하여 정유성분과 화학구조를 규명한 결과, (E)-시남알데하이드의 피크를 관찰하였고 화학구조를 규명한 결과는 도 1과 같다. 시남알데하이드 함량을 산출한 결과는 표 2에 나타내었다. 표 2의 결과에 의하면, 80％ 메탄올 추출물에 비해 계피 초임계 추출물(SFE) 오일에서의 시남알데하이드의 함량이 약 30-60배 이상 많이 함유되어 있었고, 특히 300 bar에서 시남알데하이드 함량이 가장 높음을 알 수 있었다. 계피 초임계 박 메탄올 추출물(SFM)에서는 80％ 메탄올 추출물보다 시남알데하이드 함량이 적었고 압력이 높을수록 함량이 줄어드는 것을 확인하였다. 본 발명의 초임계 추출법에 의하면, 기존의 오일을 추출하는 soxhlet 추출법에 비해 더 많은 시남알데하이드를 얻을 수 있었다. As a result of identifying the essential oil components and chemical structure of the cinnamon supercritical extract for each condition using GC / MS, the peaks of (E) -cinnamaldehyde were observed and the results of the chemical structure are shown in FIG. 1. The results of calculating the cinnamaldehyde content are shown in Table 2. According to the results of Table 2, the cinnamic aldehyde content of cinnamon supercritical extract (SFE) oil contained about 30-60 times more than the 80% methanol extract, and especially the highest cinnamic aldehyde content at 300 bar. Could know. In cinnamon supercritical gourd methanol extract (SFM), the content of cinnamic aldehyde was lower than that of 80% methanol extract, and it was confirmed that the content decreases with higher pressure. According to the supercritical extraction method of the present invention, it was possible to obtain more cinnamic aldehyde than the soxhlet extraction method for extracting the existing oil.
DPPHDPPH 자유 freedom 라디칼Radical 소거활성 Scavenging activity
DPPH는 분자 내 자유 라디칼을 가지고 있는 수용성 물질로 아스코르빈산, 토코페롤, 폴리하이드록시 방향족 화합물 등에 의해 환원되어 짙은 자색이 탈색되는데, 이 때 분자의 움직임은 하이드록실 라디칼과 유사하여 다양한 천연 소재로부터 항산화 물질을 검색하는데 많이 이용되고 있다(4, 9). ROS(reactive oxygen species)는 체내 방어기전에 의해 대부분 제거되지만 제거되지 못할 경우 생체분자들과 신속하게 반응하여 단백질의 변성이나 생체막의 지질 과산화, DNA 손상 등을 일으키며, 세포 내로 확산되거나 혈류를 통해 이동된 지질 과산화물은 새로운 라디칼 반응을 촉진시켜 각종 질환의 원인으로 작용한다(7). 계피 메탄올 추출물 및 계피 초임계 추출물, 계피 초임계 박 추출물의 DPPH 자유 라디칼 소거활성을 합성 항산화제인 BHA와 비교한 결과를 표 3에 나타내었다. 계피 초임계 추출물을 제외한 계피 메탄올 추출물, 계피 초임계 박 메탄올 추출물에서 DPPH 소거활성이 높게 나타났으며, 특히 메탄올 추출물 100 /mL에서 93.98％의 DPPH 소거활성이 나타났으며, 계피 초임계 박 메탄올 추출물(SFM) 중 200 bar 100 /mL 에서 89.45％로 SFM 중 가장 높은 소거활성을 가지는 것으로 나타났다. 시남알데하이드와 계피 초계 추출물(SFE) 오일은 DPPH 활성이 나타나지 않았다(표 3). DPPH is a water-soluble substance with free radicals in the molecule, reduced by ascorbic acid, tocopherols, polyhydroxy aromatics, etc., and dark purple decolorizes. At this time, the movement of the molecule is similar to hydroxyl radicals, which are antioxidants from various natural materials. It is widely used to search for substances (4, 9). Reactive oxygen species (ROS) are mostly eliminated by the body's defense mechanisms, but when they are not removed, they react rapidly with biomolecules, causing protein denaturation, biofilm lipid peroxidation, and DNA damage. Lipid peroxides promote new radical reactions and cause various diseases (7). Table 3 shows the results of comparing DPPH free radical scavenging activity of methanol extract, cinnamon supercritical extract and cinnamon supercritical gourd extract with synthetic antioxidant BHA. Cinnamon methanol extracts except cinnamon supercritical extracts and cinnamon supercritical gourd methanol extracts showed high DPPH scavenging activity, especially 93.98% DPPH scavenging activity at 100 / mL methanol extract. It was found to have the highest scavenging activity in SFM at 89.45% at 200 bar 100 / mL in (SFM). Cinnamic aldehyde and cinnamon herb extract (SFE) oil did not show DPPH activity (Table 3).
a메탄올, SFE, SFM, 시남알데하이드의 농도 단위는 μg/mL이며, BHA는 이다. a Concentration units of methanol, SFE, SFM and cinnamaldehyde are μg / mL, and BHA is.
b반응 시작 30분 후 DPPH 라디칼의 50％ 감소를 나타내는 농도. b Concentration showing a 50% reduction in DPPH radicals 30 minutes after the start of the reaction.
각 값은 표준편차±S.D(≥3)로 나타내었다.
Each value is expressed as standard deviation ± SD (≧ 3).
ABTSABTS 자유 freedom 라디칼Radical 소거활성 Scavenging activity
ABTS 라디칼을 이용한 항산화능 측정은 과황화칼륨과 반응하여 암소에 방치하면 ABTS 라디칼이 생성되는데 추출물의 항산화력에 의해 ABTS 라디칼이 소거되어 라디칼 특유의 색인 청록색이 탈색되는 원리를 이용한다. ABTS 라디칼 탈색 반응은 1분 안에 종료 되므로 단시간에 측정할 수 있고, 극성과 비극성 물질 모두에 적용 가능하다(22). 본 실험에서는 80％ 메탄올 추출물, 계피 초임계 추출물(SFE) 오일, 계피 초임계 박 추출물(SFM), 시남알데하이드 및 트로록스(trolox)의 ABTS+의 소거활성을 측정하여 표 4에 나타내었다. 계피 메탄올 추출물은 100 /mL의 농도에서 93.12％의 높은 ABTS+소거 활성을 보였고, 계피 초임계 추출물(SFM) 중 200 bar 100 /mL의 농도에서 93.21％의 높은 ABTS+소거 활성을 보였다. 계피 메탄올 추출물과 계피 초임계 박 메탄올 추출물(SFM)에서 높은 활성을 나타낸 반면에 시남알데하이드 및 계피 초임계 추출물(SFE) 오일은 ABTS+소거활성이 없는 것으로 나타났다(표 4). 이러한 항산화 결과는 시남알데하이드 함량이 높은 SFE 오일보다 80％ 메탄올 추출물 및 SFM에 폴리페놀과 같은 항산화 성분이 많이 포함되어 있기 때문이라 생각된다. Antioxidant activity using ABTS radicals is generated when reacted with potassium persulfide and left in the dark to generate ABTS radicals. It utilizes the principle of elimination and decolorization of the radical cyan color. The ABTS radical decolorization reaction can be measured in a short time since it is completed in 1 minute and is applicable to both polar and nonpolar materials (22). In this experiment, the scavenging activity of ABTS + of 80% methanol extract, cinnamon supercritical extract (SFE) oil, cinnamon supercritical gourd extract (SFM), cinnaaldehyde and trolox was measured and shown in Table 4. Cinnamon methanol extract showed a high ABTS + clearing activity of 93.12% at a concentration of 100 / mL, and 93.21% high ABTS + clearing activity at a concentration of 200 bar 100 / mL in cinnamon supercritical extract (SFM). While cinnamon methanol extract and cinnamon supercritical gourd methanol extract (SFM) showed high activity, cinnamic aldehyde and cinnamon supercritical extract (SFE) oil were found to have no ABTS + elimination activity (Table 4). These antioxidant results are thought to be due to the fact that 80% methanol extract and SFM contain more antioxidant components such as polyphenols than SFE oils with high content of cinnamic aldehyde.
a메탄올, SFE, SFM, (E)-시나말데하이드의 농도 단위는 μg/mL이며, 트로록스는 이다. a Concentration units of methanol, SFE, SFM and (E) -cinnamaldede are μg / mL and trolox is.
b반응 시작 1분 후 ABTS 라디칼의 50% 감소를 나타내는 농도. b Concentration showing a 50% reduction in ABTS radicals 1 minute after the start of the reaction.
각 값은 표준편차± S.D(≥3)로 나타내었다.
Each value is expressed as standard deviation ± SD (≥3).
계피 조건별 추출물 및 단일성분의 균 생육억제 효과Inhibitory Effects of Extracts and Single Components on Cinnamon Condition
계피 추출물을 이용하여 그람(+)균과 그람(-)균에 대한 항균효과를 검색한 결과는 표 5에서 보는 것과 같이 계피 초임계 추출물(SFE) 오일, 시남알데하이드에서 모든 식중독 균에 대해 억제대를 나타냈다. 그러나, 80％ 메탄올 추출물과 계피 초임계 박 메탄올 추출물(SFM)에서는 항균활성이 없었다. 그람(+)균에서는 바실러스 세레우스(B. cereus), 리스테리아 모노사이토제네스(L. monocytogenes)균에 대해 SFE 오일 200 bar, 300 bar 에서 높은 억제대를 보였고, 나머지 그람(+)균에서는 SFE 오일의 모든 압력조건에서 높은 억제대를 보였다. 특히 그람(-)균 중 대장균(E. coli)에서는 시남알데하이드 2.5 mg/mL의 농도에서 가장 높은 억제대를 나타냈으며, SFE 오일에서는 압력 조건에 관계없이 200, 300, 400 bar 2.5 mg/mL 이상의 농도에서 높은 항균력을 보였다. 이에 반해 시남알데하이드 성분이 적게 함유된 80％ 메탄올 추출물, SFM에서는 항균력이 없었다.
The results of searching for antimicrobial effects on gram (+) and gram (-) bacteria using cinnamon extracts are shown in Table 5 to show the inhibitors against all food poisoning bacteria in cinnamon supercritical extract (SFE) oil and sinamaldehyde. Indicated. However, 80% methanol extract and cinnamon supercritical thin methanol extract (SFM) had no antimicrobial activity. B. cereus and L. monocytogenes bacteria showed high inhibitory effects on SFE oil at 200 bar and 300 bar, and the rest of Gram (+) bacteria. All the pressure conditions showed a high suppression band. In particular, E. coli among Gram (-) bacteria showed the highest inhibitory concentration at the concentration of 2.5 mg / mL of cinnamic aldehyde, and more than 200, 300, 400 bar 2.5 mg / mL of SFE oil regardless of the pressure condition. Showed high antimicrobial activity. On the other hand, 80% methanol extract containing less cinnamic aldehyde and SFM had no antimicrobial activity.
aBC: Bacillus cereus, SA: Staphylococcus aureus, SM: Streptococcus mutans, LM: Listeriamonocytogenes, EC: Escherichia coli, ST: Sallmonella typhimurium, PA: Pseudomoans aeruginosa, VP: Vibrio parahaemolyticus a BC: Bacillus cereus , SA: Staphylococcus aureus , SM: Streptococcus mutans , LM: Listeriamonocytogenes , EC: Escherichia coli , ST: Sallmonella typhimurium , PA: Pseudomoans aeruginosa , VP: Vibrio parahaemolyticus
b종이 디스크(5 mm)가 포함됨. b Paper discs (5 mm) are included.
c억제 효과 없음.
c No inhibitory effect.
이상으로 본 발명의 특정한 부분을 상세히 기술하였는바, 당업계의 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아닌 점은 명백하다. 따라서, 본 발명의 실질적인 범위는 첨부된 청구항과 그의 등가물에 의하여 정의된다고 할 것이다.
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the same is by way of illustration and example only and is not to be construed as limiting the scope of the present invention. Thus, the substantial scope of the present invention will be defined by the appended claims and equivalents thereof.
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Claims (13)
(a) 계피를 파쇄하는 단계;
(b) 상기 단계 (a)에서 얻어진 계피 파쇄물을 초임계 추출용기에 넣고, 초임계유체 및 보조 용매를 계피 파쇄물에 접촉하도록 상기 추출용기에 흘려주어 초임계 추출을 행하는 단계;
(c) 상기 단계 (b)의 초임계 추출을 행하고 난 후의 계피 파쇄물의 잔여물을 얻는 단계; 및
(d) 상기 단계 (c)의 계피 파쇄물의 잔여물에 추출 용매를 가하여 추출하는 단계.
Method for preparing cinnamon supercritical gourd extract comprising the following steps:
(a) crushing cinnamon;
(b) putting the cinnamon crushed product obtained in step (a) into a supercritical extraction container, and performing supercritical extraction by flowing a supercritical fluid and an auxiliary solvent into the extraction container so as to contact the cinnamon crushed product;
(c) obtaining a residue of cinnamon crush after the supercritical extraction of step (b); And
(d) extracting by adding an extraction solvent to the residue of the cinnamon crush of step (c).
The method of claim 10, wherein the extraction solvent in step (d) is water, anhydrous or hydrous lower alcohol having 1 to 4 carbon atoms, acetone, ethyl acetate, butyl acetate, chloroform, hexane, diethyl ether or 1,3-butyl Ethylene glycol.
Functional food composition for antioxidant comprising cinnamon supercritical gourd extract prepared by the method of claim 10 or 11 as an active ingredient.
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| EP3120712B1 (en) | 2015-07-22 | 2017-09-13 | Evonik Degussa GmbH | Method for improved extraction of juniper berries, rose hips, sea buckthorn berries, sorbus |
| ES2670473T3 (en) | 2015-12-04 | 2018-05-30 | Evonik Degussa Gmbh | Improved procedure for the extraction of flavoring substances from fatty and / or aqueous liquid phases |
| KR102006258B1 (en) | 2017-11-06 | 2019-08-01 | 한국생명공학연구원 | Composition for preventing, improving or treating earyl mortality sydrome infection of shrimps and method for manufacturing the same |
| KR102129409B1 (en) * | 2018-01-18 | 2020-07-02 | 경희대학교 산학협력단 | Composition for treating hair loss and promoting hair growth |
| KR102139804B1 (en) * | 2018-07-30 | 2020-07-31 | 재단법인 전남생물산업진흥원 | A method of preparing brassica rapa extract |
| CN110613649A (en) * | 2019-10-24 | 2019-12-27 | 湖南农业大学 | Tieguanyin extract whitening sunscreen cream base solution and preparation method thereof |
| CN112998064A (en) * | 2021-04-25 | 2021-06-22 | 福建省农通科技发展有限公司 | Preservative and preparation method thereof |
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| KR20060098480A (en) * | 2005-03-03 | 2006-09-19 | 임교빈 | Formation of oil-soluble licorice extract including whitening bioactive materials |
| KR20070057108A (en) * | 2007-05-09 | 2007-06-04 | 케이엠에이치 주식회사 | Antifungal extract produced by supercritical fluid extraction |
| KR20070076802A (en) * | 2006-01-20 | 2007-07-25 | (주)원텍 | Antimicrobial compositions and rood packaging sheet using natural extracts |
| KR100841711B1 (en) * | 2006-08-31 | 2008-06-26 | 케이엠에이치 주식회사 | Method for manufacturing extracts with high content of antibiotcs by supercritical fluid extraction technology |
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| KR20060098480A (en) * | 2005-03-03 | 2006-09-19 | 임교빈 | Formation of oil-soluble licorice extract including whitening bioactive materials |
| KR20070076802A (en) * | 2006-01-20 | 2007-07-25 | (주)원텍 | Antimicrobial compositions and rood packaging sheet using natural extracts |
| KR100841711B1 (en) * | 2006-08-31 | 2008-06-26 | 케이엠에이치 주식회사 | Method for manufacturing extracts with high content of antibiotcs by supercritical fluid extraction technology |
| KR20070057108A (en) * | 2007-05-09 | 2007-06-04 | 케이엠에이치 주식회사 | Antifungal extract produced by supercritical fluid extraction |
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