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Marine Drugs
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Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and...
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Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species

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

Deadline for manuscript submissions: closed (30 June 2018) | Viewed by 59170

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

Special Issue Editors

Dr. Rosario Nicoletti

E-Mail Website
Guest Editor
1. Council for Agricultural Research and Economics, Research Center for Olive, Citrus and Fruit Crops, 81100 Caserta, Italy
2. Department of Agricultural Sciences, University of Naples Federico II, 80055 Portici, Italy
Interests: endophytes; plant pathogens; entomopathogens; biocontrol; bioactive fungal products; marine fungi
Special Issues, Collections and Topics in MDPI journals
Dr. Francesco Vinale

E-Mail Website
Guest Editor
1. Dipartimento di Agraria, Università degli Studi di Napoli Federico II, 80055 Portici (NA), Italy
2. Istituto per la Protezione Sostenibile delle Piante, Consiglio Nazionale delle Ricerche (IPSP-CNR), 80055 Portici (NA), Italy
Interests: biological control; Trichoderma; secondary metabolites; metabolite characterization; plant pathogens
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The importance of bioactive natural compounds in pharmacology and other biotechnological fields has stimulated the scientific community to explore new environmental contexts and the associated microbial diversity. As the largest frontier in biological discovery, the sea represents a significant source of organisms producing novel secondary metabolites with interesting bioactivities. Within this biological material, fungi have received an increasing consideration, both for their pervasive occurrence in several habitats and for their widespread aptitude to develop symbiotic associations with higher organisms. In many cases, fungal strains have been reported as the real producers of drugs originally extracted from marine plants and animals. The constantly-increasing number of marine-derived fungi yielding valuable bioactive products makes it now appropriate to consider more organized forms of presentation to the recipient audience.

This Special Issue of Marine Drugs entitled “Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species” is specifically focused on a few genera of ascomycetous fungi, which are quite widespread in marine contexts, and are particularly inclined to establish symbiotic relationships. Full research papers, short notes and review articles reporting the finding and the characterization of products showing antibiotic, antitumor, antiviral, insecticidal, antimalarial, antifouling, antioxidant, plant growth-promoting and/or resistance-inducing, as well as other less exploited activities, are invited for this editorial project.

Dr. Rosario Nicoletti
Dr. Francesco Vinale
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

  • Aspergillus
  • bioactive products
  • drug discovery
  • fungal diversity
  • marine-derived fungi
  • Penicillium
  • symbiosis
  • Talaromyces
  • Trichoderma

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Published Papers (10 papers)

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Editorial

Jump to: Research, Review

3 pages, 194 KiB  
Editorial
Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species
by Rosario Nicoletti and Francesco Vinale
Mar. Drugs 2018, 16(11), 408; https://doi.org/10.3390/md16110408 - 26 Oct 2018
Cited by 35 | Viewed by 3691
Abstract
The impact of bioactive compounds from natural sources on human life, particularly in pharmacology and biotechnology, has challenged the scientific community to explore new environmental contexts and the associated microbial diversity. [...] Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)

Research

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12 pages, 3849 KiB  
Article
Asperindoles A–D and a p-Terphenyl Derivative from the Ascidian-Derived Fungus Aspergillus sp. KMM 4676
by Elena V. Ivanets, Anton N. Yurchenko, Olga F. Smetanina, Anton B. Rasin, Olesya I. Zhuravleva, Mikhail V. Pivkin, Roman S. Popov, Gunhild Von Amsberg, Shamil Sh. Afiyatullov and Sergey A. Dyshlovoy
Mar. Drugs 2018, 16(7), 232; https://doi.org/10.3390/md16070232 - 9 Jul 2018
Cited by 45 | Viewed by 5395
Abstract
Four new indole-diterpene alkaloids asperindoles A–D (1–4) and the known p-terphenyl derivative 3″-hydroxyterphenyllin (5) were isolated from the marine-derived strain of the fungus Aspergillus sp., associated with an unidentified colonial ascidian. The structures of 1– [...] Read more.
Four new indole-diterpene alkaloids asperindoles A–D (1–4) and the known p-terphenyl derivative 3″-hydroxyterphenyllin (5) were isolated from the marine-derived strain of the fungus Aspergillus sp., associated with an unidentified colonial ascidian. The structures of 1–5 were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of 1–4 were determined by the combination of ROESY data, coupling constants analysis, and biogenetic considerations. Asperindoles C and D contain a 2-hydroxyisobutyric acid (2-HIBA) residue, rarely found in natural compounds. Asperindole A exhibits cytotoxic activity against hormone therapy-resistant PC-3 and 22Rv1, as well as hormone therapy-sensitive human prostate cancer cells, and induces apoptosis in these cells at low-micromolar concentrations. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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11 pages, 2407 KiB  
Article
Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
by De-Sheng Liu, Xian-Guo Rong, Hui-Hui Kang, Li-Ying Ma, Mark T. Hamann and Wei-Zhong Liu
Mar. Drugs 2018, 16(6), 213; https://doi.org/10.3390/md16060213 - 18 Jun 2018
Cited by 12 | Viewed by 4330
Abstract
Three new diastereomers of polyketides (PKs), raistrickiones A−C (1–3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an [...] Read more.
Three new diastereomers of polyketides (PKs), raistrickiones A−C (1–3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an experimental thermo-change strategy to tap its potential of producing new secondary metabolites. Metabolites 1 and 2 existed in a diastereomeric mixture in the crystal packing according to the X-ray data, and were laboriously separated by semi-preparative HPLC on a chiral column. The structures of 1–5 were determined on the basis of the detailed analyses of the spectroscopic data (UV, IR, HRESIMS, 1D, and 2D NMR), single-crystal X-ray diffractions, and comparison of the experimental and calculated electronic circular dichroism spectra. Compounds 1–5 represented the first case of 3,5-dihydroxy-4-methylbenzoyl derivatives of natural products. Compounds 1–5 exhibited moderate radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH). Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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21 pages, 11626 KiB  
Article
The Maxi-K (BK) Channel Antagonist Penitrem A as a Novel Breast Cancer-Targeted Therapeutic
by Amira A. Goda, Abu Bakar Siddique, Mohamed Mohyeldin, Nehad M. Ayoub and Khalid A. El Sayed
Mar. Drugs 2018, 16(5), 157; https://doi.org/10.3390/md16050157 - 11 May 2018
Cited by 27 | Viewed by 7409
Abstract
Breast cancer (BC) is a heterogeneous disease with different molecular subtypes. The high conductance calcium-activated potassium channels (BK, Maxi-K channels) play an important role in the survival of some BC phenotypes, via membrane hyperpolarization and regulation of cell cycle. BK channels have been [...] Read more.
Breast cancer (BC) is a heterogeneous disease with different molecular subtypes. The high conductance calcium-activated potassium channels (BK, Maxi-K channels) play an important role in the survival of some BC phenotypes, via membrane hyperpolarization and regulation of cell cycle. BK channels have been implicated in BC cell proliferation and invasion. Penitrems are indole diterpene alkaloids produced by various terrestrial and marine Penicillium species. Penitrem A (1) is a selective BK channel antagonist with reported antiproliferative and anti-invasive activities against multiple malignancies, including BC. This study reports the high expression of BK channel in different BC subtypes. In silico BK channel binding affinity correlates with the antiproliferative activities of selected penitrem analogs. 1 showed the best binding fitting at multiple BK channel crystal structures, targeting the calcium-sensing aspartic acid moieties at the calcium bowel and calcium binding sites. Further, 1 reduced the levels of BK channel expression and increased expression of TNF-α in different BC cell types. Penitrem A (1) induced G1 cell cycle arrest of BC cells, and induced upregulation of the arrest protein p27. Combination treatment of 1 with targeted anti-HER drugs resulted in synergistic antiproliferative activity, which was associated with reduced EGFR and HER2 receptor activation, as well as reduced active forms of AKT and STAT3. Collectively, the BK channel antagonists represented by penitrem A can be novel sensitizing, chemotherapeutics synergizing, and therapeutic agents for targeted BC therapy. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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10 pages, 1776 KiB  
Communication
Two New Terpenoids from Talaromyces purpurogenus
by Wenjing Wang, Xiao Wan, Junjun Liu, Jianping Wang, Hucheng Zhu, Chunmei Chen and Yonghui Zhang
Mar. Drugs 2018, 16(5), 150; https://doi.org/10.3390/md16050150 - 2 May 2018
Cited by 36 | Viewed by 6004
Abstract
A new sesquiterpenoid 9,10-diolhinokiic acid (1) and a new diterpenoid roussoellol C (2), together with 4 known compounds, were isolated from the extracts of laboratory cultures of marine-derived fungus Talaromyces purpurogenus. 9,10-diolhinokiic acid is the first thujopsene-type sesquiterpenoid [...] Read more.
A new sesquiterpenoid 9,10-diolhinokiic acid (1) and a new diterpenoid roussoellol C (2), together with 4 known compounds, were isolated from the extracts of laboratory cultures of marine-derived fungus Talaromyces purpurogenus. 9,10-diolhinokiic acid is the first thujopsene-type sesquiterpenoid containing a 9,10-diol moiety, and roussoellol C possesses a novel tetracyclic fusicoccane framework with an unexpected hydroxyl at C-4. These new structures were confirmed by spectroscopic data, chemical method, NMR data calculations and electronic circular dichroism (ECD) calculations. The selected compounds were evaluated for cytotoxicities against five human cancer cell lines, including SW480, HL-60, A549, MCF-7, and SMMC-7721 and the IC50 values of compound 2 against MCF-7 and 3 against HL-60 cells were 6.5 and 7.9 μM, respectively. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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22 pages, 3997 KiB  
Article
Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062
by Suradet Buttachon, Alice A. Ramos, Ângela Inácio, Tida Dethoup, Luís Gales, Michael Lee, Paulo M. Costa, Artur M. S. Silva, Nazim Sekeroglu, Eduardo Rocha, Madalena M. M. Pinto, José A. Pereira and Anake Kijjoa
Mar. Drugs 2018, 16(4), 119; https://doi.org/10.3390/md16040119 - 6 Apr 2018
Cited by 56 | Viewed by 7504
Abstract
A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), [...] Read more.
A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2″-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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9 pages, 2403 KiB  
Communication
A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
by Beiye Yang, Weiguang Sun, Jianping Wang, Shuang Lin, Xiao-Nian Li, Hucheng Zhu, Zengwei Luo, Yongbo Xue, Zhengxi Hu and Yonghui Zhang
Mar. Drugs 2018, 16(4), 110; https://doi.org/10.3390/md16040110 - 29 Mar 2018
Cited by 28 | Viewed by 5377
Abstract
Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known [...] Read more.
Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC50 values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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1603 KiB  
Article
Cytotoxic and Antibacterial Compounds from the Coral-Derived Fungus Aspergillus tritici SP2-8-1
by Weiyi Wang, Yanyan Liao, Chao Tang, Xiaomei Huang, Zhuhua Luo, Jianming Chen and Peng Cai
Mar. Drugs 2017, 15(11), 348; https://doi.org/10.3390/md15110348 - 7 Nov 2017
Cited by 39 | Viewed by 5397
Abstract
Three novel compounds, 4-methyl-candidusin A (1), aspetritone A (2) and aspetritone B (3), were obtained from the culture of a coral-derived fungus Aspergillus tritici SP2-8-1, together with fifteen known compounds (4–18). Their structures, [...] Read more.
Three novel compounds, 4-methyl-candidusin A (1), aspetritone A (2) and aspetritone B (3), were obtained from the culture of a coral-derived fungus Aspergillus tritici SP2-8-1, together with fifteen known compounds (4–18). Their structures, including absolute configurations, were assigned based on NMR, MS, and time-dependent density functional theory (TD-DFT) ECD calculations. Compounds 2 and 5 exhibited better activities against methicillin-resistant strains of S. aureus (MRSA) ATCC 43300 and MRSA CGMCC 1.12409 than the positive control chloramphenicol. Compound 5 displayed stronger anti-MRSA and lower cytotoxic activities than 2, and showed stronger antibacterial activities against strains of Vibrio vulnificus, Vibrio rotiferianus, and Vibrio campbellii than the other compounds. Compounds 2 and 10 exhibited significantly stronger cytotoxic activities against human cancer cell lines HeLa, A549, and Hep G2 than the other compounds. Preliminary structure–activity relationship studies indicated that prenylation of terphenyllin or candidusin and the tetrahydrobenzene moiety in anthraquinone derivatives may influence their bioactivity. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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889 KiB  
Article
Identification and Antifungal Activity of Compounds from the Mangrove Endophytic Fungus Aspergillus clavatus R7
by Wensheng Li, Ping Xiong, Wenxu Zheng, Xinwei Zhu, Zhigang She, Weijia Ding and Chunyuan Li
Mar. Drugs 2017, 15(8), 259; https://doi.org/10.3390/md15080259 - 19 Aug 2017
Cited by 34 | Viewed by 5889
Abstract
Two new coumarin derivatives, 4,4′-dimethoxy-5,5′-dimethyl-7,7′-oxydicoumarin (1), 7-(γ,γ-dimethylallyloxy)-5-methoxy-4-methylcoumarin (2), a new chromone derivative, (S)-5-hydroxy-2,6-dimethyl-4H-furo[3,4-g]benzopyran-4,8(6H)-dione (5), and a new sterone derivative, 24-hydroxylergosta-4,6,8(14),22-tetraen-3-one (6), along with two known bicoumarins, kotanin (3 [...] Read more.
Two new coumarin derivatives, 4,4′-dimethoxy-5,5′-dimethyl-7,7′-oxydicoumarin (1), 7-(γ,γ-dimethylallyloxy)-5-methoxy-4-methylcoumarin (2), a new chromone derivative, (S)-5-hydroxy-2,6-dimethyl-4H-furo[3,4-g]benzopyran-4,8(6H)-dione (5), and a new sterone derivative, 24-hydroxylergosta-4,6,8(14),22-tetraen-3-one (6), along with two known bicoumarins, kotanin (3) and orlandin (4), were isolated from an endophytic fungus Aspergillus clavatus (collection No. R7), isolated from the root of Myoporum bontioides collected from Leizhou Peninsula, China. Their structures were elucidated using 1D- and 2D- NMR spectroscopy, and HRESIMS. The absolute configuration of compound 5 was determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 6 significantly inhibited the plant pathogenic fungi Fusarium oxysporum, Colletotrichum musae and Penicillium italicum, compound 5 significantly inhibited Colletotrichum musae, and compounds 1, 3 and 4 greatly inhibited Fusarium oxysporum, showing the antifungal activities higher than those of the positive control, triadimefon. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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Review

Jump to: Editorial, Research

15 pages, 9691 KiB  
Review
Secondary Metabolites of Mangrove-Associated Strains of Talaromyces
by Rosario Nicoletti, Maria Michela Salvatore and Anna Andolfi
Mar. Drugs 2018, 16(1), 12; https://doi.org/10.3390/md16010012 - 6 Jan 2018
Cited by 57 | Viewed by 7054
Abstract
Boosted by the general aim of exploiting the biotechnological potential of the microbial component of biodiversity, research on the secondary metabolite production of endophytic fungi has remarkably increased in the past few decades. Novel compounds and bioactivities have resulted from this work, which [...] Read more.
Boosted by the general aim of exploiting the biotechnological potential of the microbial component of biodiversity, research on the secondary metabolite production of endophytic fungi has remarkably increased in the past few decades. Novel compounds and bioactivities have resulted from this work, which has stimulated a more thorough consideration of various natural ecosystems as conducive contexts for the discovery of new drugs. Thriving at the frontier between land and sea, mangrove forests represent one of the most valuable areas in this respect. The present paper offers a review of the research on the characterization and biological activities of secondary metabolites from manglicolous strains of species belonging to the genus Talaromyces. Aspects concerning the opportunity for a more reliable identification of this biological material in the light of recent taxonomic revisions are also discussed. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine-Derived Aspergillus, Penicillium, Talaromyces and Trichoderma Species)
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