KR20180021618A - Anthocyanin nanocomplex - Google Patents
Anthocyanin nanocomplex Download PDFInfo
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- KR20180021618A KR20180021618A KR1020160106428A KR20160106428A KR20180021618A KR 20180021618 A KR20180021618 A KR 20180021618A KR 1020160106428 A KR1020160106428 A KR 1020160106428A KR 20160106428 A KR20160106428 A KR 20160106428A KR 20180021618 A KR20180021618 A KR 20180021618A
- Authority
- KR
- South Korea
- Prior art keywords
- anthocyanin
- nanocomposite
- chitosan
- complex
- present
- Prior art date
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Images
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5161—Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
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- A23V2200/048—Preventing colour changes
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/20—Ingredients acting on or related to the structure
- A23V2200/25—Nanoparticles, nanostructures
Abstract
Description
본 발명은 안토시아닌의 안정성이 현저히 개선된 안토시아닌 나노 복합체에 관한 것이다.The present invention relates to an anthocyanin nanocomposite in which the stability of anthocyanin is remarkably improved.
안토시아닌은 꽃이나 과실 등에 주로 포함되어 있는 색소로, 블랙커런트, 블루베리, 아로니아, 체리, 흑미, 포도, 적양배추와 같은 식물에 많이 함유되어 있다.Anthocyanin is a pigment mainly contained in flowers and fruits. It is contained in many plants such as black currant, blueberry, aronia, cherry, black rice, grapes and red cabbage.
안토시아닌은 항산화 물질 중에서도 가장 강력한 효과를 나타낼 뿐만 아니라, 암, 노화, 면역반응, 당뇨, 박테리아 감염증, 신경계 질환 등에 약리활성이 우수하다.Anthocyanins are not only the most potent antioxidants but also have excellent pharmacological activities such as cancer, aging, immune response, diabetes, bacterial infections, and neurological diseases.
안토시아닌을 함유한 제품의 세계적인 수요 증가와 이상기후로 인하여 안토시아닌이 풍부하다고 알려진 열매들의 수확량 감소가 맞물리면서 가격 상승이 우려된다. 또한, 안토시아닌의 항산화 효과 자체는 음식으로 섭취했을 때 가장 큰 효과가 나타나지만 위장관에서 머무르는 시간, 낮은 장관 벽 투과성, 낮은 용해도 및 상업화를 위한 공정상에서의 불안정성이나, 온도, 주변 산소, 빛, 소화관 내 PH, 효소 및 다른 영양분에 의한 분해 등에 의해 생체 내에서는 5% 이하의 낮은 활성을 가지게 된다.Increased global demand for anthocyanin-containing products, coupled with reduced yields of known anthocyanins rich in anthocyanins due to unusual weather conditions, may raise prices. In addition, the antioxidant effect of anthocyanin itself has the greatest effect when ingested as food, but it has been shown to be the most effective when consumed as food, but it has been found that the gastrointestinal stays, low intestinal wall permeability, low solubility and instability in the process for commercialization, , Degradation by enzymes and other nutrients, and the like.
따라서 높은 저장 안정성을 가지며, 항산화의 활성이 증대된 안토시아닌의 개발이 절실히 필요하다.Therefore, the development of anthocyanin having high storage stability and enhanced antioxidant activity is urgently needed.
본 발명은 안토시아닌의 안정성이 현저히 개선된 안토시아닌 나노 복합체의 제공을 목적으로 한다.It is an object of the present invention to provide an anthocyanin nanocomposite in which the stability of anthocyanin is remarkably improved.
본 발명은 생체적합성 및 생분해성이 우수한 안토시아닌 나노 복합체의 제공을 목적으로 한다.An object of the present invention is to provide an anthocyanin nanocomposite having excellent biocompatibility and biodegradability.
본 발명은 가격 경쟁력이 높은 안토시아닌 나노 복합체의 제공을 목적으로 한다.The present invention aims to provide an anthocyanin nanocomposite having high price competitiveness.
1. 안토시아닌 코어 및 상기 코어를 감싸는 키토산 쉘을 포함하는 안토시아닌 나노 복합체.1. Anthocyanin nanocomposite comprising an anthocyanin core and a chitosan shell surrounding the core.
2. 위 1에 있어서, 상기 안토시아닌은 페오니딘(Peonidin), 시아니딘 3-아라비노시드(cyanidin 3-arabinoside), 시아니딘-3-(크실 로실글루코오스)-5-갈락토오스(cyanidin-3-(xylosylglucose)-5-galactose), 시아니딘 3-글루코시드(cyanidin 3-glucoside), 시아니딘 3-갈락토시드(cyanidin 3-galactoside), 시아니딘-3-(쿠마로일-크실로실글루코오스)-5-갈락토오스(cyanidin-3-(coumaroyl-xylosylglucose)-5-galactose), 델피니딘 3-글루코시드(delphinidin 3-glucoside), 델피니딘 3-루티노시드(delphinidin 3-rutinoside), 페오니딘 3-아라비노시드(peonidin 3-arabinoside), 페오니딘 3-갈락토시드(peonidin 3-galactoside), 페투니딘 3-글루코시드(petunidin 3-glucoside), 시아니딘(Cyanidin), 델피니딘(delphinidin), 말비딘(malvidin), 펠라르고니딘(pelargonidin), 페오니딘(peonidin), 시아니딘 3,5-디글루코시드(cyanidin 3,5-diglucoside), 시아니딘 3-루티노시드(cyanidin 3-rutinoside), 펠라르고니딘 3-글루코시드(pelargonidin 3-glucoside), 페오니딘 3-글루코시드(peonidin 3-glucoside), 말비딘 3-글루코시드(malvidin 3-glucoside) 및 말비딘 3,5-디글루코시드(malvidin 3,5-diglucoside)로 이루어진 군으로부터 선택되는 적어도 하나인, 안토시아닌 나노 복합체.2. The method of
3. 위 1에 있어서, 상기 안토시아닌은 펠라르고니딘인 안토시아닌 나노 복합체.3. The anthocyanin nanocomposite according to
4. 위 1에 있어서, 상기 키토산은 키토산 및 글라이콜 키토산 중 적어도 하나인 안토시아닌 나노 복합체.4. The anthocyanin nanocomposite according to
5. 위 1에 있어서, 상기 복합체는 입경이 10㎚ 내지 10㎛인, 안토시아닌 나노 복합체.5. The anthocyanin nanocomposite according to
6. 위 1 내지 5 중 어느 한 항의 안토시아닌 나노 복합체를 포함하는, 조성물.6. The composition of any one of
본 발명에 따른 안토시아닌 나노 복합체는 구조적으로 안정하다.The anthocyanin nanocomposite according to the present invention is structurally stable.
본 발명에 따른 안토시아닌 나노 복합체는 산화 및 보관 안정성이 뛰어나 체내 외 환경에 안정하다.The anthocyanin nanocomposite according to the present invention is excellent in oxidation and storage stability and is stable in an external environment.
본 발명에 따른 안토시아닌 나노 복합체는 저장 안정성이 뛰어나 생체 내 활성이 높다.The anthocyanin nanocomposite according to the present invention is excellent in storage stability and high in vivo activity.
본 발명에 다른 안토시아닌 나노 복합체는 생체적합성 및 생분해성이 우수하다.The anthocyanin nanocomposite according to the present invention is excellent in biocompatibility and biodegradability.
본 발명에 따른 안토시아닌 나노 복합체는 색도를 오랫동안 높게 유지할 수 있다.The anthocyanin nanocomposite according to the present invention can maintain a high chromaticity for a long time.
본 발명에 따른 안토시아닌 나노 복합체는 약품 또는 식품에 응용시 가공조건, 유통과 저장성을 향상시킬 수 있다.The anthocyanin nanocomposite according to the present invention can improve processing conditions, distribution and shelf life when applied to medicines or foods.
도 1은 본 발명의 일 실시예를 나타낸 모식도이다.
도 2는 안토니시아닌-클라이콜 키토산 복합체 형성 후의 색가를 비율별로 나타낸 것이다.
도 3은 안토니시아닌-클라이콜 키토산 복합체의 비율별 흡광도 그래프를 나타낸 것이다.
도 4는 안토시아닌 (10:0)과 안토니시아닌-클라이콜 키토산 복합체의 533nm에서의 흡광도 값을 나타낸 것이다.
도 5는 안토니시아닌-클라이콜 키토산 복합체 입자의 크기를 나타낸 것이다.
도 6은 안토니시아닌-클라이콜 키토산 복합체 입자의 형태를 나타낸 것이다.
도 7은 안토시아닌의 pH에 따른 구조의 변화를 나타낸 것이다.
도 8은 pH에 따른 안정성을 Λmax1 (533nm)/ Λmax2 (598nm) 값으로 나타낸 것이다.
도 9는 안토시아닌만 있을 때 pH에 따른 흡광도를 나타낸 것이다.
도 10은 안토시아닌 : 글라이콜 키토산 = 4 : 1 복합체의 pH에 따른 흡광도를 나타낸 것이다.
도 11은 안토시아닌 : 글라이콜 키토산 = 9 : 1 복합체의 pH에 따른 흡광도를 나타낸 것이다.
도 12는 안토시아닌 : 글라이콜 키토산 = 8 : 1 복합체의 pH에 따른 흡광도를 나타낸 것이다.
도 13은 안토시아닌 : 글라이콜 키토산 = 7 : 1 복합체의 pH에 따른 흡광도를 나타낸 것이다.
도 14는 안토시아닌 : 글라이콜 키토산 = 6 : 1 복합체의 pH에 따른 흡광도를 나타낸 것이다.
도 15는 안토시아닌 : 글라이콜 키토산 = 5 : 1 복합체의 pH에 따른 흡광도를 나타낸 것이다.
도 16은 안토시아닌만 있을 때 다양한 온도에서의 안정성을 나타낸 것이다.
도 17은 안토시아닌만 있을 때 100 ℃에서 시간에 따른 안정성을 나타낸 것이다.
도 18은 안토시아닌 : 글라이콜 키토산 = 9 : 1 복합체의 온도에 따른 흡광도를 나타낸 것이다.
도 19는 안토시아닌 : 글라이콜 키토산 = 8 : 1 복합체의 온도에 따른 흡광도를 나타낸 것이다.
도 20은 안토시아닌 : 글라이콜 키토산 = 7 : 1 복합체의 온도에 따른 흡광도를 나타낸 것이다.
도 21은 안토시아닌 : 글라이콜 키토산 = 6 : 1 복합체의 온도에 따른 흡광도를 나타낸 것이다.
도 22는 안토시아닌 : 글라이콜 키토산 = 5 : 1 복합체의 온도에 따른 흡광도를 나타낸 것이다.
도 23은 안토시아닌 : 글라이콜 키토산 = 4 : 1 복합체의 온도에 따른 흡광도를 나타낸 것이다.
도 24는 온도에 따른 안정성을 Λmax1 (533nm)/ Λmax2 (598nm) 값으로 나타낸 것이다.
도 25는 광에 따른 안정성을 Λmax1 (533nm)/ Λmax2 (598nm) 값으로 나타낸 것이다.
도 26은 안토시아닌만 있을 때 광 안정성을 나타낸 것이다.
도 27은 안토시아닌 : 글라이콜 키토산 = 4 : 1 복합체의 광 안정성을 나타낸 것이다.
도 28은 안토시아닌 : 글라이콜 키토산 = 9 : 1 복합체의 광 안정성을 나타낸 것이다.
도 29는 안토시아닌 : 글라이콜 키토산 = 8 : 1 복합체의 광 안정성을 나타낸 것이다.
도 30은 안토시아닌 : 글라이콜 키토산 = 7 : 1 복합체의 광 안정성을 나타낸 것이다.
도 31은 안토시아닌 : 글라이콜 키토산 = 6 : 1 복합체의 광 안정성을 나타낸 것이다.
도 32는 안토시아닌 : 글라이콜 키토산 = 5 : 1 복합체의 광 안정성을 나타낸 것이다.1 is a schematic diagram showing an embodiment of the present invention.
Fig. 2 shows the color value after the formation of the anthocyanin-clavicle chitosan complex.
FIG. 3 is a graph showing the absorbance of each of the anthocyanin-klycol chitosan complexes.
Figure 4 shows the absorbance values at 533 nm of anthocyanin (10: 0) and anthocyanin-clavicle chitosan complexes.
Figure 5 shows the size of anthocyanin-klycol chitosan complex particles.
6 shows the shape of the anthocyanin-klycol chitosan complex particle.
Fig. 7 shows the change of the structure according to the pH of anthocyanin.
Fig. 8 shows the stability with respect to pH as a value of? Max1 (533 nm) /? Max2 (598 nm).
9 shows the absorbance according to pH when only anthocyanin is present.
10 shows the absorbance of anthocyanin: glycol chitosan = 4: 1 complex according to pH.
Figure 11 shows the absorbance of anthocyanin: glycol chitosan = 9: 1 complex according to pH.
Figure 12 shows the absorbance of anthocyanin: glycol chitosan = 8: 1 complex according to pH.
13 shows the absorbance of anthocyanin: glycol chitosan = 7: 1 complex according to pH.
14 shows the absorbance of anthocyanin: glycol chitosan = 6: 1 complex according to pH.
15 shows the absorbance of anthocyanin: glycol chitosan = 5: 1 complex according to pH.
Figure 16 shows stability at various temperatures when only anthocyanins are present.
Figure 17 shows the stability over time at 100 ° C in the presence of anthocyanin only.
18 shows the absorbance of anthocyanin: glycol chitosan = 9: 1 complex according to temperature.
Figure 19 shows the absorbance of anthocyanin: glycol chitosan = 8: 1 complex according to temperature.
20 shows the absorbance of anthocyanin: glycol chitosan = 7: 1 complex according to temperature.
21 shows the absorbance of anthocyanin: glycol chitosan = 6: 1 complex according to temperature.
22 shows the absorbance of anthocyanin: glycol chitosan = 5: 1 complex according to temperature.
23 shows the absorbance of anthocyanin: glycol chitosan = 4: 1 complex according to temperature.
24 shows the stability with respect to temperature as a value of? Max1 (533 nm) /? Max2 (598 nm).
25 shows the stability with respect to light as a value of? Max1 (533 nm) /? Max2 (598 nm).
Figure 26 shows the light stability when only anthocyanins were present.
Figure 27 shows the light stability of anthocyanin: glycol chitosan = 4: 1 complex.
Figure 28 shows the light stability of anthocyanin: glycol chitosan = 9: 1 complex.
29 shows the light stability of anthocyanin: glycol chitosan = 8: 1 complex.
30 shows the light stability of anthocyanin: glycol chitosan = 7: 1 complex.
31 shows the light stability of anthocyanin: glycol chitosan = 6: 1 complex.
Figure 32 shows the light stability of anthocyanin: glycol chitosan = 5: 1 complex.
본 발명은 안토시아닌 나노 복합체에 관한 것으로서, 안토시아닌과 양전하성 다당류가 이온결합됨으로써, 구조적으로 안정하고, 산화 및 보관 안정성이 뛰어나 체내 외 환경에 안정하며, 저장 안정성이 뛰어나 생체 내 활성이 높고, 생체적합성 및 생분해성이 우수하며, 색도를 오랫동안 높게 유지할 수 있어, 약품 또는 식품에 응용시 가공조건, 유통과 저장성을 향상시킬 수 있는, 안토시아닌 나노 복합체에 관한 것이다.The present invention relates to an anthocyanin nanocomposite. The present invention relates to an anthocyanin nanocomposite having an anthocyanin and a positively charged polysaccharide which are structurally stable, stable in oxidation and storage stability, And biodegradability of the anthocyanin nanocomposite, and can maintain the chromaticity at a high level for a long time, thereby improving processing conditions, distribution and shelf life when applied to medicines or foods.
이하 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명의 안토시아닌 나노 복합체는 안토시아닌 코어 및 상기 코어를 감싸는 키토산 쉘을 포함한다.The anthocyanin nanocomposite of the present invention comprises an anthocyanin core and a chitosan shell surrounding the core.
안토시아닌(anthocyanin)은 꽃이나 과실 등에 주로 포함되어 있는 색소로서, 수소 이온 농도에 따라 빨간색, 보라색, 파란색 등을 띤다. 안토시아닌은 고등식물의 잎, 줄기, 뿌리, 꽃, 과일 등 어느 조직에나 생기는 수용성 물질로 우수한 항산화 효과를 갖는다.Anthocyanin is a pigment mainly contained in flowers and fruits. It is red, purple, blue depending on the concentration of hydrogen ions. Anthocyanin is a water-soluble substance that occurs in any plant tissues such as leaves, stems, roots, flowers and fruits of higher plants.
이러한 안토시아닌은 안정성이 낮아 pH, 온도 조건, 광 조사 등에 따라 쉽게 퇴색하는 성질이 있다.These anthocyanins are low in stability and easily fade due to pH, temperature conditions, and light irradiation.
그러나, 본 발명자들은 이러한 안토시아닌으로 코어를 형성하고, 이를 키토산 쉘로 감싸는 코어-쉘 구조를 갖는 나노복합체를 형성하는 경우에 안토시아닌의 안정성이 현저히 개선되는 것을 발견하여 본 발명을 착안하였다.However, the inventors of the present invention have found that the stability of anthocyanin is remarkably improved when a core is formed with the anthocyanin and the nanocomposite having the core-shell structure is wrapped with the chitosan shell.
본 발명에 따른 안토시아닌은 특별히 제한되지 않고, 예를 들면 페오니딘(Peonidin), 시아니딘 3-아라비노시드(cyanidin 3-arabinoside), 시아니딘-3-(크실로실글루코오스)-5-갈락토오스(cyanidin-3-(xylosylglucose)-5-galactose), 시아니딘 3-글루코시드(cyanidin 3-glucoside), 시아니딘 3-갈락토시드(cyanidin 3-galactoside), 시아니딘-3-(쿠마로일-크실로실글루코오스)- 5-갈락토오스(cyanidin-3-(coumaroyl-xylosylglucose)-5-galactose), 델피니딘 3-글루코시드(delphinidin 3-glucoside), 델피니딘 3-루티노시드(delphinidin 3-rutinoside), 페오니딘 3-아라비노시드(peonidin 3-arabinoside), 페오니딘 3-갈락토시드(peonidin 3-galactoside), 페투니딘 3-글루코시드(petunidin 3-glucoside), 시아니딘(Cyanidin), 델피니딘(delphinidin), 말비딘(malvidin), 펠라르고니딘(pelargonidin), 페오니딘(peonidin), 시아니딘 3,5-디글루코시드(cyanidin 3,5-diglucoside), 시아니딘 3-루티노시드(cyanidin 3-rutinoside), 펠라르고니딘 3-글루코시드(pelargonidin 3-glucoside), 페오니딘 3-글루코시드(peonidin 3-glucoside), 말비딘 3-글루코시드(malvidin 3-glucoside) 및 말비딘 3,5-디글루코시드(malvidin 3,5-diglucoside)로 이루어진 군으로부터 선택되는 적어도 하나일 수 있으며, 보다 구체적으로 펠라르고니딘일 수 있다.The anthocyanin according to the present invention is not particularly limited and includes, for example, peonidin, cyanidin 3-arabinoside, cyanidin-3- (xylosyl glucose) -5-galactose cyanidin 3-galactoside, cyanidin-3- (xylosylglucose-5-galactose), cyanidin 3-glucoside, cyanidin 3-galactoside, -Coumaroyl-xylosylglucose-5-galactose, delphinidin 3-glucoside, delphinidin 3-rutinoside, Peonidin 3-arabinoside, peonidin 3-galactoside, petunidin 3-glucoside, cyanidin, and the like. Delphinidin, malvidin, pelargonidin, peonidin,
펠라르고니딘은 예를 들면 자소엽으로부터 분리된 것일 수 있으나, 이에 제한되는 것은 아니다.The pelargonidine may be, for example, isolated from the natural lobes, but is not limited thereto.
본 발명에 있어서 안토시아닌은 소수성 반응에 의해 구형의 코어의 형태로 존재한다.In the present invention, anthocyanin is present in the form of a spherical core by a hydrophobic reaction.
본 발명에 따른 키토산 쉘은 상기 안토시아닌 코어를 감싼다.The chitosan shell according to the present invention envelops the anthocyanin core.
키토산은 예를 들면 키토산 및 글라이콜 키토산 중 적어도 하나일 수 있으며, 구체적으로, 글라이콜 키토산일 수 있다.The chitosan may be at least one of, for example, chitosan and glycol chitosan, and specifically may be glycol chitosan.
키토산은 예를 들면 중량평균분자량이 1000 내지 1,000,000, 10,000 내지 500,000일 수 있으나, 이에 제한되는 것은 아니다.The chitosan may be, for example, a weight average molecular weight of 1,000 to 1,000,000 or 10,000 to 500,000, but is not limited thereto.
본 발명의 안토시아닌 나노 복합체의 입경은 특별히 한정되지 않으며, 예를 들면 10nm 내지 10㎛일 수 있으며, 보다 구체적으로 100nm 내지 500nm일 수 있다.The particle size of the anthocyanin nanocomposite of the present invention is not particularly limited, and may be, for example, 10 nm to 10 탆, and more specifically, 100 nm to 500 nm.
본 발명의 복합체는 외부환경 변화로부터 불안정한 안토시아닌을 안정화하고, 그 항산화 활성을 증대시키며, 체내 반감기를 증진시킬 수 있다. 또한, 색 보존성 및 항산화 활성을 장기간 유지할 수 있다.The complex of the present invention can stabilize unstable anthocyanins from an external environment change, increase its antioxidant activity, and enhance the half-life of the body. Further, the color preservability and antioxidative activity can be maintained for a long time.
본 발명의 안토시아닌 나노 복합체는 안토시아닌이 색가를 나타낼 수 있는 양이온을 구조적으로 안정화시켜 색소로서의 이용을 가능하게 하였다. 안토시아닌 색가의 불안정성은 flavyllium 양이온 구조에 기인한다(도 1). 안토시아닌은 pH3 구조에서 적색의 색가를 띠고 항산화 활성을 가진다. 하지만 pH가 변하면 도 1 에서 보듯이 안토시아닌 구조에서 양이온을 잃어 색가를 잃게 된다. 하지만, 본 발명의 안토시아닌 나노 복합체는 중성에서도 안토시아닌 본래의 색가를 유지함으로써 안정성이 증진된 천연색소로 이용 가능하다.The anthocyanin nanocomposite of the present invention structurally stabilizes cations capable of exhibiting a color value by anthocyanin, making it possible to use the anthocyanin as a coloring matter. The instability of the anthocyanin color value is due to the flavyllium cation structure (Fig. 1). Anthocyanin has an antioxidant activity with a color value of red at
또한, 본 발명은 상기 나노 복합체를 포함하는 조성물을 제공한다.The present invention also provides a composition comprising the nanocomposite.
안토시아닌은 색소인 바, 본 발명의 조성물은 색소 조성물로 사용될 수 있다. 또한, 안토시아닌이 우수한 항산화 활성을 가지는 바, 본 발명의 조성물은 의약 조성물, 화장료 조성물, 항산화용 건강기능식품 등으로 활용될 수 있다.Since anthocyanin is a pigment, the composition of the present invention can be used as a pigment composition. Furthermore, since anthocyanin has excellent antioxidative activity, the composition of the present invention can be utilized as a pharmaceutical composition, a cosmetic composition, a health functional food for antioxidation, and the like.
본 발명에서 의약 조성물은 약제학적으로 허용 가능한 비히클(vehicle), 희석제(diluent), 부형제(excipient), 또는 이들의 조합을 포함하여 제조할 수 있다. 상기 비히클은 세포 또는 조직내로의 화합물의 부가를 용이하게 하는 화합물로 정의된다. 상기 약제학적으로 허용되는 비히클로는 예를 들어, 이온 교환 수지, 알루미나, 알루미늄 스테아레이트, 레시틴, 혈청 단백질 (예, 사람 혈청 알부민), 완충 물질 (예, 여러 인산염, 글리신, 소르브산, 칼륨 소르베이트, 포화 식물성 지방산의 부 분적인 글리세라이드 혼합물), 물, 염 또는 전해질 (예, 프로타민설페이트, 인산수소이나트륨, 인산수소캄륨, 염화나트륨 및 아연 염), 교질성 실리카, 마그네슘 트리실리케이트, 폴리비닐피롤리돈, 셀룰로즈계 기질, 폴리 에틸렌 글리콜, 나트륨 카르복시메틸셀룰로즈, 폴리아릴레이트, 왁스, 폴리에틸렌 글리콜 및 양모지 등이 포함되지만, 이에 한정되지 않는다. 또한, 상기 비히클은 식염 수, 멸균수, 링거액, 완충 식염수, 덱스트로즈 용액, 말토 덱스트린 용액, 글리세롤, 에탄올 및 이들 성분 중 1 성분 이상을 혼합하여 사용할 수 있고, 필요에 따라 항산화제, 완충액, 정균제 등 다른 통상의 첨가제를 첨가할 수 있다. In the present invention, the pharmaceutical composition may be prepared by including a pharmaceutically acceptable vehicle, a diluent, an excipient, or a combination thereof. The vehicle is defined as a compound that facilitates the addition of a compound into a cell or tissue. Such pharmaceutically acceptable vehicles include, for example, ion exchange resins, alumina, aluminum stearate, lecithin, serum proteins such as human serum albumin, buffer substances such as various phosphates, glycine, sorbic acid, Salts, or electrolytes (e.g., protamine sulfate, disodium hydrogen phosphate, potassium hydrogen phosphate, sodium chloride and zinc salts), colloidal silica, magnesium trisilicate, polyvinylpyridine But are not limited to, ralidone, a cellulose based substrate, polyethylene glycol, sodium carboxymethylcellulose, polyarylate, wax, polyethylene glycol, and wool. The vehicle may be a mixture of saline, sterilized water, Ringer's solution, buffered saline, dextrose solution, maltodextrin solution, glycerol, ethanol and one or more of these components. If necessary, the vehicle may be mixed with an antioxidant, Other conventional additives such as a bacteriostatic agent may be added.
상기 희석제는 대상 화합물의 생물학적 활성 형태를 안정화시킬 뿐만 아니라, 화합물을 용해시키게 되는 물에서 희석되는 화합물로 정의된다. 버퍼 용액에 용해되어 있는 염은 당해 분야에서 희석제로 사용된다. 통상 사용 되는 버퍼 용액은 포스페이트 버퍼 식염수이며, 이는 인간 용액의 염 상태를 모방하고 있기 때문이다. 버퍼 염 은 낮은 농도에서 용액의 pH를 제어할 수 있기 때문에, 버퍼 희석제가 화합물의 생물학적 활성을 변형하는 일은 드물다.The diluent is defined as a compound that not only stabilizes the biologically active form of the compound of interest but also dilutes it in the water in which the compound is dissolved. Salts dissolved in buffer solutions are used as diluents in the art. A commonly used buffer solution is phosphate buffered saline, since it mimics the salt state of the human solution. Since buffer salts can control the pH of the solution at low concentrations, buffer diluents rarely modify the biological activity of the compounds.
상기 부형제는 예를 들어, 전분, 탄산칼슘, 수크로스, 락토오스 및 젤라틴 등의 고형 제제용 부형제, 습윤제, 감미제, 방향제 및 보존제 등을 포함하는 개념이다. 필요에 따라, 상기 의약 조성물은 약제학적으로 허용가능한 성분으로서, 습윤제 (wetting agent), 완충제, 현탁화제, 윤활제(lubricationg agent), 에멀젼화제, 붕해제, 흡수제, 보존제, 계면활성제, 착색제, 풍미제 (flavorant), 감미제 (sweetener), 및 추가적인 치료제 중에서 선택된 1종 이상의 첨가제를 더욱 포함할 수 있다.These excipients include, for example, excipients for solid preparations such as starch, calcium carbonate, sucrose, lactose and gelatin, wetting agents, sweetening agents, fragrances and preservatives. If desired, the pharmaceutical composition may contain, as a pharmaceutically acceptable ingredient, a wetting agent, a buffer, a suspending agent, a lubrication agent, an emulsifying agent, a disintegrating agent, an absorbent, a preservative, a surfactant, a flavorant, a sweetener, and an additional therapeutic agent.
또한, 본 발명의 의약 조성물은 경구, 경피, 정맥내, 국소(topically), 흡입, 또는 직장으로 피험자에게 전달되며, 전달은 지속 방출(sustained release)에 의한 것일 수도 있다. 상기 의약 조성물은 캡슐, 정제, 분말, 과립제, 시럽, 주사가능한 유체, 크림, 연고, 친수성 연고, 흡입성 유체(inhalable fluids), 및 좌약으로 이루어진 군으로부터 선택되는 방법에 의해 투여될 수 있다.In addition, the pharmaceutical composition of the present invention may be delivered to the subject by oral, transdermal, intravenous, topically, inhaled, or rectal, and the delivery may be by sustained release. The pharmaceutical composition may be administered by a method selected from the group consisting of capsules, tablets, powders, granules, syrups, injectable fluids, creams, ointments, hydrophilic ointments, inhalable fluids, and suppositories.
본 발명에 따른 의약 조성물은 당업자에게 알려진 모든 수단에 의해 투여될 수 있다. 예를 들어, 본 발명 의 화합물은 경구, 비경구, 흡입 스프레이, 국소, 직장 투여, 비강, 협측 (buccally), 질, 또는 매식 저장소 (implanted reservoir)를 통하여 투여될 수 있다. 여기에서 사용되는 "비경구적"이란 용어는 피하, 복막내, 수 막강내, 정구강, 정맥내, 근육내, 동맥내, 골수내, 경막내, 심장내, 경피, 피하, 복강내, 장관, 설하 및 주입 기술을 포함한다. 정확한 투여 프로토콜은 환자의 연령, 체중, 전반적인 건강상태 (general health), 성별, 및 식이 (diet)를 포함하는 다양한 인자에 의존하여 변경되며 특정한 투여 절차의 결정은 이 분야의 당업자에게 일상적일 것이다. 본 발명의 의약 조성물은 일회량, 다중 분할 투여량 (multiple discrete doses), 또는 연속 주입에 의해 투여될 수 있다. 펌프 수단, 특히, 피하 펌프 수단은 연속 주입에 유용하다. 본 발명에 따른 의약 조성물의 투약 단위는, 예를 들면 개별 투약양의 1, 2, 3 또는 4배를 함유하거나 또는 1/2, 1/3 또는 1/4배를 함유할 수 있다. 개별 투약양은 유효 약물이 1회에 투여되는 양을 함유하며, 이는 통상 1일 투약양의 전부, 1/2, 1/3 또는 1/4배에 해당한다. 안토시아닌 나노 복합체의 유효용량은 농도 의존적이 나 바람직하게는 0.1 mg 내지 1,000 mg/kg이고, 더욱 바람직하게는 0.1 내지 500 mg/kg이며, 하루 1 내지 6회 투 여할 수 있다. 따라서, 성인 체중 1 kg 당 0.1 내지 6,000 mg/일 범위로 투여될 수 있다. 임의의 투약양 수준은 사용되는 특정 화합물의 활성 및 가능한 독성; 환자의 연령, 체중, 전반적 건강 상태, 성 별, 및 식이(diet); 투여 시간; 배출 속도; 약물 조합; 질병의 심각성; 및 투여의 형태를 포함하는 다양한 인자에 의존하여 변경될 수 있다. 전형적으로, 시험관내의 용량-효과 결과는 환자 투약을 위한 적당한 투여량에 대한 유용한 가이드라인을 제공한다. 적당한 투여량 수준을 결정하기 위하여 고려할 사항들은 이 분야에 잘 알려져 있으며, 일반적인 의사가 갖는 기술에 속한다. 시간을 규칙적이 되게 하며 약물 전달의 연속을 위하여 공지된 모든 투약 요법은 본 발명의 방법에 있어서 효과 적인 치료에 필요한 것으로서 사용되고 재경험될 수 있다. 상기 요법은 전처리(pretreatment) 및/또는 추가적인 치료제(들)과의 복합투여를 포함할 수 있다. 본 발명의 의약 조성물의 투여량은 환자의 체중, 연령, 성별, 건강상태, 식이, 투여시간, 투여방법, 배설율 및 질환의 중증도 등에 따라 그 범위가 다양하며, 본 기술분야의 통상의 전문가가 용이하게 결정할 수 있다. The pharmaceutical composition according to the present invention can be administered by any means known to those skilled in the art. For example, the compounds of the present invention may be administered orally, parenterally, by inhalation spray, topically, rectally, nasally, buccally, vaginally or through an implanted reservoir. As used herein, the term "parenterally" refers to any agent that is administered orally, subcutaneously, intraperitoneally, intrathecally, intrathecally, intravenously, intramuscularly, intraarterially, intrathecally, intrathecally, intracardially, transdermally, subcutaneously, Sublingual and infusion techniques. The exact administration protocol will vary depending upon various factors including the age, weight, general health, sex, and diet of the patient, and the determination of a particular administration procedure will be routine to those skilled in the art. The pharmaceutical composition of the present invention may be administered by one dose, multiple discrete doses, or continuous infusion. Pump means, in particular subcutaneous pump means, are useful for continuous infusion. The dosage unit of the pharmaceutical composition according to the present invention may contain, for example, 1, 2, 3 or 4 times, or 1/2, 1/3 or 1/4 times the amount of the individual dose. The amount of individual dosages will include the amount of the active drug administered in a single dose, which usually corresponds to the full, half, one-third, or one-fourth of the daily dosage amount. The effective dose of the anthocyanin nanocomposite is dose dependent, preferably 0.1 mg to 1,000 mg / kg, more preferably 0.1 to 500 mg / kg, and can be injected 1 to 6 times a day. Thus, it can be administered in the range of 0.1 to 6,000 mg / day per kg adult body weight. The level of any dosage amount will depend upon the activity and possible toxicity of the particular compound employed; Age, weight, general health status, sex, and diet of the patient; Time of administration; Discharge rate; Drug combination; The severity of the disease; The route of administration, and the mode of administration. Typically, in vitro dose-effect results provide a useful guideline for appropriate dosages for patient dosing. The considerations for determining the appropriate dosage level are well known in the art and fall within the skills of a general practitioner. All dosing regimens known for time sequencing and for the continuation of drug delivery can be used and re-experienced as necessary for effective treatment in the methods of the present invention. Such therapy may include pretreatment and / or combined administration with additional therapeutic agent (s). The dosage of the pharmaceutical composition of the present invention varies depending on the patient's body weight, age, sex, health condition, diet, administration time, administration method, excretion rate and severity of disease, It can be easily determined.
본 발명에서 식품 조성물은, 바람직하게는 안토시아닌이 항산화 활성을 나타낼 수 있는 건강 및 기능성 식품 조성물이다. 본 명세서에서 "건강 및 기능성 식품"이란 일반 식품에 본 발명의 복합체를 첨가함으로써 일반 식품의 기능을 향상시킨 식품이며, 본 발명의 복합체를 일반식품에 첨가하거나, 캡슐화, 분말화, 현탁액 등으로 제조할 수 있다.The food composition in the present invention is preferably a health and functional food composition in which anthocyanins can exhibit antioxidative activity. The term "health and functional food" in the present specification means a food in which the function of the general food is improved by adding the complex of the present invention to the general food, and the complex of the present invention is added to the general food or prepared by encapsulation, can do.
본 발명의 안토시아닌 나노 복합체를 식품 첨가물로 사용할 경우에는, 상기 복합체 그대로 첨가하거나, 항산화 활성을 나타내는 다른 식품 또는 식품 성분과 함께 사용될 수 있다. 그 외의 통상적인 방법에 따라 적절하게 사용할 수 있다. 유효 성분의 혼합양은 그의 사용 목적(예방, 건강 또는 치료적 처치)에 따라 적합하게 결정될 수 있다. 일반적으로, 식품 또는 음료의 제조 시에는, 원료의 전체중량에 대하여 0.0001 내지 30중량%, 바람직 하게는 0.0001 내지 10 중량%, 더욱 바람직하게는 0.1 내지 5 중량%의 양으로 첨가될 수 있다. 그러나 건강 및 위생을 목적으로 하거나 또는 건강 조절을 목적으로 하는 장기간의 섭취의 경우에는 상기 양은 상기 범위 이하로 조절할 수 있다. 또한, 본 발명의 건강식품은 상기 약학적 조성물로 이용하는 경우는 측정된 독성 범위내의 안토시아닌 나노 복합체를 함유되도록 하는 것이 바람직하다. 상기 식품의 종류에는 특별한 제한이 없으며, 예를 들면 육류, 소세지, 빵, 쵸코렛, 캔디류, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 분유, 선식, 생식, 유산균 발효유, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차, 드링크제, 알콜 음료 및 비타민 복합제 등이 있다. 예를 들어, 본 발명 안토시아닌 나노 복합체는 우유나 요쿠르트와 같은 음료, 식품 등에 대하여 일정 농도로 첨가하여 사용할 수 있다. 본 발명의 식품 조성물은 상기의 유효 성분 외에 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로 함유할 수 있으며, 그 외에 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산 음료에 사용되는 탄산화제 등을 함유할 수도 있다. 이러한 첨가제 성분은 조성물 100 중량부 당 0.0001 내지 10 중량부로 첨가될 수 있다.When the anthocyanin nanocomposite of the present invention is used as a food additive, the complex may be added as it is, or may be used together with other food or food ingredients exhibiting antioxidative activity. And can be suitably used according to other conventional methods. The amount of the active ingredient to be mixed can be suitably determined according to its intended use (prevention, health or therapeutic treatment). In general, when the food or beverage is produced, it may be added in an amount of 0.0001 to 30% by weight, preferably 0.0001 to 10% by weight, more preferably 0.1 to 5% by weight based on the total weight of the raw material. However, in the case of long-term ingestion intended for health and hygiene purposes or for the purpose of controlling health, the amount can be adjusted to the above-mentioned range. In addition, when the health food of the present invention is used as the pharmaceutical composition, it is preferable to contain the anthocyanin nanocomposite within the measured toxicity range. There is no particular limitation on the type of the food. For example, dairy products including meat, sausage, bread, chocolate, candy, snack, confectionery, pizza, ramen, other noodles, gum, powdered milk, Products, soups, drinks, tea, drinks, alcoholic beverages, and vitamin complexes. For example, the anthocyanin nanocomposite of the present invention may be added to beverage, food such as milk or yogurt at a certain concentration. The food composition of the present invention may contain various flavoring agents or natural carbohydrates in addition to the above-mentioned active ingredients, and may further contain various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and salts thereof, alginic acid And salts thereof, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonating agents used in carbonated drinks, and the like. Such an additive component may be added in an amount of 0.0001 to 10 parts by weight per 100 parts by weight of the composition.
상기 화장료 조성물에서, 안토시아닌 나노 복합체는 그대로 첨가하거나 다른 화장품 성분과 함께 사용되고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효 성분의 혼합양은 그의 사용 목적에 따라 적합하게 결정 될 수 있다. 일반적으로, 안토시아닌 나노 복합체를 화장품 제조 시에 원료의 전체중량에 대하여 0.0001 내지 10 중량%, 바람직하게는 0.1 내지 5 중량%의 양으로 첨가될 수 있다. 화장품으로는 스킨, 로션, 크림, 팩 및 색조화장품 등에 적용할 수 있으며, 이에 한정되는 것은 아니다.In the above-mentioned cosmetic composition, the anthocyanin nanocomposite may be added as it is or may be used together with other cosmetic ingredients, and suitably used according to a conventional method. The amount of the active ingredient to be mixed can be suitably determined according to the purpose of use thereof. In general, the anthocyanin nanocomposite may be added in an amount of 0.0001 to 10% by weight, preferably 0.1 to 5% by weight, based on the total weight of the starting material in cosmetics production. The cosmetics can be applied to skins, lotions, creams, packs, and color cosmetics, but the present invention is not limited thereto.
본 발명은 또한 안토시아닌 나노 복합체의 제조방법을 제공한다.The present invention also provides a process for preparing anthocyanin nanocomposites.
본 발명의 안토시아닌 나노 복합체는 안토시아닌과 키토산을 용매에 넣고 교반하여 제조될 수 있다.The anthocyanin nanocomposite of the present invention can be prepared by stirring anthocyanin and chitosan in a solvent.
구체적으로, 안토시아닌을 먼저 용매에 녹이면, 안토시아닌이 고리 구조 사이의 인력으로 뭉쳐져 안토시아닌 코어를 형성하게 된다. 안토시아닌 코어를 포함한 용매에 키토산을 넣고 교반할 수 있다.Specifically, when anthocyanin is first dissolved in a solvent, anthocyanins are aggregated into an anthocyanin core by the attraction between the ring structures. Chitosan can be added to a solvent containing anthocyanin core and stirred.
키토산도 용매에 녹여서 제공될 수 있다.Chitosan may also be provided by dissolving in a solvent.
용매는 예를 들면 물일 수 있으나, 이에 제한되는 것은 아니다.The solvent may be, for example, water, but is not limited thereto.
안토시아닌과 키토산의 혼합비는 특별히 한정되지 않으며, 예를 들면 키토산과 안토시아닌의 부피비가 1: 1 내지 20, 구체적으로, 1: 2 내지 15, 보다 구체적으로 1: 4 내지 9일 수 있다. The mixing ratio of anthocyanin to chitosan is not particularly limited. For example, the volume ratio of chitosan and anthocyanin may be 1: 1 to 20, specifically 1: 2 to 15, more specifically 1: 4 to 9.
이후, 건조 공정을 거쳐 나노 복합체를 얻을 수 있다.Thereafter, the nanocomposite can be obtained through a drying process.
건조 방법은 특별히 한정되지 않으며, 예를 들면 분무 건조에 의할 수 있다.The drying method is not particularly limited, and can be carried out, for example, by spray drying.
분무 건조는 스케일업 (scale-up)이 쉬운 장점을 가지고 이지고 있고, 동일한 양의 액상 시료를 건조하는 과정에서 동결 건조와 같은 다른 건조 방법에 비해 액상 제품의 건조 분말화가 빠르다. 또한, 단일 단계에서 이루어지기 때문에 비용을 절감시킬 수 있다.Spray drying has the advantage of easy scale-up and drying of the liquid product is faster than other drying methods such as freeze drying in the process of drying the same amount of liquid sample. In addition, the cost can be reduced because it is performed in a single step.
본 발명에 따라 제조된 안토시아닌 나노 복합체는 산화 안정성 및 저장 안정성이 매우 뛰어나 장기간 퇴색되지 않는 천연 색소 조성물로서 활용될 수 있고, 또한 약품 또는 식품에서도 항산화 활성을 장시간 나타낼 수 있다. 상기 안토시아닌 나노 복합체는 안토시아닌의 환원에 의한 구조적 변이를 방지할 수 있어 안토시아닌 나노 복합체의 색가를 유지할 뿐만 아니라 안정성을 증진시킬 수 있다. 또한 안토시아닌 나노 복합체를 외부환경, 즉 산소, 빛, 자외선, 증발, 분자간의 상호작용 등으로부터 보호하여 손실을 줄이고, 반응성이 큰 물질로부터 안토시아닌 나노 복합체를 격리시킬 수도 있으며, 냄새나 맛 등을 은폐시킬 뿐만 아니라 고형화 시켜 취급을 간편하게 하는 등 그 응용성이 다양하다. 또한 안토시아닌의 색도를 오랫동안 높게 유지할 수 있고 안토시아닌의 보관 기간을 늘릴 수 있으며, 생체 내 활성을 크게 높일 수 있다.The anthocyanin nanocomposite prepared according to the present invention is excellent in oxidation stability and storage stability, and can be used as a natural colorant composition which does not fade for a long time, and also exhibits antioxidative activity for a long time in drugs or foods. The anthocyanin nanocomposite can prevent the structural change due to the reduction of anthocyanin, thereby maintaining the color value of the anthocyanin nanocomposite and improving the stability. In addition, the anthocyanin nanocomposite can be protected from external environment such as oxygen, light, ultraviolet rays, evaporation, intermolecular interaction, etc. to reduce loss, isolate the anthocyanin nanocomposite from a highly reactive substance, In addition, it has various applications such as solidification and easy handling. In addition, the color of anthocyanin can be maintained high for a long time, the storage period of anthocyanin can be increased, and the in vivo activity can be greatly increased.
실시예Example
1. 실험 방법1. Experimental Method
1) One) 자소엽Lobular leaf 추출물과 다당류인 Extracts and polysaccharides 글라이콜Glycoll 키토산과의 복합체 형성 Complex formation with chitosan
자소엽에서 추출한 안토시아닌 100mg 을 100ml D.W (deionized water) 에 녹이고, 글라이콜 키토산을 D.W에 녹였다. 이때 안토시아닌과 글라이콜 키토산의 복합체 형성 비율을 (안토시아닌 : 글라이콜 키토산 (v/v) = 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1) 로 하여 각각 11 mg, 13 mg, 14 mg, 17 mg, 20 mg, 25 mg, 33 mg, 500 mg 및 100 mg을 100ml D.W에 녹였다.100 mg of anthocyanin extracted from lobules was dissolved in 100 ml of deionized water (W), and glycol chitosan was dissolved in D.W. At this time, the complex formation ratio of anthocyanin and glycol chitosan (anthocyanin: glycol chitosan (v / v) = 9: 1, 8: 1, 7: 1, 6: 1, 5: 1, 4: , 11, 13, 14, 17, 20, 25, 33, 500 and 100 mg were dissolved in 100 ml of DW.
2) 두 용액을 고르게 2) Mix the two solutions evenly 교반하고Stirring 4 에서 24시간 동안 보관하여 안토시아닌- 4 to 24 hours to obtain anthocyanin- 글라이콜Glycoll 키토산 복합체를 제조 Manufacture of chitosan complex
복합체 크기 분포 확인은 Dynamic Light Scattering (DLS)로 하였고, 복합체 형태 확인은 Scanning Electron Microscope (SEM)로 하였다.Complex size distribution was confirmed by Dynamic Light Scattering (DLS), and complex type was confirmed by Scanning Electron Microscope (SEM).
3) 안토시아닌-3) Anthocyanin- 글라이콜Glycoll 키토산 복합체의 안정성 시험 Stability test of chitosan complex
글라이콜 키토산과 복합체를 형성하지 않은 안토시아닌과 다양한 비율별로 형성된 안토시아닌-글라이콜 키토산 복합체를 각각 5 mg/ml의 농도로 녹인 후 UV spectrophotometer를 이용하여 안토시아닌 색소가 활성을 나타내는 파장대인 400 내지 700 nm 에서의 흡광도 값을 비교하였다.Anthocyanins which did not complex with glycolated chitosan and anthocyanin-glycol chitosan complexes formed at various ratios were dissolved at a concentration of 5 mg / ml, respectively. Then, using an UV spectrophotometer, 400 to 700 nm were compared.
4) pH 에 따른 안정성 시험4) Stability test according to pH
pH 3, pH 4, pH 5, pH 6, pH 7 및 pH 8 조건에서 흡광도 값을 비교하였다.The absorbance values were compared at
5) 온도에 따른 안정성 시험5) Stability test according to temperature
20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃ 및 100 ℃의 조건에서 흡광도 값을 비교하고, 100 에서 10 분, 30 분, 1 시간 및 2 시간 별로 흡광도 값을 비교하였다.The absorbance values at 20 ° C., 30 ° C., 40 ° C., 50 ° C., 60 ° C., 70 ° C., 80 ° C., 90 ° C. and 100 ° C. were compared and the absorbance values at 100 min, 10 min, 30 min, The values were compared.
6) 광에서의 안정성 시험6) Stability test in light
시료를 해가 잘 드는 곳에 두어, 0일, 1일, 3일, 5일까지의 광 안정성을 시험하였다.The specimens were placed in well-exposed areas and tested for light stability up to 0, 1, 3 and 5 days.
2. 결과2. Results
1) 안토시아닌-1) Anthocyanin- 글라이콜Glycoll 키토산 복합체 형성 후 After chitosan complex formation 색가Color value 확인 Confirm
안토시아닌(10:0)과 안토시아닌-글라이콜 키토산 복합체(Chitosan complex)를 같은 농도(5mg/ml)로 D.W에 녹여 색가를 비교해 보았을 때, 안토시아닌이 붉은색의 색가를 유지하는 것을 눈으로 확인하였다.When anthocyanin (10: 0) and anthocyanin-glychol chitosan complex (Chitosan complex) were dissolved in DW at the same concentration (5 mg / ml), the anthocyanin was visually confirmed to maintain a red color value .
안토시아닌이 색가를 나타내는 파장대인 533nm에서 안토시아닌-글라이콜 키토산 복합체가 안토시아닌 자체와 같이 (10:0) 흡광도 값을 가지는 것을 확인하였으며, 흡광도 수치 또한 안토시아닌과 같이 복합체에서도 유지되는 것을 확인하였다.The anthocyanin-glycol chitosan complex was found to have an absorbance value (10: 0) similar to that of anthocyanin itself at 533 nm, the wavelength range at which the anthocyanin exhibits the color value, and the absorbance value was also maintained in the complex such as anthocyanin.
2) 안토시아닌-2) Anthocyanin- 글라이콜Glycoll 키토산 복합체 형성 확인 Confirmation of chitosan complex formation
혼합된 가루를 생리식염수에 녹여 생체 내의 조건에서 형성된 복합체의 크기를 확인하였다. 가루를 5 mg/mL 농도로 녹였을 때 217.2 nm (± 4.4 nm) 크기의 입자가 형성된 것을 확인하였고, 형성된 복합체의 형태는 구형이었다(도 5 및 6).The mixed powders were dissolved in physiological saline to confirm the size of the complex formed in vivo conditions. When the powder was dissolved at a concentration of 5 mg / mL, it was confirmed that particles of 217.2 nm (± 4.4 nm) were formed, and the shape of the formed complex was spherical (FIGS. 5 and 6).
3) pH 안정성 시험3) pH stability test
도 7 및 8에 나타난 바와 같이, 안토시아닌은 pH 에 따라 구조와 최대 흡광도 값이 변하는데 붉은 색을 나타내는 구조에서는 최대 흡광도 값이 533nm (Λmax1)이었고, pH 7 내지 8에서 나타나는 구조에서의 최대 흡광도 값은 598nm (Λmax2)이었다.As shown in FIGS. 7 and 8, the maximum absorption value of the anthocyanin was 533 nm (Λmax1) in the structure in which the structure and the maximum absorbance value changed depending on the pH and the structure showing red color, and the maximum absorbance value Was 598 nm (? Max 2).
도 9 내지 15에 나타난 것과 같이, 안토시아닌만 있는 경우, 흡광도 값이 pH 5까지 급격히 떨어지다가 pH 6부터는 최대 흡광도 값이 이동하는 것을 볼 수 있었다(도 9). 안토시아닌-글라이콜 키토산 복합체의 경우, pH에 따른 최대 흡광도 값의 기울기가 안토시아닌 : 글라이콜 키토산 = 4:1의 비율에서 가장 완만한 것으로 보아 pH 에서의 안정성을 확보하였고, 기존 안토시아닌은 최대 흡광도 값이 이동한 것에 비해 안토시아닌-글라이콜 키토산 복합체는 최대 흡광도 값이 이동하지 않은 것을 확인하였다(도 10).As shown in Figs. 9 to 15, when anthocyanin alone was present, the absorbance value rapidly dropped to
4) 온도 안정성 시험4) Temperature stability test
도 16 내지 17에 나타난 바와 같이, 글라이콜 키토산과 복합체를 형성하지 않은 안토시아닌을 20 ℃부터 100 ℃까지 30분이 지난 후에 각 온도별로 흡광도 값을 비교하였다(도 16). 또한, 100 ℃의 온도에서 10분, 30분, 60분 및 120분의 시간별로 글라이콜 키토산과 복합체를 형성하지 않은 안토시아닌의 안정성 여부를 확인하였다(도 17).As shown in Figs. 16 to 17, the absorbance values of the anthocyanins not complexed with glycol chitosan were measured at 20 [deg.] C to 100 [deg.] C for 30 minutes (Fig. 16). In addition, it was confirmed whether the anthocyanin which did not complex with glycol chitosan was stable at a temperature of 100 ° C for 10 minutes, 30 minutes, 60 minutes and 120 minutes (FIG. 17).
도 18 내지 23에 나타난 바와 같이, 안토시아닌-글라이콜 키토산 복합체 또한 다양한 온도에서 안정성을 나타내었다.As shown in Figures 18-23, anthocyanin-glycol chitosan complexes also exhibited stability at various temperatures.
도 24에 안토시아닌-글라이콜 키토산 복합체의 온도별 안정성을 Λmax1 (533nm)/Λmax2 (598nm) 비율로 나타낸 결과, 안토시아닌과 안토시아닌-글라이콜 키토산 복합체(4:1) 각각에서 온도 안정성을 나타내는 것을 확인하였다.24 shows the temperature stability of the anthocyanin-glycol chitosan complex (4: 1) in anthocyanin and anthocyanin-glycol chitosan complexes (4: 1) as a result of the temperature stability of the anthocyanin-glycol chitosan complex in terms of the ratio of Λ max (533 nm) / Λ max2 Respectively.
5) 광 안정성 시험5) Light stability test
도 25에 나타난 바와 같이, 안토시아닌만 있을 때 안토시아닌이 활성을 나타내는 파장대인 533nm에서 시간이 지날수록 흡광도 값이 낮아지는 것에 비해, 안토시아닌-글라이콜 키토산 복합체에서는 흡광도 값이 낮아지는 폭이 줄어드는 것을 확인하였다.As shown in Fig. 25, it was confirmed that the absorbance value decreases with time at 533 nm, which is the wavelength range in which anthocyanin is active when anthocyanin is present, whereas it decreases with the decrease in the absorbance value in the anthocyanin-glycol chitosan complex Respectively.
고찰Review
실험 결과 양이온성 다당류인 글라이콜 키토산과 복합체를 형성하였을 때 안토시아닌의 색가 유지가 잘되는 것을 확인하였다. 또한, 다양한 조건에서의 안정성 시험에서 안토시아닌 색소의 취약점인 pH에서의 안정성을 확보하였다. 실험 결과 안토시아닌만 있을 때는 pH가 올라감에 따라 안토시아닌의 활성을 나타내는 파장대인 533nm에서 흡광도 값이 낮아지다가 pH 6의 조건에서 구조적 변화를 일으켜 흡광도 값이 이동하는 것을 확인하였다. 그에 비해 안토시아닌-글라이콜 키토산 복합체는 다양한 pH에서도 533nm에서 최대 흡광도 값을 유지하였고 흡광도 값이 이동하지 않는 것으로 보아 안토시아닌 색소와 글라이콜 키토산 복합체를 형성함으로써 기존의 안토시아닌이 활성을 가지는 구조를 안정화 시킨다는 것을 확인하였다.As a result of the experiment, it was confirmed that the anthocyanin color was maintained well when the complex was formed with the cationic polysaccharide glycollicholite. In addition, the stability of the anthocyanin pigment in the stability test at various conditions was secured. As a result of the experiment, it was confirmed that when the anthocyanin was only present, the absorbance value was lowered at 533 nm, which indicates the activity of anthocyanin, and the absorbance value was shifted due to the structural change at
온도 안정성 시험에서는 안토시아닌 자체의 온도 안정성을 확인함으로써 안토시아닌 추출과정에서 안토시아닌의 활성이 유지 된다는 것을 확인하였다.In the temperature stability test, the anthocyanin activity was maintained in the anthocyanin extraction process by confirming the temperature stability of the anthocyanin itself.
광 안정성 시험에서는 안토시아닌과 안토시아닌-글라이콜 키토산 복합체를 각각 자연광에 날짜별로 노출시켰을 때, 안토시아닌만 있을 때는 최대 흡광도 값이 줄어드는 것을 확인하였지만 안토시아닌-글라이콜 키토산 복합체는 최대 흡광도 값이 크게 줄어들지 않는 것으로 보아 광 조건 하에서도 안정성을 가지는 것을 확인하였다.In the light stability test, when the anthocyanin and anthocyanin-glycol chitosan complexes were exposed to natural light on a date basis, the maximum absorbance value was found to decrease when only anthocyanin was present. However, the anthocyanin-glycol chitosan complex did not significantly decrease the maximum absorbance value And it was found that it was stable even under light condition.
실험 결과 안토시아닌과 글라이콜 키토산 복합체를 다양한 비율로 형성하였을 때 안토시아닌 : 글라이콜 키토산 복합체 = 4:1 의 비율에서 pH 및 광조건 하에서 가장 안정성이 높은 것을 확인하였다.Experimental results showed that when anthocyanin and glycol chitosan complexes were formed at various ratios, the stability was the highest at an anthocyanin: glycol chitosan complex = 4: 1 ratio under pH and light conditions.
결론conclusion
본 발명에 따라 안토시아닌과 양이온성 다당류인 글라이콜 키토산과 복합체를 형성함으로써 안토시아닌의 구조적 안정성을 향상시킬 수 있으며, 다양한 환경조건(pH, 온도, 광)에서 안정화 시킬 수 있다.According to the present invention, by forming a complex with anthocyanin and glycolated chitosan, which is a cationic polysaccharide, the structural stability of anthocyanin can be improved and stabilized under various environmental conditions (pH, temperature, light).
Claims (6)
An anthocyanin nanocomposite comprising an anthocyanin core and a chitosan shell surrounding the core.
The method of claim 1, wherein the anthocyanin is selected from the group consisting of peonidin, cyanidin 3-arabinoside, cyanidin-3- (cyanosylglucose) -5-galactose xylosylglucose-5-galactose, cyanidin 3-glucoside, cyanidin 3-galactoside, cyanidin-3- (coumaroyl-xylosylglucose) But are not limited to, cyanidin-3-coumaroyl-xylosylglucose-5-galactose, delphinidin 3-glucoside, delphinidin 3-rutinoside, Peonidin 3-arabinoside, peonidin 3-galactoside, petunidin 3-glucoside, cyanidin, delphinidin, But are not limited to, malvidin, pelargonidin, peonidin, cyanidin 3,5-diglucoside, cyanidin 3- ru tinoside, pelargonidin 3-glucoside, peonidin 3-glucoside, malvidin 3-glucoside and malvidin 3,5 Wherein the anthocyanin nanocomposite is at least one selected from the group consisting of malvidin 3,5-diglucoside.
The anthocyanin nanocomposite according to claim 1, wherein the anthocyanin is pelargonidine.
The anthocyanin nanocomposite according to claim 1, wherein the chitosan is at least one of chitosan and glycol chitosan.
The anthocyanin nanocomposite according to claim 1, wherein the composite has a particle diameter of 10 nm to 10 μm.
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KR20200066443A (en) * | 2018-11-30 | 2020-06-10 | 한국기초과학지원연구원 | A pharmaceutical composition for preventing or treating aging or an aging-related disease comprising an anthocyanin-polysaccharide complex as an active ingredient |
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