New <i>p</i>-Terphenyl and Polyketide Metabolites from the Sclerotia of <i>Penicillium raistrickii</i>

Belofsky, Gilbert N.; Gloer, Katherine B.; Gloer, James B.; Wicklow, Donald T.; Dowd, Patrick F.

doi:10.1021/np980188o

Cited by 74 publications

(75 citation statements)

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“…NMR analysis of the proton ( 1 H), heteronuclear multiple quantam coherence (HSQC), and heteronuclear multiple bond correlation (HMBC) data proved the hypothesis of a further hydroxyl group since only three aromatic protons could be detected. The additional hydroxy group could be assigned to the 5 position, since a singlet proton at 6.62 ppm was assigned to position 7 due to clear HMBC correlations to C5, C8a, and 8-CH 3 in accordance with the work of Belofsky et al, who also reported that 1,3,5,6-tetrahydroxy-8-methyl-xanthone has antibacterial activity against Staphyloccocus aureus (4).…”

supporting

confidence: 83%

Method for Screening Compounds That Influence Virulence Gene Expression in Staphylococcus aureus

Nielsen

Frees

et al. 2010

Antimicrob Agents Chemother

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We present a simple assay to examine effects of compounds on virulence gene expression in the human pathogen Staphylococcus aureus. The assay employs transcriptional reporter strains carrying lacZ fused to central virulence genes. Compounds affecting virulence gene expression and activity of the agr locus are scored based on color change in the presence of a chromogenic ␤-galactosidase substrate. The assay can be used to screen for novel antivirulence compounds from many different sources, such as fungi, as demonstrated here.Staphylococcus aureus is a significant human pathogen that causes a variety of diseases ranging from minor skin infections to life-threatening endocarditis and septicemia (2). A contributing factor to the severity of staphylococcal infections is the ability of the organism to acquire resistance to numerous antibiotics (22). The growing problems of antibiotic-resistant microorganisms have necessitated alternative therapeutic strategies, including antivirulence therapy (3, 6). The aim of antivirulence therapy is to silence virulence gene expression, allowing the host immune system time to act and eradicate the pathogen. In S. aureus, the ability to cause disease relies on the timely production of an impressive collection of virulence factors. During exponential growth, the cell surface-located virulence factors are expressed, including spa, encoding protein A, while upon entry into stationary phase, transcription of hla, encoding ␣-hemolysin, and other genes encoding extracellular factors are induced (15). This regulation is mediated partly by the agr quorum sensing system, composed of a two-component system and a regulatory RNA molecule, RNAIII, that is synthesized in response to increasing concentrations of autoinducer peptide (AIP), also encoded by the agr locus (17, 18). In order to search for new agents that interfere with S. aureus virulence gene expression, we have developed a simple plate assay that allows an easy screen of compounds from a diverse range of biological sources.Results and Discussion. In order to examine the influence of novel compounds on hla and spa gene expression in S. aureus, we incorporated the 8325-4 (16)-derived hla::lacZ (PC322; Ery r ) (5) and spa::lacZ (PC203; Ery r ) (5) fusion strains in tryptic soy agar (TSA) (Oxoid) plates containing erythromycin and 5-bromo-4-chloro-3-indolyl-␤-D-galactopyranoside (X-Gal). Briefly, 1 ml of 10 Ϫ3 -diluted overnight culture (tryptone soya broth [TSB]; Oxoid) was placed in a petri dish to which 25 ml of TSA (ϳ40°C) containing 150 g ml Ϫ1 X-Gal and 5 g ⅐ ml Ϫ1 erythromycin was added and mixed by careful whirling. The plates were dried, and wells were formed with a sterile drill. When incubated at 37°C for optimized periods of time, the plates containing PC203 (spa::lacZ) became light blue while those containing PC322 (hla::lacZ) became intensely blue, consistent with the Agr-dependent reciprocal regulation of cell-associated and secreted virulence determinants (15) (Fig. 1).To verify that the assay can visualize established e...

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supporting

confidence: 83%

Method for Screening Compounds That Influence Virulence Gene Expression in Staphylococcus aureus

Nielsen

Frees

et al. 2010

Antimicrob Agents Chemother

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“…Ding et al (2008) have recently reported the isolation of a urea derivative, hualisyn from P. herquei, an aromatic compound that also is not related to the compounds related herein. Nevertheless producing secondary metabolites holding aromatic rings, metabolites previously described for P. raistrickii (Belofsky et al 1998) are also not related to naphalenoids isolated in the present work.…”

Section: Secondary Metabolites Isolatedcontrasting

confidence: 48%

Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil

Petit¹,

Lucas²,

Abreu³

et al. 2009

Electro Journal of Biotech

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The morphological features of a Penicillium, isolated from Brazilian cerrado soil, were characterized and showed to be distinctly different from all well-defined Penicillium species. Chemical and biological investigation on the ethyl acetate extract of this Penicillium isolate resulted in the isolation of three new naphthalenoids: a major metabolite, methyl 6-acetyl-4-*Corresponding author methoxy-5, 7, 8-trihydroxynaphthalene-2-carboxylate and two minor ones, methyl 6-acetyl-4-methoxy-7,8 dihydroxynaphthalene-2-carboxylate and methyl 6 acetyl-4-methoxy-5, 8-dihydroxynaphthalene-2 carboxylate. Their structures were determined based on their mono and bidimensional nuclear magnetic resonance data. Acetyl, allyl and methoxyl derivatives of

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“…From an unidentified marine sponge sample, the fungal strain ZSDS1-F3, which was identified as Arthrinium sp., was isolated and selected for chemical study because its culture broth produced a series of metabolites that displayed similar UV absorptions by HPLC -UV analysis at 256 and 318 nm. Detailed chemical investigation resulted in the isolation of a new naphthalene derivative, 1,8-dihydroxynaphthol-1-O-a-rhamnopyranoside (1), one known a-dibenzopyrone, alternariol (2) (Aly 2008), and five known xanthones, 1,3,6-trihydroxy-8-methylxanthone (3) (Mutanyatta et al 2003), 1,3,5,6-tetrahydroxy-8-methylxanthone (4) (Belofsky et al 1998), anomalins A (5) and B (6) (Abdel et al 2003), fischexanthone (7) , were also isolated (Figure 1). Herein, we report the isolation and structural elucidation of the new naphthalene derivative, 1,8-dihydroxynaphthol-1-O-a-L-rhamnopyranoside (1) from Arthrinium sp.…”

Section: Introductionmentioning

confidence: 99%

A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3

Wang

et al. 2014

Natural Product Research

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(2014) A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3, Natural Product Research: Formerly Natural Product Letters, 28:14, 1070-1074, DOI: 10.1080/14786419.2014 To link to this article: http://dx.doi.org/10.1080/14786419.2014.905935 PLEASE SCROLL DOWN FOR ARTICLETaylor & Francis makes every effort to ensure the accuracy of all the information (the "Content") contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content.This One new naphthalene derivative, 1,8-dihydroxynaphthol-1-O-a-L-rhamnopyranoside (1), together with one known a-dibenzopyrone, alternariol (2), and five xanthones (3 -7) were isolated from the sponge-derived fungus Arthrinium sp. ZSDS1-F3. All the isolated compounds (1 -7) were established by comprehensive analysis of the spectral data, especially 1D and 2D NMR (HMQC and HMBC) spectra. In the primary bioassays, compound 3 exhibited moderate COX-2 inhibition, with IC 50 values of 12.2 mM.article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is

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New p-Terphenyl and Polyketide Metabolites from the Sclerotia of Penicillium raistrickii

Cited by 74 publications

References 24 publications

Method for Screening Compounds That Influence Virulence Gene Expression in Staphylococcus aureus

Method for Screening Compounds That Influence Virulence Gene Expression in Staphylococcus aureus

Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil

A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3

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