Citreamicins with Potent Gram-Positive Activity

Hopp, D. Craig; Milanowski, Dennis; Rhea, Joshua; Jacobsen, Daniel E.; Rabenstein, John; Smith, Chris; Romari, Khadidja; Clarke, Midori; Francis, Linda; Irigoyen, Macarena; Luche, Michele; Carr, Grant; Mocek, Ursula

doi:10.1021/np800503z

Cited by 18 publications

(18 citation statements)

References 7 publications

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“…Citreamicin δ and ε were also isolated in 2008 from Streptomyces vinaceus from a soil sample obtained from a river. They were observed to be structurally similar to citreamicin η except for the relocation of a methoxy group but yet showed anti-MRSA activity in the range of ≤ 0.5–2 and 0.12–0.25 μg/mL (Hopp et al, 2008 ). Despite its potent anti-MRSA activity, its mechanism of action remains unknown at present time.…”

Section: Anti-mrsa Compounds Derived From Streptomyces mentioning

confidence: 99%

Streptomyces as a Prominent Resource of Future Anti-MRSA Drugs

et al. 2018

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Methicillin-resistant Staphylococcus aureus (MRSA) pose a significant health threat as they tend to cause severe infections in vulnerable populations and are difficult to treat due to a limited range of effective antibiotics and also their ability to form biofilm. These organisms were once limited to hospital acquired infections but are now widely present in the community and even in animals. Furthermore, these organisms are constantly evolving to develop resistance to more antibiotics. This results in a need for new clinically useful antibiotics and one potential source are the Streptomyces which have already been the source of several anti-MRSA drugs including vancomycin. There remain large numbers of Streptomyces potentially undiscovered in underexplored regions such as mangrove, deserts, marine, and freshwater environments as well as endophytes. Organisms from these regions also face significant challenges to survival which often result in the production of novel bioactive compounds, several of which have already shown promise in drug development. We review the various mechanisms of antibiotic resistance in MRSA and all the known compounds isolated from Streptomyces with anti-MRSA activity with a focus on those from underexplored regions. The isolation of the full array of compounds Streptomyces are potentially capable of producing in the laboratory has proven a challenge, we also review techniques that have been used to overcome this obstacle including genetic cluster analysis. Additionally, we review the in vivo work done thus far with promising compounds of Streptomyces origin as well as the animal models that could be used for this work.

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Section: Anti-mrsa Compounds Derived From Streptomyces mentioning

confidence: 99%

Streptomyces as a Prominent Resource of Future Anti-MRSA Drugs

et al. 2018

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“…Analysis of the 13 C NMR spectra indicated the presence of three carbonyls ( δ C 183.1, 173.7, 166.3), including a ketone at δ C 183.1; 18 sp 2 carbons in the down field region (three methines ( δ C 122.6, 118.2, 107.7) and fifteen quaternary carbons); and two sp 3 quaternary carbons ( δ C 93.6, 65.5), four methylene groups ( δ C 61.6, 40.4, 29.4, 23.6), two methyl groups ( δ C 26.5, 19.2) and one methoxy ( δ C 57.3) in the high field region. Together, these signals reveal a skeleton of xanthones very similar to that identified in citreamicin ε ( 5 ) [13] (Figure 1). A fragment ion at m / z 475 in ion source collision-induced dissociation electrospray ionization mass spectrometry (ISCID ESIMS) corresponding to citeamicin ε ( 5 ) without the G ring ion was also observed (Figure 2).…”

Section: Resultsmentioning

confidence: 90%

“…Further comparison of the 1D and 2D NMR data of compound 1 and citreamicin ε [13] indicated that they are structural isomers with the same molecular weight and similar chemical shifts. Heteronuclear multiple bond correlation (HMBC) correlations from the methyl group at δ H 1.61 (H-21) to carbons at δ C 173.7 (C-2), 65.5 (C-3), and 61.6 (C-20), together with HMBC correlations from δ H 1.67 (H-22) to δ C 40.4 (C-18) and 93.6 (C-19), reveal the G ring.…”

Section: Resultsmentioning

confidence: 99%

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Four New Antibacterial Xanthones from the Marine-Derived Actinomycetes Streptomyces caelestis

et al. 2012

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Four new polycyclic antibiotics, citreamicin θ A (1), citreamicin θ B (2), citreaglycon A (3), and dehydrocitreaglycon A (4), were isolated from marine-derived Streptomyces caelestis. The structures of these compounds were elucidated by 1D and 2D NMR spectra. All four compounds displayed antibacterial activity against Staphylococcus haemolyticus, Staphylococcus aureus, and Bacillus subtillis. Citreamicin θ A (1), citreamicin θ B (2) and citreaglycon A (3) also exhibited low MIC values of 0.25, 0.25, and 8.0 μg/mL, respectively, against methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300.

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“…and active against a variety of Gram-positive bacteria, including MRSA and vancomycin-resistant Enterococcus faecalis (VRE). [14][15][16][17][18] Plant pathogenic fungi making specic organs infection are responsible for the heavy economic loss in agriculture. Thus, different strategies have been used for the control of phytopathogenic fungi, mainly by using synthetic fungicides.…”

Section: Introductionmentioning

confidence: 99%