Inhibitory Effect Of Melanogenesis By 5-Pentyl-2-Furaldehyde ...

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Bioactive Compounds and Chemical Biology

Inhibitory Effect of Melanogenesis by 5-Pentyl-2-Furaldehyde Isolated from Clitocybe sp.

Young-Hee Kim 1, Soo-Jin Choo 1, In-Ja Ryoo 1, Bo Yeon Kim 1, Jong Seog Ahn 1 and Ick-Dong Yoo 1*

Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Korea

Received: January 31, 2012; Accepted: February 28, 2012

J. Microbiol. Biotechnol. 2012; 22(6): 814-817

Published June 28, 2012 https://doi.org/10.4014/jmb.1101.01053

Copyright © The Korean Society for Microbiology and Biotechnology.

Abstract

In the continued search for melanogenesis inhibitors from microbial metabolites, we found that the culture broth of Clitocybe sp. MKACC 53267 inhibited melanogenesis in B16F10 melanoma cells. The active component was purified by solvent extraction, silica gel chromatography, Sephadex LH-20 column chromatography, and finally by preparative HPLC. Its structure was determined as 5- pentyl-2-furaldehyde on the basis of the UV, NMR, and MS spectroscopic analysis. The 5-pentyl-2-furaldehyde potently inhibited melanogenesis in B16F10 cells with an IC50 value of 8.4 μg/ml, without cytotoxicity.

Keywords

B16F10 melanoma, Clitocybe sp., melanogenesis, 5-pentyl-2-furaldehyde

References

1. Baek, S. H., D. H. Kim, C. Y. Lee, Y. H. Kho, and C. H. Lee. 2006. Idescarpin isolated from the fruits of Idesia polycarpa inhibits melanin biosynthesis. J. Microbiol. Biotechnol. 16:667-672.
2. Curto, E. V., C. Kwong, H. Hermersdörfer, H. Glatt, C. Santis, V. Virador, V. J. Hearing Jr., and T. P. Dooley. 1999. Inhibition of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663-672.
3. Dooley, T. P., R. C. Gadwood, K. Kilgore, and L. M. Thomasco. 1994. Development of an in vitro primary screen for skin depigmentation and antimelanoma agents. Skin Pharmacol. 7: 188-200.
4. Hayashi, M., K. Wada, and K. Munakata. 1981. New nematicidal metabolites from a fungus, Irpex lacteus. Agric. Biol. Chem. 45: 1527-1529.
5. Kim, D. H., J. S. Hwang, H. S. Baek, K. J. Kim, B. G. Lee, I. S. Chang, et al. 2003. Development of 5-[(3-aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one as a novel whitening agent. Chem. Pharm. Bull. 51: 113-116.
6. Kim, K. B., S. I. Kim, and K. S. Song. 2003. Neuraminidase inhibitors from mushroom Microphors affinis. J. Microbiol. Biotechnol. 13: 778-782.
7. Kim, W. G., I. J. Ryoo, S. H. Park, D. S. Kim, S. K. Lee, K. C. Park, and I. D. Yoo. 2005. Terrein, a melanin biosynthesis inhibitor, from Penicillium sp. 20135. J. Microbiol. Biotechnol. 15: 891-894.
8. Kim, Y. H., S. M. Cho, J. W. Hyun, I. J. Ryoo, S. J. Choo, S. Lee, et al. 2008. A new antioxidant, clitocybin A, from the culture broth of Clitocybe aurantiaca. J. Antibiot. 61: 573-576.
9. Lee, N. K., K. H. Son, H. W. Chang, S. S. Kang, H. Park, Y. M. Heo, and H. P. Kim. 2004. Prenylated flavonoids as tyrosinase inhibitors. Arch. Pharm. Res. 27: 1132-1135.
10. Lim, Y. H., I. H. Kim, J. J. Seo, and J. K. Kim. 2006. Tyrosinase inhibitor from the flowers of Impatiens balsamina. J. Microbiol. Biotechnol. 16: 1977-1983.
11. Riley, P. A. 2003. Melanogenesis and melanoma. Pigment Cell Res. 16: 548-552.
12. Smalley, K. and T. Eisen. 2000. The involvement of p38 mitogen-activated protein kinase in the α-melanocyte stimulating hormone (α-MSH)-induced melanogenesis and anti-proliferative effects in B16 murine melanoma cells. FEBS Lett. 476: 198202.
13. Sutton, D. A., E. H. Thompson, M. G. Rinaldi, P. C. Iwen, K. K. Nakasone, H. S. Jung, et al. 2005. Identification and first report of Inonotus (Phellinus) tropicalis as an etiologic agent in a patient with chronic granulomatous disease. J. Clin. Microbiol. 43: 982-987.
14. Zaidman, B. Z., M. Tassin, J. Mahajna, and S. P. Wasser. 2005. Medicinal mushroom modulators of molecular targets as cancer therapeutics. Appl. Microbiol. Biotechnol. 67: 453-468.

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Note

J. Microbiol. Biotechnol. 2012; 22(6): 814-817

Published online June 28, 2012 https://doi.org/10.4014/jmb.1101.01053

Copyright © The Korean Society for Microbiology and Biotechnology.

Inhibitory Effect of Melanogenesis by 5-Pentyl-2-Furaldehyde Isolated from Clitocybe sp.

Young-Hee Kim 1, Soo-Jin Choo 1, In-Ja Ryoo 1, Bo Yeon Kim 1, Jong Seog Ahn 1 and Ick-Dong Yoo 1*

Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Korea

Received: January 31, 2012; Accepted: February 28, 2012

Abstract

In the continued search for melanogenesis inhibitors from microbial metabolites, we found that the culture broth of Clitocybe sp. MKACC 53267 inhibited melanogenesis in B16F10 melanoma cells. The active component was purified by solvent extraction, silica gel chromatography, Sephadex LH-20 column chromatography, and finally by preparative HPLC. Its structure was determined as 5- pentyl-2-furaldehyde on the basis of the UV, NMR, and MS spectroscopic analysis. The 5-pentyl-2-furaldehyde potently inhibited melanogenesis in B16F10 cells with an IC50 value of 8.4 μg/ml, without cytotoxicity.

Keywords: B16F10 melanoma, Clitocybe sp., melanogenesis, 5-pentyl-2-furaldehyde

• Abstract

References

1. Baek, S. H., D. H. Kim, C. Y. Lee, Y. H. Kho, and C. H. Lee. 2006. Idescarpin isolated from the fruits of Idesia polycarpa inhibits melanin biosynthesis. J. Microbiol. Biotechnol. 16:667-672.
2. Curto, E. V., C. Kwong, H. Hermersdörfer, H. Glatt, C. Santis, V. Virador, V. J. Hearing Jr., and T. P. Dooley. 1999. Inhibition of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663-672.
3. Dooley, T. P., R. C. Gadwood, K. Kilgore, and L. M. Thomasco. 1994. Development of an in vitro primary screen for skin depigmentation and antimelanoma agents. Skin Pharmacol. 7: 188-200.
4. Hayashi, M., K. Wada, and K. Munakata. 1981. New nematicidal metabolites from a fungus, Irpex lacteus. Agric. Biol. Chem. 45: 1527-1529.
5. Kim, D. H., J. S. Hwang, H. S. Baek, K. J. Kim, B. G. Lee, I. S. Chang, et al. 2003. Development of 5-[(3-aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one as a novel whitening agent. Chem. Pharm. Bull. 51: 113-116.
6. Kim, K. B., S. I. Kim, and K. S. Song. 2003. Neuraminidase inhibitors from mushroom Microphors affinis. J. Microbiol. Biotechnol. 13: 778-782.
7. Kim, W. G., I. J. Ryoo, S. H. Park, D. S. Kim, S. K. Lee, K. C. Park, and I. D. Yoo. 2005. Terrein, a melanin biosynthesis inhibitor, from Penicillium sp. 20135. J. Microbiol. Biotechnol. 15: 891-894.
8. Kim, Y. H., S. M. Cho, J. W. Hyun, I. J. Ryoo, S. J. Choo, S. Lee, et al. 2008. A new antioxidant, clitocybin A, from the culture broth of Clitocybe aurantiaca. J. Antibiot. 61: 573-576.
9. Lee, N. K., K. H. Son, H. W. Chang, S. S. Kang, H. Park, Y. M. Heo, and H. P. Kim. 2004. Prenylated flavonoids as tyrosinase inhibitors. Arch. Pharm. Res. 27: 1132-1135.
10. Lim, Y. H., I. H. Kim, J. J. Seo, and J. K. Kim. 2006. Tyrosinase inhibitor from the flowers of Impatiens balsamina. J. Microbiol. Biotechnol. 16: 1977-1983.
11. Riley, P. A. 2003. Melanogenesis and melanoma. Pigment Cell Res. 16: 548-552.
12. Smalley, K. and T. Eisen. 2000. The involvement of p38 mitogen-activated protein kinase in the α-melanocyte stimulating hormone (α-MSH)-induced melanogenesis and anti-proliferative effects in B16 murine melanoma cells. FEBS Lett. 476: 198202.
13. Sutton, D. A., E. H. Thompson, M. G. Rinaldi, P. C. Iwen, K. K. Nakasone, H. S. Jung, et al. 2005. Identification and first report of Inonotus (Phellinus) tropicalis as an etiologic agent in a patient with chronic granulomatous disease. J. Clin. Microbiol. 43: 982-987.
14. Zaidman, B. Z., M. Tassin, J. Mahajna, and S. P. Wasser. 2005. Medicinal mushroom modulators of molecular targets as cancer therapeutics. Appl. Microbiol. Biotechnol. 67: 453-468.