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18 pages, 3165 KiB

Open AccessArticle

Integrating Molecular Network and Culture Media Variation to Explore the Production of Bioactive Metabolites by Vibrio diabolicus A1SM3

by Natalia Conde-Martínez, Anelize Bauermeister, Alan Cesar Pilon, Norberto Peporine Lopes and Edisson Tello

Mar. Drugs 2019, 17(4), 196; https://doi.org/10.3390/md17040196 - 27 Mar 2019

Cited by 5 | Viewed by 3230

Abstract

Vibrio diabolicus A1SM3 strain was isolated from a sediment sample from Manaure Solar Saltern in La Guajira and the produced crude extracts have shown antibacterial activity against methicillin-resistant Staphylococcus aureus and cytotoxic activity against human lung cell line. Thus, the aim of this [...] Read more.

Vibrio diabolicus A1SM3 strain was isolated from a sediment sample from Manaure Solar Saltern in La Guajira and the produced crude extracts have shown antibacterial activity against methicillin-resistant Staphylococcus aureus and cytotoxic activity against human lung cell line. Thus, the aim of this research was to identify the main compound responsible for the biological activity observed and to systematically study how each carbon and nitrogen source in the growth media, and variation of the salinity, affect its production. For the characterization of the bioactive metabolites, 15 fractions obtained from Vibrio diabolicus A1SM3 crude extract were analyzed by HPLC-MS/MS and their activity was established. The bioactive fractions were dereplicated with Antibase and Marinlit databases, which combined with nuclear magnetic resonance (NMR) spectra and fragmentation by MS/MS, led to the identification of 2,2-di(3-indolyl)-3-indolone (isotrisindoline), an indole-derivative antibiotic, previously isolated from marine organisms. The influence of the variations of the culture media in isotrisindoline production was established by molecular network and MZmine showing that the media containing starch and peptone at 7% NaCl was the best culture media to produce it. Also, polyhydroxybutyrates (PHB) identification was established by MS/MS mainly in casamino acids media, contributing to the first report on PHB production by this strain. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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15 pages, 2900 KiB

Open AccessArticle

Integrated Genomic and Metabolomic Approach to the Discovery of Potential Anti-Quorum Sensing Natural Products from Microbes Associated with Marine Samples from Singapore

by Ji Fa Marshall Ong, Hui Chin Goh, Swee Cheng Lim, Li Mei Pang, Joyce Seow Fong Chin, Koh Siang Tan, Zhao-Xun Liang, Liang Yang, Evgenia Glukhov, William H. Gerwick and Lik Tong Tan

Mar. Drugs 2019, 17(1), 72; https://doi.org/10.3390/md17010072 - 21 Jan 2019

Cited by 15 | Viewed by 6160

Abstract

With 70% of the Earth’s surface covered in water, the marine ecosystem offers immense opportunities for drug discovery and development. Due to the decreasing rate of novel natural product discovery from terrestrial sources in recent years, many researchers are beginning to look seaward [...] Read more.

With 70% of the Earth’s surface covered in water, the marine ecosystem offers immense opportunities for drug discovery and development. Due to the decreasing rate of novel natural product discovery from terrestrial sources in recent years, many researchers are beginning to look seaward for breakthroughs in new therapeutic agents. As part of an ongoing marine drug discovery programme in Singapore, an integrated approach of combining metabolomic and genomic techniques were initiated for uncovering novel anti-quorum sensing molecules from bacteria associated with subtidal samples collected in the Singapore Strait. Based on the culture-dependent method, a total of 102 marine bacteria strains were isolated and the identities of selected strains were established based on their 16S rRNA gene sequences. About 5% of the marine bacterial organic extracts showed quorum sensing inhibitory (QSI) activity in a dose-dependent manner based on the Pseudomonas aeruginosa QS reporter system. In addition, the extracts were subjected to mass spectrometry-based molecular networking and the genome of selected strains were analysed for known as well as new biosynthetic gene clusters. This study revealed that using integrated techniques, coupled with biological assays, can provide an effective and rapid prioritization of marine bacterial strains for downstream large-scale culturing for the purpose of isolation and structural elucidation of novel bioactive compounds. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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14 pages, 1259 KiB

Open AccessArticle

An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria

by Lisa Ziesche, Laura Wolter, Hui Wang, Thorsten Brinkhoff, Marion Pohlner, Bert Engelen, Irene Wagner-Döbler and Stefan Schulz

Mar. Drugs 2019, 17(1), 20; https://doi.org/10.3390/md17010020 - 31 Dec 2018

Cited by 8 | Viewed by 4058

Abstract

N-acylhomoserine lactones (AHLs), bacterial signaling compounds involved in quorum-sensing, are a structurally diverse group of compounds. We describe here the identification, synthesis, occurrence and biological activity of a new AHL, N-((2E,5Z)-2,5-dodecadienoyl)homoserine lactone (11) and its [...] Read more.

N-acylhomoserine lactones (AHLs), bacterial signaling compounds involved in quorum-sensing, are a structurally diverse group of compounds. We describe here the identification, synthesis, occurrence and biological activity of a new AHL, N-((2E,5Z)-2,5-dodecadienoyl)homoserine lactone (11) and its isomer N-((3E,5Z)-3,5-dodecadienoyl)homoserine lactone (13), occurring in several Roseobacter group bacteria (Rhodobacteraceae). The analysis of 26 strains revealed the presence of 11 and 13 in six of them originating from the surface of the macroalgae Fucus spiralis or sediments from the North Sea. In addition, 18 other AHLs were detected in 12 strains. Compound identification was performed by GC/MS. Mass spectral analysis revealed a diunsaturated C₁₂ homoserine lactone as structural element of the new AHL. Synthesis of three likely candidate compounds, 11, 13 and N-((2E,4E)-2,4-dodecadienoyl)homoserine lactone (5), revealed the former to be the natural AHLs. Bioactivity test with quorum-sensing reporter strains showed high activity of all three compounds. Therefore, the configuration and stereochemistry of the double bonds in the acyl chain seemed to be unimportant for the activity, although the chains have largely different shapes, solely the chain length determining activity. In combination with previous results with other Roseobacter group bacteria, we could show that there is wide variance between AHL composition within the strains. Furthermore, no association of certain AHLs with different habitats like macroalgal surfaces or sediment could be detected. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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19 pages, 1407 KiB

Open AccessArticle

Environmentally Friendly Valorization of Solieria filiformis (Gigartinales, Rhodophyta) from IMTA Using a Biorefinery Concept

by Ana Peñuela, Daniel Robledo, Nathalie Bourgougnon, Gilles Bedoux, Emanuel Hernández-Núñez and Yolanda Freile-Pelegrín

Mar. Drugs 2018, 16(12), 487; https://doi.org/10.3390/md16120487 - 06 Dec 2018

Cited by 31 | Viewed by 4044

Abstract

Marine macroalgae (seaweed) are an excellent source of novel bioactive metabolites. The biorefinery concept applied to seaweed facilitates the extraction of many chemical constituents from the same biomass ensuring that the resource is used fully, generating few residues through a succession of extraction [...] Read more.

Marine macroalgae (seaweed) are an excellent source of novel bioactive metabolites. The biorefinery concept applied to seaweed facilitates the extraction of many chemical constituents from the same biomass ensuring that the resource is used fully, generating few residues through a succession of extraction steps. In the present study, the biomass of the carragenophyte Solieria filiformis (Rhodophyta, Gigartinales) cultured in an integrated multi-trophic aquaculture (IMTA) system was evaluated to obtain valuable products by a biorefinery approach. Enzymatic-assisted extraction (EAE) and microwave-assisted extraction (MAE) were the eco-friendly technologies used to ensure an environmentally friendly valorization of the biomass. Three valuable products were successfully recovered: a water-soluble extract rich in proteins and sulfated polysaccharides suitable as a food supplement; a lipid fraction rich in polyunsaturated fatty acids (PUFAs) with potential to be used in the nutraceutical industry; and a pure ι-carrageenan with a powerful antiviral activity against Herpes simplex virus (EC₅₀ = 6.3 µg mL⁻¹) comparable to the commercial antiviral acyclovir (EC₅₀ = 3.2–5.4 µg mL⁻¹). Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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13 pages, 1113 KiB

Open AccessArticle

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

by Alyaa Hatem Ibrahim, Eman Zekry Attia, Dina Hajjar, Mohamed A. Anany, Samar Yehia Desoukey, Mostafa Ahmed Fouad, Mohamed Salah Kamel, Harald Wajant, Tobias A. M. Gulder and Usama Ramadan Abdelmohsen

Mar. Drugs 2018, 16(9), 290; https://doi.org/10.3390/md16090290 - 21 Aug 2018

Cited by 26 | Viewed by 5562

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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8 pages, 1294 KiB

Open AccessArticle

First Evidence of Dehydroabietic Acid Production by a Marine Phototrophic Gammaproteobacterium, the Purple Sulfur Bacterium Allochromatium vinosum MT86

by Johannes F. Imhoff, Mingshuang Sun, Jutta Wiese, Marcus Tank and Axel Zeeck

Mar. Drugs 2018, 16(8), 270; https://doi.org/10.3390/md16080270 - 04 Aug 2018

Cited by 1 | Viewed by 3312

Abstract

The production of secondary metabolites by a new isolate of the purple sulfur bacterium Allochromatium vinosum, which had shown antibiotic activities during a preliminary study, revealed the production of several metabolites. Growth conditions suitable for the production of one of the compounds [...] Read more.

The production of secondary metabolites by a new isolate of the purple sulfur bacterium Allochromatium vinosum, which had shown antibiotic activities during a preliminary study, revealed the production of several metabolites. Growth conditions suitable for the production of one of the compounds shown in the metabolite profile were established and compound 1 was purified. The molecular formula of compound 1 (C₂₀H₂₈O₂) was determined by high resolution mass spectra, and its chemical structure by means of spectroscopic methods. The evaluation of these data revealed that the structure of the compound was identical to dehydroabietic acid, a compound known to be characteristically produced by conifer trees, but so far not known from bacteria, except cyanobacteria. The purified substance showed weak antibiotic activities against Bacillus subtilis and Staphylococcus lentus with IC₅₀ values of 70.5 µM (±2.9) and 57.0 µM (±3.3), respectively. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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560 KiB

Open AccessArticle

Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348

by Cheng Cheng, Eman M. Othman, Helga Stopper, RuAngelie Edrada-Ebel, Ute Hentschel and Usama Ramadan Abdelmohsen

Mar. Drugs 2017, 15(12), 383; https://doi.org/10.3390/md15120383 - 06 Dec 2017

Cited by 30 | Viewed by 6038

Abstract

A new cyclic dipeptide, petrocidin A (1), along with three known compounds—2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4)—were isolated from the solid culture of Streptomyces sp. SBT348. The strain Streptomyces sp. SBT348 had been [...] Read more.

A new cyclic dipeptide, petrocidin A (1), along with three known compounds—2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4)—were isolated from the solid culture of Streptomyces sp. SBT348. The strain Streptomyces sp. SBT348 had been prioritized in a strain collection of 64 sponge-associated actinomycetes based on its distinct metabolomic profile using liquid chromatography/high-resolution mass spectrometry (LC-HRMS) and nuclear magnetic resonance (NMR). The absolute configuration of all α-amino acids was determined by HPLC analysis after derivatization with Marfey’s reagent and comparison with commercially available reference amino acids. Structure elucidation was pursued in the presented study by mass spectrometry and NMR spectral data. Petrocidin A (1) and 2,3-dihydroxybenzamide (3) exhibited significant cytotoxicity towards the human promyelocytic HL-60 and the human colon adenocarcinoma HT-29 cell lines. These results demonstrated the potential of sponge-associated actinomycetes for the discovery of novel and pharmacologically active natural products. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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Review

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12 pages, 1230 KiB

Open AccessReview

Natural Product Potential of the Genus Nocardiopsis

by Alyaa Hatem Ibrahim, Samar Yehia Desoukey, Mostafa A. Fouad, Mohamed Salah Kamel, Tobias A. M. Gulder and Usama Ramadan Abdelmohsen

Mar. Drugs 2018, 16(5), 147; https://doi.org/10.3390/md16050147 - 29 Apr 2018

Cited by 43 | Viewed by 6480

Abstract

Actinomycetes are a relevant source of novel bioactive compounds. One of the pharmaceutically and biotechnologically important genera that attract natural products research is the genus Nocardiopsis, mainly for its ability to produce a wide variety of secondary metabolites accounting for its wide range [...] Read more.

Actinomycetes are a relevant source of novel bioactive compounds. One of the pharmaceutically and biotechnologically important genera that attract natural products research is the genus Nocardiopsis, mainly for its ability to produce a wide variety of secondary metabolites accounting for its wide range of biological activities. This review covers the literature from January 2015 until February 2018 making a complete survey of all the compounds that were isolated from the genus Nocardiopsis, their biological activities, and natural sources, whenever applicable. Full article

(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)

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