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Clitocybin D, a Novel Human Neutrophil Elastase Inhibitor from the Culture Broth of Clitocybe aurantiaca

  • Kim, Young-Hee (Korea Research Institute of Bioscience and Biotechnology) ;
  • Ryoo, In-Ja (Korea Research Institute of Bioscience and Biotechnology) ;
  • Choo, Soo-Jin (Korea Research Institute of Bioscience and Biotechnology) ;
  • Xu, Guang-Hua (Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee, Sang-Ku (Korea Research Institute of Bioscience and Biotechnology) ;
  • Seok, Soon-Ja (National Institute of Agricultural Science and Technology, RDA) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University) ;
  • Yoo, Ick-Dong (Korea Research Institute of Bioscience and Biotechnology)
  • Published : 2009.10.31

Abstract

Clitocybin D, a novel human neutrophil elastase inhibitor, was isolated from the culture broth of Clitocybe aurantiaca. This compound was purified by solvent extraction, silica gel column chromatography, Sephadex LH-20 column chromatography, and preparative HPLC. The compound was determined to be 4-(4,6-dihydroxy-3-methoxy-3H-isoindol-1-yl)-benzoic acid on the basis of 1D and 2D NMRs and MS spectroscopic analysis. Analysis of the human neutrophil elastase (HNE) inhibitory activity of the isolated compound revealed that it showed significant HNE inhibitory activity with an $IC_{50}$ value of $17.8{\mu}M$.

Keywords

References

  1. Antonicelli, F., G. Bellon, L. Debelle, and W. Hornebeck. 2007. Elastin-elastases and inflamm-aging. Curr. Top. Dev. Biol. 79:99-155 https://doi.org/10.1016/S0070-2153(06)79005-6
  2. Arnone, A., A. Colombo, G.. Nasini, and S. V. Meille. 1993. Secondary mold metabolites. Part 42. Eleganthol, a sesquiterpene from Clitocybe elegans. Phytochemistry 32: 1493-1497 https://doi.org/10.1016/0031-9422(93)85165-N
  3. Bernstein, E. F. and J. Uitto. 1996. The effect of photodamage on dermal extracellular matrix. Clin. Dermatol. 14: 143-151 https://doi.org/10.1016/0738-081X(95)00149-A
  4. Bradshaw, A. P., J. R. Hanson, and P. B. Hitchcock. 1982. 4$\alpha$-Hydroxydihydroilludin M. A new sesquiterpenoid metabolite of Clitocybe illudens. Phytochemistry 21: 942-943 https://doi.org/10.1016/0031-9422(82)80099-X
  5. Choo, S. J., B. S. Yun, I. J. Ryoo, Y. H. Kim, K. H. Bae, and I. D. Yoo. 2009. Aspochalasin I, a melanogenesis inhibitor from Aspergillus sp. J. Microbiol. Biotechnol. 19 (In press) https://doi.org/10.4014/jmb.0806.389
  6. 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 https://doi.org/10.1038/ja.2008.77
  7. Lee, K. K., J. H. Kim, J. J. Cho, and J. D. Choi. 1999. Inhibitory effects of 150 plant extracts on elastase activity, and their anti-inflammatory effects. Int. J. Cosmet. Sci. 21: 71-82 https://doi.org/10.1046/j.1467-2494.1999.181638.x
  8. Melzig, M. F., B. L$\ddot{o}$ser, and S. Ciesielski. 2001. Inhibition of neutrophil elastase activity by phenolic compounds from plants. Die Pharmazie 56: 967-970
  9. Starcher, B., R. L. Aycock, and C. H. Hill. 2005. Multiple roles for elastic fibers in the skin. J. Histochem. Cytochem. 53: 431-443 https://doi.org/10.1369/jhc.4A6484.2005
  10. Tsukahara, K., H. Nakagawa, S. Moriwaki, Y. Takema, T. Fujimura, and G. Imokawa. 2006. Inhibition of ultraviolet-Binduced wrinkle formation by an elastase-inhibiting herbal extract:Implication for the mechanism underlying elastase-associated wrinkles. Int. J. Dermatol. 45: 460-468 https://doi.org/10.1111/j.1365-4632.2006.02557.x
  11. Wiltried, M., N. Klaus, and Z. F. Lin. 1994. Elastic fiber arrangement in the skin of the pig. Arch. Derm. Res. 270: 397-401
  12. Xu, G. H., I. J. Ryoo, Y. H. Kim, S. J. Choo, and I. D. Yoo. 2009. Free radical scavenging and antielastase activities of flavonoids from the fruits of Thuja orientalis. Arch. Pharm. Res. 32: 275-282

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