KR20170003385A - Cosmetic composition containing galloyl-peptide stabilized in nanoliposome - Google Patents
Cosmetic composition containing galloyl-peptide stabilized in nanoliposome Download PDFInfo
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- KR20170003385A KR20170003385A KR1020160066622A KR20160066622A KR20170003385A KR 20170003385 A KR20170003385 A KR 20170003385A KR 1020160066622 A KR1020160066622 A KR 1020160066622A KR 20160066622 A KR20160066622 A KR 20160066622A KR 20170003385 A KR20170003385 A KR 20170003385A
- Authority
- KR
- South Korea
- Prior art keywords
- skin
- nanoliposome
- peptide
- galloyl
- cosmetic composition
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/14—Liposomes; Vesicles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/553—Phospholipids, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Abstract
Description
본 발명은 나노리포좀으로 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료 조성물에 관한 것으로, 더욱 상세하게는 항노화 및 항산화 활성이 우수한 갈로일 펩타이드를 나노리포좀으로 안정화하여 피부 침투효과가 현저히 향상된 화장료 조성물에 관한 것이다. The present invention relates to a cosmetic composition comprising a galloyl peptide stabilized with nanoliposomes as an active ingredient, and more particularly, a cosmetic composition with remarkably improved skin penetration effect by stabilizing galloyl peptide having excellent anti-aging and antioxidant activity with nanoliposomes. It relates to the composition.
산업이 발달함에 따라 환경 오염이 심각해지고, 피부의 노화 방지, 미백 등에 관한 관심이 고조되고 있다. 특히, 사람의 피부는 끊임없이 변화를 겪게 되는데, 가장 대표적인 변화가 노화에 의한 피부 기능 저하 및 시각적 아름다움의 감소이다. 피부 노화의 결과 나타나는 최종적인 피부 외관에서의 현상은 주름의 형성, 피부 탄력 저하, 노인성 반점 형성 등이 있으며, 주름의 형성이 가장 대표적인 현상으로 받아들여지고 있다.As the industry develops, environmental pollution is becoming more serious, and interest in anti-aging and whitening of the skin is increasing. In particular, human skin is constantly undergoing changes, and the most representative changes are reduction of skin function and visual beauty due to aging. The final appearance of the skin as a result of skin aging includes the formation of wrinkles, decreases in skin elasticity, and the formation of senile spots, and the formation of wrinkles is considered the most representative phenomenon.
일반적으로 피부 노화를 설명하는 이론은 여러 가지가 있으나, 그 중에서도 체내외의 여러 가지 원인에 의해서 발생되는 자유라디칼에 의해서 피부가 노화된다는 자유라디칼 이론이 가장 타당성이 있는 이론으로 받아들여지고 있다. 자유라디칼은 화학적으로 반응성이 매우 큰 화학물질로서, 인체 내에서는 여러 가지 원인 즉, 자외선, 방사선, 배기가스, 담배연기, 스트레스 등의 외부적 요인과 체내의 미토콘드리아 및 백혈구의 대사과정에 의해서 생성되어, 다단계의 연쇄반응을 통하여 세포막의 구성성분인 지질의 과산화를 일으키게 된다.In general, there are various theories explaining skin aging, but among them, the free radical theory that the skin is aged by free radicals caused by various causes inside and outside the body is accepted as the most valid theory. Free radicals are chemically highly reactive chemical substances, and are produced by external factors such as ultraviolet rays, radiation, exhaust gas, cigarette smoke, stress, and the metabolism of mitochondria and white blood cells in the body. In addition, the peroxidation of lipids, which is a component of the cell membrane, is caused through a multi-step chain reaction.
피부 노화와 관련있는 자유라디칼의 대부부은 활성 산소종(Reactive Oxygen Species, ROS)으로, 그 종류로는 수퍼옥사이드 라디칼(Super oxide radical), 과산화수소(H2O2), 하이드록시 라디칼(Hydroxy radical), 단일상태의 산소(Singlet oxygen) 등이 있다. 이들에 의해 일어나는 지질의 과산화는 라디칼, 과산화물, 알데히드(aldehyde) 및 에폭사이드(epoxide)의 다양한 활성 산소종을 발생시키고, DNA, RNA, 단백질, 세포막 및 세포 구조에 손상을 입힌다.Most of the free radicals related to skin aging are Reactive Oxygen Species (ROS), and the types include super oxide radical, hydrogen peroxide (H2O2), hydroxy radical, and single state. And singlet oxygen. Peroxidation of lipids caused by them generates various reactive oxygen species such as radicals, peroxides, aldehydes and epoxides, and damages DNA, RNA, proteins, cell membranes and cellular structures.
상기 활성 산소종들은 암, 조직 손상, 노화 등의 주원인으로 보고되고 있다(Black HS, Photochemphotobiol. 46(2):213(1987)). 예를 들어, 세포를 구성하는 막지질의 과산화는 세포막의 구조와 유동성 변화, 세포질 물질의 투과성 증가, 라이소좀 효소의 누출, 막효소와 운반 단백질의 불활성화, 지질과 단백질의 공유 가교결합 생성, 단백질 사슬 절단, DNA 손상, 돌연변이 등을 유발시키며, 이들 반응 중 피부 구성 세포막의 과산화와 진피 구성 단백질들의 변형이 피부 노화와 가장 밀접한 연관이 있는 것으로 알려져 있다.The reactive oxygen species have been reported as the main causes of cancer, tissue damage, aging, etc. (Black HS, Photochemphotobiol. 46(2):213(1987)). For example, peroxidation of membrane lipids constituting cells can result in changes in the structure and fluidity of cell membranes, increased permeability of cytoplasmic substances, leakage of lysosome enzymes, inactivation of membrane enzymes and carrier proteins, covalent crosslinking of lipids and proteins, protein. It causes chain breakage, DNA damage, mutation, etc. Among these reactions, peroxidation of skin-forming cell membranes and modification of dermal components are known to be most closely related to skin aging.
호기성 생물체들은 이러한 산화제의 생성과 지질 과산화를 막기 위한 보호 기구를 보유하고 있다. 상기 보호 기구에는 수퍼옥사이드 디스뮤타아제(super oxide dismutase, SOD), 카탈라아제(catalase) 등의 효소와 토코페롤(tocopherol, vitamin E), beta-카로틴(carotene), 아스코르빈산(ascorbic acid, vitamin C) 및 글루타치온(glutathione)과 같은 지용성 및 수용성 항산화제 또는 라디칼 소거제들이 포함된다.Aerobic organisms have protective mechanisms to prevent the formation of these oxidants and lipid peroxidation. The protective mechanism includes enzymes such as super oxide dismutase (SOD) and catalase, and tocopherol (vitamin E), beta-carotene, and ascorbic acid (vitamin C). And fat-soluble and water-soluble antioxidants or radical scavengers such as glutathione.
한편, 지금까지 알려진 피부 항노화 물질은 다음과 같은 효과를 기대하여 개발되었다. 첫째, 피부에 수분 공급, 둘째, 항산화 효능, 셋째, 피부세포의 활성화에 관여하는 섬유아세포의 증식 촉진, 넷째, 피부를 구성하는 콜라겐과 엘라스틴을 분해하여 주름의 생성 및 탄력 손실을 가속화하는 효소인 콜라게나아제와 엘라스타아제의 화성 억제, 다섯째, 콜라겐 및 엘라스틴 합성의 촉진 등이다.Meanwhile, skin anti-aging substances known so far were developed in anticipation of the following effects. First, moisture supply to the skin, second, antioxidant effect, third, promoting the proliferation of fibroblasts involved in the activation of skin cells, and fourth, an enzyme that accelerates the formation of wrinkles and loss of elasticity by decomposing collagen and elastin that make up the skin. Inhibition of synthesis of collagenase and elastase, and fifth, promotion of collagen and elastin synthesis.
즉, 자유라디칼형 산소 또는 활성 산소종은 피부 노화와 관련성이 크기 때문에 종래에는 화장료에 수퍼옥사이드 디스뮤타아제, 비타민 E 유도체, 비타민 C 및 그 유도체, 플라보노이드(flavonoid) 등을 화장료에 배합함으로써 피부 노화 방지 효과를 달성하려는 노력이 많이 있었으나, 화장료에 상기 성분들을 배합하는 경우 안전성(safety), 안정성(stability) 등이 미흡하여 실질적인 효과를 기대하기 어려웠다.In other words, since free radical oxygen or reactive oxygen species are highly related to skin aging, conventionally, skin aging by combining cosmetics with superoxide dismutase, vitamin E derivatives, vitamin C and its derivatives, and flavonoids in cosmetics. There have been many efforts to achieve the preventive effect, but when the above ingredients are blended in a cosmetic, safety, stability, etc. are insufficient, making it difficult to expect a practical effect.
한편, 피부에 유용한 비타민, 단백질 등 다양한 생리활성물질들은 원료 자체의 안정성이 일정 기간 유지될 수 있지만, 다른 성분들이 다량 함유되어 있는 제형에 첨가되면 시간의 경과 및 보관온도에 따라 색상, 점도, pH 등 물성의 경시변화가 심하게 나타나는 등의 문제점이 있으며, 특히 화장료가 에센스나 저점도의 스킨로션 등 수성베이스인 경우에는 비타민 E 등의 유용성 생리활성물질 등을 첨가하는데 있어 한계가 있었다. On the other hand, various physiologically active substances such as vitamins and proteins useful for skin can maintain the stability of the raw material for a certain period of time, but when added to a formulation containing a large amount of other ingredients, the color, viscosity, and pH are determined depending on the lapse of time and storage temperature. There is a problem such as severe change of physical properties over time, and in particular, when the cosmetic is an aqueous base such as an essence or a low-viscosity skin lotion, there is a limit to the addition of useful physiologically active substances such as vitamin E.
또한, 종래의 방법으로 제조된 화장료는 에멀젼 입자의 크기가 피부 지질의 간극보다 훨씬 더 크기 때문에 유용한 생리활성물질들이 피부로의 침투가 용이하지 못한 단점이 있었다. In addition, the cosmetic prepared by the conventional method has a disadvantage that useful physiologically active substances cannot easily penetrate into the skin because the size of the emulsion particles is much larger than that of the skin lipids.
종래의 화학적으로 합성된 유화제들을 이용하여 에멀젼을 제조할 때 피부 친화성이 미흡하여 민감한 피부에 자극을 유발할 수 있는 문제점이 있다.When preparing an emulsion using conventional chemically synthesized emulsifiers, there is a problem in that skin affinity is insufficient, which may cause irritation to sensitive skin.
상기 문제점을 해결하기 위해 제약뿐만 아니라, 화장품 및 식품 산업에 있어서 생리활성 성분이 파괴되지 않고 안정하게 전달될 수 있으며, 지용성 또는 수용성 물질을 모두 내포시킬 수 있는 나노리포좀 기술이 적극적으로 개발되고 있으며, 최근에는 나노 기술의 발달과 함께 피부 침투 효과를 극대화할 수 있는 나노리포좀에 대한 연구 개발도 활발히 진행되고 있다.In order to solve the above problems, nanoliposomal technology capable of stably delivery without destroying physiologically active ingredients in not only pharmaceuticals, but also cosmetics and food industries, and containing both fat-soluble or water-soluble substances, is being actively developed. Recently, with the development of nanotechnology, research and development on nanoliposomes that can maximize the skin penetration effect are also actively progressing.
본 발명은 전술한 문제점을 해결하기 위해 안출된 것으로, 갈로일 펩타이드를 나노리포좀으로 안정화하여 항노화 및 항산화 효과가 더욱 개선된 화장료 조성물을 제공하는 것을 목적으로 한다. The present invention was conceived to solve the above-described problems, and an object of the present invention is to provide a cosmetic composition with improved anti-aging and antioxidant effects by stabilizing galloyl peptides with nanoliposomes.
본 발명의 일 측면에 따르면, 나노리포좀으로 안정화된 하기 화학식 1의 갈로일 펩타이드 및 비타민 C 유도체를 유효성분으로 포함하는 피부 주름 개선 또는 피부 탄력 개선용 화장료 조성물이 제공된다.According to an aspect of the present invention, there is provided a cosmetic composition for improving skin wrinkles or skin elasticity, comprising as an active ingredient a galloyl peptide of Formula 1 and a vitamin C derivative stabilized with nanoliposomes.
[화학식 1][Formula 1]
상기 식에서 n은 1 내지 3 중 하나의 정수이고, L은 서열번호 1의 올리고 펩타이드이다. In the above formula, n is an integer from 1 to 3, and L is an oligopeptide of SEQ ID NO: 1.
본 발명의 다른 측면에 따르면, 나노리포좀으로 안정화된 하기 화학식 1의 갈로일 펩타이드 및 비타민 C 유도체를 유효성분으로 포함하는 피부 보습용 화장료 조성물이 제공된다.According to another aspect of the present invention, there is provided a cosmetic composition for moisturizing skin comprising a galloyl peptide of Formula 1 and a vitamin C derivative stabilized with nanoliposome as an active ingredient.
[화학식 1][Formula 1]
상기 식에서 n은 1 내지 3 중 하나의 정수이고, L은 서열번호 1의 올리고 펩타이드이다. In the above formula, n is an integer from 1 to 3, and L is an oligopeptide of SEQ ID NO: 1.
일 실시예에 따르면, 상기 나노리포좀은 포스파티딜콜린의 함량이 70 중량% 이상인 대두 유래의 레시틴에 의해 안정화될 수 있다. According to an embodiment, the nanoliposome may be stabilized by soybean-derived lecithin in which the content of phosphatidylcholine is 70% by weight or more.
일 실시예에 따르면, 상기 나노리포좀은 상기 나노리포좀 총 중량에 대하여 0.01 내지 20.0 중량%의 비타민 C 유도체를 포함할 수 있다. According to an embodiment, the nanoliposome may contain a vitamin C derivative of 0.01 to 20.0% by weight based on the total weight of the nanoliposome.
일 실시예에 따르면, 상기 나노리포좀은 조성물 총 중량에 대하여 0.1 내지 20.0 중량% 포함될 수 있다. According to an embodiment, the nanoliposome may be included in an amount of 0.1 to 20.0% by weight based on the total weight of the composition.
일 실시예에 따르면, 상기 화장료 조성물은 유연화장수, 영양화장수, 영양크림, 마사지크림, 에센스, 아이크림, 클렌징크림, 클렌징폼, 클렌징워터, 팩, 스프레이 및 파우더로 이루어진 군에서 선택된 하나 이상으로 제형화될 수 있다.According to an embodiment, the cosmetic composition is formulated with one or more selected from the group consisting of softening lotion, nutritional lotion, nutritional cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray, and powder. It can be angry.
본 발명에 따르면, 상기 화장료 조성물은 나노리포좀에 의해 안정화된 갈로일 펩타이드를 포함하여 항염, 항산화, 콜라겐 합성능이 우수하며, 나노리포좀에 포접된 갈로일 펩타이드는 피부 침투 효과가 현저히 증가될 수 있다. According to the present invention, the cosmetic composition has excellent anti-inflammatory, antioxidant, and collagen synthesis ability, including galloyl peptide stabilized by nanoliposome, and the galloyl peptide encapsulated in nanoliposome can significantly increase the skin penetration effect.
본 발명의 효과는 상기한 효과로 한정되는 것은 아니며, 본 발명의 상세한 설명 또는 특허청구범위에 기재된 발명의 구성으로부터 추론 가능한 모든 효과를 포함하는 것으로 이해되어야 한다.The effects of the present invention are not limited to the above effects, and should be understood to include all effects that can be inferred from the configuration of the invention described in the detailed description or claims of the present invention.
본 명세서에서 사용되는 용어는 본 발명에서의 기능을 고려하면서 가능한 현재 널리 사용되는 일반적인 용어들을 선택하였으나, 이는 당 분야에 종사하는 기술자의 의도 또는 판례, 새로운 기술의 출현 등에 따라 달라질 수 있다. 또한, 특정한 경우는 출원인이 임의로 선정한 용어도 있으며, 이 경우 해당되는 발명의 설명 부분에서 상세히 그 의미를 기재할 것이다. 따라서 본 발명에서 사용되는 용어는 단순한 용어의 명칭이 아닌, 그 용어가 가지는 의미와 본 발명의 전반에 걸친 내용을 토대로 정의되어야 한다.Terms used in the present specification have selected general terms that are currently widely used as possible while taking functions of the present invention into consideration, but this may vary according to the intention or precedent of a technician working in the field, the emergence of new technologies, and the like. In addition, in certain cases, there are terms arbitrarily selected by the applicant, and in this case, the meaning of the terms will be described in detail in the description of the corresponding invention. Therefore, the terms used in the present invention should be defined based on the meaning of the term and the overall contents of the present invention, not a simple name of the term.
다르게 정의되지 않는 한, 기술적이거나 과학적인 용어를 포함해서 여기서 사용되는 모든 용어들은 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에 의해 일반적으로 이해되는 것과 동일한 의미를 가지고 있다. 일반적으로 사용되는 사전에 정의되어 있는 것과 같은 용어들은 관련 기술의 문맥상 가지는 의미와 일치하는 의미를 가지는 것으로 해석되어야 하며, 본 출원에서 명백하게 정의하지 않는 한, 이상적이거나 과도하게 형식적인 의미로 해석되지 않는다. Unless otherwise defined, all terms used herein including technical or scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Terms such as those defined in a commonly used dictionary should be interpreted as having a meaning consistent with the meaning in the context of the related technology, and should not be interpreted as an ideal or excessively formal meaning unless explicitly defined in the present application. Does not.
수치 범위는 상기 범위에 정의된 수치를 포함한다. 본 명세서에 걸쳐 주어진 모든 최대의 수치 제한은 낮은 수치 제한이 명확히 쓰여져 있는 것처럼 모든 더 낮은 수치 제한을 포함한다. 본 명세서에 걸쳐 주어진 모든 최소의 수치 제한은 더 높은 수치 제한이 명확히 쓰여져 있는 것처럼 모든 더 높은 수치 제한을 포함한다. 본 명세서에 걸쳐 주어진 모든 수치 제한은 더 좁은 수치 제한이 명확히 쓰여져 있는 것처럼, 더 넓은 수치 범위 내의 더 좋은 모든 수치 범위를 포함할 것이다.The numerical range includes the numerical values defined in the above range. All maximum numerical limits given throughout this specification include all lower numerical limits as if the lower numerical limits were expressly written. All minimum numerical limits given throughout this specification include all higher numerical limits as if the higher numerical limits were expressly written. All numerical limits given throughout this specification will include all better numerical ranges within the wider numerical range, as if the narrower numerical limits were expressly written.
이하, 본 발명의 실시예를 상세히 기술하나, 하기 실시예에 의해 본 발명이 한정되지 아니함은 자명하다.Hereinafter, examples of the present invention will be described in detail, but it is obvious that the present invention is not limited by the following examples.
본 발명의 일 측면에 따르면, 나노리포좀으로 안정화된 하기 화학식 1의 갈로일 펩타이드(Galloyl peptide)를 유효성분으로 포함하는 화장료 조성물이 제공된다. According to an aspect of the present invention, there is provided a cosmetic composition comprising, as an active ingredient, a galloyl peptide of the following formula 1 stabilized with nanoliposomes.
[화학식 1][Formula 1]
상기 식에서 n은 1 내지 3 중 하나의 정수이고, L은 TYR-GLY-GLY-PHE-LEU-ARG-LYS-TYR-PRO로 구성된 올리고 펩타이드이다. In the above formula, n is an integer of 1 to 3, and L is an oligopeptide composed of TYR-GLY-GLY-PHE-LEU-ARG-LYS-TYR-PRO.
상기 펩타이드를 명명하는 일반적인 규칙은 구체적으로 지시된 예외사항이 없는 경우 3문자 또는1문자 아미노산 코드를 기초로 할 수 있다. 예컨대, 아미노산 구조의 중심부를 3문자 코드(예를 들어, Ala, Lys)로 표시하며, 3문자 코드의 앞에 "D-"를 적음으로써 D-입체형태(예를 들어, D-Ala, D-Lys)를 구체적으로 지시하지 않은 경우라면L-입체형태로 가정한다. 상기 펩타이드를 구성하는 아미노산 잔기는 천연 또는 비-천연아미노산 잔기가 모두 가능하다.The general rules for naming the peptides may be based on a three-letter or one-letter amino acid code in the absence of specifically indicated exceptions. For example, the central part of the amino acid structure is represented by a 3-letter code (eg, Ala, Lys), and by writing “D-” in front of the 3-letter code, the D-stereoscopic form (eg, D-Ala, D- Lys) is assumed to be in L-stereo form unless specifically indicated. The amino acid residues constituting the peptide may be natural or non-natural amino acid residues.
상기 갈로일 펩타이드는 갈릭산이 결합된 펩타이드를 지칭하며, 상기 펩타이드는 N말단에 갈로일 기가 결합될 수 있다. 상기 펩타이드는 TYR-GLY-GLY-PHE-LEU-ARG-LYS-TYR-PRO로 구성된 아미노산 서열을 포함하는 올리고 펩타이드일 수 있다. The galloyl peptide refers to a peptide to which gallic acid is bound, and the peptide may have a galloyl group bound to the N-terminus. The peptide may be an oligopeptide comprising an amino acid sequence consisting of TYR-GLY-GLY-PHE-LEU-ARG-LYS-TYR-PRO.
상기 올리고 펩타이드는 티로시나아제 억제능 및 항산화 활성을 보유하여 우수한 미백효과를 나타낼 수 있을 뿐만 아니라, 생체친화도가 뛰어나 피부에 자극이 없고 장시간 보관시에도 안정성이 우수하다. The oligopeptide not only exhibits excellent whitening effect by possessing tyrosinase inhibitory ability and antioxidant activity, but also has excellent biocompatibility, does not irritate the skin, and has excellent stability even when stored for a long time.
상기 갈로일 펩타이드는 펩타이드를 합성한 후 갈릭산 유도체와 결합 반응시켜 제조될 수 있다. 상기 펩타이드는 생체 내의 단백질을 추출한 다음 단백질 분해효소로 처리하여 저분자량화하거나, 유전자 재조합과 단백질 발현시스템을 이용하여 제조될 수 있으며, 펩타이드 합성기 등을 이용한 화학 합성 방법으로 제조될 수 있으나, 이에 한정되는 것은 아니다. The galloyl peptide may be prepared by synthesizing the peptide and reacting with a gallic acid derivative. The peptide may be produced by extracting a protein in a living body and then treating it with a proteolytic enzyme to reduce molecular weight, or to be prepared using a gene recombination and protein expression system, and may be prepared by a chemical synthesis method using a peptide synthesizer, etc. It does not become.
일 실시예에 따르면, 상기 올리고 펩타이드는 (a)통상의 고체상 펩타이드 합성법(solid phase peptide synthesis: SPPS)으로 NH2-보호된 펩타이드-레진을 수득하는 단계; (b)수득된 NH2-보호된 펩타이드-레진을 벤조산 유도체와 반응시키는 단계; 및 (c)레진을 제거하는 단계에 의해 제조될 수 있다. 상기 올리고 펩타이드를 구성하는 아미노산 잔기의 측쇄에 작용기가 존재하는 경우에는 상기 (a)단계에서 상기 작용기가 보호된 아미노산을 사용하여 펩타이드를 합성할 수 있으며, 상기 작용기에 결합된 보호기는 (c)단계에서 제거될 수 있다. According to an embodiment, the oligopeptide is (a) obtained by a conventional solid phase peptide synthesis (SPPS) NH 2 -protected peptide-resin; (b) reacting the obtained NH2-protected peptide-resin with a benzoic acid derivative; And (c) removing the resin. When a functional group is present in the side chain of the amino acid residue constituting the oligopeptide, the peptide can be synthesized using an amino acid whose functional group is protected in step (a), and the protecting group bound to the functional group is step (c) Can be removed from.
즉, 상기 올리고 펩타이드는 Fmoc을 이용한 고체상 합성법(Solid Phase Peptide Synthesis)에 의해 제조될 수 있다. 상기 고체상 합성법은 coupling-deprotection을 반복하여 수행될 수 있다. That is, the oligopeptide may be prepared by a solid phase synthesis method using Fmoc (Solid Phase Peptide Synthesis). The solid phase synthesis method may be performed by repeating coupling-deprotection.
구체적으로, 고체 지지체에 결합해있는 펩타이드의 보호되어 있지 않은 N-terminal인 아미드 그룹에 N-terminal이 보호되어 있는 다음 amino acid의 C-terminal인 카르복시 그룹과 반응할 수 있다. 그 후, 탈보호시켜 그 다음 amino acid가 반응할 수 있도록 N-terminal을 노출시킨다.Specifically, after the N-terminal is protected to the unprotected N-terminal amide group of the peptide bound to the solid support, it can react with the carboxy group, the C-terminal of the amino acid. After that, it is deprotected and the N-terminal is exposed so that the amino acid can react.
상기 고체상 펩타이드 합성법은 Fmoc 그리고 tert-butoxycarbonyl(Boc) 두 개의 전략이 주로 사용된다. 리보솜 단백질 합성과 다르게 고체상 펩타이드 합성법은 C-terminal에서 N-terminal로 합성될 수 있다. 아미노산의 N-terminal은 이들 보호기로 보호되어 있어 Fmoc-아미노산 및 Boc-amino acid형태로 이루어져 있고 전략에 따라 탈보호 과정이 상이하다. 그 중 Fmoc 전략은 아미노산의 N-terminal 끝에는 염기에 쉽게 제거되는 Fmoc 보호기와 산에서 쉽게 제거되는 tertiary-butyl(tBu) 보호기가 곁사슬을 보호하고 있다. 첫 번째 Fmoc-아미노산을 레진의 linker에 결합시킨 후에 Fmoc은 Piperidine을 사용하여 제거한다.The solid-phase peptide synthesis method mainly uses two strategies, Fmoc and tert-butoxycarbonyl (Boc). Unlike ribosomal protein synthesis, solid-phase peptide synthesis can be synthesized from C-terminal to N-terminal. Since the N-terminal of amino acids is protected by these protecting groups, it is composed of Fmoc-amino acid and Boc-amino acid forms, and the deprotection process is different depending on the strategy. Among them, the Fmoc strategy is that the side chain is protected by the Fmoc protecting group that is easily removed from the base and the tertiary-butyl (tBu) protecting group that is easily removed from the acid at the N-terminal end of the amino acid. After binding the first Fmoc-amino acid to the resin linker, the Fmoc is removed using Piperidine.
Kaiser test로 Fmoc 보호기가 제거되었는지 확인한 후 Fmoc-아미노산의 카로복실기를 활성화시켜 두 번째 반응을 수행한다. Kaiser test를 통해 레진에 free 아민을 확인하여 반응완료 여부를 확인한다. 합성은 Fmoc 보호기의 제거 그리고 다음 Fmoc-아미노산의 반응을 한 싸이클로 하여 펩타이드 서열에 따라 합성될 수 있다. 합성 완료된 펩타이드는 TFA를 처리하여 레진으로부터 떨어지고 곁사슬의 보호기도 제거될 수 있다. After confirming that the Fmoc protecting group has been removed by the Kaiser test, the second reaction is carried out by activating the carboxyl group of the Fmoc-amino acid. The reaction is completed by checking the free amine in the resin through the Kaiser test. Synthesis can be synthesized according to the peptide sequence by removing the Fmoc protecting group and then reacting with the Fmoc-amino acid in one cycle. The synthesized peptide can be separated from the resin by treatment with TFA, and the side chain protecting group can be removed.
상기 화장료 조성물은 상기 올리고 펩타이드를 유효성분으로 포함하며, 항산화 또는 피부 개선 효과가 우수하다. The cosmetic composition contains the oligopeptide as an active ingredient, and has excellent antioxidant or skin improvement effects.
상기 피부 개선 효과는 피부 보호 및 피부 상태 개선, 피부 미백, 피부 노화 및 주름의 예방 또는 개선, 피부 보호 및 피부의 염증 반응의 완화, 면역질환 개선능, 또는 피부 장벽 기능 개선, 피부자극 완화, 피부 세포 증식 및 재생능, 항산화능, 콜라겐 합성 증진능 등 피부에 유익한 효과를 모두 포괄 할 수 있다. The skin improvement effect is skin protection and skin condition improvement, skin whitening, skin aging and wrinkle prevention or improvement, skin protection and relief of inflammatory reactions of the skin, immune disease improvement ability, or skin barrier function improvement, skin irritation relief, skin It can cover all beneficial effects on the skin such as cell proliferation and regeneration ability, antioxidant ability, and collagen synthesis enhancement ability.
상기 “유효성분으로 포함하는”은 화장료 조성물로서 피부 개선 효과를 나타낼 수 있는, 예컨대, 주름개선효능과 관련된 콜라겐 합성, 탄력 개선 또는 항산화 활성 등을 나타낼 수 있는 정도의 유효량을 함유하는 것을 의미할 수 있다. The "contained as an active ingredient" may mean that the cosmetic composition contains an effective amount that can exhibit skin improvement effects, for example, collagen synthesis, elasticity improvement or antioxidant activity related to wrinkle improvement effect. have.
상기 화장료 조성물은 자유라디칼 소거 활성능에 따른 항산화능을 보유하며, 특히, 콜라겐 생합성 증가능, 콜라겐 분해 방지능이 우수하므로, 피부 노화 방지, 피부 주름 개선, 피부 탄력 증진 개선의 용도로 사용될 수 있다. The cosmetic composition has antioxidant activity according to the free radical scavenging activity, and in particular, it is excellent in the ability to increase collagen biosynthesis and prevent collagen degradation, so it can be used for the purpose of preventing skin aging, improving skin wrinkles, and improving skin elasticity.
한편, 상기 올리고 펩타이드는 나노리포좀으로 안정화될 수 있으며, 나노리포좀에 의해 포접된 상기 올리고 펩타이드는 피부 침투가 용이하여 피부 개선 효과가 비약적으로 개선될 수 있다. On the other hand, the oligopeptide may be stabilized with a nanoliposome, and the oligopeptide encapsulated by the nanoliposome can easily penetrate the skin, thereby dramatically improving the skin improvement effect.
상기 “나노리포좀”은 통상적인 리포좀의 형태를 갖는 것으로서 평균 입자 지름이 1 내지 150nm인 리포좀을 의미할 수 있다. The "nanoliposome" may mean a liposome having an average particle diameter of 1 to 150 nm as having a conventional liposome form.
일 실시예에 따르면, 상기 나노리포좀의 평균 입자 지름은 90 내지 130nm일 수 있다. 상기 나노리포좀의 평균입자 지름이 130nm 초과이면 피부침투 효과가 저하되고 제형 안정성이 저하될 수 있으며, 90nm 미만이면 나노리포좀 내에 유효 성분이 적절히 내포되지 않을 수 있다. According to an embodiment, the average particle diameter of the nanoliposome may be 90 to 130 nm. If the average particle diameter of the nanoliposome is more than 130nm, the skin penetration effect may be lowered and the formulation stability may be lowered, and if it is less than 90nm, the active ingredient may not be properly contained in the nanoliposome.
한편, 상기 나노리포좀은 폴리올, 유성 성분, 계면활성제, 인지질, 지방산 및 물을 포함하는 혼합물에 의해 제조될 수 있다.Meanwhile, the nanoliposome may be prepared by a mixture comprising a polyol, an oily component, a surfactant, a phospholipid, a fatty acid, and water.
상기 폴리올의 종류는 특별히 제한되지 아니하며, 예컨대, 프로필렌글리콜, 디프로필렌글리콜, 1,3-부틸렌글리콜, 글리세린, 메틸프로판디올, 이소프렌글리콜, 펜틸렌글리콜, 에리스리톨, 자일리톨, 솔비톨 또는 이의 혼합물일 수 있다. 바람직하게는 상기 폴리올은 프로필렌글리콜, 1,3-부틸렌글리콜, 또는 글리세린일 수 있으며, 상기 폴리올은 나노리포좀 총 중량에 대하여 30 내지 70 중량% 포함될 수 있다. The type of the polyol is not particularly limited, and may be, for example, propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, methylpropanediol, isoprene glycol, pentylene glycol, erythritol, xylitol, sorbitol, or mixtures thereof. have. Preferably, the polyol may be propylene glycol, 1,3-butylene glycol, or glycerin, and the polyol may be contained in an amount of 30 to 70% by weight based on the total weight of the nanoliposome.
상기 유성 성분은 당업계에 공지된 다양한 오일이 사용될 수 있으며, 예컨대, 헥사데칸 및 파라핀 오일과 같은 하이드로카본계 오일; 에스테르계의 합성오일; 디메치콘 및 사이크로메치콘계과 같은 실리콘 오일; 해바라기유, 옥수수유, 대두유, 아보카도유, 참깨유 및 어유와 같은 동식물성 오일; 에톡시레이티드 알킬에테르계오일; 프로폭시레이티드알킬에테르계 오일; 피토스핑고신, 스핑고신 및 스핑가닌과 같은 스핑고노이드 지질; 콜레스테롤; 시토스테롤; 콜레스테릴설페이트; 시토스테릴설페이트 또는 C10-40 지방알코올일 수 있다. 상기 유상 성분은 나노리포좀 총 중량에 대하여 3.0 내지 20.0 중량% 포함될 수 있다. As the oily component, various oils known in the art may be used, for example, hydrocarbon-based oils such as hexadecane and paraffin oil; Ester-based synthetic oils; Silicone oils such as dimethicone and cyclomethicone; Animal and vegetable oils such as sunflower oil, corn oil, soybean oil, avocado oil, sesame oil and fish oil; Ethoxylated alkyl ether oil; Propoxylated alkyl ether oil; Sphingoid lipids such as phytosphingosine, sphingosine and sphinganine; cholesterol; Sitosterol; Cholesteryl sulfate; It may be cytosteryl sulfate or C10-40 fatty alcohol. The oily component may be included in an amount of 3.0 to 20.0% by weight based on the total weight of the nanoliposome.
상기 계면활성제는 당업계에 공지된 다양한 계면활성제가 사용될 수 있으며, 예컨대, 음이온성 계면활성제, 양이온성 계면활성제, 양성 계면활성제 및 비이온성 계면활성제가 사용될 수 있고, 바람직하게는 음이온성 계면활성제 및 비이온성 계면활성제가 사용될 수 있다. 상기 음이온 계면활성제는 알킬아실글루타메이트, 알킬포스페이트, 알킬락틸레이트, 디알킬포스페이트 또는 트리알킬포스페이트일 수 있으며, 상기 비이온계면활성제는 알콕시레이티드알킬에테르, 알콕시레이티드알킬에스테르, 알킬폴리글리코사이드, 폴리글리세릴에스테르 및 슈가에스테르일 수 있다. 상기 계면활성제는 나노리포좀 총 중량에 대하여 0.5 내지 3.0 중량% 포함될 수 있다.As the surfactant, various surfactants known in the art may be used, for example, anionic surfactants, cationic surfactants, amphoteric surfactants and nonionic surfactants may be used, preferably anionic surfactants and Nonionic surfactants can be used. The anionic surfactant may be an alkylacyl glutamate, an alkyl phosphate, an alkyl lactylate, a dialkyl phosphate or a trialkyl phosphate, and the nonionic surfactant is an alkoxylated alkyl ether, an alkoxylated alkyl ester, an alkyl polyglycoside, It may be a polyglyceryl ester and a sugar ester. The surfactant may be included in an amount of 0.5 to 3.0% by weight based on the total weight of the nanoliposome.
또한, 상기 인지질은 양쪽친화성 지질로 이용된 것으로서, 천연 인지질(예컨대, 난황 레시틴 또는 대두 레시틴, 스핑고마이엘린) 및 합성 인지질 (예컨대, 디팔미토일포스파티딜콜린 또는 수첨 레시틴)을 사용할 수 있으나, 바람직하게는 수첨 레시틴(Hydrogenated Lecithin)을 사용할 수 있다. In addition, the phospholipid is used as an amphiphilic lipid, and natural phospholipids (eg, egg yolk lecithin or soybean lecithin, sphingomyelin) and synthetic phospholipids (eg, dipalmitoylphosphatidylcholine or hydrogenated lecithin) may be used, but preferred Hydrogenated Lecithin can be used for the sake of clarity.
일 실시예에 따르면, 상기 나노리포좀은 포스파티딜콜린의 함량이 70 중량% 이상인 대두 유래의 레시틴에 의해 안정화될 수 있으며, 상기 대두 유래의 레시틴은 수화 단계를 거쳐 임의적으로 수소가 첨가된 수첨 레시틴일 수 있다. According to an embodiment, the nanoliposome may be stabilized by soybean-derived lecithin having a phosphatidylcholine content of 70% by weight or more, and the soybean-derived lecithin may be hydrogenated lecithin to which hydrogen is optionally added through a hydration step. .
상기 대두 유래의 수첨 레시틴은 안정성이 우수하고 피부에 대한 자극이 없으며, 피부 침투능이 우수하므로 상기 갈로일 펩타이드의 피부 흡수를 촉진할 수 있다. 상기 대두 유래의 수첨 레시틴은 단단하게 결합된 분자들 사이에 물분자가 도입되어 팽윤되므로 유화시 오일입자를 둘러쌓음으로써 안정한 에멀전을 형성할 수 있다. The soybean-derived hydrogenated lecithin has excellent stability, no irritation to the skin, and excellent skin penetration ability, so that the galloyl peptide can promote skin absorption. The soybean-derived hydrogenated lecithin is swelled by introducing water molecules between tightly bound molecules, so it is possible to form a stable emulsion by surrounding oil particles during emulsification.
또한, 상기 나노리포좀은 포스파티딜콜린의 함량이 70 중량% 미만인 경우 불순물이 과도하게 포함되어 평균입자크기가 증가할 수 있으므로, 피부 흡수가 용이하도록 포스파티딜콜린의 함량을 적정 비율 이상 유지하는 것이 바람직하다. In addition, when the content of phosphatidylcholine is less than 70% by weight of the nanoliposome, impurities may be excessively contained and the average particle size may increase, so it is preferable to maintain the content of phosphatidylcholine in an appropriate ratio or higher to facilitate skin absorption.
일 실시예에 따르면, 상기 나노리포좀은 조성물 총 중량에 대하여 0.1 내지 20.0 중량% 포함될 수 있다. 상기 나노리포좀의 함량이 총 중량에 대하여 0.1 중량% 미만인 경우 상기 갈로일 펩타이드에 의한 피부 개선 효과가 충분히 구현되지 않을 수 있고, 20.0 중량% 이상인 경우 첨가량 대비 피부 개선효과가 증가되지 않아 비용 효율이 저하될 수 있으므로 적정 비율로 유지하는 것이 바람직하다.According to an embodiment, the nanoliposome may be included in an amount of 0.1 to 20.0% by weight based on the total weight of the composition. When the content of the nanoliposome is less than 0.1% by weight based on the total weight, the skin improvement effect by the galloyl peptide may not be sufficiently realized, and when the content of the nanoliposome is more than 20.0% by weight, the skin improvement effect compared to the amount added is not increased, resulting in a decrease in cost efficiency. It is desirable to keep it at an appropriate ratio.
한편, 상기 지방산은 고급 지방산으로서, 바람직하게는 C12-22 알킬 체인의 포화 또는 불포화 지방산이며, 예컨대, 라우린산, 미리스트산, 팔미트산, 스테아린산, 올레인산 또는 리놀레산일 수 있다. 상기 지방산은 나노리포좀 총 중량에 대하여 0.1 내지 1.0 중량% 포함될 수 있다. Meanwhile, the fatty acid is a higher fatty acid, preferably a saturated or unsaturated fatty acid having a C12-22 alkyl chain, and may be, for example, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, or linoleic acid. The fatty acid may be included in an amount of 0.1 to 1.0% by weight based on the total weight of the nanoliposome.
또한, 상기 나노리포좀의 제조에 사용되는 물은 일반적으로 탈이온화된 증류수일 수 있으며, 나노리포좀 총 중량에 대하여 5.0 내지 20.0 중량% 포함될 수 있다. In addition, water used in the preparation of the nanoliposome may be generally deionized distilled water, and may be included in an amount of 5.0 to 20.0% by weight based on the total weight of the nanoliposome.
일 실시예에 따르면, 상기 나노리포좀은 비타민 C 유도체를 포함할 수 있으며, 상기 비타민 C 유도체는 상기 나노리포좀 총 중량에 대하여 0.01 내지 20.0 중량% 포함될 수 있다. According to an embodiment, the nanoliposome may include a vitamin C derivative, and the vitamin C derivative may be included in an amount of 0.01 to 20.0% by weight based on the total weight of the nanoliposome.
상기 비타민 C는 피부 노화를 억제시키는 효과가 있는 성분으로 자외선(UV) 차단 효과, 항산화 효과, 콜라겐 형성 촉진을 통한 피부 주름 개선, 색소 침착개선 효과, 면역 체계 강화 효과가 우수하다. 그러나, 상기 비타민 C는 수용성 물질로 수용액이 아닌 피부와 같은 유기적인 환경에서는 흡수가 제한될 수 있다. Vitamin C is a component that has an effect of inhibiting skin aging, and has excellent ultraviolet (UV) blocking effect, antioxidant effect, skin wrinkle improvement through collagen formation promotion, pigmentation improvement effect, and immune system strengthening effect. However, the vitamin C is a water-soluble substance, and absorption may be limited in an organic environment such as skin rather than an aqueous solution.
또한, 상기 비타민 C는 통상적으로 사용되는 유기용매, 예컨대, 글리세린, 프로필렌 글리콜, 다양한 지방 등에 잘 녹지 않으며, 비타민C가 이온화 되지 않았을 때 피부 장벽을 통과하여 흡수시 비이온 상태를 유지하기 위해서는 pH가 4.2 이하로 유지되어야 하는 한계점이 있다. In addition, the vitamin C does not dissolve well in commonly used organic solvents, such as glycerin, propylene glycol, and various fats. When vitamin C is not ionized, the pH is adjusted to maintain a nonionic state when absorbed through the skin barrier. There is a limitation that should be kept below 4.2.
상기 비타민 C는 경구 투여보다 외용제로 사용하였을 때 피부 축적량이 20배 내지 40배 정도 증가하지만, 안정성 및 피부 흡수율이 낮으므로 경피 흡수율을 증가시킬 필요가 있다. When vitamin C is used for external application than oral administration, the skin accumulation amount increases by 20 to 40 times, but the stability and skin absorption rate are low, so it is necessary to increase the transdermal absorption rate.
상기 갈로일 펩타이드를 포함하는 나노리포좀은 리포좀 제조 과정에서 비타민 C를 함께 투입함으로써 비타민 C를 포함할 수 있다. 상기 비타민 C는 상기 나노리포좀에 포접되어 안정성 및 피부 흡수율이 현저히 증가될 수 있다. The nanoliposome containing the galloyl peptide may contain vitamin C by adding vitamin C together during the liposome manufacturing process. The vitamin C may be enclosed in the nanoliposome to significantly increase stability and skin absorption rate.
특히, 상기 비타민 C는 상기 갈로일 펩타이드와 피부에 동시에 적용되는 경우 피부 광택, 피부색 개선, 주름 감소, 피부 탄력 증가 등의 상승효과를 발휘할 수 있으며, 상기 비타민 C 및 갈로일 펩타이드를 내포하는 나노리포좀에 의해 두 성분 모두 피부 흡수율이 증가함으로써 상승 효과가 극대화될 수 있다. In particular, when the vitamin C is applied to both the galloyl peptide and the skin at the same time, it can exhibit synergistic effects such as skin gloss, skin color improvement, wrinkle reduction, and skin elasticity increase, and nanoliposomes containing the vitamin C and galloyl peptide As a result, the synergistic effect can be maximized by increasing the skin absorption rate of both ingredients.
상기 나노리포좀은 당업계에 공지된 다양한 방법을 통해 이루어질 수 있으나, 가장 바람직하게는 상기 성분들을 포함하는 혼합물을 고압 호모게나이저에 적용하여 제조될 수 있다. The nanoliposome may be formed through various methods known in the art, but most preferably, it may be prepared by applying a mixture containing the above components to a high-pressure homogenizer.
상기 나노리포좀은 목적하는 나노 입자 크기에 따라 다양한 조건(예: 압력, 횟수 등)으로 균질화될 수 있으며, 바람직하게는 600 내지 1200bar의 압력 하에서 1 내지 5회 고압 호모게나이저를 통과시켜 제조될 수 있다. The nanoliposome may be homogenized under various conditions (eg, pressure, number of times, etc.) according to the desired nanoparticle size, and may be prepared by passing through a high-pressure homogenizer 1 to 5 times, preferably under a pressure of 600 to 1200 bar. have.
일 실시예에 따르면, 상기 화장료 조성물은 피부 주름 개선 또는 피부 탄력 개선용일 수 있다. According to an embodiment, the cosmetic composition may be for improving skin wrinkles or improving skin elasticity.
상기 화장료 조성물은 피부 세포의 증식 촉진, 항산화 효능, 콜라겐 합성의 촉진에 의한 피부 주름 개선과 피부 탄력 개선, 보습력 향상 및 피부 면역 증강을 통하여 피부 노화를 방지하는 효과가 우수하며, 상기 효과는 하기 실시예에 의해 뒷받침된다. The cosmetic composition has an excellent effect of preventing skin aging by promoting skin cell proliferation, antioxidant effect, and collagen synthesis by promoting skin wrinkles and skin elasticity, moisturizing power, and skin immunity. Supported by examples.
일 실시예에 따르면, 상기 화장료 조성물은 유연화장수, 영양화장수, 영양크림, 마사지크림, 에센스, 아이크림, 클렌징크림, 클렌징폼, 클렌징워터, 팩, 스프레이 및 파우더로 이루어진 군에서 선택된 하나 이상으로 제형화될 수 있다. According to an embodiment, the cosmetic composition is formulated with one or more selected from the group consisting of softening lotion, nutritional lotion, nutritional cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray, and powder. It can be angry.
상기 화장료 조성물은 각각의 제형에 있어서 상기 필수성분 외에 제형의 종류 또는 사용 목적 등에 따라 본 발명에 따른 목적을 저해하지 않는 범위 내에서 다른 성분들이 적절히 배합될 수 있다. In each formulation, the cosmetic composition may be appropriately blended with other components within a range that does not impair the object according to the present invention depending on the type of formulation or purpose of use, in addition to the essential components.
또한, 상기 화장료 조성물은 최종 제품의 품질이나 기능에 따라 업계에서 통상적으로 사용되는 지방 물질, 유기용매, 용해제, 농축제, 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온봉 쇄제, 킬레이트화제, 보존제, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 화장품에 통상적으로 사용되는 임의의 다른 성분과 같은 화장품학 또는 피부과학 분야에서 통상적으로 사용되는 보조제를 추가적으로 함유할 수 있다. In addition, the cosmetic composition is a fatty substance, an organic solvent, a solubilizer, a thickener, a gelling agent, an emollient, an antioxidant, a suspending agent, a stabilizer, a foaming agent, which is commonly used in the industry depending on the quality or function of the final product. , Fragrances, surfactants, water, ionic or nonionic emulsifiers, fillers, sequestering agents, chelating agents, preservatives, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic actives, usually in cosmetics It may additionally contain adjuvants commonly used in the field of cosmetology or dermatology, such as any other ingredients used.
다만, 상기 보조제 및 그 혼합 비율은 본 발명에 따른 화장료 조성물의 바람직한 성질에 영향을 미치지 않도록 적절히 선택하는 것이 바람직하다. However, it is preferable to appropriately select the adjuvant and its mixing ratio so as not to affect the desirable properties of the cosmetic composition according to the present invention.
이하 실시예를 통해, 본 발명을 더욱 상술하나 하기 실시예에 의해 본 발명이 제한되지 아니함은 자명하다.It is apparent that the present invention is further elaborated through the following examples, but the present invention is not limited by the following examples.
제조예 1-1: 노나펩타이드(YGGFLRKYP)의 합성Preparation Example 1-1: Synthesis of nonapeptide (YGGFLRKYP)
노나펩타이드는 9-플루오레닐메톡시카르보닐(9-fluorenylmethoxycarbonyl; Fmoc)을 아미노산의 보호기로 사용하여 통상의 고체상 펩타이드 합성법(solid phase peptide synthesis: SPPS)에 의해 합성하였으며, N-히드록시벤조 트리아졸(N-hydroxybenzotriazole; HOBt)와 N,N-디아이소프로필카보 디이미드(N,N'-diisopropylcarbodiimide; DIC)를 활성화제로 사용하여 아미노산 잔기를 연장하였다[참고문헌 : Wang C. Chan, Perter D. White, 'Fmoc-solid phase peptide synthesis', Oxford].Nonapeptide was synthesized by conventional solid phase peptide synthesis (SPPS) using 9-fluorenylmethoxycarbonyl (Fmoc) as an amino acid protecting group, and N-hydroxybenzotriazole (N-hydroxybenzotriazole; HOBt) and N,N-diisopropylcarbodiimide (DIC) were used as activators to extend amino acid residues [Reference: Wang C. Chan, Perter D. White,'Fmoc-solid phase peptide synthesis', Oxford].
구체적으로, 유리 반응기에서 아미노기가 Fmoc으로 보호된His(Trt) 레진(Nova Biochem, Inc) 0.04g을 용매인 N,N-디메틸포름아마이드(N,N-Dimethylformamide; DMF) 3ml에서 20분 동안 부풀린(swelling) 다음, 용매를 제거하고, 20% 피페리딘(piperidine) 3ml로 2회 처리하여 Fmoc를 제거하였다. Specifically, 0.04 g of His (Trt) resin (Nova Biochem, Inc) in which the amino group is protected by Fmoc in a glass reactor was inflated in 3 ml of N,N-dimethylformamide (DMF) as a solvent for 20 minutes. (swelling) Next, the solvent was removed, and Fmoc was removed by treatment twice with 3 ml of 20% piperidine.
상기 Fmoc이 제거된 His 레진을 디클로로메탄(dichloromethane: DCM)으로 3회, DMF로 3회 처리하고, HOBt-DIC로 활성화된 Fmoc-Val-OH(발린)용액과 실온에서 약2시간 동안 반응시켰다. 이와 같은 과정으로 루신을 연속적으로 반응시켜 수득한 NH2-보호된 펩타이드(YGGFLRKYP) 레진을 DCM으로 3회, DMF로 3회 세척하였다.The His resin from which Fmoc was removed was treated with dichloromethane (DMF) three times and DMF three times, and reacted with a solution of Fmoc-Val-OH (valine) activated with HOBt-DIC at room temperature for about 2 hours. . In this process, the NH 2 -protected peptide (YGGFLRKYP) resin obtained by continuously reacting leucine was washed 3 times with DCM and 3 times with DMF.
제조예Manufacturing example 1- One- 2: 32: 3 ,4,5-,4,5- 트리하이드록시벤조일Trihydroxybenzoyl (( 갈로일Galloil )-)- 노나펩타이드(YGGFLRKYP)의Of nonapeptide (YGGFLRKYP) 합성 synthesis
상기에서 합성된 NH2-보호된 펩타이드(YGGFLRKYP 레진을DMF와 DCM으로 세척한 후 3,4,5-트리하드록시벤조산(3,4,5-Trihydroxybenzoic acid) 5당량과 HOBt(5당량), DIC(5당량)을 혼합하여, 실온에서 하룻밤 동안 커플링 반응시켰다. 반응이 종료된 후 DMF와 DCM으로 각각 3회 세척한 다음 건조시켰다. NH 2 -protected peptide synthesized above (after washing YGGFLRKYP resin with DMF and DCM, 5 equivalents of 3,4,5-trihydroxybenzoic acid) and HOBt (5 equivalents), DIC (5 equivalents) was mixed, and the coupling reaction was carried out overnight at room temperature After the reaction was completed, the mixture was washed three times with DMF and DCM, and then dried.
건조된 3,4,5-트리하이드록시벤조일(갈로일)-노나펩타이드(YGGFLRKYP) 레진을 트리플루오로아세트산 : 페놀 : 티오아니솔 : 물 : 에탄디티올(82.5 : 5: 5 : 5 : 2.5 (v/v))의 혼합 용액으로 실온에서 2 내지 3시간 동안 반응시켜, 펩타이드를 구성하는 아미노산 잔기의 측쇄에 존재하는 작용기의 보호기인 Boc기를 제거하고 레진으로부터 3,4,5-트리하이드록시벤조일(갈로일)-노나펩타이드(YGGFLRKYP)을 분리시킨 다음, 차가운 디에틸에테르로 상기 펩타이드를 침전시켰다. Dried 3,4,5-trihydroxybenzoyl (galoyl)-nonapeptide (YGGFLRKYP) resin was mixed with trifluoroacetic acid: phenol: thioanisole: water: ethandithiol (82.5: 5: 5: 5: 2.5) (v/v)) reacted at room temperature for 2 to 3 hours at room temperature to remove the protective group Boc group of the functional group present in the side chain of the amino acid residue constituting the peptide, and 3,4,5-trihydroxyl from the resin. After separating benzoyl (galoyl)-nonapeptide (YGGFLRKYP), the peptide was precipitated with cold diethyl ether.
수득된3,4,5-트리하이드록시벤조일(갈로일)-노나펩타이드(YGGFLRKYP)을 0.1% 트리플루오로아세트산이 포함된 물과 아세토니트릴을 용매로 역상 고성능액체크로마토그래피(reverse phase high performance liquid chromatography; column: Gemini, C18 110A 25021.2mm)에서 정제 하였다.The obtained 3,4,5-trihydroxybenzoyl (galoyl)-nonapeptide (YGGFLRKYP) was used in water containing 0.1% trifluoroacetic acid and acetonitrile as a solvent in reverse phase high performance liquid chromatography. chromatography; column: Gemini, C18 110A 25021.2mm).
상기 펩타이드는 고성능액체크로마토그래피(HPLC)에 의해 정제되었으며 동결 건조되어 수득되었다. The peptide was purified by high performance liquid chromatography (HPLC) and freeze-dried to obtain.
제조예 2-1: 나노리포좀의 제조Preparation Example 2-1: Preparation of nanoliposome
나노리포좀의 제조를 위해 하기 표 1의 조성으로 A상에 B상을 첨가하고, 균일하게 습윤 시켰으며, 이후 C 상을 첨가하고 70-80℃에서 가열 혼합하였다. 상기 혼합 용액은 600-1000 bar의 조건으로 고압 호모게나이저에 3회 통과 후 냉각되었으며 평균 입자 지름 약 100nm 의 나노리포좀을 수득하였다.For the preparation of nanoliposomes, phase B was added to the A phase according to the composition shown in Table 1, and uniformly wetted, and then phase C was added and heated and mixed at 70-80°C. The mixed solution was cooled after passing through a high-pressure homogenizer three times under conditions of 600-1000 bar, and nanoliposomes having an average particle diameter of about 100 nm were obtained.
제조예 2-2: 나노리포좀의 제조Preparation Example 2-2: Preparation of nanoliposome
상기 제조예 2-1과 동일한 방법으로 나노리포좀을 제조하되, C상의 비타민 C는 제외하였다. Nanoliposome was prepared in the same manner as in Preparation Example 2-1, except for vitamin C in C phase.
제조예 3: 실시예 및 비교예의 제조Preparation Example 3: Preparation of Examples and Comparative Examples
나노리포좀으로 안정화된 갈로일 펩타이드를 포함하는 화장료 조성물을 하기 표 2의 조성비에 따라 제조하였다. 구체적으로 실시예 1은 갈로일 펩타이드 및 비타민 C가 나노리포좀에 의해 안정화된 화장료 조성물이며, 비교예 1은 갈로일 펩타이드는 나노리포좀에 의해 안정화되었으나, 비타민 C는 별개로 첨가되었다. 상기 실시예 1 및 비교예 1 양자를 비교하면, 비타민 C를 나노리포좀에 함께 포접한 본 발명에 따른 화장료 조성물의 피부 개선 효과를 확인할 수 있다. A cosmetic composition comprising a galloyl peptide stabilized with nanoliposomes was prepared according to the composition ratio shown in Table 2 below. Specifically, Example 1 is a cosmetic composition in which galloyl peptide and vitamin C are stabilized by nanoliposomes, and in Comparative Example 1, galloyl peptide is stabilized by nanoliposomes, but vitamin C is separately added. Comparing both Example 1 and Comparative Example 1, it can be seen that the skin improvement effect of the cosmetic composition according to the present invention incorporating vitamin C together with nanoliposomes.
또한, 하기 비교예 2 및 비교예 3의 갈로일 펩타이드는 하기 실시예 1 및 2의 나노리포좀에 안정화된 갈로일 펩타이드와 동일량이 첨가될 수 있도록 함량이 조절되었다. In addition, the content of the galloyl peptide of Comparative Examples 2 and 3 was adjusted so that the same amount as the stabilized galloyl peptide can be added to the nanoliposomes of Examples 1 and 2 below.
실험예 1: 피부 보습 효과 평가Experimental Example 1: Evaluation of skin moisturizing effect
나노리포좀에 의해 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료의 피부 보습력 개선효과를 알아보기 위하여 다음과 같이 실험을 하였다.In order to find out the effect of improving skin moisturizing power of cosmetics containing galloyl peptide stabilized by nanoliposome as an active ingredient, the following experiment was conducted.
피부 질환이 없는 20~40대 40명을 대상으로 1조당 20명씩 2개 조로 나누고, 각 조별로 상기 표 2의 화장료를 매일 2회씩 1개월간 얼굴 및 전반부에 도포하게 하였으며, 음성 대조군으로서 동일한 양의 정제수를 사용하였다. Targeting 40 people in their 20s to 40s without skin disease, 20 people per group were divided into 2 groups, and the cosmetics in Table 2 were applied twice daily for 1 month on the face and front part for each group, and the same amount as a negative control group. Purified water was used.
도포 전 항온, 항습 조건(24℃, 습도 40%)에서 수분측정기(Corneometer, CM820 courage Khazaka electronic GmbH, Germany)를 이용하여 피부 전도도를 측정하여 기본 값으로 삼고, 2분 단위로 피부 전도도 증가율(%)을 측정하였다. Use a moisture meter (Corneometer, CM820 courage Khazaka electronic GmbH, Germany) under constant temperature and humidity conditions (24℃, humidity 40%) before application to measure the skin conductivity as a basic value. ) Was measured.
상기 표 3에 나타난 바와 같이 실시예 1 및 2의 화장료 조성물의 피부 보습 효과가 높은 것으로 확인되었다. 특히, 비타민 C 및 갈로일 펩타이드가 나노리포좀에 의해 안정화된 화장료 조성물(실시예 1)은 비타민 C가 나노리포좀에 함유되지 않은 화장료 조성물(비교예 1) 보다 보습 효과가 현저히 높은 것으로 확인되었다. 즉, 비타민 C가 나노리포좀에 의해 상기 갈로일 펩타이드와 함께 포접되는 경우 피부 개선 효과는 더욱 개선될 수 있다. As shown in Table 3, it was confirmed that the cosmetic compositions of Examples 1 and 2 had a high skin moisturizing effect. In particular, it was confirmed that the cosmetic composition in which vitamin C and galloyl peptide were stabilized by nanoliposomes (Example 1) had a significantly higher moisturizing effect than the cosmetic composition in which vitamin C was not contained in nanoliposomes (Comparative Example 1). That is, when vitamin C is incorporated together with the galloyl peptide by nanoliposomes, the skin improvement effect may be further improved.
실험예 2: 피부 장벽 개선 효과 평가Experimental Example 2: Evaluation of skin barrier improvement effect
나노리포좀에 의해 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료의 피부 장벽 개선효과를 알아보기 위하여 다음과 같이 실험하였다. In order to investigate the effect of improving the skin barrier of cosmetics containing galloyl peptide stabilized by nanoliposome as an active ingredient, the following experiment was performed.
상기 실시예 1, 실시예 2, 및 비교예 1 내지 4의 화장료 적용에 따른 피부의 경피 수분 손실량(TEWL: Trans-Epidemal Water Loss)을 Tewameterr(TM300, Courage and Khazaka Electronic Co., Germany)를 이용하여 측정하였다. Tewameterr (TM300, Courage and Khazaka Electronic Co., Germany) was used to determine the amount of transdermal water loss (TEWL: Trans-Epidemal Water Loss) of the skin according to the application of the cosmetics of Examples 1, 2, and Comparative Examples 1 to 4 above. And measured.
20 ~ 40대 여성 40명을 대상으로 오른쪽과 왼쪽 얼굴에 각 시료를 도포하고 눈가에서 3cm 우측으로 1cm 아래에 떨어진 부위에서 도포 전 및 도포 후 1시간, 2시간, 4시간, 6시간 후 Tewameterr(TM300, Courage and Khazaka Electronic Co., Germany)를 이용하여 경피 수분 손실량을 3회 측정하였다. For 40 women in their 20s to 40s, apply each sample to the right and left faces, and apply Tewameterr( TM300, Courage and Khazaka Electronic Co., Germany) was used to measure the amount of transdermal water loss three times.
시료를 바르기 전 수분량 측정 결과는 대조군으로 설정하였으며, 상기 대조군과 비교한 경피 수분 손실량 평균값을 산출하였다. The water content measurement result before applying the sample was set as a control, and the average value of the transdermal water loss compared to the control was calculated.
상기 표 4에 나타난 바와 같이 실시예 1 및 2의 화장료 조성물의 피부 장벽 개선효과가 높은 것으로 확인되었다. 비타민 C 및 갈로일 펩타이드가 나노리포좀에 의해 안정화된 화장료 조성물(실시예 1)은 비타민 C가 나노리포좀에 함유되지 않은 화장료 조성물(비교예 1) 보다 피부 장벽 개선효과가 우수하였으며, 갈로일 펩타이드만 안정화된 화장료 조성물(실시예 2) 보다 장벽 개선효과가 현저히 우수하였다.As shown in Table 4, it was confirmed that the cosmetic compositions of Examples 1 and 2 had a high skin barrier improvement effect. The cosmetic composition in which vitamin C and galloyl peptide were stabilized by nanoliposomes (Example 1) was superior to the cosmetic composition in which vitamin C was not contained in nanoliposomes (Comparative Example 1), and only galloyl peptide was The barrier improvement effect was remarkably better than the stabilized cosmetic composition (Example 2).
실험예 3: 피부 탄력 개선 효과 평가Experimental Example 3: Evaluation of skin elasticity improvement effect
나노리포좀에 의해 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료의 피부 탄력 증진효과를 알아보기 위하여 다음과 같이 실험을 하였다.In order to investigate the effect of enhancing skin elasticity of cosmetics containing galloyl peptide stabilized by nanoliposome as an active ingredient, the following experiment was conducted.
온도 24-26℃, 습도 75의 조건에서 20세 이상의 건강한 여성 60명(평균연령 37세)을 5 그룹으로 나누고, A 그룹에는 실시예 1을, B 그룹에는 실시예 2를, C 그룹에는 비교 실시예 1을, D 그룹에는 비교 실시예 2를, E 그룹에는 비교 실시예 3을, F 그룹에는 비교 실시예 4의 제형을 눈가를 중심으로 하루 2회씩 (아침 및 저녁) 12주간 도포한 후, 피부탄력 측정기(Cutometer MPA580, Conrage + Khazaka사, 독일연방국)를 이용하여 피부 탄력을 측정하였다. 60 healthy women 20 years old or older (average age 37 years old) under the conditions of temperature 24-26°C and humidity 75 were divided into 5 groups, Example 1 in Group A, Example 2 in Group B, and Comparison in Group C After applying the formulation of Example 1, Comparative Example 2 to Group D, Comparative Example 3 to Group E, and Comparative Example 4 to Group F, twice a day (morning and evening) for 12 weeks. , Skin elasticity was measured using a skin elasticity meter (Cutometer MPA580, Conrage + Khazaka, Germany).
시험결과는 cutometer MPA580의 R8(R8(12주)-R8(0주)) 값으로 기재하였는데, R8 값은 피부 점탄성 (Vicoelasticity)의 성질을 나타내며, 결과는 하기 표 5에 나타내었다.The test result was described as the value of R8 (R8 (12 weeks)-R8 (0 weeks)) of the cutometer MPA580, and the R8 value indicates the properties of skin viscoelasticity, and the results are shown in Table 5 below.
표 5에 나타난 바와 같이, 실시예 1 및 2의 화장료 조성물의 피부 탄력 개선효과는 비교예 2 내지 4와 비교하여 증가되었다. As shown in Table 5, the skin elasticity improvement effect of the cosmetic compositions of Examples 1 and 2 was increased compared to Comparative Examples 2 to 4.
실험예 4: 피부 주름 개선 효과 평가Experimental Example 4: Evaluation of skin wrinkle improvement effect
나노리포좀에 의해 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료의 피부 주름 개선 효과를 평가하기 위하여 다음과 같이 실험을 하였다.In order to evaluate the effect of improving skin wrinkles of a cosmetic containing galloyl peptide stabilized by nanoliposome as an active ingredient, an experiment was conducted as follows.
피시험자는 30세 이상의 성인 여성 22명을 대상으로 하였으며, 피시험자는 4주 동안 매일 아침, 저녁 세안 후 상기 실시예 1, 실시예 2, 및 비교예 1 내지 4의 화장료를 안면에 고르게 도포하여 충분히 흡수되도록 하였다. The test subjects were 22 adult women aged 30 years or older, and the test subject evenly applied the cosmetics of Examples 1, 2, and Comparative Examples 1 to 4 on their face after washing their faces every morning and evening for 4 weeks. It was made to be sufficiently absorbed.
주름개선 평가를 위하여 ANTERA 3D (Miravex, Ireland)를 적용하였으며, 기기측정은 시험물질 사용 전과 2주 사용 후, 4주 사용 후의 시점에서 이루어졌다. 동일한 시험담당자가 모든 피시험자의 왼쪽 눈꼬리부위를 측정하였고, 측정의 재현성을 위하여 시험 물질 사용 전에 측정한 이미지와 오버랩시켜 동일부위를 측정하였다. 촬영된 이미지는 ANTERA 3D 전용 소프트웨어인 ANTERA pro software를 이용하여 매칭시킨 후 일치된 측정부위를 분석에 사용하였다. To evaluate wrinkle improvement, ANTERA 3D (Miravex, Ireland) was applied, and the instrument measurement was performed before, after 2 weeks of use, and after 4 weeks of use of the test substance. The same test person measured the left tail of all subjects, and for reproducibility of the measurement, the same area was measured by overlapping the image measured before use of the test substance. The photographed images were matched using ANTERA pro software, which is an exclusive software for ANTERA 3D, and then the matched measurement sites were used for analysis.
측정값은 측정변수인 Indentation index를 이용하여 피부의 주름을 나타내는 Wrinkles small값을 분석하였다. 하기 표 6에서는 실시예 1, 실시예 2, 및 비교예 1 내지 4의 화장료 사용에 따른 피시험자의 4주 후의 Wrinkles small값의 변화량을 나타내었다. 즉, 주름 개선 효과가 우수할수록 Wrinkles small 값의 변화량은 크게 나타난다. As the measured value, the small Wrinkles value representing the wrinkles of the skin was analyzed using the Indentation index, a measurement variable. Table 6 below shows the amount of change in the small value of Wrinkles after 4 weeks of the test subject according to the use of the cosmetics of Examples 1, 2, and Comparative Examples 1 to 4. That is, the better the wrinkle improvement effect, the larger the amount of change in the Wrinkles small value appears.
표 6에 나타난 바와 같이, 실시예 1 및 2의 화장료 조성물의 피부 주름 개선 효과가 우수한 것으로 확인되었다. 특히, 비타민 C 및 갈로일 펩타이드가 나노리포좀에 의해 안정화된 화장료 조성물(실시예 1)은 비타민 C가 나노리포좀에 함유되지 않은 화장료 조성물(비교예 1) 보다 피부 주름 개선 효과가 높은 것으로 분석되었다. As shown in Table 6, it was confirmed that the cosmetic compositions of Examples 1 and 2 had excellent skin wrinkle improvement effects. In particular, it was analyzed that the cosmetic composition in which vitamin C and galloyl peptide were stabilized by nanoliposomes (Example 1) had a higher effect on improving skin wrinkles than the cosmetic composition (Comparative Example 1) in which vitamin C was not contained in nanoliposomes.
실험예 5: 피부 침투 효과 평가Experimental Example 5: Evaluation of skin penetration effect
나노리포좀에 의해 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료의 피부 침투 효과를 알아보기 위하여 다음과 같이 실험을 하였다.In order to investigate the skin penetration effect of cosmetics containing galloyl peptide stabilized by nanoliposome as an active ingredient, an experiment was conducted as follows.
Dermal Equivalent (DE)-인체 정상 섬유아세포 1 X 105 cell/㎖를 인체의 결합조직을 이루는 섬유조직과 유사한 겔 구조에 콜라겐 수용액 3 mg/㎖:5 X DEM : 2:2 소듐바이카보네이트와 200 mM Hepes 완충액이 포함된 0.05 N 수산화나트륨이 7:2:1로 혼합된 배지에 접종하여 5CO2, 37℃에서 7일 동안 배양하였다. 이를 3 ㎛ 다공성폴리카보네이트 (porous polycarbonate) 재질로 된 막 (membrane)에 의해 안쪽과 바깥쪽이 구분된 플레이트의 안쪽에 넣고 섬유아세포가 배양된 Derma Equivalent(DE) 표면 위에 표피각질형성세포 (Epidermal Keratinocyte) 1 X 105 cell/㎖ 세포를 접종하여 EGF와 BPE가 함유된 K-SFM 배지를 안쪽과 바깥쪽에 넣고 7일 동안 배양하였다.Dermal Equivalent (DE)- human body normal fibroblasts 1 X 10 5 cells/ml in a gel structure similar to the fibrous tissues of the human body, collagen aqueous solution 3 mg/ml:5 X DEM: 2:2 sodium bicarbonate and 200 0.05 N sodium hydroxide containing mM Hepes buffer was inoculated into a medium mixed with 7:2:1 and incubated at 5CO2 and 37°C for 7 days. It is placed inside the plate separated from the inside and outside by a membrane made of 3 ㎛ porous polycarbonate material and placed on the surface of Derma Equivalent (DE) in which fibroblasts are cultured, and epidermal keratinocytes (Epidermal Keratinocytes) ) 1 X 10 5 cells/ml cells were inoculated, and K-SFM medium containing EGF and BPE was added inside and outside and cultured for 7 days.
그 후 플레이트 안쪽의 배지를 버려 공기가 배양세포의 표면에 접촉되도록 하고 바깥쪽에 10% FBS가 함유된 K-SFM과 EGF가 들어있지 않은 DMEM이 동량으로 혼합된 배지를 넣고 2주간 배양하여 다층의 표피와 진피가 형성된 인공피부를 얻었다. 여기에 본 발명의 실험예 및 비교예를 맨 위층의 인공피부 조직에 적용하여 4시간 배양 후 콜라겐 펩타이드 함량을 분석하였다. 결과는 하기 표 7에 나타내었다. After that, discard the medium inside the plate so that the air comes into contact with the surface of the cultured cells, and add a mixed medium of K-SFM containing 10% FBS and DMEM containing no EGF in the same amount, and incubate for 2 weeks. Artificial skin with epidermis and dermis formed was obtained. Here, the experimental examples and comparative examples of the present invention were applied to the artificial skin tissue of the top layer, and the collagen peptide content was analyzed after 4 hours incubation. The results are shown in Table 7 below.
표 7에 나타난 바와 같이, 나노리포좀으로 안정화된 갈로일 펩타이드를 포함하는 화장료(실시예 1, 실시예 2, 비교예 1)는 나노리포좀화 하지 않은 갈로일 펩타이드를 포함하는 화장료와 비교하여 피부 침투효과가 현저하게 우수한 것으로 확인되었다. 즉, 상기 갈로일 펩타이드는 나노리포좀에 의해 안정화되어 피부 침투능이 극대화될 수 있다. As shown in Table 7, cosmetics containing galloyl peptide stabilized with nanoliposomes (Example 1, Example 2, and Comparative Example 1) penetrated the skin compared to cosmetics containing galloyl peptide that were not nanoliposomal. It was confirmed that the effect was remarkably excellent. That is, the galloyl peptide can be stabilized by nanoliposomes to maximize skin penetration.
실험예 6: 제형의 안정성 평가Experimental Example 6: Evaluation of the stability of the formulation
나노리포좀에 의해 안정화된 갈로일 펩타이드를 유효성분으로 포함하는 화장료 제형의 안정성을 평가하기 위하여 다음과 같이 실험을 하였다.In order to evaluate the stability of the cosmetic formulation containing the galloyl peptide stabilized by the nanoliposome as an active ingredient, an experiment was conducted as follows.
화장료의 안정성을 시험하기 위해 상기 실시예 및 비교예의 화장료 조성물을 불투명초자 용기에 담아 45℃ 및 4℃로 온도를 일정하게 유지하면서 12주간 보관한 후, 변색 및 변취, 분리정도를 비교 측정하였다. 결과는 하기 표 8에 나타내었다. In order to test the stability of cosmetics, the cosmetic compositions of Examples and Comparative Examples were put in an opaque glass container and stored for 12 weeks while maintaining a constant temperature at 45° C. and 4° C., and then discoloration, discoloration, and degree of separation were measured. The results are shown in Table 8 below.
<평가기준><Evaluation Criteria>
0: 변화없음 / 1: 극히 조금 분리(변색) / 2: 조금 분리(변색) / 3: 조금 심하게 분리(변색) / 4: 심하게 분리(변색) / 5: 극히 심하게 분리(변색)0: No change / 1: Very little separation (discoloration) / 2: Little separation (discoloration) / 3: Little severe separation (discoloration) / 4: Very severe separation (discoloration) / 5: Extremely separation (discoloration)
표 8에 나타난 바와 같이, 나노리포좀으로 안정화된 갈로일 펩타이드를 포함하는 화장료(실시예 1, 실시예 2, 비교예 1)는 45℃에서 변색이나 변취, 분리 현상이 거의 나타나지 않고 안정한 상태로 존재하였으나, 나노리포좀화 하지 않은 갈로일 펩타이드를 제형화한 화장료(비교예 2, 3)는 분리 및 변색이 일어나 갈로일 펩타이드의 불안정성뿐만 아니라, 제형 자체가 불안정해진 것으로 확인되었다. As shown in Table 8, cosmetics containing galloyl peptides stabilized with nanoliposomes (Examples 1, 2, and Comparative Example 1) hardly exhibit any discoloration, discoloration, or separation at 45°C, and exist in a stable state. However, it was confirmed that not only the instability of the galloyl peptide but also the formulation itself was unstable due to separation and discoloration of the cosmetic composition (Comparative Examples 2 and 3) formulated with the galloyl peptide that was not nanoliposomalized.
전술한 본 발명의 설명은 예시를 위한 것이며, 본 발명이 속하는 기술분야의 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다른 구체적인 형태로 쉽게 변형이 가능하다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야만 한다. 예를 들어, 단일형으로 설명되어 있는 각 구성 요소는 분산되어 실시될 수도 있으며, 마찬가지로 분산된 것으로 설명되어 있는 구성 요소들도 결합된 형태로 실시될 수 있다.The above description of the present invention is for illustrative purposes only, and those of ordinary skill in the art to which the present invention pertains will be able to understand that other specific forms can be easily modified without changing the technical spirit or essential features of the present invention. will be. Therefore, it should be understood that the embodiments described above are illustrative in all respects and are not limiting. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as being distributed may also be implemented in a combined form.
본 발명의 범위는 후술하는 특허청구범위에 의해 나타내어지며, 특허청구범위의 의미 및 범위 그리고 그 균등 개념으로부터 도출되는 모든 변경 또는 변형된 형태가 본 발명의 범위에 포함되는 것으로 해석되어야 한다.The scope of the present invention is indicated by the claims to be described later, and all changes or modified forms derived from the meaning and scope of the claims and their equivalent concepts should be construed as being included in the scope of the present invention.
<110> AMI COSMETIC CO., LTD. <120> COSMETIC COMPOSITION CONTAINING GALLOYL-PEPTIDE STABILIZED IN NANOLIPOSOME <130> 2015PP10839 <160> 1 <170> KopatentIn 2.0 <210> 1 <211> 9 <212> PRT <213> Artificial Sequence <220> <223> Galloyl peptide <400> 1 Tyr Gly Gly Phe Leu Arg Lys Tyr Pro 1 5 <110> AMI COSMETIC CO., LTD. <120> COSMETIC COMPOSITION CONTAINING GALLOYL-PEPTIDE STABILIZED IN NANOLIPOSOME <130> 2015PP10839 <160> 1 <170> KopatentIn 2.0 <210> 1 <211> 9 <212> PRT <213> Artificial Sequence <220> <223> Galloyl peptide <400> 1 Tyr Gly Gly Phe Leu Arg Lys Tyr Pro 1 5
Claims (6)
[화학식 1]
상기 식에서 n은 1 내지 3 중 하나의 정수이고, L은 서열번호 1의 올리고 펩타이드이다.
A cosmetic composition for improving skin wrinkles or improving skin elasticity, which comprises, as an active ingredient, a galloyl peptide and a vitamin C derivative represented by the following formula (1) stabilized with a nanoliposome.
[Chemical Formula 1]
Wherein n is an integer from 1 to 3 and L is an oligopeptide of SEQ ID NO: 1.
[화학식 1]
상기 식에서 n은 1 내지 3 중 하나의 정수이고, L은 서열번호 1의 올리고 펩타이드이다.
A cosmetic composition for moisturizing skin comprising, as an active ingredient, a galloyl peptide and a vitamin C derivative represented by the following formula (1) stabilized with a nanoliposome.
[Chemical Formula 1]
Wherein n is an integer from 1 to 3 and L is an oligopeptide of SEQ ID NO: 1.
상기 나노리포좀은 포스파티딜콜린의 함량이 70 중량% 이상인 대두 유래의 레시틴에 의해 안정화된 화장료 조성물.
The method according to claim 1,
Wherein the nanoliposome is stabilized by soybean-derived lecithin having a phosphatidylcholine content of 70 wt% or more.
상기 나노리포좀은 상기 나노리포좀 총 중량에 대하여 0.01 내지 20.0 중량%의 비타민 C 유도체를 포함하는 화장료 조성물.
The method according to claim 1,
Wherein the nanoliposome comprises 0.01 to 20.0% by weight of a vitamin C derivative based on the total weight of the nanoliposome.
상기 나노리포좀은 조성물 총 중량에 대하여 0.1 내지 20.0 중량% 포함된 화장료 조성물.
The method according to claim 1,
Wherein the nanoliposome is contained in an amount of 0.1 to 20.0% by weight based on the total weight of the composition.
유연화장수, 영양화장수, 영양크림, 마사지크림, 에센스, 아이크림, 클렌징크림, 클렌징폼, 클렌징워터, 팩, 스프레이 및 파우더로 이루어진 군에서 선택된 하나 이상으로 제형화된 화장료 조성물.
The method according to claim 1,
Wherein the cosmetic composition is formulated with at least one selected from the group consisting of softening agents, nutritional lotion, nutritional cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray and powder.
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