Cyclic dipeptides exhibit synergistic, broad spectrum antimicrobial effects and have anti-mutagenic properties

Rhee, Kyu-Nam

doi:10.1016/j.ijantimicag.2004.05.005

Cited by 118 publications

(55 citation statements)

References 15 publications

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“…18,21,22 These heterocyclic compounds display several biological properties, such as: antimicrobial, antitumor, antiviral and plant growth regulation. 19,23 Fdhila et al 20 These DD-diketopiperazines presented a potent inhibitory activity against the pathogen Vibrio anguillarum, while the LL-enantiomers were completely inactive. 20 Therefore, the D-stereochemistry seems to be important for the biological activity.…”

Section: Resultsmentioning

confidence: 99%

Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Furtado¹,

Pupo²,

Carvalho³

et al. 2005

J. Braz. Chem. Soc.

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Section: Resultsmentioning

confidence: 99%

Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Furtado¹,

Pupo²,

Carvalho³

et al. 2005

J. Braz. Chem. Soc.

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“…KH-614 and Aspergillus parasiticus have been reported to produce Cyclo(L-leucyl-L-prolyl) that exhibit antimicrobial and anticancer activity. Cyclic dipeptides are known to have antiviral, antibiotic and antitumor properties (Rhee 2002, 2004, Yan et al 2004. Two species of Penicillium were isolated from leaves of Alibertia macrophylla (Rubiaceae).…”

Section: Discussionmentioning

confidence: 99%

Bioactive metabolites from an endophytic fungus Penicillium sp. isolated from Centella asiatica

Nn¹,

Jj²

2014

CREAM

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Endophytes are important sources for the discovery of bioactive compounds. The potential role of the endophyte and its biologically active metabolites in its association with its host has been investigated. In the present study the antioxidant activity of the endophytic fungus Penicillium sp. isolated from medicinal plant Centella asiatica was evaluated by its ability to scavenge DPPH free radicals. Bioactive metabolites present in the ethyl acetate extract from the endophytic fungus Penicillium sp. were analysed by using GC-MS. The metabolites were investigated for cytotoxic activity. The extract of Penicillium sp. exhibited high antioxidant activity with IC 50 value, 54.72±2.19μg/ml. The ethyl acetate extract of Penicillium sp. has high antioxidant capacity of 325.76±0.14 mg equivalent to ascorbic acid. The ethyl acetate extract of Penicillium sp. demonstrated a promising cytotoxic activity against HeLa, A431 and human breast cancer (MCF7). These results indicate that endophytic fungi isolated from medicinal plants could be a potential source for bioactive compounds.

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“…Cyclo(Leu-Gly) produced by the fungus Rosellinia necatrix inhibits the development of physical dependence on morphine (52), and cFP produced by Lactobacillus plantarum has antifungal activity (49), while a stereoisomer, cyclic(D-Phe-D-Pro), produced by marine bacteria, inhibits the growth of the fish pathogen Vibrio anguillarum (13). cFP together with cyclo(Lleucine-L-proline) inhibits the growth of pathogenic yeasts and is antimutagenic in a Salmonella mutation assay (43). Considering the relatively high concentration of cFP produced by Vibrio spp.…”

Section: Discussionmentioning

confidence: 99%

Cyclo(Phe-Pro) Modulates the Expression ofompUinVibriospp

et al. 2006

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Vibrio vulnificus was found to produce a chemical that induced the expression of Vibrio fischeri lux genes. Electron spray ionization-mass spectrometry and 1 H nuclear magnetic resonance analyses indicated that the compound was cyclo(L-Phe-L-Pro) (cFP). The compound was produced at a maximal level when cell cultures reached the onset of stationary phase. Sodium dodecyl sulfate-polyacrylamide gel analysis of the total proteins of V. vulnificus indicated that expression of OmpU was enhanced by exogenously added synthetic or purified cFP. A toxR-null mutant failed to express ompU despite the addition of cFP. The related Vibrio spp. V. cholerae, V. parahaemolyticus, and V. harveyi also produced cFP, which induced the expression of their own ompU genes. cFP also enhanced the expression in V. cholerae of the ctx genes, which are known to be regulated by ToxR. Our results suggest that cFP is a signal molecule controlling the expression of genes important for the pathogenicity of Vibrio spp.Communication between cells via diffusible chemicals is a general phenomenon found in virtually all living organisms. However, it is only in the last 2 decades that it has been intensively studied in bacteria. One of the best-known examples is quorum sensing. A number of bacteria associated with eukaryotic hosts employ quorum-sensing systems to sense their population density, thereby modulating the expression of sets of genes involved in physiological responses associated with survival, propagation, and/or virulence (9,21,44). N-Acylhomoserine lactones (AHLs) are the most prevalent signal molecules for quorum sensing in gram-negative bacteria, but not all signal molecules belong to this group. For instance, Vibrio harveyi employs a furanosyl borate diester molecule in addition to AHL (7). The plant pathogen Ralstonia solanacearum uses 3-hydroxypalmitic acid methyl ester together with AHL to control the expression of virulence factors (14), and several gram-positive bacteria utilize peptides or ␥-butyrolactone as signals (for a review, see reference 12). Xanthomonas campestris also uses non-AHL signal molecules, which have been identified as fatty acid derivatives, to regulate the expression of virulence factors (3, 54). In addition, cyclic dipeptides produced by Pseudomonas spp. and some other genera can activate AHL bioindicator strains (22). They probably activate or antagonize signaling components implicated in AHL-dependent quorum sensing by cross talk with the associated sensors. However, the actual biological roles of these cyclic dipeptide molecules remain to be clarified.Vibrio vulnificus is an opportunistic human pathogen that causes severe wound infection and primary septicemia (50). It has been reported to possess a functional luxS and produce a signal molecule that induces bioluminescence in a V. harveyi AI-2 reporter strain (25). It is also known to possess smcR, a homolog of the positive regulatory gene luxR of V. harveyi (29). SmcR induces the expression of vvpE, encoding a metalloprotease, and represses vvhAB, encodin...

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Cyclic dipeptides exhibit synergistic, broad spectrum antimicrobial effects and have anti-mutagenic properties

Cited by 118 publications

References 15 publications

Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Diketopiperazines produced by an Aspergillus fumigatus Brazilian strain

Bioactive metabolites from an endophytic fungus Penicillium sp. isolated from Centella asiatica

Cyclo(Phe-Pro) Modulates the Expression ofompUinVibriospp

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