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Special Issue "Bioactive Compounds from Marine Fungi"

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

Deadline for manuscript submissions: closed (31 March 2015)

Special Issue Editor

Guest Editor
Prof. Dr. Johannes F. Imhoff

Marine Mikrobiologie, Helmholtz Centre for Ocean Research GEOMAR, Düsternbrooker Weg 20, D-24105 Kiel, Germany
Fax: +0431-600-4452

Special Issue Information

Dear Colleagues,

Nature continues to be most important in the delivery of new drugs or lead structures and the oceans are important sources of structurally unique natural products. Among the biota from the oceans marine-derived fungi are an outstanding source for secondary metabolites, many of which have highly complex structures, making them difficult to be supplied economically via chemical synthesis.

Fungi derived from marine sources are considered to represent a huge reservoir of secondary metabolites, many of which are biologically active and are produced e.g. by multifunctional enzyme complexes such as polyketide synthases (PKS) and non-ribosomal peptide synthetases (NRPS). Marine fungi are highly potent producers of bioactive substances with antifungal, antibacterial, antiviral, cytotoxic and immunosuppressive activity. The various biological activities make them a valuable source for pharmaceutical applications.

From an ecological point of view fungal secondary metabolites may act specifically in interspecies interactions to protect the host and/or the producer against competitors and/or diseases. On the other hand, fungal metabolites are considered of great importance in the ecology of marine communities and the analysis of fungal genetics, fungal physiology and fungal natural compound profiles will be essential to understand the interrelationships between fungi and their environment.

In addition, the rapid progress in genomic information significantly stimulates the search for secondary metabolite producers and secondary metabolite biosynthesis. It greatly improves our knowledge on the potential of secondary metabolite production in fungi and already has demonstrated that fungi encode the genetic information for the biosynthesis of many as yet unknown compounds.

This is good reason to devote a special issue of Marine Drugs to the bioactive compounds from marine fungi.

Prof. Dr. Johannes F. Imhoff
Guest Editor

Submission

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a 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 1800 CHF (Swiss Francs).

Keywords

  • marine fungi
  • fungal genomics
  • polyketide synthases
  • non-ribosomal peptide synthesis
  • antitumoral activity
  • antibiotic activity
  • fungal secondary metabolites
  • secondary metabolite biosynthesis
  • fungal secondary metabolites
  • fungal interactions
  • fungal drugs

Published Papers (23 papers)

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Open AccessArticle Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae
Mar. Drugs 2015, 13(8), 4617-4632; doi:10.3390/md13084617
Received: 11 June 2015 / Revised: 11 July 2015 / Accepted: 16 July 2015 / Published: 27 July 2015
Cited by 4 | PDF Full-text (504 KB) | HTML Full-text | XML Full-text
Abstract
An unusual polyketide with a new carbon skeleton, lindgomycin (1), and the recently described ascosetin (2) were extracted from mycelia and culture broth of different Lindgomycetaceae strains, which were isolated from a sponge of the Kiel Fjord in the Baltic Sea (Germany) [...] Read more.
An unusual polyketide with a new carbon skeleton, lindgomycin (1), and the recently described ascosetin (2) were extracted from mycelia and culture broth of different Lindgomycetaceae strains, which were isolated from a sponge of the Kiel Fjord in the Baltic Sea (Germany) and from the Antarctic. Their structures were established by spectroscopic means. In the new polyketide, two distinct domains, a bicyclic hydrocarbon and a tetramic acid, are connected by a bridging carbonyl. The tetramic acid substructure of compound 1 was proved to possess a unique 5-benzylpyrrolidine-2,4-dione unit. The combination of 5-benzylpyrrolidine-2,4-dione of compound 1 in its tetramic acid half and 3-methylbut-3-enoic acid pendant in its decalin half allow the assignment of a new carbon skeleton. The new compound 1 and ascosetin showed antibiotic activities with IC50 value of 5.1 (±0.2) µM and 3.2 (±0.4) μM, respectively, against methicillin-resistant Staphylococcus aureus. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Identification of the Scopularide Biosynthetic Gene Cluster in Scopulariopsis brevicaulis
Mar. Drugs 2015, 13(7), 4331-4343; doi:10.3390/md13074331
Received: 20 March 2015 / Revised: 2 July 2015 / Accepted: 3 July 2015 / Published: 14 July 2015
Cited by 6 | PDF Full-text (1549 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Scopularide A is a promising potent anticancer lipopeptide isolated from a marine derived Scopulariopsis brevicaulis strain. The compound consists of a reduced carbon chain (3-hydroxy-methyldecanoyl) attached to five amino acids (glycine, l-valine, d-leucine, l-alanine, and l-phenylalanine). Using the newly sequenced S. brevicaulis [...] Read more.
Scopularide A is a promising potent anticancer lipopeptide isolated from a marine derived Scopulariopsis brevicaulis strain. The compound consists of a reduced carbon chain (3-hydroxy-methyldecanoyl) attached to five amino acids (glycine, l-valine, d-leucine, l-alanine, and l-phenylalanine). Using the newly sequenced S. brevicaulis genome we were able to identify the putative biosynthetic gene cluster using genetic information from the structurally related emericellamide A from Aspergillus nidulans and W493-B from Fusarium pseudograminearum. The scopularide A gene cluster includes a nonribosomal peptide synthetase (NRPS1), a polyketide synthase (PKS2), a CoA ligase, an acyltransferase, and a transcription factor. Homologous recombination was low in S. brevicaulis so the local transcription factor was integrated randomly under a constitutive promoter, which led to a three to four-fold increase in scopularide A production. This indirectly verifies the identity of the proposed biosynthetic gene cluster. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessCommunication Bioactive 7-Oxabicyclic[6.3.0]lactam and 12-Membered Macrolides from a Gorgonian-Derived Cladosporium sp. Fungus
Mar. Drugs 2015, 13(7), 4171-4178; doi:10.3390/md13074171
Received: 12 May 2015 / Revised: 22 June 2015 / Accepted: 23 June 2015 / Published: 7 July 2015
Cited by 2 | PDF Full-text (250 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
One new bicyclic lactam, cladosporilactam A (1), and six known 12-membered macrolides (27) were isolated from a gorgonian-derived Cladosporium sp. fungus collected from the South China Sea. Their complete structural assignments were elucidated by comprehensive spectroscopic [...] Read more.
One new bicyclic lactam, cladosporilactam A (1), and six known 12-membered macrolides (27) were isolated from a gorgonian-derived Cladosporium sp. fungus collected from the South China Sea. Their complete structural assignments were elucidated by comprehensive spectroscopic investigation. Quantum chemistry calculations were used in support of the structural determination of 1. The absolute configuration of 1 was determined by calculation of its optical rotation. Cladosporilactam A (1) was the first example of 7-oxabicyclic[6.3.0]lactam obtained from a natural source. Compound 1 exhibited promising cytotoxic activity against cervical cancer HeLa cell line with an IC50 value of 0.76 μM. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle Investigation of Marine-Derived Fungal Diversity and Their Exploitable Biological Activities
Mar. Drugs 2015, 13(7), 4137-4155; doi:10.3390/md13074137
Received: 31 March 2015 / Revised: 8 June 2015 / Accepted: 15 June 2015 / Published: 30 June 2015
Cited by 2 | PDF Full-text (593 KB) | HTML Full-text | XML Full-text
Abstract
Marine fungi are potential producers of bioactive compounds that may have pharmacological and medicinal applications. Fungi were cultured from marine brown algae and identified using multiple target genes to confirm phylogenetic placement. These target genes included the internal transcribed spacer (ITS), the [...] Read more.
Marine fungi are potential producers of bioactive compounds that may have pharmacological and medicinal applications. Fungi were cultured from marine brown algae and identified using multiple target genes to confirm phylogenetic placement. These target genes included the internal transcribed spacer (ITS), the nuclear large subunit (LSU), and the β-tubulin region. Various biological activities of marine-derived fungi were evaluated, including their antifungal, antioxidant and cellulolytic enzyme activities. As a result, a total of 50 fungi was isolated from the brown algae Sargassum sp. Among the 50 isolated fungi, Corollospora angusta was the dominant species in this study. The genus Arthrinium showed a relatively strong antifungal activity to all of the target plant pathogenic fungi. In particular, Arthrinium saccharicola KUC21221 showed high radical scavenging activity and the highest activities in terms of filter paper units (0.39 U/mL), endoglucanase activity (0.38 U/mL), and β-glucosidase activity (1.04 U/mL). Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Production of Calcaride A by Calcarisporium sp. in Shaken Flasks and Stirred Bioreactors
Mar. Drugs 2015, 13(7), 3992-4005; doi:10.3390/md13073992
Received: 30 March 2015 / Revised: 19 May 2015 / Accepted: 15 June 2015 / Published: 24 June 2015
Cited by 2 | PDF Full-text (1329 KB) | HTML Full-text | XML Full-text
Abstract
Increased interest in marine resources has led to increased screening of marine fungi for novel bioactive compounds and considerable effort is being invested in discovering these metabolites. For compound discovery, small-scale cultures are adequate, but agitated bioreactors are desirable for larger-scale production. [...] Read more.
Increased interest in marine resources has led to increased screening of marine fungi for novel bioactive compounds and considerable effort is being invested in discovering these metabolites. For compound discovery, small-scale cultures are adequate, but agitated bioreactors are desirable for larger-scale production. Calcarisporium sp. KF525 has recently been described to produce calcaride A, a cyclic polyester with antibiotic activity, in agitated flasks. Here, we describe improvements in the production of calcaride A in both flasks (13-fold improvement) and stirred bioreactors (200-fold improvement). Production of calcaride A in bioreactors was initially substantially lower than in shaken flasks. The cultivation pH (reduced from 6.8 to <5.4), carbon source (sucrose replacing glucose), C/N ratio and nature of mycelial growth (pellets or filaments) were important in improving calcaride A production. Up to 4.5 mg·g−1 biomass (85 mg·L−1) calcaride A were produced in the bioreactor, which was only slightly less than in shaken flasks (14 mg·g−1, 100 mg·L−1). The results demonstrate that a scalable process for calcaride A production could be developed using an iterative approach with flasks and bioreactors. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides
Mar. Drugs 2015, 13(6), 3640-3652; doi:10.3390/md13063640
Received: 28 April 2015 / Revised: 24 May 2015 / Accepted: 27 May 2015 / Published: 5 June 2015
Cited by 2 | PDF Full-text (1390 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Peniciadametizine A (1); a new dithiodiketopiperazine derivative possessing a unique spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] skeleton, together with a highly oxygenated new analogue, peniciadametizine B (2); as well as two known compounds, brasiliamide A (3); and viridicatumtoxin (4), were isolated and identified [...] Read more.
Peniciadametizine A (1); a new dithiodiketopiperazine derivative possessing a unique spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] skeleton, together with a highly oxygenated new analogue, peniciadametizine B (2); as well as two known compounds, brasiliamide A (3); and viridicatumtoxin (4), were isolated and identified from Penicillium adametzioides AS-53, a fungus obtained from an unidentified marine sponge. The unambiguous assignment of the relative and absolute configuration for the spiro center C-2 of compound 1 was solved by the combination of NMR and ECD measurements with Density-Functional Theory (DFT) conformational analysis and Time-Dependent Density-Functional Theory-Electronic Circular Dichroism (TDDFT-ECD) calculations. The spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] skeleton of 1 has not been reported yet among natural products and the biosynthetic pathway for 1 and 2 was discussed. Compounds 1 and 2 showed inhibitory activity against the pathogenic fungus Alternaria brassicae. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle New Polyphenols from a Deep Sea Spiromastix sp. Fungus, and Their Antibacterial Activities
Mar. Drugs 2015, 13(4), 2526-2540; doi:10.3390/md13042526
Received: 11 February 2015 / Revised: 7 April 2015 / Accepted: 13 April 2015 / Published: 22 April 2015
Cited by 1 | PDF Full-text (655 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Eleven new polyphenols namely spiromastols A–K (111) were isolated from the fermentation broth of a deep sea-derived fungus Spiromastix sp. MCCC 3A00308. Their structures were determined by extensive NMR data and mass spectroscopic analysis in association with chemical [...] Read more.
Eleven new polyphenols namely spiromastols A–K (111) were isolated from the fermentation broth of a deep sea-derived fungus Spiromastix sp. MCCC 3A00308. Their structures were determined by extensive NMR data and mass spectroscopic analysis in association with chemical conversion. The structures are classified as diphenyl ethers, diphenyl esters and isocoumarin derivatives, while the n-propyl group in the analogues is rarely found in natural products. Compounds 13 exhibited potent inhibitory effects against a panel of bacterial strains, including Xanthomanes vesicatoria, Pseudomonas lachrymans, Agrobacterium tumefaciens, Ralstonia solanacearum, Bacillus thuringensis, Staphylococcus aureus and Bacillus subtilis, with minimal inhibitory concentration (MIC) values ranging from 0.25 to 4 µg/mL. The structure-activity relationships are discussed, while the polychlorinated analogues 13 are assumed to be a promising structural model for further development as antibacterial agents. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle Identification and Bioactivity of Compounds from the Fungus Penicillium sp. CYE-87 Isolated from a Marine Tunicate
Mar. Drugs 2015, 13(4), 1698-1709; doi:10.3390/md13041698
Received: 26 December 2014 / Revised: 13 March 2015 / Accepted: 18 March 2015 / Published: 25 March 2015
Cited by 4 | PDF Full-text (592 KB) | HTML Full-text | XML Full-text
Abstract
In the course of our continuous interest in identifying bioactive compounds from marine microbes, we have investigated a tunicate-derived fungus, Penicillium sp. CYE-87. A new compound with the 1,4-diazepane skeleton, terretrione D (2), together with the known compounds, methyl-2-([2-(1H-indol-3-yl)ethyl]carbamoyl)acetate ( [...] Read more.
In the course of our continuous interest in identifying bioactive compounds from marine microbes, we have investigated a tunicate-derived fungus, Penicillium sp. CYE-87. A new compound with the 1,4-diazepane skeleton, terretrione D (2), together with the known compounds, methyl-2-([2-(1H-indol-3-yl)ethyl]carbamoyl)acetate (1), tryptamine (3), indole-3-carbaldehyde (4), 3,6-diisobutylpyrazin-2(1H)-one (5) and terretrione C (6), were isolated from Penicillium sp. CYE-87. The structures of the isolated compounds were established by spectral analysis, including 1D (1H, 13C) and 2D (COSY, multiplicity edited-HSQC and HMBC) NMR and HRESIMS, as well as comparison of their NMR data with those in the literature. The compounds were evaluated for their antimigratory activity against the human breast cancer cell line (MDA-MB-231) and their antiproliferation activity against HeLa cells. Compounds 2 and 6 showed significant antimigratory activity against MDA-MB-231, as well as antifungal activity against C. albicans. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013
Mar. Drugs 2015, 13(3), 1432-1450; doi:10.3390/md13031432
Received: 27 January 2015 / Revised: 4 March 2015 / Accepted: 9 March 2015 / Published: 17 March 2015
Cited by 6 | PDF Full-text (624 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus [...] Read more.
A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 2 the stereochemistry of its amino acid constituents was determined by chiral HPLC analysis of the hydrolysate by co-injection with the d and l amino acids standards. Compounds 2 and 3 were evaluated for their in vitro growth inhibitory activity against MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A373 (melanoma) cell lines, as well as antibacterial activity against reference strains and the environmental multidrug-resistant isolates (MRS and VRE). Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Territrem and Butyrolactone Derivatives from a Marine-Derived Fungus Aspergillus Terreus
Mar. Drugs 2014, 12(12), 6113-6124; doi:10.3390/md12126113
Received: 17 September 2014 / Revised: 24 November 2014 / Accepted: 8 December 2014 / Published: 17 December 2014
Cited by 6 | PDF Full-text (567 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Seventeen lactones including eight territrem derivatives (18) and nine butyrolactone derivatives (917) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 13 and 91 [...] Read more.
Seventeen lactones including eight territrem derivatives (18) and nine butyrolactone derivatives (917) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 13 and 910 were new, and their structures were elucidated by spectroscopic analysis. The acetylcholinesterase inhibitory activity and antiviral activity of compounds 117 were evaluated. Among them, compounds 1 and 2 showed strong inhibitory activity against acetylcholinesterase with IC50 values of 4.2 ± 0.6, 4.5 ± 0.6 nM, respectively. This is the first time it has been reported that 3, 6, 10, 12 had evident antiviral activity towards HSV-1 with IC50 values of 16.4 ± 0.6, 6.34 ± 0.4, 21.8 ± 0.8 and 28.9 ± 0.8 μg·mL−1, respectively. Antifouling bioassay tests showed that compounds 1, 11, 12, 15 had potent antifouling activity with EC50 values of 12.9 ± 0.5, 22.1 ± 0.8, 7.4 ± 0.6, 16.1 ± 0.6 μg·mL−1 toward barnacle Balanus amphitrite larvae, respectively. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Inhibition of Bacterial Quorum Sensing by Extracts from Aquatic Fungi: First Report from Marine Endophytes
Mar. Drugs 2014, 12(11), 5503-5526; doi:10.3390/md12115503
Received: 19 September 2014 / Revised: 7 November 2014 / Accepted: 7 November 2014 / Published: 19 November 2014
Cited by 4 | PDF Full-text (1177 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In our search for quorum-sensing (QS) disrupting molecules, 75 fungal isolates were recovered from reef organisms (endophytes), saline lakes and mangrove rhizosphere. Their QS inhibitory activity was evaluated in Chromobacterium violaceum CVO26. Four strains of endophytic fungi stood out for their potent [...] Read more.
In our search for quorum-sensing (QS) disrupting molecules, 75 fungal isolates were recovered from reef organisms (endophytes), saline lakes and mangrove rhizosphere. Their QS inhibitory activity was evaluated in Chromobacterium violaceum CVO26. Four strains of endophytic fungi stood out for their potent activity at concentrations from 500 to 50 μg mL−1. The molecular characterization, based on the internal transcribed spacer (ITS) region sequences (ITS1, 5.8S and ITS2) between the rRNA of 18S and 28S, identified these strains as belonging to four genera: Sarocladium (LAEE06), Fusarium (LAEE13), Epicoccum (LAEE14), and Khuskia (LAEE21). Interestingly, three came from coral species and two of them came from the same organism, the coral Diploria strigosa. Metabolic profiles obtained by Liquid Chromatography-High Resolution Mass Spectrometry (LC-HRMS) suggest that a combination of fungal secondary metabolites and fatty acids could be the responsible for the observed activities. The LC-HRMS analysis also revealed the presence of potentially new secondary metabolites. This is, to the best of our knowledge, the first report of QS inhibition by marine endophytic fungi. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans
Mar. Drugs 2013, 11(6), 2054-2068; doi:10.3390/md11062054
Received: 1 April 2013 / Revised: 10 May 2013 / Accepted: 14 May 2013 / Published: 10 June 2013
Cited by 17 | PDF Full-text (540 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
One new phenylalanine derivative 4′-OMe-asperphenamate (1), along with one known phenylalanine derivative (2) and two new cytochalasins, aspochalasin A1 (3) and cytochalasin Z24 (4), as well as eight known cytochalasin analogues (5 [...] Read more.
One new phenylalanine derivative 4′-OMe-asperphenamate (1), along with one known phenylalanine derivative (2) and two new cytochalasins, aspochalasin A1 (3) and cytochalasin Z24 (4), as well as eight known cytochalasin analogues (512) were isolated from the fermentation broth of Aspergillus elegans ZJ-2008010, a fungus obtained from a soft coral Sarcophyton sp. collected from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods. The absolute configuration of 1 was determined by chemical synthesis and Marfey’s method. All isolated metabolites (112) were evaluated for their antifouling and antibacterial activities. Cytochalasins 5, 6, 8 and 9 showed strong antifouling activity against the larval settlement of the barnacle Balanus amphitrite, with the EC50 values ranging from 6.2 to 37 μM. This is the first report of antifouling activity for this class of metabolites. Additionally, 8 exhibited a broad spectrum of antibacterial activity, especially against four pathogenic bacteria Staphylococcus albus, S. aureus, Escherichia coli and Bacillus cereus. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle PTP1B Inhibitory and Anti-Inflammatory Effects of Secondary Metabolites Isolated from the Marine-Derived Fungus Penicillium sp. JF-55
Mar. Drugs 2013, 11(4), 1409-1426; doi:10.3390/md11041409
Received: 24 January 2013 / Revised: 11 March 2013 / Accepted: 3 April 2013 / Published: 23 April 2013
Cited by 16 | PDF Full-text (498 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Protein tyrosine phosphatase 1B (PTP1B) plays a major role in the negative regulation of insulin signaling, and is thus considered as an attractive therapeutic target for the treatment of diabetes. Bioassay-guided investigation of the methylethylketone extract of marine-derived fungus Penicillium sp. JF-55 [...] Read more.
Protein tyrosine phosphatase 1B (PTP1B) plays a major role in the negative regulation of insulin signaling, and is thus considered as an attractive therapeutic target for the treatment of diabetes. Bioassay-guided investigation of the methylethylketone extract of marine-derived fungus Penicillium sp. JF-55 cultures afforded a new PTP1B inhibitory styrylpyrone-type metabolite named penstyrylpyrone (1), and two known metabolites, anhydrofulvic acid (2) and citromycetin (3). Compounds 1 and 2 inhibited PTP1B activity in a dose-dependent manner, and kinetic analyses of PTP1B inhibition suggested that these compounds inhibited PTP1B activity in a competitive manner. In an effort to gain more biological potential of the isolated compounds, the anti-inflammatory effects of compounds 13 were also evaluated. Among the tested compounds, only compound 1 inhibited the production of NO and PGE2, due to the inhibition of the expression of iNOS and COX-2. Penstyrylpyrone (1) also reduced TNF-α and IL-1β production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of IκB-α, NF-κB nuclear translocation, and NF-κB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), an inhibitor of HO-1, it was verified that the inhibitory effects of penstyrylpyrone (1) on the pro-inflammatory mediators and NF-κB DNA binding activity were associated with the HO-1 expression. Therefore, these results suggest that penstyrylpyrone (1) suppresses PTP1B activity, as well as the production of pro-inflammatory mediators via NF-κB pathway, through expression of anti-inflammatory HO-1. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550
Mar. Drugs 2013, 11(3), 800-816; doi:10.3390/md11030800
Received: 18 December 2012 / Revised: 17 January 2013 / Accepted: 6 February 2013 / Published: 12 March 2013
Cited by 11 | PDF Full-text (615 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Microbial studies of the Mediterranean sponge Tethya aurantium led to the isolation of the fungus Bartalinia robillardoides strain LF550. The strain produced a number of secondary metabolites belonging to the chloroazaphilones. This is the first report on the isolation of chloroazaphilones of [...] Read more.
Microbial studies of the Mediterranean sponge Tethya aurantium led to the isolation of the fungus Bartalinia robillardoides strain LF550. The strain produced a number of secondary metabolites belonging to the chloroazaphilones. This is the first report on the isolation of chloroazaphilones of a fungal strain belonging to the genus Bartalinia. Besides some known compounds (helicusin A (1) and deacetylsclerotiorin (2)), three new chloroazaphilones (helicusin E (3); isochromophilone X (4) and isochromophilone XI (5)) and one new pentaketide (bartanolide (6)) were isolated. The structure elucidations were based on spectroscopic analyses. All isolated compounds revealed different biological activity spectra against a test panel of four bacteria: three fungi; two tumor cell lines and two enzymes. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.
Mar. Drugs 2013, 11(2), 551-558; doi:10.3390/md11020551
Received: 21 January 2013 / Revised: 13 February 2013 / Accepted: 18 February 2013 / Published: 22 February 2013
Cited by 9 | PDF Full-text (543 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The marine fungus Chondrostereum sp. was collected from a soft coral of the species Sarcophyton tortuosum from the South China Sea. Three new compounds, chondrosterins F–H (1, 4 and 5), together with three known compounds, incarnal (2), [...] Read more.
The marine fungus Chondrostereum sp. was collected from a soft coral of the species Sarcophyton tortuosum from the South China Sea. Three new compounds, chondrosterins F–H (1, 4 and 5), together with three known compounds, incarnal (2), arthrosporone (3), and (2E)-decene-4,6,8-triyn-1-ol (6), were isolated. Their structures were elucidated primarily based on NMR and MS data. Incarnal (2) exhibited potent cytotoxic activity against various cancer cell lines. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Xyloketal B Exhibits Its Antioxidant Activity through Induction of HO-1 in Vascular Endothelial Cells and Zebrafish
Mar. Drugs 2013, 11(2), 504-522; doi:10.3390/md11020504
Received: 28 November 2012 / Revised: 22 January 2013 / Accepted: 31 January 2013 / Published: 18 February 2013
Cited by 15 | PDF Full-text (1166 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We previously reported that a novel marine compound, xyloketal B, has strong antioxidative actions in different models of cardiovascular diseases. Induction of heme oxygenase-1 (HO-1), an important endogenous antioxidant enzyme, has been considered as a potential therapeutic strategy for cardiovascular diseases. We [...] Read more.
We previously reported that a novel marine compound, xyloketal B, has strong antioxidative actions in different models of cardiovascular diseases. Induction of heme oxygenase-1 (HO-1), an important endogenous antioxidant enzyme, has been considered as a potential therapeutic strategy for cardiovascular diseases. We here investigated whether xyloketal B exhibits its antioxidant activity through induction of HO-1. In human umbilical vein endothelial cells (HUVECs), xyloketal B significantly induced HO-1 gene expression and translocation of the nuclear factor-erythroid 2-related factor 2 (Nrf-2) in a concentration- and time-dependent manner. The protection of xyloketal B against angiotensin II-induced apoptosis and reactive oxygen species (ROS) production could be abrogated by the HO-1 specific inhibitor, tin protoporphyrin-IX (SnPP). Consistently, the suppressive effects of xyloketal B on NADPH oxidase activity could be reversed by SnPP in zebrafish embryos. In addition, xyloketal B induced Akt and Erk1/2 phosphorylation in a concentration- and time-dependent manner. Furthermore, PI3K inhibitor LY294002 and Erk1/2 inhibitor U0126 suppressed the induction of HO-1 and translocation of Nrf-2 by xyloketal B, whereas P38 inhibitor SB203580 did not. In conclusion, xyloketal B can induce HO-1 expression via PI3K/Akt/Nrf-2 pathways, and the induction of HO-1 is mainly responsible for the antioxidant and antiapoptotic actions of xyloketal B. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus
Mar. Drugs 2012, 10(12), 2912-2935; doi:10.3390/md10122912
Received: 9 November 2012 / Revised: 29 November 2012 / Accepted: 5 December 2012 / Published: 19 December 2012
Cited by 8 | PDF Full-text (1010 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The marine-derived filamentous fungus Asteromyces cruciatus 763, obtained off the coast of La Jolla, San Diego, USA, yielded the new pentapeptide lajollamide A (1), along with the known compounds regiolone (2), hyalodendrin (3), gliovictin (4 [...] Read more.
The marine-derived filamentous fungus Asteromyces cruciatus 763, obtained off the coast of La Jolla, San Diego, USA, yielded the new pentapeptide lajollamide A (1), along with the known compounds regiolone (2), hyalodendrin (3), gliovictin (4), 1N-norgliovicitin (5), and bis-N-norgliovictin (6). The planar structure of lajollamide A (1) was determined by Nuclear Magnetic Resonance (NMR) spectroscopy in combination with mass spectrometry. The absolute configuration of lajollamide A (1) was unambiguously solved by total synthesis which provided three additional diastereomers of 1 and also revealed that an unexpected acid-mediated partial racemization (2:1) of the l-leucine and l-N-Me-leucine residues occurred during the chemical degradation process. The biological activities of the isolated metabolites, in particular their antimicrobial properties, were investigated in a series of assay systems. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle Phylogenetic Identification of Fungi Isolated from the Marine Sponge Tethya aurantium and Identification of Their Secondary Metabolites
Mar. Drugs 2011, 9(4), 561-585; doi:10.3390/md9040561
Received: 17 February 2011 / Revised: 1 March 2011 / Accepted: 25 March 2011 / Published: 6 April 2011
Cited by 39 | PDF Full-text (496 KB) | HTML Full-text | XML Full-text
Abstract
Fungi associated with the marine sponge Tethya aurantium were isolated and identified by morphological criteria and phylogenetic analyses based on internal transcribed spacer (ITS) regions. They were evaluated with regard to their secondary metabolite profiles. Among the 81 isolates which were characterized, [...] Read more.
Fungi associated with the marine sponge Tethya aurantium were isolated and identified by morphological criteria and phylogenetic analyses based on internal transcribed spacer (ITS) regions. They were evaluated with regard to their secondary metabolite profiles. Among the 81 isolates which were characterized, members of 21 genera were identified. Some genera like Acremonium, Aspergillus, Fusarium, Penicillium, Phoma, and Trichoderma are quite common, but we also isolated strains belonging to genera like Botryosphaeria, Epicoccum, Parasphaeosphaeria, and Tritirachium which have rarely been reported from sponges. Members affiliated to the genera Bartalinia and Volutella as well as to a presumably new Phoma species were first isolated from a sponge in this study. On the basis of their classification, strains were selected for analysis of their ability to produce natural products. In addition to a number of known compounds, several new natural products were identified. The scopularides and sorbifuranones have been described elsewhere. We have isolated four additional substances which have not been described so far. The new metabolite cillifuranone (1) was isolated from Penicillium chrysogenum strain LF066. The structure of cillifuranone (1) was elucidated based on 1D and 2D NMR analysis and turned out to be a previously postulated intermediate in sorbifuranone biosynthesis. Only minor antibiotic bioactivities of this compound were found so far. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessArticle Isolation of a New Natural Product and Cytotoxic and Antimicrobial Activities of Extracts from Fungi of Indonesian Marine Habitats
Mar. Drugs 2011, 9(3), 294-306; doi:10.3390/md9030294
Received: 13 January 2011 / Revised: 11 February 2011 / Accepted: 24 February 2011 / Published: 25 February 2011
Cited by 14 | PDF Full-text (183 KB) | HTML Full-text | XML Full-text
Abstract
In the search for bioactive compounds, 11 fungal strains were isolated from Indonesian marine habitats. Ethyl acetate extracts of their culture broth were tested for cytotoxic activity against a urinary bladder carcinoma cell line and for antifungal and antibacterial activities against fish [...] Read more.
In the search for bioactive compounds, 11 fungal strains were isolated from Indonesian marine habitats. Ethyl acetate extracts of their culture broth were tested for cytotoxic activity against a urinary bladder carcinoma cell line and for antifungal and antibacterial activities against fish and human pathogenic bacteria as well as against plant and human pathogenic fungi. The crude extract of a sterile algicolous fungus (KT31), isolated from the red seaweed Kappaphycus alvarezii (Doty) Doty ex P.C. Silva exhibited potent cytotoxic activity with an IC50 value of 1.5 µg/mL. Another fungal strain (KT29) displayed fungicidal properties against the plant pathogenic fungus Cladosporium cucumerinum Ell. et Arth. at 50 µg/spot. 2-Carboxy-8-methoxy-naphthalene-1-ol (1) could be isolated as a new natural product. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessArticle Low Water Activity Induces the Production of Bioactive Metabolites in Halophilic and Halotolerant Fungi
Mar. Drugs 2011, 9(1), 43-58; doi:10.3390/md9010043
Received: 8 November 2010 / Revised: 15 December 2010 / Accepted: 22 December 2010 / Published: 27 December 2010
Cited by 13 | PDF Full-text (320 KB) | HTML Full-text | XML Full-text
Abstract
The aim of the present study was to investigate indigenous fungal communities isolated from extreme environments (hypersaline waters of solar salterns and subglacial ice), for the production of metabolic compounds with selected biological activities: hemolysis, antibacterial, and acetylcholinesterase inhibition. In their natural [...] Read more.
The aim of the present study was to investigate indigenous fungal communities isolated from extreme environments (hypersaline waters of solar salterns and subglacial ice), for the production of metabolic compounds with selected biological activities: hemolysis, antibacterial, and acetylcholinesterase inhibition. In their natural habitats, the selected fungi are exposed to environmental extremes, and therefore the production of bioactive metabolites was tested under both standard growth conditions for mesophilic microorganisms, and at high NaCl and sugar concentrations and low growth temperatures. The results indicate that selected halotolerant and halophilic species synthesize specific bioactive metabolites under conditions that represent stress for non-adapted species. Furthermore, adaptation at the level of the chemical nature of the solute lowering the water activity of the medium was observed. Increased salt concentrations resulted in higher hemolytic activity, particularly within species dominating the salterns. The appearance of antibacterial potential under stress conditions was seen in the similar pattern of fungal species as for hemolysis. The active extracts exclusively affected the growth of the Gram-positive bacterium tested, Bacillus subtilis. None of the extracts tested showed inhibition of acetylcholinesterase activity. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)

Review

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Open AccessReview Potential Antiviral Agents from Marine Fungi: An Overview
Mar. Drugs 2015, 13(7), 4520-4538; doi:10.3390/md13074520
Received: 3 June 2015 / Revised: 12 June 2015 / Accepted: 15 June 2015 / Published: 22 July 2015
PDF Full-text (265 KB) | HTML Full-text | XML Full-text
Abstract
Biodiversity of the marine world is only partially subjected to detailed scientific scrutiny in comparison to terrestrial life. Life in the marine world depends heavily on marine fungi scavenging the oceans of lifeless plants and animals and entering them into the nutrient [...] Read more.
Biodiversity of the marine world is only partially subjected to detailed scientific scrutiny in comparison to terrestrial life. Life in the marine world depends heavily on marine fungi scavenging the oceans of lifeless plants and animals and entering them into the nutrient cycle by. Approximately 150 to 200 new compounds, including alkaloids, sesquiterpenes, polyketides, and aromatic compounds, are identified from marine fungi annually. In recent years, numerous investigations demonstrated the tremendous potential of marine fungi as a promising source to develop new antivirals against different important viruses, including herpes simplex viruses, the human immunodeficiency virus, and the influenza virus. Various genera of marine fungi such as Aspergillus, Penicillium, Cladosporium, and Fusarium were subjected to compound isolation and antiviral studies, which led to an illustration of the strong antiviral activity of a variety of marine fungi-derived compounds. The present review strives to summarize all available knowledge on active compounds isolated from marine fungi with antiviral activity. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
Open AccessReview Can Some Marine-Derived Fungal Metabolites Become Actual Anticancer Agents?
Mar. Drugs 2015, 13(6), 3950-3991; doi:10.3390/md13063950
Received: 15 April 2015 / Revised: 4 June 2015 / Accepted: 9 June 2015 / Published: 19 June 2015
Cited by 11 | PDF Full-text (457 KB) | HTML Full-text | XML Full-text
Abstract
Marine fungi are known to produce structurally unique secondary metabolites, and more than 1000 marine fungal-derived metabolites have already been reported. Despite the absence of marine fungal-derived metabolites in the current clinical pipeline, dozens of them have been classified as potential chemotherapy [...] Read more.
Marine fungi are known to produce structurally unique secondary metabolites, and more than 1000 marine fungal-derived metabolites have already been reported. Despite the absence of marine fungal-derived metabolites in the current clinical pipeline, dozens of them have been classified as potential chemotherapy candidates because of their anticancer activity. Over the last decade, several comprehensive reviews have covered the potential anticancer activity of marine fungal-derived metabolites. However, these reviews consider the term “cytotoxicity” to be synonymous with “anticancer agent”, which is not actually true. Indeed, a cytotoxic compound is by definition a poisonous compound. To become a potential anticancer agent, a cytotoxic compound must at least display (i) selectivity between normal and cancer cells (ii) activity against multidrug-resistant (MDR) cancer cells; and (iii) a preferentially non-apoptotic cell death mechanism, as it is now well known that a high proportion of cancer cells that resist chemotherapy are in fact apoptosis-resistant cancer cells against which pro-apoptotic drugs have more than limited efficacy. The present review thus focuses on the cytotoxic marine fungal-derived metabolites whose ability to kill cancer cells has been reported in the literature. Particular attention is paid to the compounds that kill cancer cells through non-apoptotic cell death mechanisms. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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Open AccessReview Antibacterial and Antifungal Compounds from Marine Fungi
Mar. Drugs 2015, 13(6), 3479-3513; doi:10.3390/md13063479
Received: 8 April 2015 / Revised: 17 May 2015 / Accepted: 20 May 2015 / Published: 2 June 2015
Cited by 7 | PDF Full-text (2645 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
This paper reviews 116 new compounds with antifungal or antibacterial activities as well as 169 other known antimicrobial compounds, with a specific focus on January 2010 through March 2015. Furthermore, the phylogeny of the fungi producing these antibacterial or antifungal compounds was [...] Read more.
This paper reviews 116 new compounds with antifungal or antibacterial activities as well as 169 other known antimicrobial compounds, with a specific focus on January 2010 through March 2015. Furthermore, the phylogeny of the fungi producing these antibacterial or antifungal compounds was analyzed. The new methods used to isolate marine fungi that possess antibacterial or antifungal activities as well as the relationship between structure and activity are shown in this review. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)

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