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Marine Drugs
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Marine Natural Products from Symbiotic Ecosystems
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Marine Natural Products from Symbiotic Ecosystems

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

Deadline for manuscript submissions: closed (20 July 2018) | Viewed by 35811

Special Issue Editor

Dr. Ipek Kurtboke

E-Mail Website
Guest Editor
School of Science, Technology and Engineering, University of the Sunshine Coast, Maroochydore, QLD 4558, Australia
Interests: microbial ecology and diversity; microbial systematics; biodiscovery; microbial biotechnology applied; environmental and industrial microbiology; marine microbiology; biological control; actinomycetology; bacteriophages
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine-derived bioactive compounds have been reported to have functional roles within their symbiotic environments and can chemically range from antimicrobials, pigments, vitamins and enzymes. These compounds can exhibit antibacterial, antiviral, antifungal, antimicrobial or cytotoxic properties. They can also be produced as defense compounds against competitors of their hosts, predators and pathogens thus providing the host with competitive advantages in the environment by increasing their access to space and nutrients through elimination of the competitors.  As a result, most symbionts are believed to produce unique compounds for their hosts, and such potent compounds might also have further use in industry. Accordingly, in this Special Issue, the author would like to invite manuscripts specialized in discovery of medicinal and biotechnologically important compounds deriving from symbiosis between marine macro-organisms and microorganisms.

Dr. Ipek Kurtboke
Guest Editor

Manuscript Submission Information

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

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

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

Keywords

  • marine microorganisms
  • marine symbiosis
  • marine biodiscovery
  • marine biotechnology
  • marine environments

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Related Special Issue

Published Papers (7 papers)

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Research

9 pages, 6191 KiB  
Article
Halogenated and Nonhalogenated Metabolites from the Marine-Alga-Endophytic Fungus Trichoderma asperellum cf44-2
by Yin-Ping Song, Feng-Ping Miao, Sheng-Tao Fang, Xiu-Li Yin and Nai-Yun Ji
Mar. Drugs 2018, 16(8), 266; https://doi.org/10.3390/md16080266 - 2 Aug 2018
Cited by 42 | Viewed by 4437
Abstract
One new bisabolane sesquiterpene, bisabolan-1,10,11-triol (1), one new norbisabolane sesquiterpene, 12-nor-11-acetoxybisabolen-3,6,7-triol (2), two new naturally occurring monoterpenes, (7S)- and (7R)-1-hydroxy-3-p-menthen-9-oic acids (3 and 4), one new naturally occurring trichodenone, dechlorotrichodenone C [...] Read more.
One new bisabolane sesquiterpene, bisabolan-1,10,11-triol (1), one new norbisabolane sesquiterpene, 12-nor-11-acetoxybisabolen-3,6,7-triol (2), two new naturally occurring monoterpenes, (7S)- and (7R)-1-hydroxy-3-p-menthen-9-oic acids (3 and 4), one new naturally occurring trichodenone, dechlorotrichodenone C (5), one new chlorine-containing trichodenone, 3-hydroxytrichodenone C (6), one new diketopiperazine, methylcordysinin A (7), and one new naturally occurring oxazole derivative, 4-oxazolepropanoic acid (8), were isolated from the culture of a marine brown alga-endophytic strain (cf44-2) of Trichoderma asperellum. Their structures and relative configurations were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of 3–6 were assigned by analysis of the ECD spectra aided by quantum chemical computations. Compounds 1, 2, 5, and 6 showed growth inhibition of some marine phytoplankton species and pathogenic bacteria. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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11 pages, 2723 KiB  
Article
Four New C9 Metabolites from the Sponge-Associated Fungus Gliomastix sp. ZSDS1-F7-2
by Jun Zhang, Zhiqiang Yang, Yan Liang, Liping Zhong, Huiting Lin, Balian Zhong, Liangchun Li, Shihai Xu and Yonghong Liu
Mar. Drugs 2018, 16(7), 231; https://doi.org/10.3390/md16070231 - 9 Jul 2018
Cited by 4 | Viewed by 4109
Abstract
Four new structurally related metabolites, one γ-lactone named gliomasolide F (1), one δ-lactone named gliomasolide G (2), and two medium-chain fatty acids named gliomacids A–B (3–4), each containing nine carbons in total, were identified from [...] Read more.
Four new structurally related metabolites, one γ-lactone named gliomasolide F (1), one δ-lactone named gliomasolide G (2), and two medium-chain fatty acids named gliomacids A–B (3–4), each containing nine carbons in total, were identified from the sponge-associated fungus Gliomastix sp. ZSDS1-F7-2. The planar chemical structures of these novel C9 metabolites were elucidated by nuclear magnetic resonance (NMR) spectroscopic methods, in connection with the analysis of high-resolution mass spectrometry (HRMS) and infrared (IR) data. The absolute configuration of 1, was determined by comparisons of experimental circular dichroism (CD) and optical rotation (OR) value with corresponding ones computed by quantum chemistry. The relative configuration of 2 was determined by the Nuclear Overhauser effect spectroscopy (NOESY) spectrum, while its absolute configuration was tentatively determined in view of the biogenetic and biosynthetic relationships between 1 and 2. Compounds 3–4, originally as an inseparable mixture, were successfully isolated after chemical modifications. The stereo-chemistries of compounds 3–4 were assumed by comparison of 13C NMR with those of the similar moiety reported in literature, in addition to the biogenetic and biosynthetic relationships with 1. The plausible biosynthetic relationships among these four C9 metabolites were supposed. Biologically, compounds 1–4 showed no cytotoxic effect against HeLa cell line at concentrations up to 25 μg/mL, while 1 exhibited moderate antifouling activity against the settlement of Balanus amphitrite larvae with IC50 being 12.8 μg/mL and LC50 > 25 μg/mL. The co-occurrence of macrolides gliomasolides A—E and four C9 metabolites in the same fermentation culture made us assume that these C9 metabolites might be biosynthetic building blocks toward the construction of more complex macrolides such as gliomasolides A—E or other unidentified polyketides. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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15 pages, 2305 KiB  
Article
Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum
by Junjun Meng, Wei Cheng, Hajar Heydari, Bin Wang, Kui Zhu, Belma Konuklugil and Wenhan Lin
Mar. Drugs 2018, 16(7), 226; https://doi.org/10.3390/md16070226 - 4 Jul 2018
Cited by 31 | Viewed by 5224
Abstract
Antibacterial activity assessment and high performance liquid chromatography associated with nuclear magnetic resonance (HPLC/NMR) data revealed that the EtOAc extract of the fermented endophytic fungus Trichoderma saturnisporum DI-IA, obtained from the marine sponge Dictyonella incisa, contained conjugated olefinic metabolites with antibacterial activity. [...] Read more.
Antibacterial activity assessment and high performance liquid chromatography associated with nuclear magnetic resonance (HPLC/NMR) data revealed that the EtOAc extract of the fermented endophytic fungus Trichoderma saturnisporum DI-IA, obtained from the marine sponge Dictyonella incisa, contained conjugated olefinic metabolites with antibacterial activity. Chemical examination of the fungal strain resulted in the isolation of eight new sorbicillinoid-based compounds, namely saturnispols A–H (1–8). Their structures were determined on the basis of extensive spectroscopic analysis, including the experimental and calculated electronic circular dichroism (ECD) data for the configurational assignments. Saturnispol F exerted significant inhibition against a panel of bacteria strains including vancomycin-resistant enterococci (VRE) with a minimum inhibitory concentrations (MIC) ranging from 1.63 to 12.9 μg/mL, while saturnispol H showed selective effects against VRE and B. subtilis. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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13 pages, 2989 KiB  
Article
Butyrolactone-I from Coral-Derived Fungus Aspergillus terreus Attenuates Neuro-Inflammatory Response via Suppression of NF-κB Pathway in BV-2 Cells
by Yuan Yuan Zhang, Yi Zhang, Yuan-Bei Yao, Xiao-Ling Lei and Zhong-Ji Qian
Mar. Drugs 2018, 16(6), 202; https://doi.org/10.3390/md16060202 - 7 Jun 2018
Cited by 28 | Viewed by 4992
Abstract
Butyrolactone-I (ZB5-1) from the coral-derived fungus Aspergillus terreus was investigated in this study to estimate its anti-neuroinflammatory effects on lipopolysaccharide (LPS)-induced BV-2 microglia cells. MTT assay indicated that ZB5-1 in tested concentrations had no cytotoxicity on BV-2 cells, and significantly reduced the production [...] Read more.
Butyrolactone-I (ZB5-1) from the coral-derived fungus Aspergillus terreus was investigated in this study to estimate its anti-neuroinflammatory effects on lipopolysaccharide (LPS)-induced BV-2 microglia cells. MTT assay indicated that ZB5-1 in tested concentrations had no cytotoxicity on BV-2 cells, and significantly reduced the production of nitric oxide (NO), measured using Griess reagent, and interleukin-1 beta (IL-1β), detected by enzyme-linked immunosorbent assay (ELISA). ZB5-1 also down-regulated the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in a dose-dependent manner by Western blot analysis. Moreover, the effect of ZB5-1 on the nuclear factor-κB (NF-κB) signaling pathway was studied via the expression of phosphorylation of NF-κB p65 and inhibitor of NF-κB (IκB), and the nuclear translocation of NF-κB p65 respectively. The results showed that ZB5-1 could inhibit the phosphorylation of p65 and IκB. Furthermore, molecular docking study suggested that ZB5-1 bound at the active sites of NF-κB to prevent its translocation to the nucleus. Therefore, we suggest ZB5-1 has a potential to reduce the anti-inflammatory response in LPS-induced BV-2 cells. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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11 pages, 1677 KiB  
Article
HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)
by Larissa Buedenbender, Luke P. Robertson, Leonardo Lucantoni, Vicky M. Avery, D. İpek Kurtböke and Anthony R. Carroll
Mar. Drugs 2018, 16(6), 189; https://doi.org/10.3390/md16060189 - 30 May 2018
Cited by 18 | Viewed by 5190
Abstract
Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). [...] Read more.
Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the compounds were elucidated based on 1D/2D NMR and MS data. The absolute configuration of 1 was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Antiplasmodial activities were tested for the natural products against chloroquine sensitive (3D7) and chloroquine resistant (Dd2) Plasmodium falciparum strains; the two polyketides (1–2) demonstrated an inhibition of >75% against both parasite strains and while 2 was highly cytotoxic, herbimycin G (1) showed no cytotoxicity and good predicted water solubility. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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13 pages, 2665 KiB  
Article
Molecular Characterization of a Novel N-Acetylneuraminate Lyase from a Deep-Sea Symbiotic Mycoplasma
by Shao-lu Wang, Yun-liang Li, Zhuang Han, Xi Chen, Qi-jia Chen, Yong Wang and Li-sheng He
Mar. Drugs 2018, 16(3), 80; https://doi.org/10.3390/md16030080 - 5 Mar 2018
Cited by 9 | Viewed by 4927
Abstract
N-acetylneuraminic acid (Neu5Ac) based novel pharmaceutical agents and diagnostic reagents are highly required in medical fields. However, N-acetylneuraminate lyase（NAL）for Neu5Ac synthesis is not applicable for industry due to its low catalytic efficiency. In this study, we biochemically characterized a deep-sea NAL [...] Read more.
N-acetylneuraminic acid (Neu5Ac) based novel pharmaceutical agents and diagnostic reagents are highly required in medical fields. However, N-acetylneuraminate lyase（NAL）for Neu5Ac synthesis is not applicable for industry due to its low catalytic efficiency. In this study, we biochemically characterized a deep-sea NAL enzyme (abbreviated form: MyNal) from a symbiotic Mycoplasma inhabiting the stomach of a deep-sea isopod, Bathynomus jamesi. Enzyme kinetic studies of MyNal showed that it exhibited a very low Km for both cleavage and synthesis activities compared to previously described NALs. Though it favors the cleavage process, MyNal out-competes the known NALs with respect to the efficiency of Neu5Ac synthesis and exhibits the highest kcat/Km values. High expression levels of recombinant MyNal could be achieved (9.56 mol L−1 culture) with a stable activity in a wide pH (5.0–9.0) and temperature (40–60 °C) range. All these features indicated that the deep-sea NAL has potential in the industrial production of Neu5Ac. Furthermore, we found that the amino acid 189 of MyNal (equivalent to Phe190 in Escherichia coli NAL), located in the sugar-binding domain, GX189DE, was also involved in conferring its enzymatic features. Therefore, the results of this study improved our understanding of the NALs from different environments and provided a model for protein engineering of NAL for biosynthesis of Neu5Ac. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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10 pages, 1224 KiB  
Article
Dichloroisocoumarins with Potential Anti-Inflammatory Activity from the Mangrove Endophytic Fungus Ascomycota sp. CYSK-4
by Yan Chen, Zhaoming Liu, Hongju Liu, Yahong Pan, Jing Li, Lan Liu and Zhigang She
Mar. Drugs 2018, 16(2), 54; https://doi.org/10.3390/md16020054 - 9 Feb 2018
Cited by 53 | Viewed by 5263
Abstract
Three new isocoumarins—dichlorodiaportintone (1), desmethyldichlorodiaportintone (2) and desmethyldichlorodiaportinol (3)—as well as six known analogues (4–9) were isolated from the culture of the mangrove endophytic fungus Ascomycota sp. CYSK-4 from Pluchea indica. Their structures were [...] Read more.
Three new isocoumarins—dichlorodiaportintone (1), desmethyldichlorodiaportintone (2) and desmethyldichlorodiaportinol (3)—as well as six known analogues (4–9) were isolated from the culture of the mangrove endophytic fungus Ascomycota sp. CYSK-4 from Pluchea indica. Their structures were elucidated by analysis of spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by the modified Mosher’s method. Compound 2 showed significant anti-inflammatory activity by inhibiting the production of NO in LPS-induced RAW 264.7 cells with IC50 value of 15.8 μM, while compounds 1, 5, and 6 exhibited weak activities with IC50 values of 41.5, 33.6, and 67.2 μM, respectively. In addition, compounds 1, 5, and 6 showed antibacterial effects against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae, and Acinetobacter calcoaceticus with the MIC values in the range of 25–50 μg·mL−1. Full article
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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