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Tyrosinase Inhibitory Compounds Isolated from Persicaria tinctoria Flower

쪽 꽃에서 분리한 타이로시네이즈 저해 화합물

  • Woo, Young-Min (Department of Bioscience and Biotechnology and Bio/Molecular Informatics Center, Konkuk University) ;
  • Kim, Ah-Jin (Department of Bioscience and Biotechnology and Bio/Molecular Informatics Center, Konkuk University) ;
  • Kim, Ji-Young (Department of Bioscience and Biotechnology and Bio/Molecular Informatics Center, Konkuk University) ;
  • Lee, Choong-Hwan (Department of Bioscience and Biotechnology and Bio/Molecular Informatics Center, Konkuk University)
  • Received : 2010.10.09
  • Accepted : 2011.01.21
  • Published : 2011.03.31

Abstract

To develop a new natural whitening agent, we investigated the tyrosinase inhibitory effects of Persicaria tinctoria Flower extracts (PTFE). PTFE showed inhibitory activity on mushroom tyrosinase with the $IC_{50}$ values of $70.8{\pm}2.2{\mu}g/mL$. We purified two active compounds from PTFE by LH-20 column chromatography and prep-high performance liquid chromatography (HPLC) and identified as quercetin-3-O-rhamnoside (Q3R) and myricetin-3-O-rhamnoside (M3R) by $^1H$nuclear magnetic resonance (NMR) and liquid chromatography-mass spectrometry (LC-MS) analysis. Q3R and M3R showed tyrosinase inhibitory activities with the $IC_{50}$ values of $47.0{\pm}0.1{\mu}g/mL$ and $150.5{\pm}1.6{\mu}g/mL$, respectively. These results suggest that PTFE and its active compounds reduced melanin formation by the inhibition of tyrosinase activity. Thus, P. tinctoria flower extracts may be a candidate for cosmetic use.

본 연구에서는 천연 미백소재 탐색을 위하여 쪽(P. tinctoria) 꽃 추출물의 tyrosinase 저해활성을 검증하였으며, 쪽 꽃 추출물은 $70.8{\pm}2.2{\mu}g/mL$$IC_{50}$ 값을 나타내었다. LH-20 chromatography와 HPLC분석을 통해 쪽으로부터 두 개의 활성물질을 정제하였고, 이 물질들의 구조 분석은 LC-MS와 NMR 데이터 해석을 바탕으로 진행하여 두 가지 화합물은 각각 quercetin-3-Orhamnoside (Q3R), myricetin-3-O-rhamnoside (M3R)로 밝혀졌다. Q3R과 M3R은 순서대로 $47.0{\pm}0.1$, $150.5{\pm}1.6{\mu}g/mL$$IC_{50}$ 값을 나타내었다. 이로 미루어 보아, 쪽 꽃 추출물과 두 활성물질의 멜라닌 생합성 저해활성을 확인할 수 있었으며, 쪽 꽃추출물의 미백소재로서의 적용 가능성을 확인할 수 있었다.

Keywords

References

  1. Ando S, Ando O, Suemoto Y, and Mishima Y (1993) Tyrosinase gene transcription and its control by melanogenetic inhibitor. J Invest Dermatol 100, 150-155. https://doi.org/10.1038/jid.1993.68
  2. Baek SH, Kim JH, Kim DH, Lee CY, Kim JY, Chung DK, and Lee CH (2008) Inhibitory Effect of Dalbergioidin Isolated from the Trunk of Lespedeza cyrtobotrya on Melanin Biosynthesis. J Microbiol Biotechnol 18, 874-879.
  3. Fitton A (1991) Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders. Drugs 41, 780-798. https://doi.org/10.2165/00003495-199141050-00007
  4. Hayder N, Bouhlel I, Skandrani I, Kadri M, Steiman R, Guiraud P, Mariotte AM, Ghedira K, Franca MG, and Leila C (2008) In vitro antioxidant and antigenotoxic potentials of myricetin-3-Ogalactoside and myricetin-3-O-rhamnoside from Myrtus communis: Modulation of expression of genes involved in cell defence system using cDNA microarray. Toxicol in Vitro 22, 567-581. https://doi.org/10.1016/j.tiv.2007.11.015
  5. Hyun SH, Jung SK, Jwa MK, Song CK, Kim JH, and Lim SB (2007) Screening of Antioxidants and Cosmeceuticals from Natural Plant Resources in Jeju Island. Korean J Food Sci Technol 39, 200-208.
  6. Imokawa G and Mishima Y (1982) Loss of melanogenic properties in tyrosinase induced by glycosilation inhibitors within malignant melanoma cells. Cancer Res 42, 1994-2002.
  7. Jeong CH and Shim KH (2004) Tyrosinase Inhibitor Isolated From the Leaves of Zanthoxylum piperitum. Biosci Biotechnol Biochem 68, 1984-1987. https://doi.org/10.1271/bbb.68.1984
  8. Kim SS, Hyun CG, Lee JS, Lim JH, Kim JY, and Park DH (2007) In vitro Screening of Jeju Medicinal Plants for Cosmeceutical Materials. J Appl Biol Chem 50, 215-220.
  9. Kim YJ and Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62, 1707. https://doi.org/10.1007/s00018-005-5054-y
  10. Lee SH, Kim SY, Kim JJ, Jang TS, and Chung SY (1999) The isolation of the inhibitory constituents on melanin polymer formation from the leaves of Cercis chinensis. Korean J Pharmacogn 30, 397-403.
  11. Lee YS, Park JH, Kim MH, and Kim HJ (2006) Synthesis of tyrosinase inhibitory kojic acid derivative. Arch Pharm (Weinheim) 339, 111-114. https://doi.org/10.1002/ardp.200500213
  12. Lopez J, Tudela R, Varon F, Carmona G, and Canovas FG (1992) Analysis of a kinetic model for melanin biosynthesis pathway. J Biol Chem 267, 381-390.
  13. Maeda K and Fukuda M (1996) Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 276, 765-769.
  14. Masuda M, Tejima T, and Suzuki T (1996) Skin lighteners. Cosmet Toiletries 111, 65-77.
  15. Pavel S and Muskiet FA (1980) Eumelanin metabolites as markers for pigmented malignant melanoma, a preliminary report. Cancer Detect Prev 6, 311-318.
  16. Parvez S, Kang M, Chung HS, Cho C, Hong MC, Shin MK, and Bae H (2006) Survey and mechanism of skin depigmenting and lightening agents. Phytother Res 20, 921-934. https://doi.org/10.1002/ptr.1954
  17. Prota G (1980) Recent advances in the chemistry of melanogenesis in mammals. J Invest Dermatol 75, 122-127. https://doi.org/10.1111/1523-1747.ep12521344
  18. Samah S, Azusa K, Kenji K, Kohki A, and Hideo H (2010) Inhibitory Activity against Urease of Quercetin Glycosides Isolated from Allium cepa and Psidium guajava. Biosci Biotechnol Biochem 74, 878-880. https://doi.org/10.1271/bbb.90895

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