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Marine Drugs
Special Issues
Bioactive Molecules from Marine Microorganisms
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Bioactive Molecules from Marine Microorganisms

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (20 November 2020) | Viewed by 38213

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editors

Prof. Dr. Hanna Mazur-Marzec

E-Mail Website
Guest Editor
1. Division of Marine Biotechnology, Institute of Oceanography, University of Gdańsk, Marszałka J. Piłsudskiego 46, PL-81378 Gdynia, Poland
2. Laboratory of Marine Biochemistry, Institute of Oceanology, Polish Academy of Sciences, Powstańców Warszawy 55, PL-81712 Sopot, Poland
Interests: bioactive natural products; marine drugs; nonribosomal peptides structure and activity; cyanobacteria toxins; peptidomics
Special Issues, Collections and Topics in MDPI journals
Dr. Anna Toruńska-Sitarz

E-Mail Website1 Website2
Guest Editor
Division of Marine Biotechnology, Institute of Oceanography, University of Gdańsk, , Marszałka J. Piłsudskiego 46, PL-81378 Gdynia, Poland
Interests: marine microbes; bioactive natural products; marine drugs; nonribosomal peptides; antibacterial activity; molecular ecology
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine microorganisms, including bacteria, fungi, and microalgae, represent an untapped source of bioactive metabolites. Considering their great metabolic diversity and the fact that only a small fraction of all marine microorganisms has been identified, many products are still waiting to be discovered. These compounds not only help the microorganisms to survive in different conditions and habitats, but they can also be used as templates for the development of new pharmaceuticals, and as components of cosmeceuticals, nutraceuticals, and other health-related products. Among the effects most frequently attributed to natural products of marine microorganisms, cytotoxic, anticoagulant, antibacterial, antiviral, neurotoxic, and immune-modulating activities have been observed.

This Special Issue aims to collect papers on the most recent findings in the field of “Bioactive Molecules from Marine Microorganisms”. We are interested in new data on the source organisms and biosynthetic pathways of the bioactive metabolites and their chemical structures, biological activity, mode of action, isolation, and alternative methods of production as well as biotechnological potential, especially as medical agents. Comprehensive review papers that present up-to-date knowledge on bioactive products from marine microorganisms are also welcome.

Prof. Dr. Hanna Mazur-Marzec
Dr. Anna Toruńska-Sitarz
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • marine microorganisms
  • natural products
  • biosynthesis
  • genome mining
  • biological activity
  • structure elucidation
  • bioprospecting
  • bacteria
  • fungi
  • actinomycetes
  • cyanobacteria
  • microalgae

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Published Papers (10 papers)

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Research

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18 pages, 34771 KiB  
Article
Rare Chromone Derivatives from the Marine-Derived Penicillium citrinum with Anti-Cancer and Anti-Inflammatory Activities
by Yi-Cheng Chu, Chun-Hao Chang, Hsiang-Ruei Liao, Ming-Jen Cheng, Ming-Der Wu, Shu-Ling Fu and Jih-Jung Chen
Mar. Drugs 2021, 19(1), 25; https://doi.org/10.3390/md19010025 - 8 Jan 2021
Cited by 19 | Viewed by 3310
Abstract
Three new and rare chromone derivatives, epiremisporine C (1), epiremisporine D (2), and epiremisporine E (3), were isolated from marine-derived Penicillium citrinum, together with four known compounds, epiremisporine B (4), penicitrinone A (5 [...] Read more.
Three new and rare chromone derivatives, epiremisporine C (1), epiremisporine D (2), and epiremisporine E (3), were isolated from marine-derived Penicillium citrinum, together with four known compounds, epiremisporine B (4), penicitrinone A (5), 8-hydroxy-1-methoxycarbonyl-6-methylxanthone (6), and isoconiochaetone C (7). Among the isolated compounds, compounds 2–5 significantly decreased fMLP-induced superoxide anion generation by human neutrophils, with IC50 values of 6.39 ± 0.40, 8.28 ± 0.29, 3.62 ± 0.61, and 2.67 ± 0.10 μM, respectively. Compounds 3 and 4 exhibited cytotoxic activities with IC50 values of 43.82 ± 6.33 and 32.29 ± 4.83 μM, respectively, against non-small lung cancer cell (A549), and Western blot assay confirmed that compounds 3 and 4 markedly induced apoptosis of A549 cells, through Bcl-2, Bax, and caspase 3 signaling cascades. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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13 pages, 2623 KiB  
Article
Eighteen New Aeruginosamide Variants Produced by the Baltic Cyanobacterium Limnoraphis CCNP1324
by Marta Cegłowska, Karolia Szubert, Ewa Wieczerzak, Alicja Kosakowska and Hanna Mazur-Marzec
Mar. Drugs 2020, 18(9), 446; https://doi.org/10.3390/md18090446 - 27 Aug 2020
Cited by 13 | Viewed by 3026
Abstract
Cyanobactins are a large family of ribosomally synthesized and post-translationally modified cyanopeptides (RiPPs). Thus far, over a hundred cyanobactins have been detected in different free-living and symbiotic cyanobacteria. The majority of these peptides have a cyclic structure. The occurrence of linear cyanobactins, aeruginosamides [...] Read more.
Cyanobactins are a large family of ribosomally synthesized and post-translationally modified cyanopeptides (RiPPs). Thus far, over a hundred cyanobactins have been detected in different free-living and symbiotic cyanobacteria. The majority of these peptides have a cyclic structure. The occurrence of linear cyanobactins, aeruginosamides and virenamide, has been reported sporadically and in few cyanobacterial taxa. In the current work, the production of cyanobactins by Limnoraphis sp. CCNP1324, isolated from the brackish water Baltic Sea, has been studied for the first time. In the strain, eighteen new aeruginosamide (AEG) variants have been detected. These compounds are characterized by the presence of prenyl and thiazole groups. A common element of AEGs produced by Limnoraphis sp. CCNP1324 is the sequence of the three C-terminal residues containing proline, pyrrolidine and methyl ester of thiazolidyne-4-carboxylic acid (Pro-Pyr-TzlCOOMe) or thiazolidyne-4-carboxylic acid (Pro-Pyr-TzlCOOH). The aeruginosamides with methylhomotyrosine (MeHTyr1) and with the unidentified N-terminal amino acids showed strong cytotoxic activity against human breast cancer cells (T47D). Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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18 pages, 3660 KiB  
Article
Nostoc edaphicum CCNP1411 from the Baltic Sea—A New Producer of Nostocyclopeptides
by Anna Fidor, Michał Grabski, Jan Gawor, Robert Gromadka, Grzegorz Węgrzyn and Hanna Mazur-Marzec
Mar. Drugs 2020, 18(9), 442; https://doi.org/10.3390/md18090442 - 26 Aug 2020
Cited by 7 | Viewed by 4400
Abstract
Nostocyclopeptides (Ncps) constitute a small class of nonribosomal peptides, exclusively produced by cyanobacteria of the genus Nostoc. The peptides inhibit the organic anion transporters, OATP1B3 and OATP1B1, and prevent the transport of the toxic microcystins and nodularin into hepatocytes. So far, only [...] Read more.
Nostocyclopeptides (Ncps) constitute a small class of nonribosomal peptides, exclusively produced by cyanobacteria of the genus Nostoc. The peptides inhibit the organic anion transporters, OATP1B3 and OATP1B1, and prevent the transport of the toxic microcystins and nodularin into hepatocytes. So far, only three structural analogues, Ncp-A1, Ncp-A2 and Ncp-M1, and their linear forms were identified in Nostoc strains as naturally produced cyanometabolites. In the current work, the whole genome sequence of the new Ncps producer, N. edaphicum CCNP1411 from the Baltic Sea, has been determined. The genome consists of the circular chromosome (7,733,505 bps) and five circular plasmids (from 44.5 kb to 264.8 kb). The nostocyclopeptide biosynthetic gene cluster (located between positions 7,609,981–7,643,289 bps of the chromosome) has been identified and characterized in silico. The LC-MS/MS analyzes of N. edaphicum CCNP1411 cell extracts prepared in aqueous methanol revealed several products of the genes. Besides the known peptides, Ncp-A1 and Ncp-A2, six other compounds putatively characterized as new noctocyclopeptide analogues were detected. This includes Ncp-E1 and E2 and their linear forms (Ncp-E1-L and E2-L), a cyclic Ncp-E3 and a linear Ncp-E4-L. Regardless of the extraction conditions, the cell contents of the linear nostocyclopeptides were found to be higher than the cyclic ones, suggesting a slow rate of the macrocyclization process. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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18 pages, 2925 KiB  
Article
Bioactive Bianthraquinones and Meroterpenoids from a Marine-Derived Stemphylium sp. Fungus
by Ji-Yeon Hwang, Sung Chul Park, Woong Sub Byun, Dong-Chan Oh, Sang Kook Lee, Ki-Bong Oh and Jongheon Shin
Mar. Drugs 2020, 18(9), 436; https://doi.org/10.3390/md18090436 - 21 Aug 2020
Cited by 11 | Viewed by 2946
Abstract
Three new bianthraquinones, alterporriol Z1–Z3 (1–3), along with three known compounds of the same structural class, were isolated from the culture broth of a marine-derived Stemphylium sp. fungus. Based upon the results of spectroscopic analyses and ECD measurements, the [...] Read more.
Three new bianthraquinones, alterporriol Z1–Z3 (1–3), along with three known compounds of the same structural class, were isolated from the culture broth of a marine-derived Stemphylium sp. fungus. Based upon the results of spectroscopic analyses and ECD measurements, the structures of new compounds were determined to be the 6-6′- (1 and 2) and 1-5′- (3) C–C connected pseudo-dimeric anthraquinones, respectively. Three new meroterpenoids, tricycloalterfurenes E–G (7–9), isolated together with the bianthraquinones from the same fungal culture broth, were structurally elucidated by combined spectroscopic methods. The relative and absolute configurations of these meroterpenoids were determined by modified Mosher’s, phenylglycine methyl ester (PGME), and computational methods. The bianthraquinones significantly inhibited nitric oxide (NO) production and suppressed inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression in LPS-stimulated RAW 264.7 cells. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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11 pages, 1717 KiB  
Article
Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635
by Yi Ding, Xiaojing Zhu, Liling Hao, Mengyao Zhao, Qiang Hua and Faliang An
Mar. Drugs 2020, 18(7), 338; https://doi.org/10.3390/md18070338 - 28 Jun 2020
Cited by 22 | Viewed by 3464
Abstract
Four new indolyl diketopiperazines, aspamides A–E (1–4) and two new diketopiperazines, aspamides F–G (5–6), along with 11 known diketopiperazines and intermediates were isolated from the solid culture of Aspergillus versicolor, which is an endophyte with the [...] Read more.
Four new indolyl diketopiperazines, aspamides A–E (1–4) and two new diketopiperazines, aspamides F–G (5–6), along with 11 known diketopiperazines and intermediates were isolated from the solid culture of Aspergillus versicolor, which is an endophyte with the sea crab (Chiromantes haematocheir). Further chiral high-performance liquid chromatography resolution gave enantiomers (+)- and (−)-4, respectively. The structures and absolute configurations of compounds 1–6 were determined by the comprehensive analyses of nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and electronic circular dichroism (ECD) calculation. All isolated compounds were selected for the virtual screening on the coronavirus 3-chymoretpsin-like protease (Mpro) of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2), and the docking scores of compounds 1–2, 5, 6, 8 and 17 were top among all screened molecules, may be helpful in fighting with Corona Virus Disease-19 (COVID-19) after further studies. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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11 pages, 1924 KiB  
Article
Bioactive Molecules from Mangrove Streptomyces qinglanensis 172205
by Dongbo Xu, Erli Tian, Fandong Kong and Kui Hong
Mar. Drugs 2020, 18(5), 255; https://doi.org/10.3390/md18050255 - 13 May 2020
Cited by 9 | Viewed by 3262
Abstract
Five new compounds 15R-17,18-dehydroxantholipin (1), (3E,5E,7E)-3-methyldeca-3,5,7-triene-2,9-dione (2) and qinlactone A–C (3–5) were identified from mangrove Streptomyces qinglanensis 172205 with “genetic dereplication,” which deleted the highly expressed secondary [...] Read more.
Five new compounds 15R-17,18-dehydroxantholipin (1), (3E,5E,7E)-3-methyldeca-3,5,7-triene-2,9-dione (2) and qinlactone A–C (3–5) were identified from mangrove Streptomyces qinglanensis 172205 with “genetic dereplication,” which deleted the highly expressed secondary metabolite-enterocin biosynthetic gene cluster. The chemical structures were established by spectroscopic methods, and the absolute configurations were determined by electronic circular dichroism (ECD). Compound 1 exhibited strong anti-microbial and antiproliferative bioactivities, while compounds 2–4 showed weak antiproliferative activities. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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11 pages, 1983 KiB  
Communication
Lysophosphatidylcholines and Chlorophyll-Derived Molecules from the Diatom Cylindrotheca closterium with Anti-Inflammatory Activity
by Chiara Lauritano, Kirsti Helland, Gennaro Riccio, Jeanette H. Andersen, Adrianna Ianora and Espen H. Hansen
Mar. Drugs 2020, 18(3), 166; https://doi.org/10.3390/md18030166 - 17 Mar 2020
Cited by 55 | Viewed by 4908
Abstract
Microalgae have been shown to be excellent producers of lipids, pigments, carbohydrates, and a plethora of secondary metabolites with possible applications in the pharmacological, nutraceutical, and cosmeceutical sectors. Recently, various microalgal raw extracts have been found to have anti-inflammatory properties. In this study, [...] Read more.
Microalgae have been shown to be excellent producers of lipids, pigments, carbohydrates, and a plethora of secondary metabolites with possible applications in the pharmacological, nutraceutical, and cosmeceutical sectors. Recently, various microalgal raw extracts have been found to have anti-inflammatory properties. In this study, we performed the fractionation of raw extracts of the diatom Cylindrotheca closterium, previously shown to have anti-inflammatory properties, obtaining five fractions. Fractions C and D were found to significantly inhibit tumor necrosis factor alpha (TNF-⍺) release in LPS-stimulated human monocyte THP-1 cells. A dereplication analysis of these two fractions allowed the identification of their main components. Our data suggest that lysophosphatidylcholines and a breakdown product of chlorophyll, pheophorbide a, were probably responsible for the observed anti-inflammatory activity. Pheophorbide a is known to have anti-inflammatory properties. We tested and confirmed the anti-inflammatory activity of 1-palmitoyl-sn-glycero-3-phosphocholine, the most abundant lysophosphatidylcholine found in fraction C. This study demonstrated the importance of proper dereplication of bioactive extracts and fractions before isolation of compounds is commenced. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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12 pages, 2041 KiB  
Article
Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388
by Lu-Ping Chi, Xiao-Ming Li, Li Li, Xin Li and Bin-Gui Wang
Mar. Drugs 2020, 18(3), 160; https://doi.org/10.3390/md18030160 - 13 Mar 2020
Cited by 28 | Viewed by 3499
Abstract
Four new thiodiketopiperazine alkaloids, namely, 5’-hydroxy-6’-ene-epicoccin G (1), 7-methoxy-7’-hydroxyepicoccin G (2), 8’-acetoxyepicoccin D (3), and 7’-demethoxyrostratin C (4), as well as a pair of new enantiomeric diketopiperazines, (±)-5-hydroxydiphenylalazine A (5), along with five [...] Read more.
Four new thiodiketopiperazine alkaloids, namely, 5’-hydroxy-6’-ene-epicoccin G (1), 7-methoxy-7’-hydroxyepicoccin G (2), 8’-acetoxyepicoccin D (3), and 7’-demethoxyrostratin C (4), as well as a pair of new enantiomeric diketopiperazines, (±)-5-hydroxydiphenylalazine A (5), along with five known analogues (6–10), were isolated and identified from the culture extract of Epicoccum nigrum SD-388, a fungus obtained from deep-sea sediments (−4500 m). Their structures were established on the basis of detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis confirmed the structures and established the absolute configurations of compounds 1–3, while the absolute configurations for compounds 4 and 5 were determined by ECD calculations. Compounds 4 and 10 showed potent activity against Huh7.5 liver tumor cells, which were comparable to that of the positive control, sorafenib, and the disulfide bridge at C-2/C-2’ is likely essential for the activity. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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10 pages, 1517 KiB  
Article
New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus
by Jing-Shuai Wu, Xiao-Hui Shi, Guang-Shan Yao, Chang-Lun Shao, Xiu-Mei Fu, Xiu-Li Zhang, Hua-Shi Guan and Chang-Yun Wang
Mar. Drugs 2020, 18(3), 132; https://doi.org/10.3390/md18030132 - 26 Feb 2020
Cited by 29 | Viewed by 3926
Abstract
Aspergillus terreus has been reported to produce many secondary metabolites that exhibit potential bioactivities, such as antibiotic, hypoglycemic, and lipid-lowering activities. In the present study, two new thiodiketopiperazines, emestrins L (1) and M (2), together with five known analogues [...] Read more.
Aspergillus terreus has been reported to produce many secondary metabolites that exhibit potential bioactivities, such as antibiotic, hypoglycemic, and lipid-lowering activities. In the present study, two new thiodiketopiperazines, emestrins L (1) and M (2), together with five known analogues (3–7), and five known dihydroisocoumarins (8–12), were obtained from the marine-derived fungus Aspergillus terreus RA2905. The structures of the new compounds were elucidated by analysis of the comprehensive spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), and electronic circular dichroism (ECD) data. This is the first time that the spectroscopic data of compounds 3, 8, and 9 have been reported. Compound 3 displayed antibacterial activity against Pseudomonas aeruginosa (minimum inhibitory concentration (MIC) = 32 μg/mL) and antifungal activity against Candida albicans (MIC = 32 μg/mL). In addition, compound 3 exhibited an inhibitory effect on protein tyrosine phosphatase 1 B (PTP1B), an important hypoglycemic target, with an inhibitory concentration (IC)50 value of 12.25 μM. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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Review

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29 pages, 6213 KiB  
Review
Current Knowledge on Microviridin from Cyanobacteria
by Samuel Cavalcante do Amaral, Patrick Romano Monteiro, Joaquim da Silva Pinto Neto, Gustavo Marques Serra, Evonnildo Costa Gonçalves, Luciana Pereira Xavier and Agenor Valadares Santos
Mar. Drugs 2021, 19(1), 17; https://doi.org/10.3390/md19010017 - 4 Jan 2021
Cited by 28 | Viewed by 4547
Abstract
Cyanobacteria are a rich source of secondary metabolites with a vast biotechnological potential. These compounds have intrigued the scientific community due their uniqueness and diversity, which is guaranteed by a rich enzymatic apparatus. The ribosomally synthesized and post-translationally modified peptides (RiPPs) are among [...] Read more.
Cyanobacteria are a rich source of secondary metabolites with a vast biotechnological potential. These compounds have intrigued the scientific community due their uniqueness and diversity, which is guaranteed by a rich enzymatic apparatus. The ribosomally synthesized and post-translationally modified peptides (RiPPs) are among the most promising metabolite groups derived from cyanobacteria. They are interested in numerous biological and ecological processes, many of which are entirely unknown. Microviridins are among the most recognized class of ribosomal peptides formed by cyanobacteria. These oligopeptides are potent inhibitors of protease; thus, they can be used for drug development and the control of mosquitoes. They also play a key ecological role in the defense of cyanobacteria against microcrustaceans. The purpose of this review is to systematically identify the key characteristics of microviridins, including its chemical structure and biosynthesis, as well as its biotechnological and ecological significance. Full article
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
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