KR20100092150A - Composition for skin whitening containing dipeptide - Google Patents

Composition for skin whitening containing dipeptide Download PDF

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KR20100092150A
KR20100092150A KR1020090011378A KR20090011378A KR20100092150A KR 20100092150 A KR20100092150 A KR 20100092150A KR 1020090011378 A KR1020090011378 A KR 1020090011378A KR 20090011378 A KR20090011378 A KR 20090011378A KR 20100092150 A KR20100092150 A KR 20100092150A
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arginine
cysteine
tryptophan
tyrosine
valine
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KR1020090011378A
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KR101222685B1 (en
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박소희
이현경
최혜령
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주식회사 웰스킨
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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

PURPOSE: A composition containing dipeptide for skin whitening is provided to reduce cost by using small peptide. CONSTITUTION: A composition for skin whitening contains dipeptide comprising two amino acids among the group selected from amino acid groups. A composition for skin whitening contains 0.001-30 weight% of dipeptide based on total weight. The composition is used in the form of skin, lotion, cream, foundation, essence, gel, pack, foam cleanser, and soap.

Description

다이펩타이드를 포함하는 피부 미백용 조성물{Composition for skin whitening containing dipeptide}Composition for skin whitening containing dipeptides

본 발명은 펩타이드를 포함하는 피부 미백용 조성물에 관한 것으로, 더욱 상세하게는 아미노산 2개로 구성된 펩타이드를 포함하는 피부 미백용 조성물에 관한 것이다. The present invention relates to a composition for skin whitening comprising a peptide, and more particularly to a composition for skin whitening comprising a peptide consisting of two amino acids.

인간의 피부색을 결정하는 색소로는 멜라닌, 헤모글로빈, 카로티노이드가 있으며, 이들 색소에 의해 인간의 피부, 모발, 눈 등의 색이 다양하게 나타난다. The pigments that determine human skin color include melanin, hemoglobin, and carotenoids, and various pigments of human skin, hair, and eyes appear by these pigments.

현재 미용적 목적을 위하여 멜라닌 생성을 억제하기 위한 다양한 방법들이 사용되고 있는데, 멜라닌은 멜라닌세포(melanocytes)에서 아미노산인 티로신(tyrosine)이 티로시나제(tyrosinase)에 의해 도파퀴논(dopa-quinone)으로 전환되는 것을 시작으로, 계속되는 일련의 산화 과정을 거쳐 갈색(pheomelanin) 또는 흑색(eumelanin)의 중합체로 형성된다. 이처럼 멜라닌의 생성 과정은 티로시나제(tyrosinase)라는 속도 조절 단계의 효소가 관여하는 반응으로서, 티로시나제의 활성을 억제하여 피부의 미백 효과를 기대할 수 있다.Various methods are currently used to suppress melanin production for cosmetic purposes. Melanin is the conversion of tyrosine, an amino acid from melanocytes, to dopa-quinone by tyrosinase. Beginning, a series of oxidation processes are followed to form a brown (pheomelanin) or black (eumelanin) polymer. The melanin production process is a reaction involving an enzyme in a rate control step called tyrosinase, and it can be expected to whiten the skin by inhibiting the activity of tyrosinase.

한편, 펩타이드의 미백 효과에 대해서는 잘 알려지지 않았는데, 대한민국 특허출원 10-2002-0016298(멜라닌 생성 억제 펩티드, 그 제조방법, 및 이를 함유하는 피부외용제조성물)을 보면, 4개의 아미노산으로 구성된 펩타이드로서, 특히 첫 번째 아미노산 및 두 번째 아미노산이 티로신 또는 트립토판에서 선택되고, 세 번째 아미노산이 트립토판, 네 번째 아미노산이 아르기닌으로 구성되는 4개의 아미노산으로 구성된 펩타이드에 미백 효능이 있음이 보고된 바 있다. On the other hand, the whitening effect of the peptide is not well known, Korean Patent Application No. 10-2002-0016298 (Melanin Production Inhibition Peptides, Method of Preparation, and External Skin Composition Containing the Same), as a peptide consisting of four amino acids, in particular It has been reported that the first amino acid and the second amino acid are selected from tyrosine or tryptophan, and the third amino acid has a whitening effect on a peptide consisting of four amino acids consisting of tryptophan and fourth amino acid.

또한, 대한민국 등록특허 10-0760875(공고일자: 2007년10월04일)호에는 세포 내의 멜라닌 생성을 억제하여 기미, 주근깨 개선 등의 피부 미백을 위하여 어류로부터 유래한 젤라틴 펩티드를 함유하는 화장품 조성물로서, 펩타이드 화합물은 분자 중에 글리신-프롤린-하이드록실프롤린(Glycine-Proline-Hydroxyproline)의 아미노산 서열을 갖고, 아미노산 3~20개로 이루어져 있는 것을 특징으로 하는 피부 미백능 화장품 조성물이 보고된 바 있다. In addition, the Republic of Korea Patent No. 10-0760875 (announced: October 04, 2007) is a cosmetic composition containing a gelatin peptide derived from fish for skin whitening such as blemishes, freckles, etc. by inhibiting the production of melanin in the cells , The peptide compound has an amino acid sequence of glycine-proline-hydroxyproline (Glycine-Proline-Hydroxyproline) in the molecule, has been reported skin whitening cosmetic composition, characterized in that consisting of 3 to 20 amino acids.

그런데, 펩타이드는 길이에 따라 분자량이 커지고, 그에 따라 생산 가격도 상승하며, 세포 투과성이 감소하므로, 가급적 길이가 짧은 펩타이드가 유용한데, 근래까지 많은 연구자들은 펩타이드의 길이가 짧으면 특별한 기능을 하기 어려울 것이라 쉽게 단정하고, 이들의 효능 특히 피부 미백능을 적극적으로 연구하지는 않았다. However, since the peptide has a large molecular weight along its length, the production price increases accordingly, and the cell permeability decreases, a short peptide is useful. Until now, many researchers will find it difficult to perform a special function if the peptide length is short. Easily neat and did not actively study their efficacy, particularly skin whitening.

이에 본 발명은 길이가 짧은 펩타이드, 즉 아미노산 2개로 구성된 펩타이드에 피부 미백능이 있는지 여부를 규명하고, 그 효능이 확인된 펩타이드를 포함하는 피부 미백용 조성물을 개발하여 제공하는데 그 목적이 있다. Accordingly, an object of the present invention is to determine whether a skin whitening ability is present in a short peptide, that is, a peptide consisting of two amino acids, and to develop and provide a composition for skin whitening including a peptide whose efficacy has been confirmed.

상기 목적을 달성하기 위하여 본 발명은, 하기의 그룹 A~C 중 선택되는 어느 하나의 그룹에 속하는 아미노산 2개로 구성된 다이펩타이드를 하나 이상 포함하는 것을 특징으로 하는 피부 미백용 조성물을 제공한다. In order to achieve the above object, the present invention provides a composition for skin whitening comprising at least one dipeptide consisting of two amino acids belonging to any one group selected from the following groups A to C.

[그룹 A] : AL(알라닌-류신), AK(알라닌-라이신), AW(알라닌-트립토판), CM(시스테인-메티오닌), CS(시스테인-세린), DV(아스파트산-발린), EA(글루탐산-알라닌), EL(글루탐산-류신), EQ(글루탐산-글루타민), FK(페닐알라닌-라이신), FW(페닐알라닌-트립토판), GD(글라이신-아스파트산), GR(글라이신-아르기닌), GW(글라이신-트립토판), HA(히스티딘-알라닌), HC(히스티딘-시스테인), HD(히스티딘-아스파트산), HG(히스티딘-글라이신), HH(히스티딘-히스티딘), HS(히스티딘-세린), HV(히스티딘-발린), HW(히스티딘-트립토판), IA(이소류신-알라닌), IF(이소류신-페닐알라닌), II(이소류신-이소류신), IL(이소류신-류신), KD(라이신-아스파트산), LE(류신-글루탐산), MQ(메티오닌-글루타민), MY(메티오닌-타이로신), NP(아스파라진-프로린), NR(아스파라진-아르기닌), PF(프로린-페닐알라닌), PH(프로린-히 스티딘), PR(프로린-아르기닌), PT(프로린-트레오닌), QR(글루타민-아르기닌), QS(글루타민-세린), QV(글루타민-발린), RG(아르기닌-글라이신), RH(아르기닌-히스티딘), RI(아르기닌-이소류신), RN(아르기닌-아스파라진), RP(아르기닌-프로린), SI(세린-이소류신), SK(세린-라이신), TI(트레오닌-이소류신), TK(트레오닌-라이신), TL(트레오닌-류신), TM(트레오닌-메티오닌), TN(트레오닌-아스파라진), VG(발린-글라이신), VP(발린-프로린), VV(발린-발린), VY(발린-타이로신), WD(트립토판-아스파트산), WI(트립토판-이소류신), WK(트립토판-라이신), WM(트립토판-메티오닌), WN(트립토판-아스파라진), WP(트립토판-프로린), WY(트립토판-타이로신), YD(타이로신-아스파트산), YE(타이로신-글루탐산), YG(타이로신-글라이신), YK(타이로신-라이신), YP(타이로신-프로린), YT(타이로신-트레오닌) [Group A]: AL (alanine-leucine), AK (alanine-lysine), AW (alanine-tryptophan), CM (cysteine-methionine), CS (cysteine-serine), DV (aspartic acid-valine), EA (Glutamic acid-alanine), EL (glutamic acid-leucine), EQ (glutamic acid-glutamine), FK (phenylalanine-lysine), FW (phenylalanine-tryptophan), GD (glycine-aspartic acid), GR (glycine-arginine), GW (glycine-tryptophan), HA (histidine-alanine), HC (histidine-cysteine), HD (histidine-aspartic acid), HG (histidine-glycine), HH (histidine-histidine), HS (histidine-serine) , HV (histidine-valine), HW (histidine-tryptophan), IA (isoleucine-alanine), IF (isoleucine-phenylalanine), II (isoleucine-isoleucine), IL (isoleucine-leucine), KD (lysine-aspartic acid ), LE (leucine-glutamic acid), MQ (methionine-glutamine), MY (methionine-tyrosine), NP (asparagine-proline), NR (asparagine-arginine), PF (proline-phenylalanine), PH (proline- Stidine), PR (proline-arginine), PT (proline-threonine), QR (glutamine-arginine), QS (glutamine-serine), QV (glutamine-valine), RG (arginine-glycine), RH (arginine- Histidine), RI (arginine-isoleucine), RN (arginine-asparagine), RP (arginine-proline), SI (serine-isoleucine), SK (serine-lysine), TI (threonine-isoleucine), TK (threonine- Lysine), TL (threonine-leucine), TM (threonine-methionine), TN (threonine-asparagine), VG (valine-glycine), VP (valine-proline), VV (valine-valine), VY (valine- Tyrosine), WD (tryptophan-aspartic acid), WI (tryptophan-isoleucine), WK (tryptophan- lysine), WM (tryptophan-methionine), WN (tryptophan-asparagine), WP (tryptophan-proline), WY Tryptophan-tyrosine), YD (tyrosine-aspartic acid), YE (tyrosine-glutamic acid), YG (tyrosine-glycine), YK (tyrosine-lysine), YP (tyrosine-proline), YT (tyrosine-threonine)

[그룹 B] : AG(알라닌-글라이신), AR(알라닌-아르기닌), AS(알라닌-세린), AT(알라닌-트레오닌), CE(시스테인-글루탐산), CQ(시스테인-글루타민), DE(아스파트산-글루탐산), DI(아스파트산-이소류신), DL(아스파트산-류신), DN(아스파트산-아스파라진), DT(아스파트산-트레오닌), DY(아스파트산-타이로신), ER(글루탐산-아르기닌), EK(글루탐산-라이신), FF(페닐알라닌-페닐알라닌), FM(페닐알라닌-메티오닌), FR(페닐알라닌-아르기닌), FY(페닐알라닌-타이로신), GK(글라이신-라이신), GQ(글라이신-글루타민), GY(글라이신-타이로신), IG(이소류신-글라이신), IP(이소류신-프로린), IQ(이소류신-글루타민), KC(라이신-시스테인), KW(라이신-트립토판), PK(프로린-라이신), QD(글루타민-아스파트산), SG(세린-글라이신), SL(세린-류신), SH(세린-히스티딘), SQ(세린-글루타민), SS(세린-세린), TD(트레오닌-아스 파트산), TP(트레오닌-프로린), VK(발린-라이신), VN(발린-아스파라진), VQ(발린-글루타민), WV(트립토판-발린), YM(타이로신-메티오닌), YN(타이로신-아스파라진), YS(타이로신-세린) [Group B]: AG (alanine-glycine), AR (alanine-arginine), AS (alanine-serine), AT (alanine-threonine), CE (cysteine-glutamic acid), CQ (cysteine-glutamine), DE (as Partsic acid-glutamic acid), DI (aspartic acid-isoleucine), DL (aspartic acid-leucine), DN (aspartic acid-asparagine), DT (aspartic acid-threonine), DY (aspartic acid-tyrosine) ), ER (glutamic acid-arginine), EK (glutamic acid-lysine), FF (phenylalanine-phenylalanine), FM (phenylalanine-methionine), FR (phenylalanine-arginine), FY (phenylalanine-tyrosine), GK (glycine-lysine) , GQ (glycine-glutamine), GY (glycine-tyrosine), IG (isoleucine-glycine), IP (isoleucine-proline), IQ (isoleucine-glutamine), KC (lysine-cysteine), KW (lysine-tryptophan), PK (proline-lysine), QD (glutamine-aspartic acid), SG (serine-glycine), SL (serine-leucine), SH (serine-histidine), SQ (serine-glutamine), SS (serine-serine) , TD (t Onin-aspartic acid), TP (threonine-proline), VK (valine-lysine), VN (valine-asparagine), VQ (valine-glutamine), WV (tryptophan-valine), YM (tyrosine-methionine), YN (tyrosine-asparagine), YS (tyrosine-serine)

[그룹 C] : AF(알라닌-페닐알라닌), AM(알라닌-메티오닌), AP(알라닌-프로린), AV(알라닌-발린), CA(시스테인-알라닌), CC(시스테인-시스테인), CD(시스테인-아스파트산), CF(시스테인-페닐알라닌), CG(시스테인-글라이신), CI(시스테인-이소류신), CK(시스테인-라이신), CL(시스테인-류신), CP(시스테인-프로린), CR(시스테인-아르기닌), CT(시스테인-트레오닌), CV(시스테인-발린), CW(시스테인-트립토판), CY(시스테인-타이로신), DC(아스파트산-시스테인), DR(아스파트산-아르기닌), DQ(아스파트산-글루타민), DW(아스파트산-트립토판), EY(글루탐산-타이로신), FD(페닐알라닌-아스파트산), FG(페닐알라닌-글라이신), FH(페닐알라닌-히스티딘), FL(페닐알라닌-류신), FP(페닐알라닌-프로린), FV(페닐알라닌-발린), GG(글라이신-글라이신), GH(글라이신-히스티딘), GI(글라이신-이소류신), GN(글라이신-아스파라진), HF(히스티딘-페닐알라닌), HK(히스티딘-라이신), HL(히스티딘-류신), ID(이소류신-아스파트산), IV(이소류신-발린), LI(류신-이소류신), LR(류신-아르기닌), MD(메티오닌-아스파트산), NA(아스파라진-알라닌), ND(아스파라진-아스파트산), NG(아스파라진-글라이신), NH(아스파라진-히스티딘), NK(아스파라진-라이신), NW(아스파라진-트립토판), PD(프로린-아스파트산), PQ(프로린-글루타민), QE(글루타민-글루탐산), QM(글루타민-메티오닌), QW(글루타민-트립토판), RA(아르기닌-알라닌), RC(아르기닌-시스테인), RD(아르기닌-아스파트산), RF(아르기닌-페닐알라 닌), RK(아르기닌-라이신), RQ(아르기닌-글루타민), RR(아르기닌-아르기닌), RV(아르기닌-발린), RY(아르기닌-타이로신), SR(세린-아르기닌), SY(세린-타이로신), TR(트레오닌-아르기닌), TT(트레오닌-트레오닌), TW(트레오닌-트립토판), VC(발린-시스테인), VL(발린-류신), VM(발린-메티오닌), VS(발린-세린), VT(발린-트레오닌), VW(발린-트립토판), WA(트립토판-알라닌), WC(트립토판-시스테인), WE(트립토판-글루탐산), WH(트립토판-히스티딘), WS(트립토판-세린), YA(타이로신-알라닌), YC(타이로신-시스테인), YH(타이로신-히스티딘), YL(타이로신-류신), YW(타이로신-트립토판)[Group C]: AF (alanine-phenylalanine), AM (alanine-methionine), AP (alanine-proline), AV (alanine-valine), CA (cysteine-alanine), CC (cysteine-cysteine), CD (cysteine Aspartic acid), CF (cysteine-phenylalanine), CG (cysteine-glycine), CI (cysteine-isoleucine), CK (cysteine-lysine), CL (cysteine-leucine), CP (cysteine-proline), CR ( Cysteine-arginine), CT (cysteine-threonine), CV (cysteine-valine), CW (cysteine-tryptophan), CY (cysteine-tyrosine), DC (aspartic acid-cysteine), DR (aspartic acid-arginine) , DQ (aspartic acid-glutamine), DW (aspartic acid-tryptophan), EY (glutamic acid-tyrosine), FD (phenylalanine-aspartic acid), FG (phenylalanine-glycine), FH (phenylalanine-histidine), FL (Phenylalanine-leucine), FP (phenylalanine-proline), FV (phenylalanine-valine), GG (glycine-glycine), GH (glycine-histidine), GI (glycine-isoleucine), GN (glas Shin-asparagine), HF (histidine-phenylalanine), HK (histidine-lysine), HL (histidine-leucine), ID (isoleucine-aspartic acid), IV (isoleucine-valine), LI (leucine-isoleucine), LR (leucine-arginine), MD (methionine-aspartic acid), NA (asparagine-alanine), ND (asparagine-aspartic acid), NG (asparagine-glycine), NH (asparagine-histidine), NK (asparagine-lysine), NW (asparagine-tryptophan), PD (proline-aspartic acid), PQ (proline-glutamine), QE (glutamine-glutamic acid), QM (glutamine-methionine), QW (glutamine-methionine) Tryptophan), RA (arginine-alanine), RC (arginine-cysteine), RD (arginine-aspartic acid), RF (arginine-phenylalanine), RK (arginine-lysine), RQ (arginine-glutamine), RR (Arginine-arginine), RV (arginine-valine), RY (arginine-tyrosine), SR (serine-arginine), SY (serine-tyrosine), TR (threonine-arginine), TT (threonine-threonine), TW ( T Onin-tryptophan), VC (valine-cysteine), VL (valine-leucine), VM (valine-methionine), VS (valine-serine), VT (valine-threonine), VW (valine-tryptophan), WA (tryptophan) -Alanine), WC (tryptophan-cysteine), WE (tryptophan-glutamic acid), WH (tryptophan-histidine), WS (tryptophan-serine), YA (tyrosine-alanine), YC (tyrosine-cysteine), YH (tyrosine-cysteine) Histidine), YL (tyrosine-leucine), YW (tyrosine-tryptophan)

한편, 본 발명의 피부 미백용 조성물은 상기 그룹 A~C로부터 선택된 어느 하나 이상의 다이펩타이드를 조성물 전체 대비 0.001~30 중량% 함유하는 것이 좋은데, 그 함량이 0.001중량% 미만일 경우에는 미백 효과가 미미하고, 30중량%를 초과할 경우에는 첨가량 증진에 따른 효과의 증진 효과가 미미하기 때문이다. On the other hand, the composition for skin whitening of the present invention preferably contains 0.001 to 30% by weight of any one or more dipeptides selected from the groups A to C, when the content is less than 0.001% by weight, the whitening effect is insignificant If the amount exceeds 30% by weight, the effect of increasing the amount of addition is minimal.

한편, 본 발명의 피부 미백용 조성물에서, 조성물의 제품 형태 및 제형은 피부 외부에 적용되어 작용될 수 있는 것이라면, 팩, 화장품(또는 화장료) 또는 약품 등의 형태를 모두 포함하며, 페이스트 상, 액상 또는 액상에 현탁되어 피부에 사용될 수 있는 형태라면 분말도 포함하는 등 여타의 모든 제형을 포함한다. 화장품의 예로는 스킨, 로션, 크림, 파운데이션, 에센스, 젤, 팩, 폼 클렌징, 비누 등이 있고, 약품으로는 피부외용 연고 등이 있다. On the other hand, in the composition for skin whitening of the present invention, if the product form and formulation of the composition can be applied to the outside of the skin, including the form of a pack, cosmetics (or cosmetics) or drugs, and paste, liquid Or all other formulations, including powders, if they are suspended in liquid form and can be used on the skin. Examples of cosmetics include skins, lotions, creams, foundations, essences, gels, packs, foam cleansing, soaps, and the like.

또한, 제조하고자 하는 제형에 따라 추가로 또는 필요에 의해 유분, 물, 계면활성제, 보습제, 저급알콜, 점증제, 킬레이트제, 색소, 방부제, 향료 등을 선택하여 적정량 첨가할 수도 있다. 특히 멜라닌 형성의 주요한 요인이 자외선임을 고려할 때, 본 발명의 조성물은 자외선 차단제, 광산란제 등을 첨가할 수도 있다.In addition, depending on the formulation to be prepared, an appropriate amount may be additionally selected and optionally selected from oils, water, surfactants, humectants, lower alcohols, thickeners, chelating agents, pigments, preservatives, fragrances, and the like. In particular, considering that the main factor of melanin formation is ultraviolet light, the composition of the present invention may add a sunscreen, a light scattering agent and the like.

한편, 본 발명의 다이펩타이드를 포함하는 피부 미백용 조성물은 비경구(피하) 투여용 약제 조성물일 수 있는데, 제제 및 사용방법에 따라 약학적으로 허용 가능한 담체를 포함할 수 있다. 약제 조성물로는 1일 10~50 ㎎으로 1회 내지 3회 사용하는 것이 바람직하며, 건강 상태에 따라 또는 의사의 처방에 의해 투약 회수 및 투여량을 조절할 수도 있다Meanwhile, the composition for skin whitening comprising the dipeptide of the present invention may be a pharmaceutical composition for parenteral (subcutaneous) administration, and may include a pharmaceutically acceptable carrier according to the formulation and the method of use. The pharmaceutical composition is preferably used once or three times at 10 to 50 mg per day, and the number of doses and dosages may be adjusted according to a medical condition or by a doctor's prescription.

이하, 본 발명의 내용을 하기에서 더욱 상세히 설명하고자 한다. Hereinafter, the content of the present invention will be described in more detail below.

본 발명자들은 20종의 아미노산 중 2개를 선택 및 연결하여 모두 400개의 다이펩타이드(dipeptide)를 제조한 후, 이들을 대상으로 하여 미백능 존재 여부를 조사하였다. 본 발명에서는 시험관 내 티로시나제 효소 억제법이 아니라, 세포를 대상으로 미백 효능을 확인하여 실제 작용할 수 있는 미백 소재를 발굴하고자 하였다. 본 발명에서 미백 효능 확인을 위해 사용한 세포는 B16 악성흑색종 세포주와 불멸화된 마우스 멜라닌세포주인 Mel-Ab cell이다. The present inventors selected and linked two of 20 amino acids to prepare 400 dipeptides, and then examined the presence of whitening ability. In the present invention, in vitro tyrosinase enzyme inhibition method, to determine the whitening effect on the cells to find a whitening material that can actually work. Cells used to confirm the whitening efficacy in the present invention is a B16 malignant melanoma cell line and an immortalized mouse melanocyte cell line Mel-Ab cell.

B16 악성흑색종세포주는 미백효능 검색을 위해 가장 많이 사용되는 흑색종세포주로 미백 효능 검색시 alpha-MSH를 처리하여 멜라닌 생성을 증가시킨 후, 이 의 억제 효과를 측정하므로 신호 전달 과정 중의 PKA(Protein Kinase A) 기전을 억제하여 작용하는 미백 소재를 탐색할 수 있는 좋은 세포주라 할 수 있다. (Choi MY, Song HS, Hur HS, Sim SS. Whitening activity of luteolin related to the inhibition of cAMP pathway in alpha-MSH-stimulated B16 melanoma cells. Arch Pharm Res. 2008 Sep;31(9):1166-71. Epub 2008 Sep 20) B16 malignant melanoma cell line is the most frequently used melanoma cell line to detect whitening efficacy. In the whitening efficacy test, BKA treated with alpha-MSH increases melanin production and then measures its inhibitory effect. Kinase A) It is a good cell line that can search for whitening materials that act by inhibiting the mechanism. (Choi MY, Song HS, Hur HS, Sim SS.Whitening activity of luteolin related to the inhibition of cAMP pathway in alpha-MSH-stimulated B16 melanoma cells.Arch Pharm Res. 2008 Sep; 31 (9): 1166-71. Epub 2008 Sep 20)

한편, 마우스의 불멸화세포주인 Mel-Ab cell은 세포 배양시 TPA를 첨가하여 배양하기 때문에 PKC(Protein Kinase C) 기전을 억제하여 작용하는 미백 소재를 탐색할 수 있는 좋은 세포주라 할 수 있다. (Park HY, Russakovsky V, Ao Y, Fernandez E, Gilchrest BA. Alpha-melanocyte stimulating hormone-induced pigmentation is blocked by depletion of protein kinase C, Exp Cell Res. 1996 Aug 25;227(1):70-9)/ Park HY, Lee J, GonzS, Middelkamp-Hup MA, Kapasi S, Peterson S, Gilchrest BA. Topical application of a protein kinase C inhibitor reduces skin and hair pigmentation. J Invest Dermatol. 2004 Jan;122(1):159-66). On the other hand, Mel-Ab cells, which are immortalized cell lines of mice, are cultured by adding TPA at the time of cell culture, which is a good cell line to search for whitening materials that act by inhibiting PKC (Protein Kinase C) mechanism. (Park HY, Russakovsky V, Ao Y, Fernandez E, Gilchrest BA.Alpha-melanocyte stimulating hormone-induced pigmentation is blocked by depletion of protein kinase C, Exp Cell Res. 1996 Aug 25; 227 (1): 70-9) / Park HY, Lee J, GonzS, Middelkamp-Hup MA, Kapasi S, Peterson S, Gilchrest BA. Topical application of a protein kinase C inhibitor reduces skin and hair pigmentation. J Invest Dermatol. 2004 Jan; 122 (1): 159-66).

이에 본 발명에서는 상기 두 가지 다른 특성을 가진 세포주를 이용하여 미백 효능을 탐색함으로써 다양한 작용 기작에 근거한 미백 소재를 탐색하고자 하였다. Therefore, the present invention was to search for whitening materials based on various mechanisms of action by searching for whitening efficacy using cell lines having two different characteristics.

B16 악성흑색종세포주를 사용한 실험 결과, 많은 종류의 다이펩타이드에 미백 효과가 있는 것으로 나타났다. 총 400종 가운데 32종에서 50% 이상의 미백 효능을 보여주었고, 19종은 30~50%, 56종은 10~30%의 억제 효능이 있었다. Mel-Ab 세포 를 사용한 실험에 대해서는 모두 34종에서 50% 이상의 미백 효능을 보였으며, 24종은 30~50%, 34종은 10~30%의 억제 효능을 보였다. Experiments with B16 malignant melanoma cell lines have shown that they have a whitening effect on many types of dipeptides. Of the 400 species, 32 showed more than 50% whitening efficacy, and 19 had 30-50% and 56 had 10-30% inhibitory effects. In the experiments using Mel-Ab cells, all of the 34 species showed more than 50% whitening efficacy, 24 of them showed 30-50%, 34 of them showed 10-30% inhibitory effect.

미백 효과를 나타내는 많은 수의 다이펩타이드는 두 가지 세포에서 서로 상이한 효과를 보여주었는데, 이는 다이펩타이드들이 단순히 티로시나제만을 억제하는 것이 아니라, 서로 다른 기전에 의해 미백 효과를 보였기 때문인 것으로 판단되었다. The large number of dipeptides showing whitening effect showed different effects in the two cells, which was judged to be due to the different mechanisms of dipeptides, not just tyrosinase.

실험에 따라 미백 효과를 나타내는 다이펩타이드들을 50% 이상 효과군(상기의 그룹 A), 30~50% 효과군(상기의 그룹 B), 10~30% 효과군(상기의 그룹 C)으로 분류하였고, 두 가지 세포에서 다른 효과를 보인 경우는 좋은 효과를 보인 군으로 분류하였다. According to the experiment, the dipeptides showing the whitening effect were classified into more than 50% effect group (Group A above), 30-50% effect group (Group B above), and 10-30% effect group (Group C above). In the case of different cells, the two cells were classified as having good effects.

본 발명에서는 아미노산이 2개 결합하여 생성된 다이펩타이드의 미백능을 규명하였는데, 4개의 아미노산으로 구성된 펩타이드로서, 특히 첫 번째 아미노산 및 두 번째 아미노산이 티로신 또는 트립토판에서 선택되고, 세 번째 아미노산이 트립토판, 네 번째 아미노산이 아르기닌으로 구성되는 총 4개의 아미노산으로 구성된 펩타이드에 미백 효능이 있음이 보고된 대한민국 특허 10-2002-0016298(멜라닌 생성 억제 펩티드, 그 제조방법, 및 이를 함유하는 피부외용제조성물)와는 펩타이드의 개수에 있어 차이가 있다. 즉, 펩타이드는 길이에 따라 분자량이 커지고 그에 따라 생산 가격이 상승하고, 세포투과성의 감소가 예상되는데, 본 발명자들은 4개의 아미노산으로 구성된 펩타이드가 아니라 단지 2개의 아미노산으로 구성된 펩타이드를 사용하였을 때 뛰어난 미백 효능을 확인할 수 있었고, 티로신이나 트립토판 에서 선택되지 않더라고 다양한 서열의 펩타이드에 미백 효능이 있음을 확인할 수 있었다. In the present invention, the whitening ability of the dipeptide produced by combining two amino acids was identified. As a peptide consisting of four amino acids, the first amino acid and the second amino acid are selected from tyrosine or tryptophan, and the third amino acid is tryptophan, Peptides with Korean Patent No. 10-2002-0016298 (Melanin Production Inhibition Peptide, Method for Producing It, and External Skin Composition Containing the Same), in which the fourth amino acid has a whitening effect on a peptide consisting of a total of four amino acids consisting of arginine There is a difference in the number of. In other words, the peptide is expected to increase in molecular weight along its length, increase the production price, and decrease the cell permeability. The inventors have excellent whitening when using a peptide consisting of only two amino acids instead of a peptide consisting of four amino acids. Efficacy was confirmed, and even though it was not selected from tyrosine or tryptophan, it was confirmed that the peptides of various sequences had whitening efficacy.

또한, 대한민국 특허 10-2002-0016298에서는 단지 4가지의 아미노산으로 구성된 펩타이드에 대한 미백능 검색을 시행하여 모두 76종의 펩타이드를 대상으로 하였지만, 본 발명에서는 2개의 아미노산으로 구성된 다이펩타이드 라이브러리 400개를 대상으로 하여 미백 효능 검색을 시행한 특징이 있다. In addition, the Republic of Korea Patent 10-2002-0016298 performed a whitening search for a peptide consisting of only four amino acids to target all 76 peptides, in the present invention 400 dipeptide library consisting of two amino acids There is a characteristic of conducting a whitening efficacy search.

또한, 대한민국 특허 10-2002-0016298에서는 시험관 내에서 티로시나제 효소를 억제하는 펩타이드를 검색하였으나, 본 발명자들은 멜라닌 세포주를 사용하여 세포 수준에서 미백능 확인 실험을 시행하였다. In addition, the Republic of Korea Patent 10-2002-0016298 searched for a peptide that inhibits the tyrosinase enzyme in vitro, the present inventors conducted a whitening ability identification experiment at the cellular level using melanin cell line.

본 발명자들의 실험에 의하면 시험관 내에서 티로시나제 효소를 전혀 억제하지 못하는 경우에도 세포 차원에서는 미백 효능이 있는 예도 많았다. 이는 본 발명에서 새롭게 미백 효능을 규명한 다이펩타이드들이 티로시나제 효소의 활성을 단순 억제하는 것이 아니라, 세포 신호 전달 기전을 조절하여 미백 효능을 나타낸 것이라 할 수 있다. (Kim DS et al. Sphingosine-1-phosphate Decreases Melanin Synthesis via Sustained ERK Activation and Subsequent MITF Degradation. J of Cell Sci, 2003) According to the experiments of the present inventors, even in the case of not inhibiting the tyrosinase enzyme at all in vitro, there were many examples of the whitening effect at the cellular level. This can be said that the dipeptides newly identified whitening efficacy in the present invention does not simply inhibit the activity of tyrosinase enzyme, but exhibits whitening efficacy by regulating cellular signal transduction mechanisms. (Kim DS et al. Sphingosine-1-phosphate Decreases Melanin Synthesis via Sustained ERK Activation and Subsequent MITF Degradation. J of Cell Sci, 2003)

또한, 대한민국특허 10-2002-0016298에서는 최고농도 1000uM에서 30~40% 억제의 낮은 미백 효능을 보인데 반하여, 본 발명의 다이펩타이드는 30~50uM (펩타이드 실험 농도 10ug/ml)의 낮은 농도에서도 최대 약 80%에 가까운 미백 효능을 보였다. 이와 같은 결과는 작은 펩타이드가 세포에 용이하게 침투했기 때문에 발생한 현상인 것으로 추측되었다. In addition, the Republic of Korea Patent 10-2002-0016298 shows a low whitening effect of 30-40% inhibition at the highest concentration of 1000uM, whereas the dipeptide of the present invention maximum at a low concentration of 30 ~ 50uM (peptide experiment concentration 10ug / ml) Almost 80% showed whitening efficacy. This result was presumed to be a phenomenon caused by the small peptide easily penetrated the cells.

본 발명은 그룹 A~C에 속하는 다이펩타이드를 포함하는 미백용 조성물을 제공하는데, 이미 알려진 테트라펩타이드(tetrapeptide)에 비하여 미백 효능이 크게 증가하고, 작은 펩타이드를 이용하게 됨으로써 비용을 크게 감소시킬 수 있는 효과가 있다. The present invention provides a composition for whitening comprising a dipeptide belonging to groups A to C, the whitening efficacy is greatly increased compared to the known tetrapeptide (tetrapeptide), and by using a small peptide can greatly reduce the cost It works.

미백능이 있는 본 발명의 그룹 A~C에 속하는 펩타이드는 단독 또는 여타의 피부 미백능이 있는 성분과의 혼합 사용에 의하여 화장품(화장료) 조성물 또는 연고와 같은 피부용 의약품으로 사용될 수 있다.Peptides belonging to Groups A to C of the present invention with whitening ability can be used as dermatological medicines such as cosmetic (cosmetic) compositions or ointments by use alone or in combination with other skin whitening ingredients.

이하, 본 발명의 내용을 하기 실시예를 통해 더욱 상세히 설명하고자 한다. 다만, 본 발명의 권리범위는 하기의 실시예에만 한정되는 것은 아니고, 그와 등가의 기술적 사상의 변형까지를 포함한다. Hereinafter, the content of the present invention will be described in more detail through the following examples. However, the scope of the present invention is not limited only to the following examples, but includes modifications of equivalent technical ideas.

하기 실시예에서 사용한 다이펩타이드(dipeptide) 라이브러리는 Ala, Asn, Arg, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, Val의 20개의 아미노산을 2개씩 연결시켜 제조한 총 400개의 다이펩타이드 라이브러리이며, 국내제조사 주)비드테크로부터 구매하여 사용하였다. Dipeptide libraries used in the following examples are Ala, Asn, Arg, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, A total of 400 dipeptide libraries prepared by linking 20 amino acids of Val 2 by 2 each, were purchased from the domestic manufacturer beadtech.

실시예 1: 다이펩타이드의 B16 악성흑색종세포주 및 Mel-Ab 세포를 대상으로 한 멜라닌 생성 억제 효능 조사Example 1 Investigation of the Inhibitory Effect of Dipeptide on Melanogenesis in B16 Malignant Melanoma Cell Line and Mel-Ab Cells

다이펩타이드의 B16 악성흑색종세포주를 대상으로 한 멜라닌 생성 억제 효능 실험을 위해 B16 악성흑색종세포주를 96 웰 플레이트에 1x104 개씩 접종하고, 하루 배양 한 후, alpha-MSH 1uM을 처리한 phenol red free DMEM 배지에 시료를 10ug/ml의 농도로 첨가하고 3일 배양하였다. 3일 배양 후, 세포의 상태를 현미경으로 관찰하고 흡광도 400nm에서 멜라닌 양을 측정하였다. 총 세포수를 계산하여 흡광도를 보정하였다. Phenolic red free treated with alpha-MSH 1uM was inoculated with 1 × 10 4 B16 malignant melanoma cell lines in 96 well plates for the melanin production inhibition test of B16 malignant melanoma cell line. Samples were added to DMEM medium at a concentration of 10 ug / ml and incubated for 3 days. After 3 days of incubation, the state of the cells was observed under a microscope and melanin amount was measured at an absorbance of 400 nm. Total cell number was calculated to correct the absorbance.

한편, 다이펩타이드의 Mel-Ab 멜라닌세포를 대상으로 한 멜라닌 생성 억제 효능 실험을 위해 Mel-Ab 멜라닌세포를 96 웰 플레이트에 1x105 개씩 접종하고, 하루 배양한 후, 시료를 10ug/ml의 농도로 첨가하고 4일 동안 배양하였다. 그 후, 세포를 1N NaOH에 녹이고, 30분 동안 100℃에서 끓여 완전히 용해시킨 후, 흡광도 400nm에서 멜라닌 양을 측정하였다. On the other hand, 1x10 5 Mel-Ab melanocytes were inoculated into 96 well plates for melanin production inhibition experiments on Mel-Ab melanocytes of dipeptides, and then cultured daily. Add and incubate for 4 days. Thereafter, the cells were dissolved in 1N NaOH, boiled at 100 ° C. for 30 minutes to completely dissolve, and the melanin amount was measured at an absorbance of 400 nm.

Figure 112009008685718-PAT00001
Figure 112009008685718-PAT00001

상기 식에서, C는 대조시료의 멜라닌농도(ug of melanin / ug of protein)이고, A는 검체의 멜라닌농도(ug of melanin / ug of protein)이다.In the above formula, C is the melanin concentration of the control sample (ug of melanin / ug of protein), A is the sample melanin concentration (ug of melanin / ug of protein).

B16 악성흑색종세포주를 사용한 실험 결과, 많은 종류의 다이펩타이드에 미백 효과가 있는 것으로 나타났다. 총 400종 가운데 32종에서 50% 이상의 미백효능이 나타났고, 19종은 30~50%, 56종은 10~30%의 억제 효능이 나타났다(표 1). 10% 이하의 효능을 보이는 군은 효능이 없는 것으로 판단하였으며, 그 중 일부 샘플의 실혐 결과를 도 1에 도시하였다. Experiments with B16 malignant melanoma cell lines have shown that they have a whitening effect on many types of dipeptides. Of the total 400 species, 32 showed more than 50% of whitening efficacy, 19 of 30 ~ 50%, 56 of 10 ~ 30% of the inhibitory effect was shown (Table 1). The group showing an efficacy of 10% or less was determined to be ineffective, and the demonstration results of some of the samples are shown in FIG. 1.

Figure 112009008685718-PAT00002
Figure 112009008685718-PAT00002

(상기 표 1은 다음 페이지로 이어짐)(Table 1 above continues to next page)

Figure 112009008685718-PAT00003
Figure 112009008685718-PAT00003

한편, Mel-Ab 세포를 사용한 실험에 대해서는 모두 34종에서 50% 이상의 미백 효능을 보였으며, 24종은 30~50%의 효능을 보였다(표 2 참조). 또한, 34종이 10~30%의 억제 효능을 보였다. 역시 10% 이하의 효능을 보이는 종류는 효능이 없는 것으로 판단하였다. On the other hand, all experiments using Mel-Ab cells showed more than 50% whitening efficacy in 34 species, and 24 species showed 30-50% efficacy (see Table 2). In addition, 34 species showed an inhibitory effect of 10-30%. Also, the species showing less than 10% of efficacy was judged to be ineffective.

Figure 112009008685718-PAT00004
Figure 112009008685718-PAT00004

(상기 표2는 다음 페이지로 이어짐)  (Table 2 above continues to next page)

Figure 112009008685718-PAT00005
Figure 112009008685718-PAT00005

상기 표 1과 표 2에서 많은 수의 다이펩타이드는 두 가지 세포에서 서로 상이한 효과를 보여주었는데, 이는 다이펩타이드들이 단순히 티로시나제를 억제하는 것만이 아니라, 서로 다른 기전에 의해 미백 효과를 보이기 때문일 것으로 판단되었다. In Table 1 and Table 2, a large number of dipeptides showed different effects in the two cells, which was judged to be due to not only inhibition of tyrosinase but also whitening effects by different mechanisms. .

실험에 따라 효과를 나타내는 다이펩타이드들을 50% 이상 효과군(그룹 A), 30~50% 효과군(그룹 B), 10~30% 효과군(그룹 C)으로 분류하였다. 이때, 두 가지 세포에서 다른 효과를 보인 경우는 좋은 효과를 보인 군으로 분류하였다. Experimental dipeptides were classified into more than 50% effect group (Group A), 30-50% effect group (Group B), 10-30% effect group (Group C). At this time, when the two cells showed different effects were classified into a group showing a good effect.

[그룹 A] : AL(알라닌-류신), AK(알라닌-라이신), AW(알라닌-트립토판), CM(시스테인-메티오닌), CS(시스테인-세린), DV(아스파트산-발린), EA(글루탐산-알라닌), EL(글루탐산-류신), EQ(글루탐산-글루타민), FK(페닐알라닌-라이신), FW(페닐알라닌-트립토판), GD(글라이신-아스파트산), GR(글라이신-아르기닌), GW(글라이신-트립토판), HA(히스티딘-알라닌), HC(히스티딘-시스테인), HD(히스티딘-아스파트산), HG(히스티딘-글라이신), HH(히스티딘-히스티딘), HS(히스티딘-세린), HV(히스티딘-발린), HW(히스티딘-트립토판), IA(이소류신-알라닌), IF(이소류신-페닐알라닌), II(이소류신-이소류신), IL(이소류신-류신), KD(라이신-아스파트산), LE(류신-글루탐산), MQ(메티오닌-글루타민), MY(메티오닌-타이로신), NP(아스파라진-프로린), NR(아스파라진-아르기닌), PF(프로린-페닐알라닌), PH(프로린-히스티딘), PR(프로린-아르기닌), PT(프로린-트레오닌), QR(글루타민-아르기닌), QS(글루타민-세린), QV(글루타민-발린), RG(아르기닌-글라이신), RH(아르기닌-히스티딘), RI(아르기닌-이소류신), RN(아르기닌-아스파라진), RP(아르기닌-프로린), SI(세린-이소류신), SK(세린-라이신), TI(트레오닌-이소류신), TK(트레오닌-라이신), TL(트레오닌-류신), TM(트레오닌-메티오닌), TN(트레오닌-아스파라진), VG(발린-글라이신), VP(발린-프로린), VV(발린-발린), VY(발린-타이로신), WD(트립토판-아스파트산), WI(트립토판-이소류신), WK(트립토판-라이신), WM(트립토판-메티오닌), WN(트립토판-아스파라진), WP(트립토판-프로린), WY(트립토판-타이로신), YD(타이로신-아스파트산), YE(타이로신-글루탐산), YG(타이로신-글라이신), YK(타이로신-라이신), YP(타이로신-프로린), YT(타이로신-트레오닌) [Group A]: AL (alanine-leucine), AK (alanine-lysine), AW (alanine-tryptophan), CM (cysteine-methionine), CS (cysteine-serine), DV (aspartic acid-valine), EA (Glutamic acid-alanine), EL (glutamic acid-leucine), EQ (glutamic acid-glutamine), FK (phenylalanine-lysine), FW (phenylalanine-tryptophan), GD (glycine-aspartic acid), GR (glycine-arginine), GW (glycine-tryptophan), HA (histidine-alanine), HC (histidine-cysteine), HD (histidine-aspartic acid), HG (histidine-glycine), HH (histidine-histidine), HS (histidine-serine) , HV (histidine-valine), HW (histidine-tryptophan), IA (isoleucine-alanine), IF (isoleucine-phenylalanine), II (isoleucine-isoleucine), IL (isoleucine-leucine), KD (lysine-aspartic acid ), LE (leucine-glutamic acid), MQ (methionine-glutamine), MY (methionine-tyrosine), NP (asparagine-proline), NR (asparagine-arginine), PF (proline-phenylalanine), PH (proline- Stidine), PR (proline-arginine), PT (proline-threonine), QR (glutamine-arginine), QS (glutamine-serine), QV (glutamine-valine), RG (arginine-glycine), RH (arginine- Histidine), RI (arginine-isoleucine), RN (arginine-asparagine), RP (arginine-proline), SI (serine-isoleucine), SK (serine-lysine), TI (threonine-isoleucine), TK (threonine- Lysine), TL (threonine-leucine), TM (threonine-methionine), TN (threonine-asparagine), VG (valine-glycine), VP (valine-proline), VV (valine-valine), VY (valine- Tyrosine), WD (tryptophan-aspartic acid), WI (tryptophan-isoleucine), WK (tryptophan- lysine), WM (tryptophan-methionine), WN (tryptophan-asparagine), WP (tryptophan-proline), WY Tryptophan-tyrosine), YD (tyrosine-aspartic acid), YE (tyrosine-glutamic acid), YG (tyrosine-glycine), YK (tyrosine-lysine), YP (tyrosine-proline), YT (tyrosine-threonine)

[그룹 B] : AG(알라닌-글라이신), AR(알라닌-아르기닌), AS(알라닌-세린), AT(알라닌-트레오닌), CE(시스테인-글루탐산), CQ(시스테인-글루타민), DE(아스파트산-글루탐산), DI(아스파트산-이소류신), DL(아스파트산-류신), DN(아스파트산-아스파라진), DT(아스파트산-트레오닌), DY(아스파트산-타이로신), ER(글루탐산-아르기닌), EK(글루탐산-라이신), FF(페닐알라닌-페닐알라닌), FM(페닐알라닌-메티오닌), FR(페닐알라닌-아르기닌), FY(페닐알라닌-타이로신), GK(글라이신-라이신), GQ(글라이신-글루타민), GY(글라이신-타이로신), IG(이소류신-글라이신), IP(이소류신-프로린), IQ(이소류신-글루타민), KC(라이신-시스테인), KW(라이신-트립토판), PK(프로린-라이신), QD(글루타민-아스파트산), SG(세린-글라이신), SL(세린-류신), SH(세린-히스티딘), SQ(세린-글루타민), SS(세린-세린), TD(트레오닌-아스파트산), TP(트레오닌-프로린), VK(발린-라이신), VN(발린-아스파라진), VQ(발린-글루타민), WV(트립토판-발린), YM(타이로신-메티오닌), YN(타이로신-아스파라진), YS(타이로신-세린) [Group B]: AG (alanine-glycine), AR (alanine-arginine), AS (alanine-serine), AT (alanine-threonine), CE (cysteine-glutamic acid), CQ (cysteine-glutamine), DE (as Partsic acid-glutamic acid), DI (aspartic acid-isoleucine), DL (aspartic acid-leucine), DN (aspartic acid-asparagine), DT (aspartic acid-threonine), DY (aspartic acid-tyrosine) ), ER (glutamic acid-arginine), EK (glutamic acid-lysine), FF (phenylalanine-phenylalanine), FM (phenylalanine-methionine), FR (phenylalanine-arginine), FY (phenylalanine-tyrosine), GK (glycine-lysine) , GQ (glycine-glutamine), GY (glycine-tyrosine), IG (isoleucine-glycine), IP (isoleucine-proline), IQ (isoleucine-glutamine), KC (lysine-cysteine), KW (lysine-tryptophan), PK (proline-lysine), QD (glutamine-aspartic acid), SG (serine-glycine), SL (serine-leucine), SH (serine-histidine), SQ (serine-glutamine), SS (serine-serine) , TD (t Onin-aspartic acid), TP (threonine-proline), VK (valine-lysine), VN (valine-asparagine), VQ (valine-glutamine), WV (tryptophan-valine), YM (tyrosine-methionine), YN (tyrosine-asparagine), YS (tyrosine-serine)

[그룹 C] : AF(알라닌-페닐알라닌), AM(알라닌-메티오닌), AP(알라닌-프로린), AV(알라닌-발린), CA(시스테인-알라닌), CC(시스테인-시스테인), CD(시스테인-아스파트산), CF(시스테인-페닐알라닌), CG(시스테인-글라이신), CI(시스테인-이소류신), CK(시스테인-라이신), CL(시스테인-류신), CP(시스테인-프로린), CR(시스테인-아르기닌), CT(시스테인-트레오닌), CV(시스테인-발린), CW(시스테인-트립토판), CY(시스테인-타이로신), DC(아스파트산-시스테인), DR(아스파트산-아르기닌), DQ(아스파트산-글루타민), DW(아스파트산-트립토판), EY(글루탐산-타이로신), FD(페닐알라닌-아스파트산), FG(페닐알라닌-글라이신), FH(페닐알라닌-히스티딘), FL(페닐알라닌-류신), FP(페닐알라닌-프로린), FV(페닐알라닌-발린), GG(글라이신-글라이신), GH(글라이신-히스티딘), GI(글라이신-이소류신), GN(글라이신-아스파라진), HF(히스티딘-페닐알라닌), HK(히스티딘-라이신), HL(히스티딘-류신), ID(이소류신-아스파트산), IV(이소류신-발린), LI(류신-이소류신), LR(류신-아르기닌), MD(메티오닌-아스파트산), NA(아스파라진-알라닌), ND(아스파라진-아스파트산), NG(아스파라진-글라이신), NH(아스파라진-히스티딘), NK(아스파라진-라이신), NW(아스파라진-트립토판), PD(프로린-아스파트산), PQ(프로린-글루타민), QE(글루타민-글루탐산), QM(글루타민-메티오닌), QW(글루타민-트립토판), RA(아르기닌-알라닌), RC(아르기닌-시스테인), RD(아르기닌-아스파트산), RF(아르기닌-페닐알라닌), RK(아르기닌-라이신), RQ(아르기닌-글루타민), RR(아르기닌-아르기닌), RV(아르기닌-발린), RY(아르기닌-타이로신), SR(세린-아르기닌), SY(세린-타이로신), TR(트레오닌-아르기닌), TT(트레오닌-트레오닌), TW(트레오닌-트립토판), VC(발린-시스테인), VL(발린-류신), VM(발린-메티오닌), VS(발린-세린), VT(발린-트레오닌), VW(발린-트립토판), WA(트립토판-알라닌), WC(트립토판-시스테인), WE(트립토판-글루탐산), WH(트립토판-히스티딘), WS(트립토판-세린), YA(타이로신-알라닌), YC(타이로신-시스테인), YH(타이로신-히스티딘), YL(타이로신-류신), YW(타이로신-트립토판)[Group C]: AF (alanine-phenylalanine), AM (alanine-methionine), AP (alanine-proline), AV (alanine-valine), CA (cysteine-alanine), CC (cysteine-cysteine), CD (cysteine Aspartic acid), CF (cysteine-phenylalanine), CG (cysteine-glycine), CI (cysteine-isoleucine), CK (cysteine-lysine), CL (cysteine-leucine), CP (cysteine-proline), CR ( Cysteine-arginine), CT (cysteine-threonine), CV (cysteine-valine), CW (cysteine-tryptophan), CY (cysteine-tyrosine), DC (aspartic acid-cysteine), DR (aspartic acid-arginine) , DQ (aspartic acid-glutamine), DW (aspartic acid-tryptophan), EY (glutamic acid-tyrosine), FD (phenylalanine-aspartic acid), FG (phenylalanine-glycine), FH (phenylalanine-histidine), FL (Phenylalanine-leucine), FP (phenylalanine-proline), FV (phenylalanine-valine), GG (glycine-glycine), GH (glycine-histidine), GI (glycine-isoleucine), GN (glas Shin-asparagine), HF (histidine-phenylalanine), HK (histidine-lysine), HL (histidine-leucine), ID (isoleucine-aspartic acid), IV (isoleucine-valine), LI (leucine-isoleucine), LR (leucine-arginine), MD (methionine-aspartic acid), NA (asparagine-alanine), ND (asparagine-aspartic acid), NG (asparagine-glycine), NH (asparagine-histidine), NK (asparagine-lysine), NW (asparagine-tryptophan), PD (proline-aspartic acid), PQ (proline-glutamine), QE (glutamine-glutamic acid), QM (glutamine-methionine), QW (glutamine-methionine) Tryptophan), RA (arginine-alanine), RC (arginine-cysteine), RD (arginine-aspartic acid), RF (arginine-phenylalanine), RK (arginine-lysine), RQ (arginine-glutamine), RR (arginine) Arginine), RV (arginine-valine), RY (arginine-tyrosine), SR (serine-arginine), SY (serine-tyrosine), TR (threonine-arginine), TT (threonine-threonine), TW (t Onin-tryptophan), VC (valine-cysteine), VL (valine-leucine), VM (valine-methionine), VS (valine-serine), VT (valine-threonine), VW (valine-tryptophan), WA (tryptophan) -Alanine), WC (tryptophan-cysteine), WE (tryptophan-glutamic acid), WH (tryptophan-histidine), WS (tryptophan-serine), YA (tyrosine-alanine), YC (tyrosine-cysteine), YH (tyrosine-cysteine) Histidine), YL (tyrosine-leucine), YW (tyrosine-tryptophan)

제형예 1~2: 미백 화장품의 제조Formulation Examples 1-2: Preparation of Whitening Cosmetics

하기 표 3의 제형예 1 및 제형예 2의 조성 비율로 수상 성분과 유상 성분을 각각 75℃까지 가열하고, 유상 성분을 수상 성분에 혼합하였다. 상기 혼합물에 중화제를 첨가하여 40℃까지 냉각시킨 후, 향료 및 그룹 A~C에서 선택되는 어느 하나의 다이펩타이드를 넣어 크림상의 에멀젼을 제조하였다.The aqueous phase component and oil phase component were heated to 75 ° C. at the composition ratios of Formulation Example 1 and Formulation Example 2 shown in Table 3 below, and the oil phase component was mixed with the aqueous phase component. After adding a neutralizing agent to the mixture and cooling to 40 ° C., a creamy emulsion was prepared by adding a perfume and any one dipeptide selected from groups A to C.

Figure 112009008685718-PAT00006
Figure 112009008685718-PAT00006

상기 표 3에서 첨가되는 '펩타이드'는 그룹 A~C에서 선택되는 어느 하나의 펩타이드이다.'Peptide' added in Table 3 is any one peptide selected from Groups A to C.

제형예 3: 미백 연고의 제조Formulation Example 3: Preparation of Whitening Ointment

그룹 A~C에서 선택되는 어느 하나의 펩타이드 0.01%(w/w), 디에틸세바케이트 8.0%(w/w), 경납 5.0%(w/w), 폴리옥시에틸렌올레일-에테르 포스페이트(EO4) 6.0%(w/w), 파라옥시안식향산에스테르 적량, 바세린 잔량으로 통상의 연고 제조방법에 따라 연고를 제조하였다. 0.01% (w / w) of any of the peptides selected from groups A to C, 8.0% (w / w) of diethyl sebacate, 5.0% (w / w) of lead lead, polyoxyethylene oleyl-ether phosphate (EO4) Ointment was prepared according to a conventional ointment preparation method with 6.0% (w / w), an amount of paraoxybenzoic acid ester and a residual amount of petrolatum.

도 1은 B16 세포에서 본 발명에 따른 다이펩타이드의 멜라닌 생성 억제 효과를 나타낸 것으로, 배양한 B16 악성흑색종세포주에 다이펩타이드를 처리한 실험결과를 촬영한 것이다. 대조군 세포에 비하여 alpha-MSH를 처리한 군은 검게 나타나 멜라닌 생성이 증가한 것으로 보이며, 양성대조군으로 코직산(kojic acid, 도 1에서 'KA'로 표시)을 사용한 샘플은 미백 효능이 잘 나타나고 있다. 다이펩타이드를 처리한 세포들은 종류에 따라 다양한 미백 효능을 보여주고 있다. Figure 1 shows the melanin production inhibitory effect of the dipeptide according to the present invention in B16 cells, photographed the experimental results of dipeptide treatment in cultured B16 malignant melanoma cell line. Compared with the control cells, the group treated with alpha-MSH appeared black and increased melanin production, and the sample using kojic acid (marked with 'KA' in FIG. 1) as a positive control group showed good whitening efficacy. Cells treated with dipeptides show various whitening effects depending on the type.

Claims (3)

하기의 그룹 A~C 중 선택되는 어느 하나의 그룹에 속하는 아미노산 2개로 구성된 다이펩타이드를 하나 이상 포함하는 것을 특징으로 하는 피부 미백용 조성물.A composition for skin whitening comprising at least one dipeptide consisting of two amino acids belonging to any one group selected from the following groups A to C. [그룹 A] : AL(알라닌-류신), AK(알라닌-라이신), AW(알라닌-트립토판), CM(시스테인-메티오닌), CS(시스테인-세린), DV(아스파트산-발린), EA(글루탐산-알라닌), EL(글루탐산-류신), EQ(글루탐산-글루타민), FK(페닐알라닌-라이신), FW(페닐알라닌-트립토판), GD(글라이신-아스파트산), GR(글라이신-아르기닌), GW(글라이신-트립토판), HA(히스티딘-알라닌), HC(히스티딘-시스테인), HD(히스티딘-아스파트산), HG(히스티딘-글라이신), HH(히스티딘-히스티딘), HS(히스티딘-세린), HV(히스티딘-발린), HW(히스티딘-트립토판), IA(이소류신-알라닌), IF(이소류신-페닐알라닌), II(이소류신-이소류신), IL(이소류신-류신), KD(라이신-아스파트산), LE(류신-글루탐산), MQ(메티오닌-글루타민), MY(메티오닌-타이로신), NP(아스파라진-프로린), NR(아스파라진-아르기닌), PF(프로린-페닐알라닌), PH(프로린-히스티딘), PR(프로린-아르기닌), PT(프로린-트레오닌), QR(글루타민-아르기닌), QS(글루타민-세린), QV(글루타민-발린), RG(아르기닌-글라이신), RH(아르기닌-히스티딘), RI(아르기닌-이소류신), RN(아르기닌-아스파라진), RP(아르기닌-프로린), SI(세린-이소류신), SK(세린-라이신), TI(트레오닌-이소류신), TK(트레오닌-라이신), TL(트레오닌-류신), TM(트레오닌-메티오닌), TN(트레오닌-아스파라진), VG(발 린-글라이신), VP(발린-프로린), VV(발린-발린), VY(발린-타이로신), WD(트립토판-아스파트산), WI(트립토판-이소류신), WK(트립토판-라이신), WM(트립토판-메티오닌), WN(트립토판-아스파라진), WP(트립토판-프로린), WY(트립토판-타이로신), YD(타이로신-아스파트산), YE(타이로신-글루탐산), YG(타이로신-글라이신), YK(타이로신-라이신), YP(타이로신-프로린), YT(타이로신-트레오닌) [Group A]: AL (alanine-leucine), AK (alanine-lysine), AW (alanine-tryptophan), CM (cysteine-methionine), CS (cysteine-serine), DV (aspartic acid-valine), EA (Glutamic acid-alanine), EL (glutamic acid-leucine), EQ (glutamic acid-glutamine), FK (phenylalanine-lysine), FW (phenylalanine-tryptophan), GD (glycine-aspartic acid), GR (glycine-arginine), GW (glycine-tryptophan), HA (histidine-alanine), HC (histidine-cysteine), HD (histidine-aspartic acid), HG (histidine-glycine), HH (histidine-histidine), HS (histidine-serine) , HV (histidine-valine), HW (histidine-tryptophan), IA (isoleucine-alanine), IF (isoleucine-phenylalanine), II (isoleucine-isoleucine), IL (isoleucine-leucine), KD (lysine-aspartic acid ), LE (leucine-glutamic acid), MQ (methionine-glutamine), MY (methionine-tyrosine), NP (asparagine-proline), NR (asparagine-arginine), PF (proline-phenylalanine), PH (proline- Stidine), PR (proline-arginine), PT (proline-threonine), QR (glutamine-arginine), QS (glutamine-serine), QV (glutamine-valine), RG (arginine-glycine), RH (arginine- Histidine), RI (arginine-isoleucine), RN (arginine-asparagine), RP (arginine-proline), SI (serine-isoleucine), SK (serine-lysine), TI (threonine-isoleucine), TK (threonine- Lysine), TL (threonine-leucine), TM (threonine-methionine), TN (threonine-asparagine), VG (valine-glycine), VP (valine-proline), VV (valine-valine), VY (valine Tyrosine), WD (tryptophan-aspartic acid), WI (tryptophan-isoleucine), WK (tryptophan-lysine), WM (tryptophan-methionine), WN (tryptophan-asparagine), WP (tryptophan-proline), WY (Tryptophan-tyrosine), YD (tyrosine-aspartic acid), YE (tyrosine-glutamic acid), YG (tyrosine-glycine), YK (tyrosine-lysine), YP (tyrosine-proline), YT (tyrosine-threonine) [그룹 B] : AG(알라닌-글라이신), AR(알라닌-아르기닌), AS(알라닌-세린), AT(알라닌-트레오닌), CE(시스테인-글루탐산), CQ(시스테인-글루타민), DE(아스파트산-글루탐산), DI(아스파트산-이소류신), DL(아스파트산-류신), DN(아스파트산-아스파라진), DT(아스파트산-트레오닌), DY(아스파트산-타이로신), ER(글루탐산-아르기닌), EK(글루탐산-라이신), FF(페닐알라닌-페닐알라닌), FM(페닐알라닌-메티오닌), FR(페닐알라닌-아르기닌), FY(페닐알라닌-타이로신), GK(글라이신-라이신), GQ(글라이신-글루타민), GY(글라이신-타이로신), IG(이소류신-글라이신), IP(이소류신-프로린), IQ(이소류신-글루타민), KC(라이신-시스테인), KW(라이신-트립토판), PK(프로린-라이신), QD(글루타민-아스파트산), SG(세린-글라이신), SL(세린-류신), SH(세린-히스티딘), SQ(세린-글루타민), SS(세린-세린), TD(트레오닌-아스파트산), TP(트레오닌-프로린), VK(발린-라이신), VN(발린-아스파라진), VQ(발린-글루타민), WV(트립토판-발린), YM(타이로신-메티오닌), YN(타이로신-아스파라진), YS(타이로신-세린) [Group B] : AG (alanine-glycine), AR (alanine-arginine), AS (alanine-serine), AT (alanine-threonine), CE (cysteine-glutamic acid), CQ (cysteine-glutamine), DE (aspartic acid-glutamic acid) ), DI (aspartic acid-isoleucine), DL (aspartic acid-leucine), DN (aspartic acid-asparagine), DT (aspartic acid-threonine), DY (aspartic acid-tyrosine), ER ( Glutamic acid-arginine), EK (glutamic acid-lysine), FF (phenylalanine-phenylalanine), FM (phenylalanine-methionine), FR (phenylalanine-arginine), FY (phenylalanine-tyrosine), GK (glycine-lysine), GQ (glycine) -Glutamine), GY (glycine-tyrosine), IG (isoleucine-glycine), IP (isoleucine-proline), IQ (isoleucine-glutamine), KC (lysine-cysteine), KW (lysine-tryptophan), PK (proline- Lysine), QD (glutamine-aspartic acid), SG (serine-glycine), SL (serine-leucine), SH (serine-histidine), SQ (serine-glutamine), SS (serine-serine), TD (threonine -As Trisane), TP (threonine-proline), VK (valine-lysine), VN (valine-asparagine), VQ (valine-glutamine), WV (tryptophan-valine), YM (tyrosine-methionine), YN (tyrosine- Asparagine), YS (tyrosine-serine) [그룹 C] : AF(알라닌-페닐알라닌), AM(알라닌-메티오닌), AP(알라닌-프로린), AV(알라닌-발린), CA(시스테인-알라닌), CC(시스테인-시스테인), CD(시스테인 -아스파트산), CF(시스테인-페닐알라닌), CG(시스테인-글라이신), CI(시스테인-이소류신), CK(시스테인-라이신), CL(시스테인-류신), CP(시스테인-프로린), CR(시스테인-아르기닌), CT(시스테인-트레오닌), CV(시스테인-발린), CW(시스테인-트립토판), CY(시스테인-타이로신), DC(아스파트산-시스테인), DR(아스파트산-아르기닌), DQ(아스파트산-글루타민), DW(아스파트산-트립토판), EY(글루탐산-타이로신), FD(페닐알라닌-아스파트산), FG(페닐알라닌-글라이신), FH(페닐알라닌-히스티딘), FL(페닐알라닌-류신), FP(페닐알라닌-프로린), FV(페닐알라닌-발린), GG(글라이신-글라이신), GH(글라이신-히스티딘), GI(글라이신-이소류신), GN(글라이신-아스파라진), HF(히스티딘-페닐알라닌), HK(히스티딘-라이신), HL(히스티딘-류신), ID(이소류신-아스파트산), IV(이소류신-발린), LI(류신-이소류신), LR(류신-아르기닌), MD(메티오닌-아스파트산), NA(아스파라진-알라닌), ND(아스파라진-아스파트산), NG(아스파라진-글라이신), NH(아스파라진-히스티딘), NK(아스파라진-라이신), NW(아스파라진-트립토판), PD(프로린-아스파트산), PQ(프로린-글루타민), QE(글루타민-글루탐산), QM(글루타민-메티오닌), QW(글루타민-트립토판), RA(아르기닌-알라닌), RC(아르기닌-시스테인), RD(아르기닌-아스파트산), RF(아르기닌-페닐알라닌), RK(아르기닌-라이신), RQ(아르기닌-글루타민), RR(아르기닌-아르기닌), RV(아르기닌-발린), RY(아르기닌-타이로신), SR(세린-아르기닌), SY(세린-타이로신), TR(트레오닌-아르기닌), TT(트레오닌-트레오닌), TW(트레오닌-트립토판), VC(발린-시스테인), VL(발린-류신), VM(발린-메티오닌), VS(발린-세린), VT(발린-트레오닌), VW(발린-트립토판), WA(트립토판-알라닌), WC(트립토판-시스테인), WE(트립토판 -글루탐산), WH(트립토판-히스티딘), WS(트립토판-세린), YA(타이로신-알라닌), YC(타이로신-시스테인), YH(타이로신-히스티딘), YL(타이로신-류신), YW(타이로신-트립토판)[Group C]: AF (alanine-phenylalanine), AM (alanine-methionine), AP (alanine-proline), AV (alanine-valine), CA (cysteine-alanine), CC (cysteine-cysteine), CD (cysteine Aspartic acid), CF (cysteine-phenylalanine), CG (cysteine-glycine), CI (cysteine-isoleucine), CK (cysteine-lysine), CL (cysteine-leucine), CP (cysteine-proline), CR ( Cysteine-arginine), CT (cysteine-threonine), CV (cysteine-valine), CW (cysteine-tryptophan), CY (cysteine-tyrosine), DC (aspartic acid-cysteine), DR (aspartic acid-arginine) , DQ (aspartic acid-glutamine), DW (aspartic acid-tryptophan), EY (glutamic acid-tyrosine), FD (phenylalanine-aspartic acid), FG (phenylalanine-glycine), FH (phenylalanine-histidine), FL (Phenylalanine-leucine), FP (phenylalanine-proline), FV (phenylalanine-valine), GG (glycine-glycine), GH (glycine-histidine), GI (glycine-isoleucine), GN (glas Isine-asparagine), HF (histidine-phenylalanine), HK (histidine-lysine), HL (histidine-leucine), ID (isoleucine-aspartic acid), IV (isoleucine-valine), LI (leucine-isoleucine), LR (leucine-arginine), MD (methionine-aspartic acid), NA (asparagine-alanine), ND (asparagine-aspartic acid), NG (asparagine-glycine), NH (asparagine-histidine), NK (asparagine-lysine), NW (asparagine-tryptophan), PD (proline-aspartic acid), PQ (proline-glutamine), QE (glutamine-glutamic acid), QM (glutamine-methionine), QW (glutamine-methionine) Tryptophan), RA (arginine-alanine), RC (arginine-cysteine), RD (arginine-aspartic acid), RF (arginine-phenylalanine), RK (arginine-lysine), RQ (arginine-glutamine), RR (arginine) Arginine), RV (arginine-valine), RY (arginine-tyrosine), SR (serine-arginine), SY (serine-tyrosine), TR (threonine-arginine), TT (threonine-threonine), TW (t Onin-tryptophan), VC (valine-cysteine), VL (valine-leucine), VM (valine-methionine), VS (valine-serine), VT (valine-threonine), VW (valine-tryptophan), WA (tryptophan) -Alanine), WC (tryptophan-cysteine), WE (tryptophan-glutamic acid), WH (tryptophan-histidine), WS (tryptophan-serine), YA (tyrosine-alanine), YC (tyrosine-cysteine), YH (tyrosine-cysteine) Histidine), YL (tyrosine-leucine), YW (tyrosine-tryptophan) 제1항에 있어서,The method of claim 1, 상기 피부 미백용 조성물은, 상기 선택된 어느 하나 이상의 다이펩타이드를 조성물 전체 대비 0.001~30 중량% 함유하는 것을 특징으로 하는 피부 미백용 조성물The skin whitening composition is a skin whitening composition, characterized in that it contains 0.001 to 30% by weight of the selected one or more dipeptides relative to the total composition 제1항에 있어서,The method of claim 1, 상기 피부 미백용 조성물은, 스킨, 로션, 크림, 파운데이션, 에센스, 젤, 팩, 폼 클렌징, 비누와 같은 화장료, 또는 피부외용 연고와 같은 약품 연고인 것을 특징으로 하는 피부 미백용 조성물.The skin whitening composition is skin, lotion, cream, foundation, essence, gel, pack, foam cleansing, cosmetics such as soap, or skin ointment composition, characterized in that the ointment for the skin ointment.
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