Journal of the Society of Cosmetic Scientists of Korea (대한화장품학회지)

Society of Cosmetic Scientists of Korea (대한화장품학회)
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Preparation of Natural Compounds-tripeptides Derivatives and Their Melanogensis Inhibitory Activity

천연유래물질 펩타이드 유도체의 제조와 멜라닌 생성 저해 효과 탐색

  • Shin, Kyong-Hoon (Central Research, Aekyung R&D Center) ;
  • Lee, Jae-Ho (Structural Biology Lab., Gwangju Institute of Science and Technology) ;
  • Ryu, Geun-Seok (Central Research, Aekyung R&D Center) ;
  • Jee, Kyung-Yup (Central Research, Aekyung R&D Center) ;
  • Park, Soo-Nam (Research Center for Development of Green Cosmetic, Seoul National University of Science and Technology) ;
  • Kim, Jae-Il (Structural Biology Lab., Gwangju Institute of Science and Technology) ;
  • Cho, In-Shik (Central Research, Aekyung R&D Center) ;
  • Kim, Han-Young (Central Research, Aekyung R&D Center)
  • 신경훈 (애경산업(주) 중앙연구소) ;
  • 이재호 (광주과학기술원) ;
  • 류근석 (애경산업(주) 중앙연구소) ;
  • 지경엽 (애경산업(주) 중앙연구소) ;
  • 박수남 (서울과학기술대학교 그린코스메틱연구개발센터) ;
  • 김재일 (광주과학기술원) ;
  • 조인식 (애경산업(주) 중앙연구소) ;
  • 김한영 (애경산업(주) 중앙연구소)
  • Received : 2010.09.08
  • Accepted : 2010.09.25
  • Published : 2010.09.30
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Abstract

Derivatives of a novel natural compunds, melanostatin (PLG-$NH_2$) were prepared by solid phase synthesis[1,2] and assayed to evaluate their melanogensis inhibitory activity. Also, a small library (natural compound-XLG-$NH_2$, natural compound-X LG-OH) was prepared with same method for increasing synthetic yield and cost-reduction. PLG-$NH_2$ (Proline-Leucine-Glycine-$NH_2$) was well-known tripeptide as its $\alpha$-MSH release-inhibiting activity and tyrosinase inhibitory activity[3-5]. In order to choose best candidate for peptide derivatization, various natural compounds were screened by their tyrosinase inhibitory activity. As a result, caffeic acid and coumaric acid were selected. Most of these derivatives showed better activities than the parent natural compound, melanostatin.

신규 미백 소재 개발을 위하여 tyrosinase의 활성을 억제하는 천연물과, alpha-melanocyte stimulating hormone ($\alpha$-MSH)을 저해하는 펩타이드를 결합한 소재를 고체상 합성법으로 제조하였다[1,2]. Tyrosinase 활성 억제 효능이 있는 천연유래물질을 기존 연구를 바탕으로 선정하였으며, 이중에서 상업화 된 물질 17종에 대해 Mushroom Tyrosinase 활성 억제 효과를 측정하여, 그 중 caffeic acid, coumaric acid를 선별하였다. 펩타이드는 $\alpha$-MSH 분비를 억제하며, tyrosinase활성을 억제하는 것으로 알려진 melanostatin을 선정하였으며[3-5], PLG-$NH_2$ (Proline-Leucine-Glycine-$NH_2$) 중에서 유도체화 수율의 저하 원인으로 예상되는 Proline (Pro)의 서열을 다른 아미노산으로 변경하면서 선별된 천연물인 coumaric acid와 caffeic acid에 도입하였다. 또한 최종물질의 원가를 고려하여 acid-amide 형태를 acid형태로 전환한 유도체를 합성하였다. 이들 펩타이드 유도체들에 대해서 B16F1 melanoma cell에서의 멜라닌 생성 억제 효능을 평가하여 유도체화된 물질이 기존의 천연유래물질이나 펩타이드에 비하여 높은 저해효과를 가지는 것을 확인하였다.

Keywords

References

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