Marine Drugs

Research

Jump to: Review

504 KiB

Open AccessArticle

Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae

by Bin Wu, Jutta Wiese, Antje Labes, Annemarie Kramer, Rolf Schmaljohann and Johannes F. Imhoff

Mar. Drugs 2015, 13(8), 4617-4632; https://doi.org/10.3390/md13084617 - 27 Jul 2015

Cited by 68 | Viewed by 8086

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) and [...] 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)

► Show Figures

Figure 1

1549 KiB

Open AccessArticle

Identification of the Scopularide Biosynthetic Gene Cluster in Scopulariopsis brevicaulis

by Mie Bech Lukassen, Wagma Saei, Teis Esben Sondergaard, Anu Tamminen, Abhishek Kumar, Frank Kempken, Marilyn G. Wiebe and Jens Laurids Sørensen

Mar. Drugs 2015, 13(7), 4331-4343; https://doi.org/10.3390/md13074331 - 14 Jul 2015

Cited by 26 | Viewed by 9337

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 genome [...] 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)

► Show Figures

Figure 1

250 KiB

Open AccessCommunication

Bioactive 7-Oxabicyclic[6.3.0]lactam and 12-Membered Macrolides from a Gorgonian-Derived Cladosporium sp. Fungus

by Fei Cao, Qin Yang, Chang-Lun Shao, Chui-Jian Kong, Juan-Juan Zheng, Yun-Feng Liu and Chang-Yun Wang

Mar. Drugs 2015, 13(7), 4171-4178; https://doi.org/10.3390/md13074171 - 7 Jul 2015

Cited by 36 | Viewed by 6704

Abstract

One new bicyclic lactam, cladosporilactam A (1), and six known 12-membered macrolides (2–7) 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. [...] Read more.

One new bicyclic lactam, cladosporilactam A (1), and six known 12-membered macrolides (2–7) 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)

► Show Figures

Graphical abstract

593 KiB

Open AccessArticle

Investigation of Marine-Derived Fungal Diversity and Their Exploitable Biological Activities

by Joo-Hyun Hong, Seokyoon Jang, Young Mok Heo, Mihee Min, Hwanhwi Lee, Young Min Lee, Hanbyul Lee and Jae-Jin Kim

Mar. Drugs 2015, 13(7), 4137-4155; https://doi.org/10.3390/md13074137 - 30 Jun 2015

Cited by 73 | Viewed by 8144

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 nuclear [...] 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)

► Show Figures

Figure 1

1329 KiB

Open AccessArticle

Production of Calcaride A by Calcarisporium sp. in Shaken Flasks and Stirred Bioreactors

by Anu Tamminen, Yanming Wang and Marilyn G. Wiebe

Mar. Drugs 2015, 13(7), 3992-4005; https://doi.org/10.3390/md13073992 - 24 Jun 2015

Cited by 4 | Viewed by 6513

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. Calcarisporium [...] 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)

► Show Figures

Graphical abstract

1390 KiB

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

by Yang Liu, Attila Mándi, Xiao-Ming Li, Ling-Hong Meng, Tibor Kurtán and Bin-Gui Wang

Mar. Drugs 2015, 13(6), 3640-3652; https://doi.org/10.3390/md13063640 - 5 Jun 2015

Cited by 58 | Viewed by 8203

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 from [...] 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)

► Show Figures

Graphical abstract

655 KiB

Open AccessArticle

New Polyphenols from a Deep Sea Spiromastix sp. Fungus, and Their Antibacterial Activities

by Siwen Niu, Dong Liu, Peter Proksch, Zongze Shao and Wenhan Lin

Mar. Drugs 2015, 13(4), 2526-2540; https://doi.org/10.3390/md13042526 - 22 Apr 2015

Cited by 28 | Viewed by 7452

Abstract

Eleven new polyphenols namely spiromastols A–K (1–11) 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. [...] Read more.

Eleven new polyphenols namely spiromastols A–K (1–11) 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 1–3 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 1–3 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)

► Show Figures

Graphical abstract

592 KiB

Open AccessArticle

Identification and Bioactivity of Compounds from the Fungus Penicillium sp. CYE-87 Isolated from a Marine Tunicate

by Lamiaa A. Shaala and Diaa T. A. Youssef

Mar. Drugs 2015, 13(4), 1698-1709; https://doi.org/10.3390/md13041698 - 25 Mar 2015

Cited by 51 | Viewed by 8327

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 (1 [...] 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)

► Show Figures

Graphical abstract

624 KiB

Open AccessArticle

A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013

by Chadaporn Prompanya, Carla Fernandes, Sara Cravo, Madalena M. M. Pinto, Tida Dethoup, Artur M. S. Silva and Anake Kijjoa

Mar. Drugs 2015, 13(3), 1432-1450; https://doi.org/10.3390/md13031432 - 17 Mar 2015

Cited by 70 | Viewed by 7940

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 Aspergillus [...] 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)

► Show Figures

Figure 1

567 KiB

Open AccessArticle

Territrem and Butyrolactone Derivatives from a Marine-Derived Fungus Aspergillus Terreus

by Xu-Hua Nong, Yi-Fei Wang, Xiao-Yong Zhang, Mu-Ping Zhou, Xin-Ya Xu and Shu-Hua Qi

Mar. Drugs 2014, 12(12), 6113-6124; https://doi.org/10.3390/md12126113 - 17 Dec 2014

Cited by 87 | Viewed by 8425

Abstract

Seventeen lactones including eight territrem derivatives (1–8) and nine butyrolactone derivatives (9–17) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 1–3 and 9–10 [...] Read more.

Seventeen lactones including eight territrem derivatives (1–8) and nine butyrolactone derivatives (9–17) were isolated from a marine-derived fungus Aspergillus terreus SCSGAF0162 under solid-state fermentation of rice. Compounds 1–3 and 9–10 were new, and their structures were elucidated by spectroscopic analysis. The acetylcholinesterase inhibitory activity and antiviral activity of compounds 1–17 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)

► Show Figures

Figure 1

1177 KiB

Open AccessArticle

Inhibition of Bacterial Quorum Sensing by Extracts from Aquatic Fungi: First Report from Marine Endophytes

by Alberto J. Martín-Rodríguez, Fernando Reyes, Jesús Martín, Juan Pérez-Yépez, Milagros León-Barrios, Alan Couttolenc, César Espinoza, Ángel Trigos, Víctor S. Martín, Manuel Norte and José J. Fernández

Mar. Drugs 2014, 12(11), 5503-5526; https://doi.org/10.3390/md12115503 - 19 Nov 2014

Cited by 49 | Viewed by 12118

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 activity [...] 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)

► Show Figures

Figure 1

540 KiB

Open AccessArticle

Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans

by Cai-Juan Zheng, Chang-Lun Shao, Lu-Yong Wu, Min Chen, Kai-Ling Wang, Dong-Lin Zhao, Xue-Ping Sun, Guang-Ying Chen and Chang-Yun Wang

Mar. Drugs 2013, 11(6), 2054-2068; https://doi.org/10.3390/md11062054 - 10 Jun 2013

Cited by 79 | Viewed by 9657

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 (5–12 [...] 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 (5–12) 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 (1–12) 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)

► Show Figures

Figure 1

498 KiB

Open AccessArticle

PTP1B Inhibitory and Anti-Inflammatory Effects of Secondary Metabolites Isolated from the Marine-Derived Fungus Penicillium sp. JF-55

by Dong-Sung Lee, Jae-Hyuk Jang, Wonmin Ko, Kyoung-Su Kim, Jae Hak Sohn, Myeong-Suk Kang, Jong Seog Ahn, Youn-Chul Kim and Hyuncheol Oh

Mar. Drugs 2013, 11(4), 1409-1426; https://doi.org/10.3390/md11041409 - 23 Apr 2013

Cited by 58 | Viewed by 9107

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 cultures [...] 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 1–3 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)

► Show Figures

Figure 1

615 KiB

Open AccessArticle

Helicusin E, Isochromophilone X and Isochromophilone XI: New Chloroazaphilones Produced by the Fungus Bartalinia robillardoides Strain LF550

by Nils Jansen, Birgit Ohlendorf, Arlette Erhard, Torsten Bruhn, Gerhard Bringmann and Johannes F. Imhoff

Mar. Drugs 2013, 11(3), 800-816; https://doi.org/10.3390/md11030800 - 12 Mar 2013

Cited by 32 | Viewed by 9949

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 a [...] 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)

► Show Figures

Figure 1

543 KiB

Open AccessArticle

Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

by Hou-Jin Li, Ting Chen, Ying-Lu Xie, Wen-Dan Chen, Xiao-Feng Zhu and Wen-Jian Lan

Mar. Drugs 2013, 11(2), 551-558; https://doi.org/10.3390/md11020551 - 22 Feb 2013

Cited by 33 | Viewed by 7248

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), arthrosporone [...] 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)

► Show Figures

Figure 1

1166 KiB

Open AccessArticle

Xyloketal B Exhibits Its Antioxidant Activity through Induction of HO-1 in Vascular Endothelial Cells and Zebrafish

by Zhen-Xing Li, Jian-Wen Chen, Feng Yuan, Yun-Ying Huang, Li-Yan Zhao, Jie Li, Huan-Xing Su, Jie Liu, Ji-Yan Pang, Yong-Cheng Lin, Xi-Lin Lu, Zhong Pei, Guan-Lei Wang and Yong-Yuan Guan

Mar. Drugs 2013, 11(2), 504-522; https://doi.org/10.3390/md11020504 - 18 Feb 2013

Cited by 37 | Viewed by 6802

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 here [...] 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)

► Show Figures

Figure 1

1010 KiB

Open AccessArticle

Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus

by Tobias A. M. Gulder, Hanna Hong, Jhonny Correa, Ekaterina Egereva, Jutta Wiese, Johannes F. Imhoff and Harald Gross

Mar. Drugs 2012, 10(12), 2912-2935; https://doi.org/10.3390/md10122912 - 19 Dec 2012

Cited by 50 | Viewed by 11827

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)

► Show Figures

Graphical abstract

496 KiB

Open AccessArticle

Phylogenetic Identification of Fungi Isolated from the Marine Sponge Tethya aurantium and Identification of Their Secondary Metabolites

by Jutta Wiese, Birgit Ohlendorf, Martina Blümel, Rolf Schmaljohann and Johannes F. Imhoff

Mar. Drugs 2011, 9(4), 561-585; https://doi.org/10.3390/md9040561 - 6 Apr 2011

Cited by 113 | Viewed by 15405

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, members [...] 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)

► Show Figures

183 KiB

Open AccessArticle

Isolation of a New Natural Product and Cytotoxic and Antimicrobial Activities of Extracts from Fungi of Indonesian Marine Habitats

by Kustiariyah Tarman, Ulrike Lindequist, Kristian Wende, Andrea Porzel, Norbert Arnold and Ludger A. Wessjohann

Mar. Drugs 2011, 9(3), 294-306; https://doi.org/10.3390/md9030294 - 25 Feb 2011

Cited by 45 | Viewed by 14865

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 and [...] 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)

► Show Figures

Graphical abstract

320 KiB

Open AccessArticle

Low Water Activity Induces the Production of Bioactive Metabolites in Halophilic and Halotolerant Fungi

by Kristina Sepcic, Polona Zalar and Nina Gunde-Cimerman

Mar. Drugs 2011, 9(1), 43-58; https://doi.org/10.3390/md9010043 - 27 Dec 2010

Cited by 43 | Viewed by 11429

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 habitats, [...] 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)

► Show Figures

Review

Jump to: Research

265 KiB

Open AccessReview

Potential Antiviral Agents from Marine Fungi: An Overview

by Soheil Zorofchian Moghadamtousi, Sonia Nikzad, Habsah Abdul Kadir, Sazaly Abubakar and Keivan Zandi

Mar. Drugs 2015, 13(7), 4520-4538; https://doi.org/10.3390/md13074520 - 22 Jul 2015

Cited by 90 | Viewed by 12785

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 cycle [...] 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)

► Show Figures

Figure 1

457 KiB

Open AccessReview

Can Some Marine-Derived Fungal Metabolites Become Actual Anticancer Agents?

by Nelson G. M. Gomes, Florence Lefranc, Anake Kijjoa and Robert Kiss

Mar. Drugs 2015, 13(6), 3950-3991; https://doi.org/10.3390/md13063950 - 19 Jun 2015

Cited by 103 | Viewed by 14913

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 candidates [...] 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)

► Show Figures

Graphical abstract

2645 KiB

Open AccessReview

Antibacterial and Antifungal Compounds from Marine Fungi

by Lijian Xu, Wei Meng, Cong Cao, Jian Wang, Wenjun Shan and Qinggui Wang

Mar. Drugs 2015, 13(6), 3479-3513; https://doi.org/10.3390/md13063479 - 2 Jun 2015

Cited by 112 | Viewed by 14171

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 analyzed. [...] 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)

► Show Figures

Figure 1

Journal Menu

Journal Browser

Bioactive Compounds from Marine Fungi

Share This Special Issue

Special Issue Editor

Special Issue Information

Keywords

Benefits of Publishing in a Special Issue

Published Papers (23 papers)

Research

Review

Further Information

Guidelines

MDPI Initiatives

Follow MDPI