Bacicyclin, a new antibacterial cyclic hexapeptide from Bacillus sp. strain BC028 isolated from Mytilus edulis

Wiese, Jutta; Abdelmohsen, Usama Ramadan; Motiei, Asa; Hentschel, Ute; Imhoff, Johannes F.

doi:10.1016/j.bmcl.2018.01.062

Cited by 20 publications

(23 citation statements)

References 18 publications

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“…The 1 H-NMR spectrum ( Figures S1–S3 ) revealed the presence of six α-amino acid hydrogen resonances (δ H 3.35–4.37). Additionally, the 13 C NMR spectrum ( Figure S4 ) contained six amide carbonyl signals resonating between δ C 171 and 179 ppm and six α-amino acid carbon signals between δ C 41 and 60 ppm, thus corroborating the presence of six amino acid moieties [ 38 , 39 ]. The 1 H-NMR and COSY spectra ( Figures S1 and S7 ) showed two distinct aromatic spin systems (δ H 6.85–7.55), and the 13 C-NMR and 13 C-DEPT-135 spectrum ( Figures S4 and S5 ) displayed ten methines and six quaternary carbons consistent with two tryptophan moieties.…”

Section: Resultsmentioning

confidence: 88%

“…Detailed analysis of the 1 D ( 1 H, 13 C and DEPT-135) and 2 D (HSQC, HMBC and NOE) NMR spectroscopic data ( Table 2 ) revealed that nocardiotide A ( 1 ) was a hexapeptide containing Ile, Leu, Val, Ala, and two Trp residues. The amino acid sequence was elucidated to be Ile-Trp 1 -Ala-Val-Leu-Trp 2 on the basis of the following HMBC correlations ( Figures S10 and S11 ): α-Trp 1 (δ H 4.37)/Ala-CO (δ C 173.9), α-Val (δ H 4.22)/Leu-CO (δ C 171.5) and the following NOE correlations ( Figures S8 and S9 ): Trp 1 H-2(δ H 7.02)/α-Ile (δ H 4.20), α-Ala (δ H 4.31)/α-Val (δ H 4.22), α-Val (δ H 4.22)/α-Leu (δ H 3.81), α-Ile (δ H 4.20)/β,β′ Trp 2 (δ H 2.82) and Trp 2 H-4′ (δ H 7.45)/α-Leu (δ H 3.81) ( Table 2 , Figure 3 ) [ 38 , 41 ].…”

Section: Resultsmentioning

confidence: 99%

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New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67

et al. 2018

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A new cyclic hexapeptide, nocardiotide A (1), together with three known compounds—tryptophan (2), kynurenic acid (3), and 4-amino-3-methoxy benzoic acid (4)—were isolated and identified from the broth culture of Nocardiopsis sp. UR67 strain associated with the marine sponge Callyspongia sp. from the Red Sea. The structure elucidation of the isolated compounds were determined based on detailed spectroscopic data including 1D and 2D nuclear magnetic resonance (NMR) experimental analyses in combination with high resolution electrospray ionization mass spectrometry (HR-ESI-MS), while the absolute stereochemistry of all amino acids components of nocardiotide A (1) was deduced using Marfey’s method. Additionally, ten known metabolites were dereplicated using HR-ESI-MS analysis. Nocardiotide A (1) displayed significant cytotoxic effects towards the murine CT26 colon carcinoma, human HeLa cervix carcinoma, and human MM.1S multiple myeloma cell lines. The results obtained revealed sponge-associated Nocardiopsis as a substantial source of lead natural products with pronounced pharmacological activities.

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67

et al. 2018

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“…The novel molecule bacicyclin ( 4 ) ( Figure 2 ), which is a cyclic peptide, was isolated from a Bacillus sp. strain BC028 isolated from the common mussel ( Mytilus edulis ) [ 64 ]. It displays antibacterial activity against E. faecalis and S. aureus with minimal inhibitory concentration (MIC) values of 8 and 12 µM, respectively, and can help in the design of analogues with increased antibiotic efficacy [ 64 ].…”

Section: Natural Productsmentioning

confidence: 99%

“…strain BC028 isolated from the common mussel ( Mytilus edulis ) [ 64 ]. It displays antibacterial activity against E. faecalis and S. aureus with minimal inhibitory concentration (MIC) values of 8 and 12 µM, respectively, and can help in the design of analogues with increased antibiotic efficacy [ 64 ]. Anthracimycin B ( 5 ), a polyketide with powerful anti-Gram-positive bacteria activity that was obtained from a marine-derived Streptomyces cyaneofuscatus M-169, has expanded the knowledge of how the methyl group at C-2 of anthracimycins plays a role in its antibacterial effect [ 65 ].…”

Section: Natural Productsmentioning

confidence: 99%

From Ocean to Medicine: Pharmaceutical Applications of Metabolites from Marine Bacteria

et al. 2020

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Oceans cover seventy percent of the planet’s surface and besides being an immense reservoir of biological life, they serve as vital sources for human sustenance, tourism, transport and commerce. Yet, it is estimated by the National Oceanic and Atmospheric Administration (NOAA) that eighty percent of the oceans remain unexplored. The untapped biological resources present in oceans may be fundamental in solving several of the world’s public health crises of the 21st century, which span from the rise of antibiotic resistance in bacteria, pathogenic fungi and parasites, to the rise of cancer incidence and viral infection outbreaks. In this review, health risks as well as how marine bacterial derived natural products may be tools to fight them will be discussed. Moreover, an overview will be made of the research pipeline of novel molecules, from identification of bioactive bacterial crude extracts to the isolation and chemical characterization of the molecules within the framework of the One Health approach. This review highlights information that has been published since 2014, showing the current relevance of marine bacteria for the discovery of novel natural products.

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“…Bacicyclin, a cyclic hexapeptide obtained from Bacillus sp. BC028, originated from the mussel Mytilus edulis , an inhabitant of the Baltic Sea (Wiese, Abdelmohsen, Motiei, Hentschel Humeida, & Imhoff, ). This compound inhibited Enterococcus faecalis JH21 and Staphylococcus aureus NCTC 8325 with MIC values of 8 μM and 12 μM, respectively.…”

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confidence: 99%

Marine bacteria and fungi as promising source for new antibiotics

Wiese

Imhoff

2018

Drug Development Research

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Natural products and derivatives thereof are of considerable importance in the discovery of new pharmaceuticals, for example, for the treatment of cancer, diabetes, inflammation diseases, and infection diseases caused by bacteria, fungi, viruses, or parasites. The great biodiversity of marine microorganisms is reflected in their huge chemical diversity, which provides a rich source of biologically active compounds. An increasing interest in marine microorganisms as promising producers of new compounds with potential medical applications has raised increasing interest in the sustainable exploration of marine microbial resources for the discovery of new antibiotics, which is highlighted. The bottlenecks in the development of drugs using the large marine natural product pipeline are also discussed.

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Bacicyclin, a new antibacterial cyclic hexapeptide from Bacillus sp. strain BC028 isolated from Mytilus edulis

Cited by 20 publications

References 18 publications

New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67

New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67

From Ocean to Medicine: Pharmaceutical Applications of Metabolites from Marine Bacteria

Marine bacteria and fungi as promising source for new antibiotics

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