Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
권호 표지
DOI QR코드

DOI QR Code

Tyrosinase Inhibitory Activities of Safrole from Myristica fragrans Houtt.

  • Cho, Soo Jeong (Department of Pharmaceutical Engineering, Gyeongnam National University of Science and Technology) ;
  • Kwon, Hyun Sook (Korea Promotion Institute for Traditional Medicine Industry)
  • Received : 2015.06.30
  • Accepted : 2015.08.17
  • Published : 2015.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

Five phenylpropanoids (1-5), a benzofuran neolignan (6), two 8-O-4'-neolignans (7-8), and five tetrahydrofuran lignans (9-13) were isolated from a methanol extract of Myristica fragrans seeds. The structures of 1-13 were determined by $^1H$- and $^{13}C$-NMR spectroscopic data analyses and a comparison with the literature data. Compound 3 was isolated for the first time from this plant. All the isolated compounds were evaluated for their inhibitory activity against tyrosinase. Among them, safrole (1) showed significant inhibitions against both the monophenolase ($IC_{50}=32.11{\mu}M$) and diphenolase ($IC_{50}=27.32{\mu}M$) activities of tyrosinase. The kinetic analysis shows that safrole (1) is competitive inhibitors for both monophenolase and diphenolase. The apparent inhibition constant ($K_i$) for safrole (1) binding with free enzyme was determined to be 16.05 and $13.66{\mu}M$ for monophenolase and diphenolase, respectively.

Keywords

References

  1. Bandara Herath HM and Anoma Priyadarshani AM (1996) Two lignans and an aryl alkanone from Myristica dactyloides. Phytochemistry 42, 1439-42. https://doi.org/10.1016/0031-9422(96)00113-6
  2. Benevides JC, Sartorelli P, and Kato MJ (1999) Phenylpropanoids and neolignans from Piper regnellii. Phytochemistry 52, 339-43. https://doi.org/10.1016/S0031-9422(99)00177-6
  3. Cavalcante SH, Fernandes D, Paulino Fo HF, Yoshida M, and Gottlieb OR (1985) Lignoids from the fruit of three Virola species. Phytochemistry 24, 1865-6. https://doi.org/10.1016/S0031-9422(00)82577-7
  4. Cho JY, Choi GJ, Son SW, Jang KS, Lim HK, Lee SO et al. (2007) Isolation and antifungal activity of lignans from Myristica fragrans against various plant pathogenic fungi. Pest Manag Sci 63, 935-40. https://doi.org/10.1002/ps.1420
  5. Davis DV and Graham CR (1982) Direct characterization of nutmeg constituents by mass spectrometry-mass spectrometry. J Agric Food Chem 30, 495-504. https://doi.org/10.1021/jf00111a021
  6. Friedman M (1996) Food browning and its prevent; an overview. J Agric Food Chem 44, 631-53. https://doi.org/10.1021/jf950394r
  7. Ha TJ, Tamura S, and Kubo I (2005) Effects of mushroom tyrosinase on anisaldehyde. J Agric Food Chem 53, 7024-8. https://doi.org/10.1021/jf047943q
  8. Hada S, Hattori M, Tezuka Y, Kikuchi T, and Namba T (1988) New neolignans and lignans from the aril of Myristica fragrans. Phytochemistry 27, 563-8. https://doi.org/10.1016/0031-9422(88)83142-X
  9. Hattori M, Hada S, Shu YZ, Kakiuchi N, and Namba T (1987) New acyclic bis-phenylpropanoids from the aril of Myristica fragrans. Chem Pharm Bull 35, 668-74. https://doi.org/10.1248/cpb.35.668
  10. Kahn V and Andrawis A (1985) Inhibition of mushroom tyrosinase by tropolone. Phytochemistry 24, 905-8. https://doi.org/10.1016/S0031-9422(00)83150-7
  11. Konishi T, Konoshima T, Daikonya A, and Kitanaka S (2005) Neolignans from Piper futokadsura and their inhibition of nitric oxide production. Chem Pharm Bull 53, 121-4. https://doi.org/10.1248/cpb.53.121
  12. Kubo I and Kinst-Hori I (1999a) Flavonols from saffron flower. J Agric Food Chem 47, 4121-5. https://doi.org/10.1021/jf990201q
  13. Kubo I and Kinst-Hori I (1999b) Tyrosinase inhibitory activity of the olive oil flavor compounds. J Agric Food Chem 47, 4574-8. https://doi.org/10.1021/jf990165v
  14. Kwon HS, Kim MJ, Jeong HJ, Yang MS, Park KH, Jeong TS et al. (2008) Low-density lipoprotein (LDL)-antioxidant lignans from Myristica fragrans seeds. Bioorg Med Chem Lett 18, 194-8. https://doi.org/10.1016/j.bmcl.2007.10.098
  15. Lee HS (2002) Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J Agric Food Chem 50, 1400-3. https://doi.org/10.1021/jf011230f
  16. Maeda K and Fukuda M (1991) In vitro effectiveness of several whitening cosmetic components in human melanocytes. J Soc Cosmet Chem 42, 361-8.
  17. Nguyen PH, Thu Le TV, Kang HW, Chae J, Kim SK, Kwon KI et al. (2010) AMP-activated protein kinase (AMPK) activators from Myristica fragrans (nutmeg) and their anti-obesity effect. Bioorg Med Chem Lett 20, 4128-31. https://doi.org/10.1016/j.bmcl.2010.05.067
  18. Orabi KY, Mossa JS, and El Feraly FS (1991) Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans). J Nat Prod 54, 856-9 https://doi.org/10.1021/np50075a017
  19. Sabudak T, Demirkiran O, Ozturk M, and Topcu G (2013) Phenolic compounds from Trifolium echinatum Bieb. and investigation of their tyrosinase inhibitory and antioxidant activities. Phytochemistry 96, 305-11. https://doi.org/10.1016/j.phytochem.2013.08.014
  20. Sadhu SK, Okuyama E, Fujimoto H, and Ishibashi M (2003) Separation of Leucas aspera, a medicinal plant of bangladesh, guided by prostaglandin inhibitory and antioxidant activities. Chem Pharm Bull 51, 595-8. https://doi.org/10.1248/cpb.51.595
  21. Seiberg M, Paine C, Sharlow E, Andrade-Gordun P, Costanzo M, Eisinger M et al. (2000) Inhibition of melanosome transfer results in skin lightening. J Invest Dermatol 115, 162-7. https://doi.org/10.1046/j.1523-1747.2000.00035.x
  22. Seo SY, Sharma VK, and Sharma N (2003) Mushroom tyrosinase: recent prospects. J Agric Food Chem 51, 2837-53. https://doi.org/10.1021/jf020826f
  23. Shimomura H, Sashida Y, and Oohara M (1987) Lignans from Machilus thunbergii. Phytochemistry 26, 1513-5. https://doi.org/10.1016/S0031-9422(00)81847-6
  24. Son SM, Moon KD, and Lee CY (2000) Rhubarb juice as a natural antibrowing agent. J Food Sci 65, 1288-9. https://doi.org/10.1111/j.1365-2621.2000.tb10598.x
  25. Urzua A, Freyer AJ, and Shamma M (1987) 2,5-Diaryl-3,4-dimethyltetrahydrofuranoid lignans. Phytochemistry 26, 1509-11. https://doi.org/10.1016/S0031-9422(00)81846-4
  26. Yang SM, Na MK, Jang JP, Kim KA, Kim BY, Sung NJ et al. (2006) Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans. Phytother Res 20, 680-2. https://doi.org/10.1002/ptr.1935

Cited by

  1. Functionalized Tyrosinase-Lignin Nanoparticles as Sustainable Catalysts for the Oxidation of Phenols vol.8, pp.6, 2018, https://doi.org/10.3390/nano8060438