KR102561745B1 - Composition for anti-oxidation comprising microsphere - Google Patents
Composition for anti-oxidation comprising microsphere Download PDFInfo
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- KR102561745B1 KR102561745B1 KR1020170156333A KR20170156333A KR102561745B1 KR 102561745 B1 KR102561745 B1 KR 102561745B1 KR 1020170156333 A KR1020170156333 A KR 1020170156333A KR 20170156333 A KR20170156333 A KR 20170156333A KR 102561745 B1 KR102561745 B1 KR 102561745B1
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Abstract
본 명세서에는 키토산 또는 그 분해물을 포함하는 층 내부에 버섯 추출물이 담지되어 있는 마이크로스피어를 포함하는 항산화용 조성물이 개시된다. 본 발명의 일 측면인 항산화용 조성물은 키토산 층 내부에 버섯 추출물이 담지되어 있는 마이크로스피어를 포함하여, 체내 흡수가 용이하고 인체 내에서 안정성이 우수하다. 따라서, 일반적인 버섯 추출물을 섭취할 때와 비교하여 우수한 항산화 활성을 제공할 수 있으며, 식품 분야 또는 의약 분야 등 다양한 분야에서 널리 활용될 수 있다. 또한, 본 발명의 조성물에 사용된 유효성분은 천연물로부터 유래한 것이므로 인체 부작용이 없다.Disclosed herein is an antioxidant composition comprising microspheres in which a mushroom extract is supported in a layer containing chitosan or a decomposition product thereof. An antioxidant composition, which is an aspect of the present invention, includes microspheres in which a mushroom extract is supported in a chitosan layer, and thus is easily absorbed into the body and has excellent stability in the human body. Therefore, it can provide excellent antioxidant activity compared to when ingesting a general mushroom extract, and can be widely used in various fields such as food or medicine. In addition, since the active ingredient used in the composition of the present invention is derived from natural products, there is no side effect on the human body.
Description
본 명세서에는 키토산 또는 그 분해물을 포함하는 층 내부에 버섯 추출물이 담지되어 있는 마이크로스피어를 포함하는 항산화용 조성물이 개시된다.Disclosed herein is an antioxidant composition comprising microspheres in which a mushroom extract is supported in a layer containing chitosan or a decomposition product thereof.
자유 라디칼 또는 활성산소종(reactive oxygen species, ROS)은 미토콘드리아, 식세포 또는 세포질 중 크산틴 산화효소(xanthine oxidase)나 글루타티온 환원 효소(glutathion reductase)에 의한 정상적인 대사 과정 또는 자외선, 외부자극에 의한 염증 반응 등 여러 가지 생물학적 반응에 의해 형성된다. 자유 라디칼 또는 활성산소종이 인체 내에 과량으로 축적되면, 염증 반응 이외에도 세포의 노화를 비롯하여 뇌졸중, 심근경색, 당뇨병성 혈관 장애, 고지혈증, 당뇨병, 신경퇴행성 질환 등 각종 인체 질환을 일으키게 된다. 따라서, 상기 활성산소 또는 자유 라디칼을 제거할 수 있는 물질은 이들 질병을 예방 또는 치료하는 효과가 있는 것으로 보고되고 있으다. 이에 미생물 및 식물체와 같은 천연물로부터 활성산소 또는 자유 라디칼 소거 물질을 개발하기 위한 연구가 계속되고 있으며, 부틸 히드록시아니솔(butylated hydroxyanisole, BHA), 부틸 히드록시톨루엔(butylated hydroxytoluene, BHT)과 같은 합성물질도 개발되고 있다. Free radicals or reactive oxygen species (ROS) are involved in normal metabolic processes by xanthine oxidase or glutathione reductase in mitochondria, phagocytic cells or cytoplasm, or inflammatory responses caused by ultraviolet light or external stimuli. formed by several biological reactions. When free radicals or reactive oxygen species are excessively accumulated in the human body, various human diseases such as stroke, myocardial infarction, diabetic vascular disorder, hyperlipidemia, diabetes, and neurodegenerative diseases, as well as cell aging, are caused in addition to inflammatory reactions. Therefore, it has been reported that substances capable of removing the active oxygen or free radical have an effect of preventing or treating these diseases. Accordingly, research to develop active oxygen or free radical scavengers from natural products such as microorganisms and plants continues, and synthetic methods such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) are being conducted. Materials are also being developed.
그러나 합성 항산화제들은 인체 내에서 불안정하고, 독성이 있으며, 암 등 인체에심각한 악영향을 미치는 부작용이 있는 것으로 밝혀졌고, 천연물 유래 물질 중에 아직까지는 만족할 만한 수준의 항산화 효능을 보이는 물질은 발견되지 않았다. However, synthetic antioxidants have been found to be unstable in the human body, toxic, and have side effects that seriously adversely affect the human body, such as cancer.
이에 합성 항산화제보다 안전하고 항산화에 효과적인 천연물 유래 항산화 물질의 개발이 절실히 필요하다.Therefore, it is urgently needed to develop natural antioxidants that are safer and more effective than synthetic antioxidants.
일 측면에서, 본 발명의 목적은 항산화 효과가 우수한 천연물 유래 물질을 제공하는 것이다.In one aspect, an object of the present invention is to provide a natural product-derived material with excellent antioxidant effect.
일 측면에서, 본 발명의 목적은 체내에서 안정성이 우수한 항산화 물질을 제공하는 것이다.In one aspect, an object of the present invention is to provide an antioxidant having excellent stability in the body.
일 측면에서, 본 발명의 목적은 타겟 기관(organ)에 전달율이 우수한 항산화 물질을 제공하는 것이다.In one aspect, an object of the present invention is to provide an antioxidant material with excellent delivery rate to a target organ.
일 측면에서, 본 발명의 목적은 체내에서 오랜시간 동안 지속적으로 유효물질을 방출할 수 있는 마이크로스피어와 이를 포함하는 조성물을 제공하는 것이다.In one aspect, an object of the present invention is to provide microspheres capable of continuously releasing active substances for a long time in the body and a composition comprising the same.
일 측면에서, 본 발명은, 마이크로스피어(microsphere)를 포함하며, 상기 마이크로스피어는, 키토산 또는 그 분해물을 포함하는 외층(outer layer); 및 외층으로 형성된 내부 공간에 담지되어 있는 버섯 추출물을 포함하는, 항산화용 조성물을 제공한다.In one aspect, the present invention includes microspheres, the microspheres comprising: an outer layer comprising chitosan or a decomposition product thereof; And it provides a composition for antioxidant, including a mushroom extract supported in the inner space formed by the outer layer.
일 측면에서, 본 발명의 항산화용 조성물은 키토산 층 내부에 버섯 추출물이 담지되어 있는 마이크로스피어를 포함하여, 체내 흡수가 용이하고 인체 내에서 안정성이 우수하다. 따라서, 일반적인 버섯 추출물을 섭취할 때와 비교하여 우수한 항산화 활성을 제공할 수 있으며, 식품 분야 또는 의약 분야 등 다양한 분야에서 널리 활용될 수 있다. 또한, 본 발명의 조성물에 사용된 유효성분은 천연물로부터 유래한 것이므로 인체 부작용이 없다.In one aspect, the antioxidant composition of the present invention includes microspheres in which the mushroom extract is supported on the inside of the chitosan layer, and thus is easily absorbed into the body and has excellent stability in the human body. Therefore, it can provide excellent antioxidant activity compared to when ingesting a general mushroom extract, and can be widely used in various fields such as food or medicine. In addition, since the active ingredient used in the composition of the present invention is derived from natural products, there is no side effect on the human body.
도 1은 키토산 올리고당의 분획 결과를 보이는 도이다.
도 2는 분획된 키토산 올리고당의 구조적 특성을 보이는 도이다.
도 3은 마이크로스피어 내부에 표고 버섯 추출물의 담지 여부를 UV를 이용하여 확인한 도로서, 도 3a 는 표고 버섯추출물, 버섯추출물 미담지 마이크로스피어, 표고 버섯추출물 담지 마이크로 스피어를 증류수에 분산시킨 경우를 보이며, 도 3b와 도 3c는 마이크로스피어 표면에 존재하는 표고 버섯 추출물을 에탄올로 세척한 후 측정한 도이다.
도 4는 표고 버섯 추출물이 마이크로스피어 내부에 담지되었는지 여부를 H-NMR을 이용하여 확인한 도이다(도 4a: 표고 버섯 추출물 미담지 마이크로스피어, 도 4b: 표고버섯 추출물, 도 4c: 20%의 표고 버섯 추출물이 담지된 마이크로스피어, 도 4d: 40% 표고버섯 추출물이 담지된 마이크로스피어).
도 5는, 표고 버섯 추출물의 부위에 따른 ABTS 라디컬 소거능(도 5a), DPPH 라디컬 소거능(도5b), ROS 발생율(도 5c), H2O2에 대한 세포 생존율(도 5d)을 보이는 도이다.1 is a diagram showing the results of fractionation of chitosan oligosaccharide.
2 is a diagram showing structural characteristics of fractionated chitosan oligosaccharide.
3 is a diagram confirming whether the shiitake mushroom extract is supported inside the microspheres using UV, and FIG. 3a shows the case in which the shiitake mushroom extract, the mushroom extract unsupported microspheres, and the shiitake mushroom extract supported microspheres are dispersed in distilled water. , Figures 3b and 3c are measurements after washing the shiitake mushroom extract present on the microsphere surface with ethanol.
Figure 4 is a diagram confirming whether or not the shiitake mushroom extract is loaded inside the microspheres using H-NMR (Fig. 4a: microspheres unloaded with shiitake mushroom extract, Fig. 4b: shiitake mushroom extract, Fig. 4c: 20% shiitake) Microspheres loaded with mushroom extract, Fig. 4d: Microspheres loaded with 40% shiitake mushroom extract).
5 shows ABTS radical scavenging activity (FIG. 5a), DPPH radical scavenging activity (FIG. 5b), ROS generation rate (FIG. 5c), and cell viability against H 2 O 2 (FIG. 5d) according to the site of the shiitake mushroom extract. It is also
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 일 측면에서, 본 발명은, 마이크로스피어(microsphere)를 포함하며, 상기 마이크로스피어는, 키토산 또는 그 분해물을 포함하는 외층(outer layer); 및 외층으로 형성된 내부 공간에 담지되어 있는 버섯 추출물을 포함하는, 항산화용 조성물이다.In one aspect, the present invention includes microspheres, wherein the microspheres include an outer layer containing chitosan or a decomposition product thereof; And a composition for antioxidation comprising a mushroom extract supported in the inner space formed as an outer layer.
본 명세서에서 항산화란 당업계에 알려진 산화 과정을 늦추거나 막거나 또는 예방할 수 있는 효능을 의미할 수 있다. As used herein, antioxidant may refer to an efficacy capable of slowing down, preventing, or preventing an oxidation process known in the art.
일 측면에서, 상기 조성물은 항산화용 조성물로서, 뇌신경계 또는 심혈관계 질환의 개선에 사용될 수 있고, 예컨대, 상기 뇌신경계 또는 심혈관계 질환은 알츠하이머병, 루게릭병, 파킨슨씨병, 크로이츠펠트-야곱병, 뇌졸중, 뇌경색 및 뇌출혈 중 하나 이상을 포함할 수 있다.In one aspect, the composition is an antioxidative composition, which can be used to improve the cerebral nervous system or cardiovascular disease, for example, the cerebral nervous system or cardiovascular disease is Alzheimer's disease, Lou Gehrig's disease, Parkinson's disease, Creutzfeldt-Jacob disease, stroke, cerebral infarction, and cerebral hemorrhage.
일 측면인 조성물은, 버섯 추출물과 키토산 또는 그 분해물을 유효성분으로 포함하여, 버섯 추출물과 키토산 또는 그 분해물이 갖는 생물화학적 효과를 극대화할 수 있다. One aspect of the composition may include a mushroom extract and chitosan or a decomposition product thereof as active ingredients, thereby maximizing the biochemical effects of the mushroom extract and chitosan or a decomposition product thereof.
상기와 같은 측면에서, 상기 마이크로스피어는 그 직경이 1~8㎛인 마이크로스피어를 포함할 수 있다.In the above aspects, the microspheres may include microspheres having a diameter of 1 to 8 μm.
상기 마이크로스피어는, 키토산 또는 그 분해물을 포함하는 직경이 1~6㎛인 스피어 내에 버섯 추출물이 봉입된 것을 포함할 수 있다.The microsphere may include a mushroom extract encapsulated in a sphere having a diameter of 1 to 6 μm containing chitosan or a decomposition product thereof.
본 명세서에서 마이크로스피어의 직경은, 모든 마이크로스피어의 직경의 평균값을 의미하는 것이 아니라, 개개 마이크로스피어의 직경을 의미한다. 즉, 본 발명의 일 측면인 조성물은 직경이 1~8㎛인 마이크로스피어를 포함하는데, 본 발명의 조성물에 포함된 모든 마이크로스피어의 직경은 1~8㎛의 범위 내에 포함되는 것을 의미할 수 있다. In the present specification, the diameter of microspheres does not mean the average value of the diameters of all microspheres, but means the diameter of individual microspheres. That is, the composition of one aspect of the present invention includes microspheres having a diameter of 1 to 8 μm, and the diameter of all microspheres included in the composition of the present invention may mean that the diameter is included in the range of 1 to 8 μm. .
상기 직경은, 각각의 마이크로스피어 내에서 측정한 직경 중 최단축과 최장축의 길이를 제외한 임의의 2개의 직경의 평균 값을 의미할 수 있다.The diameter may mean an average value of two arbitrary diameters excluding the lengths of the shortest axis and the longest axis among diameters measured within each microsphere.
일 측면에서, 상기 마이크로스피어는, 직경이 1~3㎛(마이크로미터)인 마이크로스피어를 포함하는 제1군; 직경이 3~5㎛(마이크로미터)인 마이크로스피어를 포함하는 제2군; 및 직경이 5~8㎛(마이크로미터)인 마이크로스피어를 포함하는 제3군을 포함할 수 있다.In one aspect, the microspheres include a first group including microspheres having a diameter of 1 to 3 μm (micrometer); a second group comprising microspheres with a diameter of 3 to 5 μm (micrometers); and a third group including microspheres having a diameter of 5 to 8 μm (micrometer).
일 측면에서, 상기 마이크로스피어는, 더욱 바람직하게, 직경이 2.5~3㎛인 제1군, 직경이 3.5~4.5㎛인 제2군, 및 6~7㎛인 제3군을 포함할 수 있다.In one aspect, the microspheres, more preferably, may include a first group having a diameter of 2.5 to 3 μm, a second group having a diameter of 3.5 to 4.5 μm, and a third group having a diameter of 6 to 7 μm.
일 측면에서, 상기 제1군, 제2군 및 제3군의 마이크로스피어는, 마이크로스피어의 총 중량을 기준으로, 순서대로 각각 5~15 중량%, 5~15 중량%, 및 70~90 중량%로 포함될 수 있다. 바람직하게는, 순서대로 7~13 중량%, 7~13 중량%, 및 75~85 중량%로 포함될 수 있다.In one aspect, the microspheres of the first group, the second group, and the third group are 5 to 15% by weight, 5 to 15% by weight, and 70 to 90% by weight, respectively, in that order, based on the total weight of the microspheres. % can be included. Preferably, it may be included in the order of 7 to 13% by weight, 7 to 13% by weight, and 75 to 85% by weight.
본 발명의 마이크로스피어는, 입자 직경이 상이한 상기 제1군, 제2군 및 제3군을 상기와 같은 비율로 포함함으로써, 더욱 개선된 항산화 효과를 가질 수 있으며, 또한, 체내에서 오랜시간 동안 일정한 수준의 항산화 효과를 유지할 수 있다.The microspheres of the present invention, by including the first group, the second group, and the third group having different particle diameters in the ratio as described above, can have a further improved antioxidant effect, and also can have a constant antioxidative effect in the body for a long time. level of antioxidants can be maintained.
또한, 일 측면에서, 상기 버섯 추출물은 키토산 또는 그 분해물의 중량을 100으로 했을 때, 10~50 중량부로 포함될 수 있다. In addition, in one aspect, the mushroom extract may be included in 10 to 50 parts by weight when the weight of chitosan or its decomposition product is 100.
상기 버섯 추출물의 함량은, 바람직하게는 키토산 또는 그 분해물의 중량을 기준으로 바람직하게는 30~50 중량부로 포함될 수 있다.The content of the mushroom extract may be preferably included in an amount of 30 to 50 parts by weight based on the weight of chitosan or a decomposition product thereof.
버섯 추출물의 함량이 10 중량부 미만일 경우에는 항산화 효과가 미미하며, 50 중량부를 초과할 경우에는, 마이크로스피어의 사이즈가 커지면서, 표적 기관으로의 전달율, 표적 기관에서의 흡수율 등이 저하되어, 항산화 효과가 떨어지는 한계가 발생할 수 있다.If the content of the mushroom extract is less than 10 parts by weight, the antioxidant effect is insignificant, and if it exceeds 50 parts by weight, the size of the microspheres increases, the delivery rate to the target organ, the absorption rate in the target organ, etc. decrease, and the antioxidant effect A falling limit may occur.
일 측면에서, 상기 키토산의 분해물은 효소 또는 화학적 분해 과정을 통하여 생성되어, 키토산 내 포함된 당의 분자수를 2~10여개까지 낮춘 물질을 의미할 수 있다. 예컨대, 키토산의 분해물은 키토산 올리고당(chitosanoligosaccharide)을 포함할 수 있다. 또한, 상기 키토산 올리고당의 분자량은 1kDa~15kDa일 수 있고, 바람직하게는, 1~10kDa일 수 있다. 일 구현예에서, 상기 키토산 올리고당은 더욱 바람직하게는, 2kDa, 4kDa 및 10kDa의 키토산 올리고당의 혼합물을 포함할 수 있다.In one aspect, the chitosan decomposition product is produced through an enzymatic or chemical decomposition process, and may refer to a material in which the number of sugar molecules included in chitosan is reduced to 2 to 10. For example, chitosan degradation products may include chitosanoligosaccharides. In addition, the chitosan oligosaccharide may have a molecular weight of 1 kDa to 15 kDa, preferably 1 to 10 kDa. In one embodiment, the chitosan oligosaccharide may more preferably include a mixture of 2 kDa, 4 kDa, and 10 kDa chitosan oligosaccharide.
일 측면에서, 상기 2kDa의 키토산 올리고당으로 제조한 마이크로 스피어의 직경은 2㎛일 수 있고, 4kDa의 키토산 올리고당으로 제조한 마이크로 스피어의 직경은 3㎛일 수 있고, 10kDa의 키토산 올리고당으로 제조한 마이크로 스피어의 직경은 5㎛일 수 있다.In one aspect, the diameter of the microspheres made of the 2 kDa chitosan oligosaccharide may be 2 μm, the diameter of the microspheres made of the 4 kDa chitosan oligosaccharide may be 3 μm, and the microspheres made of the 10 kDa chitosan oligosaccharide The diameter of may be 5 μm.
키토산 또는 키토산 올리고당은, 독성이 없어 생체 재료로서 사용이 가능하다는 많은 연구논문이 보고가 되어지만, 고분자량 키토산의 경우 구조내에 많은 아민그룹의 영향으로 농도에 의해서 일정 부분 세포 독성이 나타난다. 따라서 키토산을 생체에 적용하기 위해서는 세포 독성을 나타내지 않은 분자량 및 농도의 확립이 필요하며, 상기 1~10kDa의 키토산 올리고당은 세포 독성이 없는 것일 수 있다.Many research papers have reported that chitosan or chitosan oligosaccharide is non-toxic and can be used as a biomaterial. Therefore, in order to apply chitosan to a living body, it is necessary to establish a molecular weight and concentration that do not exhibit cytotoxicity, and the 1-10 kDa chitosan oligosaccharide may be non-cytotoxic.
키토산은 게나 새우 등의 갑각류, 오징어 연골 연체류 등에 분포되어 있는 천연 고분자인 키틴을 농축 알칼리로 처리하여 얻어지는 물질로서 β-(1,4)-glycosidic 결합으로 연결된 D-glucosamine과 N-acetyl D-glucosamine 두 단위체로 구성된 생분해성 천연 다당류이다. 키토산은 항암효과, 콜레스테롤 감소, 면역 활성 및 향균성 등 우수한 생리활성을 갖는 것으로 잘 알려져 있다. 키토산 응용 분야로는 화장품, 수처리, 의약품, 식품, 바이오산업 등이 있으며 최근에는 의료용 분야로의 연구가 확대되고 있다. 특히 생체 적합성이 우수하고, 독성이 낮으며, 세포부착 능력이 우수하다. Chitosan is a substance obtained by treating chitin, a natural polymer distributed in crustaceans such as crabs and shrimps, cartilage and molluscs such as squid, with concentrated alkali. D-glucosamine and N-acetyl D-glucosamine linked by β-(1,4)-glycosidic bonds It is a biodegradable natural polysaccharide composed of two units. Chitosan is well known to have excellent physiological activities such as anticancer effect, cholesterol reduction, immune activity and antibacterial properties. Applications of chitosan include cosmetics, water treatment, medicine, food, and bio industries, and recently, research into the medical field is expanding. In particular, it has excellent biocompatibility, low toxicity, and excellent cell adhesion ability.
또한, 일 측면에서, 상기 버섯은 표고버섯을 포함할 수 있다. 표고버섯은 담자균류 주름버섯목 느타리과에 속하는 버섯이다. 표고버섯은 일반적으로 참나무, 밤나무, 서어나무 등 활엽수의 고목에서 발생하고, 한국, 일본, 중국 등 동북아시아 지역에서 주로 재배된다. 버섯갓의 지름은 약 4~10cm 이고, 처음에 반구 모양이나 점차 펴져서 편평해진다. 갓 가장자리는 어렸을 때 안쪽으로 감기고 흰색 또는 연한 갈색의 피막으로 덮여 있다가 터지면 갓 가장자리와 버섯대에 떨어져 붙는다. 버섯대에 붙은 것은 불완전한 버섯대 고리가 되고, 주름살은 흰색이며 촘촘하다. 버섯대는 3~6cm×1cm이고 나무에 붙어 있는 상태에 따라 한쪽으로 기울어진다. 버섯대 표면은 위쪽이 흰색, 아래쪽이 갈색이고 섬유처럼 질긴 편이다. 홀씨는 한쪽이 뾰족한 타원 모양이고 색이 없으며 홀씨 무늬는 흰색이다.Also, in one aspect, the mushroom may include a shiitake mushroom. Shiitake mushroom is a mushroom belonging to the family Pleurotusaceae. Shiitake mushrooms generally occur in old trees of broad-leaved trees such as oak, chestnut, and hornbeam, and are mainly cultivated in Northeast Asian regions such as Korea, Japan, and China. The diameter of the mushroom cap is about 4-10 cm, and it is hemispherical at first, but gradually spreads and becomes flat. The edge of the cap is wrapped inward when young and covered with a white or light brown film, and when it bursts, it falls off and sticks to the edge of the cap and the mushroom stand. Attached to the mushroom stem becomes an incomplete mushroom stem ring, and the wrinkles are white and dense. The mushroom stand is 3-6 cm × 1 cm, and tilts to one side depending on the state attached to the tree. The surface of the mushroom stem is white on the top and brown on the bottom, and is tough like fiber. The spore is an oval shape with one side pointed, and there is no color, and the spore pattern is white.
표고버섯은 특유의 향과 맛을 띠어 기호성이 높은 식품소재이다.Shiitake mushrooms are highly palatable food materials with their unique aroma and taste.
일 측면에서, 상기 버섯 추출물은 버섯 갓 추출물을 포함할 수 있다. 본 발명의 일 측면에서, 버섯 갓 추출물은, 버섯대 추출물에 비하여 현저히 우수한 항산화 효과를 나타낼 수 있다.In one aspect, the mushroom extract may include a mushroom cap extract. In one aspect of the present invention, the mushroom cap extract may exhibit a significantly superior antioxidant effect compared to the mushroom stem extract.
일 측면에서, 상기 버섯 추출물의 추출 용매는 물, 유기용매 또는 유기용매 수용액을 포함할 수 있다. In one aspect, the extraction solvent of the mushroom extract may include water, an organic solvent or an organic solvent aqueous solution.
상기 유기용매는, 헥산, 메틸렌클로라이드, 알코올 등일 수 있으나, 이에 한정되는 것은 아니다. 상기에서 물은 증류수 또는 정제수를 포함하고, 유기 용매는 C1~5의 저급 알코올을 예로 들 수 있는 에탄올, 아세톤, 에테르, 에틸아세테이트, 디에틸에테르, 메탄올, 에틸메틸케톤 및 클로로포름으로 이루어진 군에서 선택된 하나 이상을 포함하나, 이에 제한되는 것은 아니다.The organic solvent may be hexane, methylene chloride, alcohol or the like, but is not limited thereto. In the above, the water includes distilled water or purified water, and the organic solvent is selected from the group consisting of ethanol, acetone, ether, ethyl acetate, diethyl ether, methanol, ethyl methyl ketone and chloroform, for example, lower alcohols of C 1-5 Including one or more selected, but not limited thereto.
일 구현예에서, 상기 버섯 추출물은 버섯의 에탄올 추출물이며, 이 경우 열수 추출, 초음파 추출, 다른 종류의 유기 용매를 사용하는 추출법에 의하여 제조되는 추출물에 비하여 월등히 우수한 항산화 효과를 가질 수 있다.In one embodiment, the mushroom extract is an ethanol extract of mushrooms, and in this case, it may have a significantly superior antioxidant effect compared to extracts prepared by hot water extraction, ultrasonic extraction, or an extraction method using another type of organic solvent.
상기와 같은 측면에서, 상기 유기용매 수용액의 농도는 0.01% 내지 100%(v/v)일 수 있다. 예컨대, 상기 유기용매 수용액의 농도는 10~90%일 수 있고, 바람직하게는, 60~80%, 더욱 바람직하게는, 70~80%일 수 있다.In terms of the above, the concentration of the organic solvent aqueous solution may be 0.01% to 100% (v / v). For example, the concentration of the organic solvent aqueous solution may be 10 to 90%, preferably, 60 to 80%, more preferably, 70 to 80%.
상기 조성물은 자유 라디칼 소거능, 활성 산소 소거능, 또는 세포 손상 억제 또는 개선능을 포함할 수 있다. The composition may include free radical scavenging activity, active oxygen scavenging activity, or cell damage inhibition or improvement activity.
상기 세포 손상은 과산화수소로 인한 손상을 포함할 수 있고, 이에 제한되지 않고, 세포에 독성을 미치는 물질로 인한 손상을 포함할 수 있다.The cellular damage may include damage due to hydrogen peroxide, but is not limited thereto, and may include damage due to substances that are toxic to cells.
또한, 상기 활성 산소는, 과산화수소, 수퍼옥사이드 이온 및 하이드록시 라디칼 중 하나 이상을 포함할 수 있다.In addition, the active oxygen may include at least one of hydrogen peroxide, superoxide ion, and hydroxyl radical.
일 측면에서, 상기 마이크로스피어는, 조성물 총 중량을 기준으로 1~4 중량%로 포함될 수 있다.In one aspect, the microspheres may be included in an amount of 1 to 4% by weight based on the total weight of the composition.
상기 마이크로 스피어는 1 중량% 미만으로 포함시, 본 조성물로부터 목적하는 효과를 얻을 수 없고, 4 중량%를 초과하는 경우, 입자 침전 등의 문제로 제형 안정성이 떨어질 수 있다.When the microspheres are included in less than 1% by weight, desired effects cannot be obtained from the present composition, and when the amount exceeds 4% by weight, formulation stability may be deteriorated due to problems such as particle precipitation.
상기 조성물은, 일 측면에서, 피부 노화 방지 또는 개선, 또는 피부 주름 방지 또는 개선용 조성물일 수 있다.In one aspect, the composition may be a composition for preventing or improving skin aging or preventing or improving skin wrinkles.
상기 조성물은, 일 측면에서, 약학적 조성물, 화장료 조성물 또는 식품 조성물일 수 있다. The composition, in one aspect, may be a pharmaceutical composition, cosmetic composition or food composition.
본 발명의 일 관점에 의한 약학 조성물은 경구 투여제 혹은 비경구 투여제로 제제화할 수 있다.The pharmaceutical composition according to one aspect of the present invention may be formulated for oral administration or parenteral administration.
경구 투여를 위한 제제는 정제 (錠劑), 환제 (丸劑), 과립제 (顆粒劑), 연질 및 경질 캡슐제, 산제, 세립제, 분제, 유탁제 (乳濁濟), 시럽제 또는 펠렛제 등을 들 수 있다. 비경구 투여를 위한 제제는 주사제, 점적제, 연고, 로션, 스프레이, 현탁제, 유제 또는 좌제 (坐劑) 등을 들 수 있다. 본 발명의 일측면에 따른 조성물은 상법에 따라 용이하게 제제화할 수 있으며 계면 활성제, 부형제, 착색료, 향신료, 보존료, 안정제, 완충제, 현탁제 또는 기타 상용하는 보조제를 적절히 사용할 수 있다.Formulations for oral administration include tablets, pills, granules, soft and hard capsules, powders, fine granules, powders, emulsions, syrups or pellets. can Formulations for parenteral administration include injections, drops, ointments, lotions, sprays, suspensions, emulsions, suppositories, and the like. The composition according to one aspect of the present invention can be easily formulated according to a conventional method, and surfactants, excipients, coloring agents, spices, preservatives, stabilizers, buffers, suspending agents, or other commonly used adjuvants may be appropriately used.
본 발명의 일측면에 따른 조성물에 포함된 유효 성분은 담체와 함께 혼합되거나, 용기 형태의 담체 내에 봉입되어 제공될 수 있다. 희석제가 담체로 사용되는 경우 희석제는 유효 성분에 대해 담체, 부형제 또는 매질(medium)로 작용할 수 있는 고형, 반고형 또는 액상의 물질일 수 있다. 적절한 담체, 부형제 또는 희석제의 예로는, 락토오스, 덱스트로스, 수크로스, 솔비톨, 만니톨, 칼슘 실리케이트, 셀룰로즈, 메틸 셀룰로오스, 미정질 셀룰로오스, 폴리비닐피롤리돈, 물, 메틸하이드록시벤조에이트, 프로필하이드록시벤조에이트, 탈크, 마그네슘 스테아레이트 또는 광물유를 들 수 있다. 본 발명의 다른 일측면에서, 조성물은 충진제, 항응집제, 윤활제, 습윤제, 향료, 유화제 또는 방부제 등을 추가로 포함할 수 있다.The active ingredient included in the composition according to one aspect of the present invention may be provided by being mixed with a carrier or encapsulated in a carrier in the form of a container. When a diluent is used as a carrier, the diluent may be a solid, semi-solid or liquid substance that can act as a carrier, excipient or medium for the active ingredient. Examples of suitable carriers, excipients or diluents are lactose, dextrose, sucrose, sorbitol, mannitol, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydro hydroxybenzoate, talc, magnesium stearate or mineral oil. In another aspect of the present invention, the composition may further include a filler, an anti-agglomerating agent, a lubricant, a wetting agent, a flavoring agent, an emulsifier or a preservative.
본 발명의 일 관점에 의한 약학 조성물은 당업계에 잘 알려진 방법을 사용하여, 포유 동물에 투여된 후 유효 성분의 신속, 지속 또는 지연된 방출을 제공하는 제형으로 제공될 수 있다. The pharmaceutical composition according to one aspect of the present invention may be provided in a formulation that provides rapid, sustained or delayed release of the active ingredient after administration to a mammal using a method well known in the art.
본 발명의 일 관점에 의한 약학 조성물은 경구, 경피, 피하, 정맥, 복강, 근육, 국소 도포, 첩포 또는 이온토포레시스(iontophoresis)를 포함하나, 이에 제한되지 않는 여러 경로를 통해 투여될 수 있고, 본 발명의 다른 일측면에서, 약학 조성물은 국소 또는 경구 투여될 수 있다. The pharmaceutical composition according to one aspect of the present invention may be administered through various routes including, but not limited to, oral, transdermal, subcutaneous, intravenous, intraperitoneal, intramuscular, topical application, patch or iontophoresis, and However, in another aspect of the present invention, the pharmaceutical composition may be administered topically or orally.
포유 동물의 경우, 유효 성분의 통상적인 1일 투여량은 1 내지 2000 mg/kg(체중), 더 구체적으로 1~1800mg/kg, 1~1500mg/kg, 1~1000mg/kg, 1~800mg/kg, 1~600mg/kg, 1~400mg/kg, 1~200mg/kg, 1~100mg/kg, 5~100mg/kg, 또는 5 내지 70 mg/kg일 수 있고, 1회 또는 수회로 나누어 투여할 수 있다. 그러나, 유효 성분의 실제 투여량은 치료할 질환, 투여 경로, 환자의 연령, 성별 및 체중과 질환의 중증도 등과 같은 여러 관련 인자를 고려한 후 결정될 수 있다고 이해되므로, 상기 투여량은 어떠한 방법으로도 본 발명의 범위를 한정하는 것은 아니다.For mammals, a typical daily dose of the active ingredient is 1 to 2000 mg/kg (body weight), more specifically 1 to 1800 mg/kg, 1 to 1500 mg/kg, 1 to 1000 mg/kg, 1 to 800 mg/kg kg, 1 to 600 mg/kg, 1 to 400 mg/kg, 1 to 200 mg/kg, 1 to 100 mg/kg, 5 to 100 mg/kg, or 5 to 70 mg/kg, which may be administered once or divided into several times can do. However, since it is understood that the actual dosage of the active ingredient can be determined after considering various related factors such as the disease to be treated, the route of administration, the patient's age, sex, and weight, and the severity of the disease, the dosage is determined according to the present invention by any method. does not limit the scope of
또한, 본 발명의 일 관점인 조성물은, 식품 조성물일 수 있다. 본 발명의 일 관점에 의한 식품 조성물은 건강기능 식품 조성물일 수 있고, 식품 첨가제 조성물 또는 건강 식품 조성물을 포함할 수 있다. 또한, 당 분야에서 통상적으로 사용되는 성분들을 적의 선정하여, 정제, 경질 캡슐제, 연질 캡슐제, 환제, 과립제, 음료(드링크제), 다이어트바, 초콜릿, 카라멜 또는 과자 등으로 제조될 수 있다. 또한 건강 식품 조성물에 적합한 기능성 원료를 부가적으로 적절하게 포함할 수 있다.In addition, the composition of one aspect of the present invention may be a food composition. Food composition according to one aspect of the present invention may be a health functional food composition, may include a food additive composition or health food composition. In addition, by selecting ingredients commonly used in the art, tablets, hard capsules, soft capsules, pills, granules, beverages (drinks), diet bars, chocolate, caramel or confectionery can be prepared. In addition, functional ingredients suitable for health food compositions may be additionally appropriately included.
구체적으로, 화장료 조성물로는 예를 들어, 모발용 화장료, 바디용 화장료, 기초 화장료, 메이크업 화장료 등이 있을 수 있고, 그 제형은 특별히 제한되지 않으며, 목적하는 바에 따라 적절히 선택할 수 있다. Specifically, the cosmetic composition may include, for example, hair cosmetics, body cosmetics, basic cosmetics, makeup cosmetics, and the like, and the formulation is not particularly limited and may be appropriately selected according to the purpose.
예를 들면, 상기 화장료 조성물은 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클린싱, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 샴푸, 린스, 바디클렌저 등의 세정료, 헤어토닉, 젤 또는 무스 등의 정발제, 양모제 또는 염모제 등의 모발용 화장료 조성물, 유연화장수, 영양화장수, 로션, 바디로션, 영양 크림, 마사지 크림, 모이스처 크림, 핸드크림, 에센스, 아이 크림, 클렌징 크림, 클렌징 폼, 클렌징 워터, 팩, 젤, 패치, 수중유(O/W)형, 유중수(O/W)형 등의 기초 화장료로 제형화 될 수 있다. For example, the cosmetic composition is formulated into a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation and spray, etc. It may be, but is not limited thereto. More specifically, detergents such as shampoo, conditioner, and body cleanser, hair tonics, hair styling agents such as gels or mousses, cosmetic compositions for hair such as hair growth agents or hair dyes, softening lotions, nutrient lotions, lotions, body lotions, nutrient creams, Basic cosmetics such as massage cream, moisture cream, hand cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, gel, patch, oil-in-water (O/W) type, water-in-oil (O/W) type can be formulated as
상기 화장료 조성물은 화장품학적으로 허용가능한 매질 또는 기제를 함유한다. 이는 국소적용에 적합한 모든 제형으로, 예를 들면 용액, 겔, 고체 또는 반죽 무수 생성물, 수상에 유상을 분산시켜 얻은 에멀젼, 현탁액, 마이크로에멀젼, 마이크로캡슐, 미세과립구 또는 이온형(리포좀) 및/또는 비이온형의 소낭 분산제의 형태로, 또는 크림, 스킨, 로션, 파우더, 연고, 스프레이 또는 콘실 스틱의 형태로 제공될 수 있다. 이들 조성물은 당해 분야의 통상적 방법에 따라 제조될 수 있다.The cosmetic composition contains a cosmetically acceptable medium or base. These are all formulations suitable for topical application, for example solutions, gels, solid or pasty anhydrous products, emulsions obtained by dispersing an oily phase in an aqueous phase, suspensions, microemulsions, microcapsules, microgranules or ionic forms (liposomes) and/or It may be provided in the form of a non-ionic follicular dispersant, or in the form of a cream, toner, lotion, powder, ointment, spray or conceal stick. These compositions can be prepared according to conventional methods in the art.
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-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.When the formulation of the present invention is a solution or emulsion, a solvent, solubilizing agent or emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 ,3-butyl glycol oil, fatty acid esters of glycerol, polyethylene glycol or sorbitan.
본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.When the formulation of the present invention is a suspension, as a carrier component, a liquid diluent such as water, ethanol or propylene glycol, an ethoxylated isostearyl alcohol, a suspending agent such as polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystals Star cellulose, aluminum metahydroxide, bentonite, agar or tracanth and the like may be used.
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, animal oil, vegetable oil, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as a carrier component. can
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. When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component, and in particular, in the case of a spray, additional chlorofluorohydrocarbon, propane / May contain a propellant such as butane or dimethyl ether.
본 발명의 일 실시태양에서, 상기 화장료 조성물에 추가적으로 점증제를 함유할 수 있다. 본 발명의 화장료 조성물에 포함되는 점증제는 메틸 셀룰로스, 카르복시 메틸 셀룰로스, 카르복시 메틸 하이드록시 구아닌, 하이드록시 메틸 셀룰로스, 하이드록시에틸셀룰로스, 카르복시 비닐 폴리머, 폴리쿼터늄, 세테아릴 알콜, 스테아릭산, 카라기난 등을 사용할 수 있으며, 바람직하게는 카르복시 메틸 셀룰로스, 카르복시 비닐 폴리머, 폴리쿼터늄 중에서 1종 이상을 사용할 수 있으며, 가장 바람직하게는 카르복시 비닐 폴리머가 될 수 있다. In one embodiment of the present invention, a thickening agent may be additionally contained in the cosmetic composition. The thickening agent included in the cosmetic composition of the present invention is methyl cellulose, carboxy methyl cellulose, carboxy methyl hydroxyguanine, hydroxy methyl cellulose, hydroxyethyl cellulose, carboxy vinyl polymer, polyquaternium, cetearyl alcohol, stearic acid, Carrageenan and the like may be used, preferably at least one of carboxy methyl cellulose, carboxy vinyl polymer, and polyquaternium may be used, and most preferably carboxy vinyl polymer.
본 발명의 일 실시태양에서 상기 화장료 조성물은 필요에 따라 적절한 각종의 기제와 첨가제를 함유할 수 있으며, 이들 성분의 종류와 양은 발명자에 의해 용이하게 선정될 수 있다. 필요에 따라 허용 가능한 첨가제를 함유할 수 있으며, 예를 들면, 당업계에 통상적인 방부제, 색소, 첨가제 등의 성분을 추가로 포함할 수 있다.In one embodiment of the present invention, the cosmetic composition may contain various appropriate bases and additives as needed, and the types and amounts of these components may be easily selected by the inventor. Acceptable additives may be included as needed, and for example, components such as preservatives, pigments, and additives common in the art may be further included.
방부제는 구체적으로 페녹시에탄올(Phenoxyethanol) 또는 1,2-헥산디올 (1,2-Hexanediol) 등이 될 수 있고, 향료는 인공향료 등이 될 수 있다.The preservative may specifically be phenoxyethanol or 1,2-hexanediol, and the fragrance may be artificial fragrance.
그리고, 본 발명의 일 실시태양에서 화장료 조성물은 수용성 비타민, 유용성 비타민, 고분자 펩티드, 고분자 다당, 스핑고 지질 및 해초 엑기스로 이루어진 군에서 선택된 조성물을 포함할 수 있다. 이외에 첨가해도 되는 배합 성분으로서는 유지 성분, 보습제, 에몰리엔트제, 계면 활성제, 유기 및 무기 안료, 유기 분체, 자외선 흡수제, 방부제, 살균제, 산화 방지제, 식물 추출물, pH 조정제, 알콜, 색소, 향료, 혈행 촉진제, 냉감제, 제한제, 정제수 등을 들 수 있다.And, in one embodiment of the present invention, the cosmetic composition may include a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high-molecular peptides, high-molecular polysaccharides, sphingolipids, and seaweed extracts. Other ingredients that may be added include fats and oils, humectants, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, bactericides, antioxidants, plant extracts, pH adjusters, alcohols, pigments, fragrances, A blood circulation accelerator, a cooling agent, an antiperspirant, purified water, etc. are mentioned.
또한, 이외에 첨가해도 되는 배합 성분은 이에 한정되는 것은 아니며, 또, 상기 어느 성분도 본 발명의 목적 및 효과를 손상시키지 않는 범위 내에서 배합 가능하다.In addition, the blending components that may be added other than these are not limited thereto, and any of the above components can be blended within a range not impairing the objects and effects of the present invention.
이하, 본 발명을 하기의 실시예 및 실험예를 통하여 설명한다. 하기 실시예 및 실험예는 본 발명에 대한 이해를 돕기 위해 예시의 목적으로만 제공된 것일 뿐 본 발명의 범주 및 범위가 그에 의해 제한되는 것은 아니다.Hereinafter, the present invention will be described through the following examples and experimental examples. The following examples and experimental examples are provided only for illustrative purposes to aid understanding of the present invention, and the scope and scope of the present invention are not limited thereto.
[제조예] [Production Example]
[제조예 1] 버섯 추출물의 제조[Preparation Example 1] Preparation of mushroom extract
시중의 표고버섯 20g을 30% 알코올을 이용하여 25℃에서 24시간 추출하고, 여과하여 버섯 추출물을 제조하였다. 사용한 버섯의 부위는 갓과 대 부위였다.20 g of shiitake mushrooms on the market were extracted at 25 ° C. for 24 hours using 30% alcohol, and filtered to prepare a mushroom extract. The parts of the mushrooms used were cap and large parts.
[제조예 2] 키토산 올리고당의 제조[Production Example 2] Production of chitosan oligosaccharide
[제조예 2-1] 키토산 올리고당 분획[Preparation Example 2-1] Chitosan oligosaccharide fraction
좁은 분자량 분포를 갖는 키토산올리고당(COS)를 제조하기 위하여 한외여과법(ultrafiltration method)을 통하여 분리하였다. 원 물질 COS 10 g을 정제수(deionization water; DW) 30 mL에 용해시킨 후 한외여과장치에(Amicon 8400, Millipore, USA) 넣고, DW 270 mL을 추가하여 최종 부피가 300 mL이 되도록 하였다. 이때, 분자량 분리능이(molecular weight cut off; MWCO) 30 kDa, 10 kDa, 3 kDa, 1 kDa인 한외여과막(ultrafiltration membrane)을 사용하여 단계적으로 분리하였다. 자세한 방법은 다음과 같다. 먼저 30 kDa 한외여과막을 이용하여 고분자량 키토산 올리고당과 키토산 분해 효소를 제거하고, 30 kDa 한외여과막을 통과한 키토산 올리고당 용액을 10 kDa의 한외여과막을 이용하여 분자량 크기에 따라 분리하였다.In order to prepare chitosan oligosaccharide (COS) having a narrow molecular weight distribution, it was separated through an ultrafiltration method. After dissolving 10 g of raw material COS in 30 mL of deionization water (DW), it was placed in an ultrafiltration device (Amicon 8400, Millipore, USA), and 270 mL of DW was added to make the final volume to 300 mL. At this time, the molecular weight cut off (MWCO) of 30 kDa, 10 kDa, 3 kDa, 1 kDa was separated using an ultrafiltration membrane (ultrafiltration membrane) in stages. The detailed method is as follows. First, high molecular weight chitosan oligosaccharide and chitosan-degrading enzyme were removed using a 30 kDa ultrafiltration membrane, and the chitosan oligosaccharide solution passing through the 30 kDa ultrafiltration membrane was separated according to molecular weight using a 10 kDa ultrafiltration membrane.
이 과정을 통하여 COS10K를 얻었다. 계속해서 3 kDa, 1 kDa의 한외여과막을 이용하여 COS 4K와 COS 2K를 얻었다. 위의 모든 단계에서 한외여과는 한외여과장치에 한외여과막을 장치한 후 키토산 올리고당 용액 300 mL을 넣고 한외여과장치에 질소를 토출(토출 압력; 3.5 ㎏f/㎠)시켜 초기양의 1/6이 되도록 농축시킨 후 다시 DW를 넣어 300 mL이 되도록 하여 다시 동일한 과정으로 농축시켰으며, 이 과정을 3회 반복한 후 한외여과장치 내의 최종 고순도 키토산 올리고당 용액을 얻었다. 이 용액은 동결건조를 통하여 분자량 별로 키토산 올리고당 분말을 얻었다.Through this process, COS10K was obtained. Subsequently, COS 4K and COS 2K were obtained using 3 kDa and 1 kDa ultrafiltration membranes. In all of the above steps, ultrafiltration is performed by placing an ultrafiltration membrane in an ultrafiltration device, then adding 300 mL of chitosan oligosaccharide solution and discharging nitrogen (discharge pressure: 3.5 kgf/cm 2 ) into the ultrafiltration device so that 1/6 of the initial amount is After concentrating as much as possible, DW was added again to make 300 mL and concentrated again in the same process. After repeating this process three times, a final high-purity chitosan oligosaccharide solution was obtained in the ultrafilter. This solution was lyophilized to obtain chitosan oligosaccharide powder by molecular weight.
[제조예 2-2] 분획된 키토산 올리고당의 분자량 측정[Preparation Example 2-2] Measurement of molecular weight of fractionated chitosan oligosaccharide
분획된 COS의 분자량 및 분자량 분포는 광 산란 검출기가 장착된 겔 투과크로마토그래피(gel permeation chromatography equipped with multi-angle laser light scattering detector, GPC-MALLS, 18angle detector, Wyatt, USA)를 통하여 분석 하였다. 분석을 위해 Shodex SB-804 HQ, Shodex SB-802 HQ (OHpak, Wyatt, USA) 두 종류의 컬럼을 사용하여 COS를 시간에 따라 분리하였다. 이때 이동상은 amonium acetate (0.5 M, pH 5.5)를 사용하였으며, 흐름속도는 0.5 mL/min, 컬럼 온도는 40 ℃로 유지하여 분석하였다. The molecular weight and molecular weight distribution of the fractionated COS were analyzed through gel permeation chromatography equipped with multi-angle laser light scattering detector (GPC-MALLS, 18angle detector, Wyatt, USA). For analysis, COS was separated according to time using two types of columns, Shodex SB-804 HQ and Shodex SB-802 HQ (OHpak, Wyatt, USA). At this time, amonium acetate (0.5 M, pH 5.5) was used as the mobile phase, the flow rate was 0.5 mL/min, and the column temperature was maintained at 40 °C.
각각 분획된 키토산 올리고당의 분자량을 측정하기 위해 GPC-MALLS를 이용하였고, 그 결과는 도 1 에 나타내었다. COS 1~3K, COS 3~10K, COS 10~30K 각각의 분자량은 2K(kDa), 4K, 10K의 분자량을 확인 하였으며, 머무름 시간(Retention time, RT)에 따른 굴절율(reflective index, RI)을 통해 분획된 모든 키토산 올리고당이 좁은 분자량 분포를 갖음을 확인 할 수 있었다. 또한, 분획된 키토산의 다분산지수(PDI)값이 1.012 ~1.077로 1에 가까운 값을 확인 함으로써 분획된 모든 키토산 올리고당이 비슷한 분자량을 함유 하고 있음을 확인 할 수 있었다.GPC-MALLS was used to measure the molecular weight of each fractionated chitosan oligosaccharide, and the results are shown in FIG. 1 . The molecular weights of COS 1-3K, COS 3-10K, and COS 10-30K were confirmed for molecular weights of 2K (kDa), 4K, and 10K, and the reflective index (RI) according to the retention time (RT) was determined. It was confirmed that all the chitosan oligosaccharides fractionated through this method had a narrow molecular weight distribution. In addition, the polydispersity index (PDI) value of the fractionated chitosan was 1.012 to 1.077, which was close to 1, confirming that all the fractionated chitosan oligosaccharides contained similar molecular weights.
[제조예 2-3] 분획된 키토산 올리고당의 구조 분석[Preparation Example 2-3] Structural analysis of fractionated chitosan oligosaccharide
분획된 키토산의 구조는 1H NMR(400 mHz, Bruker, Germany)와 적외선 분광광도계(FT-IR 8700, Shimadzu, Japan)를 이용하여 분석하였다. 1H NMR 분석은 분리된 COS를 용매 D2O에 용해시켜 1 ~ 10 ppm 범위에서 chemical shift를 통하여 분석하였다. The structure of the fractionated chitosan was analyzed using 1 H NMR (400 mHz, Bruker, Germany) and an infrared spectrophotometer (FT-IR 8700, Shimadzu, Japan). In 1 H NMR analysis, the separated COS was dissolved in solvent D 2 O and analyzed through chemical shift in the range of 1 to 10 ppm.
그 결과 키토산 구조에서 1번 위치의 수소는 5.4 ppm, 2번 위치의 수소는 3.1 ppm, 그리고 3번 ~ 6번 위치의 수소는 3.5 ~ 4.0 ppm에서 모두 확인하였고, 키토산 구조내의 키틴의 아세틸 그룹에 의한 특성 피크를 2.1 ppm에서 확인하였으며, 키토산에 도입되어 있는 lactic acid의 특성피크를 1.2 ~ 1.5 ppm 과 4.2 ppm에서 모두 확인하였다(도 2). 이러한 결과는 분획되어 있는 세 종류의 키토산인 COS2K, 4K, 10K에서 모두 동일하게 나타났다. 따라서 이러한 구조분석 결과를 통해 분획과정에서 키토산 올리고당이 구조적으로 변화가 없음을 확인하였다.As a result, in the chitosan structure, the hydrogen at position 1 was 5.4 ppm, the hydrogen at position 2 was 3.1 ppm, and the hydrogen at position 3 to 6 was confirmed at 3.5 to 4.0 ppm. The characteristic peak of lactic acid introduced into chitosan was confirmed at 2.1 ppm, and the characteristic peaks of lactic acid introduced into chitosan were confirmed at 1.2 ~ 1.5 ppm and 4.2 ppm (FIG. 2). These results were the same in all three kinds of chitosans, COS2K, 4K, and 10K. Therefore, through the result of structural analysis, it was confirmed that there was no structural change of chitosan oligosaccharide during the fractionation process.
[제조예 2-4] 키토산 올리고당의 독성 확인[Preparation Example 2-4] Confirmation of toxicity of chitosan oligosaccharide
동물세포주 중 HEK293 cell을 이용하여 세포독성 여부를 측정하였다. 동물세포주를 37℃, 5% CO2와 습윤화된 배양기내에서 DMEM 배양액(FBS 10%와 Penicillin-Streptomycin 1% 항생제를 포함)을 함유한 culture dish에서 부착 배양한 후, Trypsin-EDTA로 떨어뜨리고 cell수를 확인하였다. 5 × 103 cells/well로 96-well microtiter에 분주하고 24시간 배양한 후 sample을 각 well에 처리하고 48시간 반응하였고, MTT를 처리하여 세포독성 여부를 측정하였다. 세포생존율은 다음과 같이 계산 되었다.Cytotoxicity was measured using HEK293 cells among animal cell lines. Animal cell lines were attached and cultured in a culture dish containing DMEM culture medium (including 10% FBS and 1% Penicillin-Streptomycin antibiotics) in a humidified incubator with 5% CO2 at 37℃, and then dropped with Trypsin-EDTA and cell culture. number was confirmed. After dividing into a 96-well microtiter at 5 × 10 3 cells/well and incubating for 24 hours, samples were treated in each well and reacted for 48 hours, and cytotoxicity was measured by treating with MTT. Cell viability was calculated as follows.
그 결과 분획된 키토산 모두 80% 이상의 세포생존율을 확인할 수 있었다. 이러한 결과는 분획된 키토산의 세포 독성은 무시할 수 있는 수준으로 안전성이 높아 생체에 적용이 가능함을 보이는 것이다.As a result, it was confirmed that all of the fractionated chitosans had a cell viability of 80% or more. These results show that the cytotoxicity of the fractionated chitosan is negligible and its safety is high, so that it can be applied to the living body.
[제조예 3] 버섯 추출물을 담지한 마이크로스피어의 제조[Preparation Example 3] Preparation of microspheres carrying mushroom extract
추출물이 담지된 마이크로스피어를 제조하기 위해 spray dry (Spray Dryers; Lab Plant, SD-06A, UK) 공법을 이용하였다. 분획된 키토산 올리고당을 증류수를 이용하여 1% 키토산 올리고당 용액을 각각 제조한 후 이 용액에 추출물을 키토산 올리고당 무게 비율로 20%와 40%를 각각 첨가 하였고 1시간동안 상온에서 교반하였다. 그 후 혼합된 용액을 spray dry nozzle에 넣어 토출 압력 20 kPa과 건조온도 200℃ 조건에서 실험을 진행 하였다. 회수된 추출물이 담지된 키토산 마이크로스피어 분말은 상온에서 1시간 건조 후 실험에 사용 하였다. To prepare the microspheres loaded with the extract, a spray drying (Spray Dryers; Lab Plant, SD-06A, UK) method was used. After preparing 1% chitosan oligosaccharide solutions using distilled water from the fractionated chitosan oligosaccharide, 20% and 40% of chitosan oligosaccharide extracts by weight were added to the solution, respectively, and stirred at room temperature for 1 hour. After that, the mixed solution was put into a spray dry nozzle and the experiment was conducted under the conditions of a discharge pressure of 20 kPa and a drying temperature of 200 °C. The recovered extract-supported chitosan microsphere powder was dried at room temperature for 1 hour and then used in the experiment.
담지 여부는, 자외선 분광광도계 (UV-Vis spectrometer, UV1601, Shimadzu, Japan)와 핵자기공명장치(1H NMR, 400 mHz, Bruker, Germany)를 이용하여 분석하였다.Whether or not supported was analyzed using a UV-Vis spectrometer (UV-Vis spectrometer, UV1601, Shimadzu, Japan) and a nuclear magnetic resonance apparatus ( 1 H NMR, 400 mHz, Bruker, Germany).
자외선 분광광도계를 이용한 경우, Sample을 에탄올에 3회 washing 한 후 건조된 분말을 증류수에 용해하였고, washing하고 남은 상층액 에탄올을 각각 220 ~ 400 nm 파장에서 흡광도 피크를 관찰하여 파장에 따른 흡광도의 변화를 확인하였다.In the case of using an ultraviolet spectrophotometer, after washing the sample in ethanol three times, the dried powder was dissolved in distilled water, and the absorbance peak of the supernatant ethanol remaining after washing was observed at a wavelength of 220 ~ 400 nm, respectively, and the change in absorbance according to the wavelength confirmed.
핵자기공명장치를 이용한 경우, 샘플을 에탄올에 3회 washing 한 후 건조된 분말 4 mg을 용매 D2O에 용해시켜 1 ~ 10 ppm 범위에서 chemical shift를 통하여 분석하였다.In the case of using a nuclear magnetic resonance device, the sample was washed three times in ethanol, and then 4 mg of the dried powder was dissolved in a solvent D 2 O and analyzed through chemical shift in the range of 1 to 10 ppm.
도 3은 추출물이 키토산 마이크로스피어 내부에 담지 여부를 확인 하기 위해 자외선 분광기를 이용하여 분석한 결과이다. 도 3a는 추출물, 키토산 올리고당 마이크로스피어, 추출물이 담지된 키토산 올리고당 마이크로스피어를 각각 증류수에 분산시켜 측정한 결과인데, 추출물의 경우 260 nm 부근에서 강한 흡수 파장을 관찰하였다. 또한, 추출물이 담지되지 않은 마이크로스피어의 경우 260 nm 부근에서 흡수 피크가 나타나지 않았으나, 추출물이 담지된 마이크로스피어의 경우 260 nm에서 강한 흡수 피크를 관찰 하였다. 도 3b, 3c는 추출물이 키토산 마이크로스피어 내부에 담지되어 있는 여부를 확인하기 위해 키토산 마이크로스피어 표면에 존재하는 표고버섯 추출물을 에탄올로 세척 후 상층액 에탄올과 추출물이 담지된 마이크로스피어를 측정한 결과이다. 그 결과 세척 후 상층액 에탄올의 경우 260 nm에서 강한 흡수 피크를 확인 함으로써 키토산 마이크로스피어 표면에 묻어 있는 추출물이 잘 제거 되었음을 확인할 수 있었고, 에탄올에 의해 세척된 추출물이 담지된 마이크로스피어는 260 nm에서 강한 흡수 피크가 관찰 됨으로써 추출물이 키토산 마이크로스피어 내부에 담지 되어 있음을 확인 할 수 있었다. 3 is an analysis result using an ultraviolet spectrometer to confirm whether the extract is supported inside the chitosan microspheres. Figure 3a shows the results obtained by dispersing the extract, the chitosan oligosaccharide microspheres, and the extract-supported chitosan oligosaccharide microspheres in distilled water, respectively. In the case of the extract, a strong absorption wavelength was observed at around 260 nm. In addition, in the case of the microspheres without the extract, no absorption peak was observed at around 260 nm, but in the case of the microspheres with the extract, a strong absorption peak was observed at 260 nm. 3b and 3c are the results of measuring the supernatant ethanol and the microspheres loaded with the extract after washing the shiitake mushroom extract present on the surface of the chitosan microspheres with ethanol to confirm whether the extract is supported inside the chitosan microspheres. . As a result, in the case of ethanol in the supernatant after washing, it was confirmed that the extract on the surface of the chitosan microspheres was well removed by confirming a strong absorption peak at 260 nm. By observing the absorption peak, it was confirmed that the extract was supported inside the chitosan microspheres.
도 4는 추출물 담지여부를 1H-NMR을 이용하여 확인한 결과이다. 추출물이 담지된 마이크로 스피어를 에탄올로 세척한 후 1H-NMR을 측정한 결과 에탄올로 세척한 후에도 추출물의 특성피크가 나타남으로써 추출물이 키토산 마이크로스피어 내부에 담지 되어 있다는 것을 확인할 수 있었다. Figure 4 is the result of confirming whether the extract was supported using 1 H-NMR. As a result of measuring 1 H-NMR after washing the microspheres loaded with the extract with ethanol, characteristic peaks of the extract appeared even after washing with ethanol, confirming that the extract was supported inside the chitosan microspheres.
한편, 버섯 추출물 담지전 2kDa의 키토산 올리고당을 이용하여 제조한 마이크로스피어의 직경은 약 2㎛이었고, 4kDa 의 키토산 올리고당을 이용하여 제조한 마이크로스피어의 직경은 약 3㎛이었으며, 10kDa의 키토산 올리고당을 이용하여 제조한 마이크로스피어의 직경은 약 5㎛이었고, 키토산 올리고당 중량을 기준으로 약 40%의 버섯 추출물을 담지한 후 마이크로 스피어의 직경은 순서대로 각각 약 2.5~3㎛, 약 3.5~4.5㎛, 약 6~7㎛였다.On the other hand, the diameter of microspheres prepared using 2 kDa chitosan oligosaccharide was about 2 μm before loading the mushroom extract, and the diameter of microspheres prepared using 4 kDa chitosan oligosaccharide was about 3 μm, using 10 kDa chitosan oligosaccharide. The diameter of the microspheres prepared was about 5 μm, and after supporting about 40% of the mushroom extract based on the weight of chitosan oligosaccharide, the diameters of the microspheres were sequentially about 2.5 to 3 μm, about 3.5 to 4.5 μm, about It was 6-7 μm.
[실험예][Experimental Example]
[실험예 1] 버섯 부위에 따른 효과 확인[Experimental Example 1] Confirmation of effects according to mushroom parts
표고 버섯 갓 추출물과 표고 버섯 대 추출물을 이용하여, 부위에 따른 ABTS 라디칼 소거능, DPPH 라디칼 소거능, ROS 발생율, H2O2에 대한 세포 생존율을 확인하였다. 실험방법은 업계에서 일반적으로 알려지 있는 방법을 이용하여 진행하였고, 버섯 추출물의 농도별로 실험 데이터를 얻었다. 그 결과, '대' 추출물에 비하여, '갓'추출물을 처리했을 때 더 우수한 라디칼 소거능, ROS 발생 제어율, H2O2에 대한 세포 생존률을 확인할 수 있었다(도 5).ABTS radical scavenging activity, DPPH radical scavenging activity, ROS generation rate, and cell survival rate for H 2 O 2 were confirmed according to the site using shiitake mushroom cap extract and shiitake mushroom stem extract. The experimental method was conducted using a method generally known in the industry, and experimental data were obtained for each concentration of mushroom extract. As a result, compared to the 'Dae' extract, when the 'God' extract was treated, it was confirmed that the radical scavenging ability, ROS generation control rate, and cell survival rate for H 2 O 2 were better (FIG. 5).
[실험예 2] 버섯 추출물과 키토산 올리고당 병용에 따른 효과 확인 [Experimental Example 2] Confirmation of effect according to combination of mushroom extract and chitosan oligosaccharide
제조예 3에서 제조된 버섯 추출물을 40% 담지한 마이크로 스피어(4kDa 키토산 올리고당 사용)를 이용하여, 실험예 1과 동일한 실험을 하였다.The same experiment as in Experimental Example 1 was conducted using microspheres (using 4kDa chitosan oligosaccharide) loaded with 40% of the mushroom extract prepared in Preparation Example 3.
실험 결과는, 버섯 추출물만 사용한 경우의 결과 데이터를 기준으로 상대적인 값으로 표시하였다.The experimental results were expressed as relative values based on the result data when only the mushroom extract was used.
*상기 수치값이 우수할수록 효과가 우수함*The higher the numerical value above, the better the effect
그 결과, 버섯 추출물만을 사용했을 때보다 마이크로 스피어 내에 버섯 추출물을 담지한 경우에, 라디컬 소거능, 세포 생존율 등이 더 우수함을 알 수 있었다.As a result, it was found that radical scavenging ability, cell viability, etc. were better when the mushroom extract was supported in the microspheres than when only the mushroom extract was used.
[실험예 3] 다양한 크기의 마이크로 스피어 병용시 효과 확인[Experimental Example 3] Confirmation of effect when microspheres of various sizes are used together
제조예 3에서 제조한, 다양한 마이크로 스피어(키토산 올리고당의 분자량이 2kDa,4kDa,10kDa인 마이크로 스피어)를 병용시 효과를 확인하였다. 분자량이 상이한 키토산 올리고당을 이용한 마이크로 스피어의 배합비율을 달리하여 효과를 확인하였다. 실험 결과는, 4kDa의 마이크로 스피어만을 사용한 경우의 결과값을 1이라고 하고, 이를 기준으로 상대적인 값으로 표시하였다.Effects of using various microspheres prepared in Preparation Example 3 (microspheres having molecular weights of chitosan oligosaccharide of 2 kDa, 4 kDa, and 10 kDa) were confirmed. The effect was confirmed by varying the blending ratio of the microspheres using chitosan oligosaccharides having different molecular weights. As for the experimental results, the resultant value in the case of using only 4 kDa microspheres was set to 1, and it was expressed as a relative value based on this.
그 결과, 2kDa, 4kDa, 10kDa를 동량 병용시에, 이들 마이크로 스피어를 단독으로 사용하는 경우에 비하여 우수한 효과를 확인하였다. 또한, 이들 중 2kDa나 4kDa는 과량 사용되어도 별다른 효과차이가 없는 반면, 10kDa는 과량 사용시 효과가 더 우수함을 확인할 수 있었다. 특히, 10kDa가 2kDa나 4kDa 에 비하여 약 8배 포함될 경우에 가장 우수한 효과를 확인할 수 있었다. As a result, when the same amounts of 2 kDa, 4 kDa, and 10 kDa were used together, superior effects were confirmed compared to the case of using these microspheres alone. In addition, it was confirmed that 2 kDa or 4 kDa of these showed no significant difference in effect even when used in excess, whereas 10 kDa was more effective when used in excess. In particular, the most excellent effect was confirmed when 10 kDa was included about 8 times as compared to 2 kDa or 4 kDa.
또한, 4kDa의 마이크로 스피어만을 사용한 경우와 비교하여, 2kDa, 4kDa, 10kDa를 동량 병용시, 마이크로 스피어 처리 직후와 유사한 정도의 효과가 장기간(약 2.5시간 이상) 유지됨을 확인할 수 있었다.In addition, compared to the case of using only 4 kDa microspheres, it was confirmed that when the same amount of 2 kDa, 4 kDa, and 10 kDa was used together, the effect similar to that immediately after microsphere treatment was maintained for a long period of time (about 2.5 hours or more).
Claims (14)
상기 마이크로스피어는,
키토산 올리고당을 포함하는 외층(outer layer); 및 외층으로 형성된 내부 공간에 담지되어 있는 표고 버섯 갓 추출물을 포함하며,
상기 표고 버섯 갓 추출물은 상기 키토산 올리고당의 중량을 100으로 했을 때, 10~50 중량부로 포함하며,
상기 마이크로스피어는,
키토산 올리고당의 분자량이 2kDa이며, 직경이 2.5~3㎛인 마이크로스피어를 포함하는 제1군; 키토산 올리고당의 분자량이 4kDa이며, 직경이 3.5~4.5㎛인 마이크로스피어를 포함하는 제2군; 및 키토산 올리고당의 분자량이 10kDa이며, 직경이 6~7㎛인 마이크로스피어를 포함하는 제3군을 포함하고, 상기 제1군, 제2군 및 제3군은, 마이크로스피어의 총 중량을 기준으로, 각각 5~15 중량%, 5~15 중량%, 및 70~90중량%로 포함하는, 조성물. Including microspheres,
The microspheres,
an outer layer comprising chitosan oligosaccharide; And a shiitake mushroom cap extract supported in the inner space formed by the outer layer,
The shiitake mushroom cap extract contains 10 to 50 parts by weight when the weight of the chitosan oligosaccharide is 100,
The microspheres,
A first group comprising microspheres having a molecular weight of chitosan oligosaccharide of 2 kDa and a diameter of 2.5 to 3 μm; a second group comprising microspheres having a molecular weight of chitosan oligosaccharide of 4 kDa and a diameter of 3.5 to 4.5 μm; and a third group comprising microspheres having a molecular weight of chitosan oligosaccharide of 10 kDa and a diameter of 6 to 7 μm, wherein the first group, second group, and third group are based on the total weight of the microspheres. , Composition comprising 5 to 15% by weight, 5 to 15% by weight, and 70 to 90% by weight, respectively.
상기 표고 버섯 갓 추출물의 추출용매는, 물, 유기용매 또는 유기용매 수용액을 포함하는, 조성물.According to claim 1,
The extraction solvent of the shiitake mushroom cap extract comprises water, an organic solvent or an organic solvent aqueous solution.
상기 유기용매는 알코올을 포함하는, 조성물.According to claim 8,
Wherein the organic solvent comprises an alcohol.
상기 조성물은,
자유 라디칼 소거능, 활성 산소 소거능, 또는 세포 손상 억제 또는 개선능을 포함하는, 조성물.According to claim 1,
The composition is
A composition comprising free radical scavenging activity, active oxygen scavenging activity, or cell damage inhibition or improvement activity.
상기 활성 산소는, 과산화수소, 수퍼옥사이드 이온 및 하이드록시 라디칼 중 하나이상을 포함하는, 조성물.According to claim 10,
Wherein the active oxygen comprises at least one of hydrogen peroxide, superoxide ions and hydroxy radicals.
상기 세포 손상은, 과산화수소로 인한 손상을 포함하는, 조성물According to claim 10,
The cell damage, including damage due to hydrogen peroxide, composition
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