Abstract
A new antibacterial dioxopiperazine, dehydroxybisdethiobis(methylthio)gliotoxin (1), and the previously described bisdethiobis(methylthio)gliotoxin (2) and gliotoxin (3), have been isolated from the broth of a marine-derived fungus of the genus Pseudallescheria. The structure and absolute stereochemistry of the new compound was assigned on the basis of NMR and CD experiments. Compounds 1~3 exhibit potent antibacterial activity against the methicillin-resistant and multidrug-resistant Staphylococcus aureus with MIC values of 31.2, 31.2, and 1.0 µg/ml, respectively. Compound 3 also exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 value of 5.2 µM.
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Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR . Marine natural products. Nat Prod Rep 22: 15–61 ( 2005) and references therein
Pietra F . Secondary metabolites from marine microorganisms: bacteria, protozoa, algae and fungi. Achievements and prospects. Nat Prod Rep 14: 453–464 ( 1997)
Jensen PR, Fenical W . Marine microorganisms and drug discovery: current status and future potential. In Drugs from the Sea. Ed., N. Fusetani, pp. 6–29 Karger, Basel, (2000)
Li Y, Li X, Son BW . Antibacterial and radical scavenging epoxycyclohexenones and aromatic polyols from a marine isolate of the fungus Aspergillus. Natural Product Sciences 11: 136–138 ( 2005)
Kirby GW, Robins DJ, Sefton MA, Talekar RR . Biosynthesis of bisdethiobis(methylthio)glitoxin, a new metabolites of Gliocladium deliquescens. JCS Perkin I. 119–121 ( 1980)
Lee HJ, Lee JH, Hwang BY, Kim HS, Lee JJ . Anti-angiogenic acitivites of glitoxin and its methylthioderivative, fungal metabolites. Arch Pharm Res 24: 397–401 ( 2001), and references therein
Cole RJ, Cox RH . Handbook of toxic fungal metabolites. pp. 571–574, Academic Press, London ( 1981)
Li Y, Li X, Son BW, Choi HD . Screening of antimicrobial activity from the marine-derived fungus. Kor J Pharmacogn 34: 142–144 ( 2003)
Li XF, Li Y, Nam KW, Kim DS, Choi HD, Son BW . Screening of radical scavenging activity from the marine-derived fungus. Kor J Pharmacogn 33: 219–223 ( 2002)
Turner WB, Aldridge DC . Fungal Metabolites II. pp. 405–423, Academic Press, London ( 1983)
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Li, X., Kim, SK., Nam, K. et al. A New Antibacterial Dioxopiperazine Alkaloid Related to Gliotoxin from a Marine Isolate of the Fungus Pseudallescheria. J Antibiot 59, 248–250 (2006). https://doi.org/10.1038/ja.2006.35
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DOI: https://doi.org/10.1038/ja.2006.35
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