Peptidolipins B–F, Antibacterial Lipopeptides from an Ascidian-Derived <i>Nocardia</i> sp.

Wyche, Thomas P.; Hou, Yunfei; Vazquez-Rivera, Emmanuel; Braun, D. C.; Bugni, Tim S.

doi:10.1021/np300016r

Cited by 66 publications

(36 citation statements)

References 33 publications

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“…33 To date, no natural products of this type have been reported with an S configuration at the β -acyloxy carbon, although NMR properties for the peptidolipin B have been predicted via DFT calculations (see Figure 4). 35 …”

Section: Resultsmentioning

confidence: 99%

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Biosynthetic Products from a Nearshore-Derived Gram-Negative Bacterium Enable Reassessment of the Kailuin Depsipeptides

et al. 2015

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Sampling of California nearshore sediments resulted in the isolation of a Gram-negative bacterium, Photobacterium halotolerans, capable of producing unusual biosynthetic products. Liquid culture in artificial seawater-based media provided cyclic depsipeptides including four known compounds, kailuins B–E (2–5), and two new analogues, kailuins G and H (7 and 8). The structures of the new and known compounds were confirmed through extensive spectroscopic and Marfey's analyses. During the course of these studies, a correction was made to the previously reported double-bond geometry of kailuin D (4). Additionally, through the application of a combination of derivatization with Mosher's reagent and extensive 13C NMR shift analysis, the previously unassigned chiral center at position C-3 of the β-acyloxy group of all compounds was determined. To evaluate bioactivity and structure–activity relationships, the kailuin core (13) and kailuin lactam (14) were prepared by chiral synthesis using an Fmoc solid-phase peptide strategy followed by solution-phase cyclization. All isolated compounds and synthetic cores were assayed for solid tumor cell cytotoxicity and showed only minimal activity, contrary to other published reports. Additional phenotypic screenings were done on 4 and 5, with little evidence of activity.

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Section: Resultsmentioning

confidence: 99%

“…As noted above, this strategy has been successfully used by others, although such an analysis failed during the evaluation of the peptidolipins. 35 As described below, Mosher's method was tenuous for the kailuins and motivated the quest for back-up analysis. This was achieved by assembling a minidatabase of 13 C NMR chemical shift values.…”

Section: Resultsmentioning

confidence: 99%

Biosynthetic Products from a Nearshore-Derived Gram-Negative Bacterium Enable Reassessment of the Kailuin Depsipeptides

et al. 2015

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“…Finally, during 2012–2013, the novel marine lipopeptides, peptidolipins B–F (MIC = 64 μg/mL), were isolated from an ascidian-derived Gram positive Nocardia sp. bacterium [116]. …”

Section: Marine Compounds With Antibacterial Antifungal Antiprotmentioning

confidence: 99%

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

et al. 2017

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The peer-reviewed marine pharmacology literature from 2012 to 2013 was systematically reviewed, consistent with the 1998–2011 reviews of this series. Marine pharmacology research from 2012 to 2013, conducted by scientists from 42 countries in addition to the United States, reported findings on the preclinical pharmacology of 257 marine compounds. The preclinical pharmacology of compounds isolated from marine organisms revealed antibacterial, antifungal, antiprotozoal, antituberculosis, antiviral and anthelmitic pharmacological activities for 113 marine natural products. In addition, 75 marine compounds were reported to have antidiabetic and anti-inflammatory activities and affect the immune and nervous system. Finally, 69 marine compounds were shown to display miscellaneous mechanisms of action which could contribute to novel pharmacological classes. Thus, in 2012–2013, the preclinical marine natural product pharmacology pipeline provided novel pharmacology and lead compounds to the clinical marine pharmaceutical pipeline, and contributed significantly to potentially novel therapeutic approaches to several global disease categories.

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“…WMMB 215 isolated from ascidian Trididemnum orbiclatum. These compounds showed bacteriostatic activity agaisnt MRSA and MSSA (methicillin sensitive Staphylococcus aureus) (Wyche et al 2012). Analysis of the NRPS sequences with registered protein in the NCBI database confirmed that the NRPS gene of isolate DR-2R-115-35 has similarity to the genus Streptomyces.…”

Section: Discussionmentioning

confidence: 77%

Bioactivity and genetic screening of marine actinobacteria associated with red algae Gelidiella acerosa

Ulfah

Kasanah

Handayani

2018

Indones. J. Biotechnol.

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Bacterial resistance to exis ng an bio cs has driven a search for new an bio cs from marine ac nobacteria. Bioac vity and gene c screening of ac nobacteria associated with red algae Gelidiella acerosa were conducted to discover new an bacterial compounds against Vibrio alginoly cus. A total of 14 ac nobacteria isolates were obtained from G. acerosa. The isolates were subjected to gene c screening for nrps (non-ribosomal pep de synthetase) and FADH 2 -dependent halogenase genes. The isolates' ability to produce secondary metabolites was examined by fermenta on in various media in a six-well mini plate. The bioac vity of the secondary metabolites was screened using a micro ter assay and the agar overlay method. The results showed that all 14 isolates had the nrps gene, whereas none had the halogenase gene. Meanwhile, eight of the ac nobacteria isolates showed an bacterial ac vity against V. alginoly cus.

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Peptidolipins B–F, Antibacterial Lipopeptides from an Ascidian-Derived Nocardia sp.

Cited by 66 publications

References 33 publications

Biosynthetic Products from a Nearshore-Derived Gram-Negative Bacterium Enable Reassessment of the Kailuin Depsipeptides

Biosynthetic Products from a Nearshore-Derived Gram-Negative Bacterium Enable Reassessment of the Kailuin Depsipeptides

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

Bioactivity and genetic screening of marine actinobacteria associated with red algae Gelidiella acerosa

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