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Development of Anti-Wrinkle Materials using Galloyl-Peptide Derivatives

갈릭산 펩타이드 유도체를 이용한 주름개선 소재 개발

  • 정해수 ((주)바이오에프디엔씨 항노화연구소) ;
  • 송미영 ((주)바이오에프디엔씨 항노화연구소) ;
  • 김형식 ((주)바이오에프디엔씨 항노화연구소) ;
  • 서효현 ((주)바이오에프디엔씨 항노화연구소) ;
  • 이정훈 ((주)바이오에프디엔씨 항노화연구소) ;
  • 이경록 ((주)아미코스메틱) ;
  • 홍일 ((주)아미코스메틱) ;
  • 모상현 ((주)바이오에프디엔씨 항노화연구소)
  • Received : 2015.05.15
  • Accepted : 2015.08.06
  • Published : 2015.08.31

Abstract

Conjugating a phytochemical, a strong antioxidant, with a functional peptide not only compensates for its stability, but also improves its solubility and anti-wrinkle effects, thereby contributing to the possibility of becoming an excellent cosmetic ingredient. Thus, in this study we examined the potential cosmetic use of a phytochemical-peptide derivative using gallic acid, a phytochemical with antioxidant, anti-inflammatory, and anti-cancer effects. To evaluate the antioxidant and wrinkle-improving efficacy of 5 synthesized gallic acids conjugated with LVH, IVH, KTTKS, YGGFM, and YGGFLRKYP respectively, we observed the expression of genes related to wrinkle improvement using DPPH radical scavenging activity and real-time PCR. As a result, all 5 derivatives had excellent free radical scavenging effects. The expression level of genes involved collagen synthesis also increased, and the secreted peptides during collagen production contributed to their antioxidant and wrinkle improving effects. These results mark the potential use of gallic acid peptide derivatives as a cosmetic ingredient for anti-oxidation and wrinkle improvement.

항산화 효능이 우수한 phytochemical에 콜라겐 합성능이 우수한 기능성 펩타이드의 결합을 통해 소재 자체의 안정성뿐만 아니라 수용액 상태에서의 분산성을 증대시켜 주름개선 효능과 더불어 우수한 화장품 소재로서의 가능성을 가진다. 이에 본 연구는 항산화, 항염 및 항암 등의 효능을 가진다고 알려져 있는 phytochemical인 갈릭산을 이용해 phytochemical-펩타이드 유도체를 개발하여 화장품 소재로서의 가능성을 시험하였다. 갈릭산에 LVH, IVH, KTTKS, YGGFM, YGGFLRKYP 총 5종의 펩타이드를 각각 합성하여 만든 갈릭산 펩타이드 유도체의 항산화 및 주름개선의 효능을 평가하고자 DPPH radical scavenging activity와 real-time PCR로 주름개선과 관련된 유전자의 발현을 확인하였다. 그 결과 5종 유도체 모두 우수한 자유 라디컬 소거능을 보였다. 또한 collagen 합성에 관여하는 유전자의 발현이 증가하였고, collagen 생성시 분비되는 펩타이드의 증가를 통해 항산화뿐만 아니라 주름개선에도 효과가 있었다. 이를 통해 갈릭산 펩타이드 유도체가 항산화 및 주름개선을 위한 화장품 소재로서의 가능성을 확인하였다.

Keywords

References

  1. Kasture VS, Sahu RK, Anjan K, Musmade DS, "Synthesis and antiparkinson activity of Gallic acid derivatives" Medicinal Chemistry and Drug Discovery, 3(2), pp. 134-139, 2012.
  2. Reynolds LD, Wilson NG "Scribes and Scholars" 3rd edition, Oxford University Press, pp. 193-194, 1991.
  3. Nguyen DM, Seo DJ, Lee HB, Kim IS, Kim KY, Park RD, Jung WJ, "Antifungal activity of gallic acid purified from Terminalia nigrovenulosa bark against Fusarium solani." Microb Pathog 56, pp. 8-15, 2013. DOI: http://dx.doi.org/10.1016/j.micpath.2013.01.001
  4. Choi HJ, Song JH, Park KS, Baek SH, "In vitro anti-enterovirus 71 activity of gallic acid from Woodfordia fruticosa flowers." Lett Appl Microbiol 50, pp. 438-440, 2010. DOI: http://dx.doi.org/10.1111/j.1472-765X.2010.02805.x
  5. Liu Z, Ma LP, Zhou B, Yang L, Liu ZL, "Antioxidative effects of green tea polyphenols on free radical initiated and photosensitized peroxidation of human low density lipoprotein." Chem Phys Lipids, 106(1), pp. 53-63, 2000. DOI: http://dx.doi.org/10.1016/S0009-3084(00)00133-X
  6. Paolo R, "Peptides and Peptidomimetics in Medicinal Chemistry", Medicinal Chemistry and Drug Design, 8, pp. 978-953, 2012.
  7. Hashimoto SI, Kyowa C, Hofu S, "Ribosome-independent Peptide Synthesis in Nature and Their Application to Dipeptide Production", J. Biol. Macromol, 8(2), pp. 28-37, 2008.
  8. Ioannis, S., F. Demosthenes, V. Katerina, G. T. Andreas, K. Valentinos, B. Evangelos "Cyanobacterial cyclopeptides as lead compounds to novel targeted cancer drugs." Mar. Drugs, 8, pp. 629-657, 2010. DOI: http://dx.doi.org/10.3390/md8030629
  9. Ruiz, M. A., B. Clares, M. E. Morales, and V. Gallardo, "Evaluation of the anti-wrinkle efficacy of cosmetic formulations with an anti-aging peptide." Ars. Pharm. 50, pp. 168-176, 2010.
  10. Robinson, L. R., N. C. Fitzgerald, D. G. Doughty, N. C. Dawes, C. A. Berge, D. L. Bissett, "Topical palmitoyl pentapeptide provides improvement in photoaged human facial skin." J. Cosmetic science 27, pp. 155-160, 2005. DOI: http://dx.doi.org/10.1111/j.1467-2494.2005.00261.x
  11. van Meerloo J1, Kaspers GJ, Cloos J, "Cell sensitivity assays: the MTT assay" Methods Mol Biol. 731, pp. 237-245, 2011. DOI: http://dx.doi.org/10.1007/978-1-61779-080-5_20
  12. Fotakis G, Timbrell JA, "In vitro cytotoxicity assays: comparison of LDH, neutral red, MTT and protein assay in hepatoma cell lines following exposure to cadmium chloride." Toxicol Lett. 160, pp. 171-177, 2006. DOI: http://dx.doi.org/10.1016/j.toxlet.2005.07.001
  13. Huang D, Ou B, Prior RL, "The chemistry behind antioxidant capacity assays." J Agric Food Chem. 53(6), pp. 1841-1856, 2005. DOI: http://dx.doi.org/10.1021/jf030723c
  14. Imai J, Ide N, Nagae S, Moriguchi T, Matsuura H, Itakura Y, "Antioxidant and radical scavenging effects of aged garlic extract and its constituents." Planta Med., 60(5), 417-420, 1994. DOI: http://dx.doi.org/10.1055/s-2006-959522
  15. Takagi M, Nishioka M, Kakihara H, Kitabayashi M, Inoue H, Kawakami B, Oka M, Imanaka T, "Characterization of DNA polymerase from Pyrococcus sp. strain KOD1 and its application to PCR." Appl Environ Microbiol. 63(11), 4504-4510, 1997.
  16. Hashimoto H, Nishioka M, Fujiwara S, Takagi M, Imanaka T, Inoue T, Kai Y, "Crystal structure of DNA polymerase from hyperthermophilic archaeon Pyrococcus kodakaraensis KOD1." J Mol Biol. 306(3), 469-477, 2001. DOI: http://dx.doi.org/10.1006/jmbi.2000.4403
  17. Atsushi Masamune, Shin Hamada, Kazuhiro Kikuta, Tetsuya Takikawa, Shin Miura, Eriko Nakano, Tooru Shimosegawa. "The angiotensin II type I receptor blocker olmesartan inhibits the growth of pancreatic cancer by targeting stellate cell activities in mice" Journal of Gastroenterology. 48, pp. 602-609, 2013. DOI: http://dx.doi.org/10.3109/00365521.2013.777776
  18. Cho S, Kim HH, Lee MJ, Lee S, Park CS, Nam SJ, Han JJ, Kim JW, Chung JH, "Phosphatidylserine prevents UV-induced decrease of type I procollagen and increase of MMP-1 in dermal fibroblasts and human skin in vivo" J Lipid Res. 49, pp. 1235-1245, 2008. DOI: http://dx.doi.org/10.1194/jlr.M700581-JLR200