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.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
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)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Issue date:
DOI: https://doi.org/10.1038/ja.2006.35
Keywords
This article is cited by
-
The intriguing chemistry and biology of sulfur-containing natural products from marine microorganisms (1987–2020)
Marine Life Science & Technology (2021)
-
Marine-Derived Fungi in Korea
Ocean Science Journal (2021)
-
Gliotoxin Analogues from Endophytic Penicillium sp. of Eucommia ulmoides and Their Antimicrobial Activity
Chemistry of Natural Compounds (2019)
-
Pharmacological significance of marine microbial bioactive compounds
Environmental Chemistry Letters (2019)
-
Non-lipopeptide fungi-derived peptide antibiotics developed since 2000
Biotechnology Letters (2019)
