Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Antifungal Activity of Valinomycin, a Cyclodepsipeptide from Streptomyces padanus TH-04

  • Lim, Tae-Heon (Regional Innovation Center, Sangju University) ;
  • Oh, Hyun-Cheol (MCBI & College of Natural Sciences, Silla University) ;
  • Kwon, Soon-Youl (Regional Innovation Center, Sangju University) ;
  • Kim, Jin-Ho (Regional Innovation Center, Sangju University) ;
  • Seo, Hyo-Won (College of Pharmacy, Catholic University of Daegu) ;
  • Lee, Jeong-Hun (College of Pharmacy, Catholic University of Daegu) ;
  • Kim, Jin-Cheol (Korea Research Institute of Chemical Technology) ;
  • Lim, Chi-Hwan (Department of Bio Environmental Chemistry, Chungnam National University) ;
  • Cha, Byeong-Jin (Department of Plant Medicine, Chungbuk National University) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu)
  • Published : 2007.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Using antifungal activity-guided fractionation, an actinomycete, Streptomyces padanus strain TH-04, which was isolated from mummified peaches infected with Monilinia fructicola, was found to produce the valinomycin (1). The structure of 1 was established using spectroscopic data, which including one- and two-dimensional NMR experimental and mass spectroscopy. Valinomycin (1) showed antifungal activity against Phytophthora capsici, with an IC$_{50}$ value of 15.9 ${\mu}$g/mL.

Keywords

References

  1. Abdalah, R., Wei, L., Francis, K., and Yu, S.P., Valinomycin-induced apoptosis in Chinese hamster ovary cells. Neurosci. Lett. 11, 68-73 (2006)
  2. Bang, K.H., Kim, Y.K., Min, B.S., Na, M.K., Rhee, Y.H., Lee, J.P., and Bae, K.H., Antifungal activity of magnolol and honokiol. Arch. Pharm. Res. 23, 46-49 (2000) https://doi.org/10.1007/BF02976465
  3. De Clercq E., Potential antivirals and antiviral strategies against SARS coronavirus infections. Expert. Rev. Anti. Infect. Ther. 4, 291-302 (2006) https://doi.org/10.1586/14787210.4.2.291
  4. Fukuda, T., Arai, M., Tomoda, H., and Omura, S., New beauvericins, potentiators of antifungal miconazole activity, produced by Beauveria sp. FKI-1366 II. Structure elucidation. J. Antibiot. 57, 117-124 (2004) https://doi.org/10.7164/antibiotics.57.117
  5. Jensen, P.R., Williams, P.G., Oh, D.C., Zeigler, L., and Fenical, W., Species-specific secondary metabolite production in marine actinomycetes of the genus Salinispora. Appl. Environ. Microbiol. 73, 1146-1152 (2007) https://doi.org/10.1128/AEM.01891-06
  6. Jeong, S.Y., Shin, H.J., Kim, T.S., Lee, H.S., Park, S.K., and Kim, H.M., Streptokordin, a new cytotoxic compound of the methylpyridine class from a marine-derived Streptomyces sp. KORDI-3238. J. Antibiot. 59, 234-240 (2006) https://doi.org/10.1038/ja.2006.33
  7. Lee, J.Y., Lee, J.Y., Moon, S.S., and Hwang, B.K., Isolation and antifungal activity of 4-phenyl-3-butenoic acid from Streptomyces koyangensis strain VK-A60. J. Agric. Food Chem. 53, 7696-7700 (2005) https://doi.org/10.1021/jf050957r
  8. Lim, T.H., Lee, J.M., Chang, T.H., and Cha, B., Antifungal activity and identification of an actinomycetes strain isolated from mummifies peaches. Kor. J. Appl. Microbiol. Biotechnol. 28, 161-166 (2000)
  9. Miyadoh, S., Research on antibiotic screening in Japan over the last decade: A producing microorganisms approach. Actinomycetologica 9, 100-106 (1993)
  10. Pettit, G.R., Tan, R., Melody, N., Kielty, J.M., Pettit, R.K., Herald, D.L., Tucker, B.E., Mallavia, L.P., Doubek, D.L., and Schmidt, J.M., Antineoplastic agents. Part 409: isolation and structure of montanastatin from a terrestrial actinomycete. Bioorg. Med Chem. Lett. 7, 895-899 (1999) https://doi.org/10.1016/S0968-0896(99)00024-3
  11. Rukachaisirikul, V., Chantaruk, S., Tansakul, C., and Saithong, S., Chaicharernwimonkoon, L., Pakawatchai, C., Isaka, M., and Intereya, K., A cyclopeptide from the insect pathogenic fungus Cordyceps sp. BCC 1788. J. Nat. Prod. 69, 305-307 (2006) https://doi.org/10.1021/np050433l
  12. Ryoo, I.J., Park, H.R., Choo, S.J., Hwang, J.H., Park, Y.M., Bae, K., Shin Ya, K., and Yoo, I.D., Selective cytotoxic activity of valinomycin against HT-29 human colon carcinoma cells via down-regulation of GRP78. Biol. Pharm. Bull. 29, 817-820 (2006) https://doi.org/10.1248/bpb.29.817
  13. Zeggaf, C., Poncet, J., Jouin, P., Dufour, M.N., and Castro, B., Isopropenyl chlorocarbonate (IPCC) in amino acid and peptide chemistry: esterification of N-protected amino acids; application to the synthesis of the depsipeptide valinomycin. Tetrahedron 45, 5039-5050 (1989) https://doi.org/10.1016/S0040-4020(01)81083-8