Marine Drugs

11 pages, 1045 KiB

Open AccessArticle

Purification and Molecular Docking Study on the Angiotensin I-Converting Enzyme (ACE)-Inhibitory Peptide Isolated from Hydrolysates of the Deep-Sea Mussel Gigantidas vrijenhoeki

by Seong-Yeong Heo, Nalae Kang, Eun-A Kim, Junseong Kim, Seung-Hong Lee, Ginnae Ahn, Je Hyeok Oh, A Young Shin, Dongsung Kim and Soo-Jin Heo

Mar. Drugs 2023, 21(8), 458; https://doi.org/10.3390/md21080458 - 21 Aug 2023

Cited by 3 | Viewed by 1520

Abstract

The objective of this study was to prepare an angiotensin I-converting enzyme (ACE)-inhibitory peptide from the hydrothermal vent mussel, Gigantidas vrijenhoeki. The G. vrijenhoeki protein was hydrolyzed by various hydrolytic enzymes. The peptic hydrolysate exhibited the highest ACE-inhibitory activity and was fractionated [...] Read more.

The objective of this study was to prepare an angiotensin I-converting enzyme (ACE)-inhibitory peptide from the hydrothermal vent mussel, Gigantidas vrijenhoeki. The G. vrijenhoeki protein was hydrolyzed by various hydrolytic enzymes. The peptic hydrolysate exhibited the highest ACE-inhibitory activity and was fractionated into four molecular weight ranges by ultrafiltration. The <1 kDa fraction exhibited the highest ACE inhibitory activity and was found to have 11 peptide sequences. Among the analyzed peptides, KLLWNGKM exhibited stronger ACE inhibitory activity and an IC₅₀ value of 0.007 μM. To investigate the ACE-inhibitory activity of the analyzed peptides, a molecular docking study was performed. KLLWNGKM exhibited the highest binding energy (−1317.01 kcal/mol), which was mainly attributed to the formation of hydrogen bonds with the ACE active pockets, zinc-binding motif, and zinc ion. These results indicate that G. vrijenhoeki-derived peptides can serve as nutritional and pharmacological candidates for controlling blood pressure. Full article

(This article belongs to the Special Issue Enzyme Inhibitors from Marine Resources)

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14 pages, 2935 KiB

Open AccessEditor’s ChoiceArticle

Lobosteroids A–F: Six New Highly Oxidized Steroids from the Chinese Soft Coral Lobophytum sp.

by Zi-Yi Xia, Man-Man Sun, Yang Jin, Li-Gong Yao, Ming-Zhi Su, Lin-Fu Liang, Hong Wang and Yue-Wei Guo

Mar. Drugs 2023, 21(8), 457; https://doi.org/10.3390/md21080457 - 19 Aug 2023

Cited by 1 | Viewed by 3118

Abstract

To explore the steroidal constituents of the soft coral Lobophytum sp. at the coast of Xuwen County, Guangdong Province, China, a chemical investigation of the above-mentioned soft coral was carried out. After repeated column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC, [...] Read more.

To explore the steroidal constituents of the soft coral Lobophytum sp. at the coast of Xuwen County, Guangdong Province, China, a chemical investigation of the above-mentioned soft coral was carried out. After repeated column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC, six new steroids, namely lobosteroids A–F (1–6), along with four known compounds 7–10, were obtained. Their structures were determined by extensive spectroscopic analysis and comparison with the spectral data reported in the literature. Among them, the absolute configuration of 1 was determined by X-ray diffraction analysis using Cu Kα radiation. These steroids were characterized by either the presence of an α,β-α′,β′-unsaturated carbonyl, or an α,β-unsaturated carbonyl moiety in ring A, or the existence of a 5α,8α-epidioxy system in ring B, as well as diverse oxidation of side chains. The antibacterial bioassays showed that all isolated steroids exhibited significant inhibitory activities against the fish pathogenic bacteria Streptococcus parauberis FP KSP28, Phoyobacterium damselae FP2244, and Streptococcus parauberis SPOF3K, with IC₉₀ values ranging from 0.1 to 11.0 µM. Meanwhile, compounds 2 and 6–10 displayed potent inhibitory effects against the vancomycin-resistant Enterococcus faecium bacterium G7 with IC₉₀ values ranging from 4.4 to 18.3 µM. Therefore, ten highly oxidized steroids with strong antibacterial activities were isolated from the Chinese soft coral Lobophytum sp., which could be developed as new chemotypes of antibacterial drug leads. Full article

(This article belongs to the Section Structural Studies on Marine Natural Products)

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29 pages, 5855 KiB

Open AccessReview

Unlocking the Potential of Octocoral-Derived Secondary Metabolites against Neutrophilic Inflammatory Response

by Ngoc Bao An Nguyen, Mohamed El-Shazly, Po-Jen Chen, Bo-Rong Peng, Lo-Yun Chen, Tsong-Long Hwang and Kuei-Hung Lai

Mar. Drugs 2023, 21(8), 456; https://doi.org/10.3390/md21080456 - 18 Aug 2023

Cited by 1 | Viewed by 1636

Abstract

Inflammation is a critical defense mechanism that is utilized by the body to protect itself against pathogens and other noxious invaders. However, if the inflammatory response becomes exaggerated or uncontrollable, its original protective role is not only demolished but it also becomes detrimental [...] Read more.

Inflammation is a critical defense mechanism that is utilized by the body to protect itself against pathogens and other noxious invaders. However, if the inflammatory response becomes exaggerated or uncontrollable, its original protective role is not only demolished but it also becomes detrimental to the affected tissues or even to the entire body. Thus, regulating the inflammatory process is crucial to ensure that it is resolved promptly to prevent any subsequent damage. The role of neutrophils in inflammation has been highlighted in recent decades by a plethora of studies focusing on neutrophilic inflammatory diseases as well as the mechanisms to regulate the activity of neutrophils during the overwhelmed inflammatory process. As natural products have demonstrated promising effects in a wide range of pharmacological activities, they have been investigated for the discovery of new anti-inflammatory therapeutics to overcome the drawbacks of current synthetic agents. Octocorals have attracted scientists as a plentiful source of novel and intriguing marine scaffolds that exhibit many pharmacological activities, including anti-inflammatory effects. In this review, we aim to provide a summary of the neutrophilic anti-inflammatory properties of these marine organisms that were demonstrated in 46 studies from 1995 to the present (April 2023). We hope the present work offers a comprehensive overview of the anti-inflammatory potential of octocorals and encourages researchers to identify promising leads among numerous compounds isolated from octocorals over the past few decades to be further developed into anti-inflammatory therapeutic agents. Full article

(This article belongs to the Special Issue Marine Anti-inflammatory and Antioxidant Agents 3.0)

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21 pages, 17892 KiB

Open AccessArticle

Echinochrome Ameliorates Physiological, Immunological, and Histopathological Alterations Induced by Ovalbumin in Asthmatic Mice by Modulating the Keap1/Nrf2 Signaling Pathway

by Islam Ahmed Abdelmawgood, Noha Ahmed Mahana, Abeer Mahmoud Badr, Ayman Saber Mohamed, Abdeljalil Mohamed Al Shawoush, Tarek Atia, Amir Elhadi Abdelrazak and Hader I. Sakr

Mar. Drugs 2023, 21(8), 455; https://doi.org/10.3390/md21080455 - 18 Aug 2023

Cited by 6 | Viewed by 3160

Abstract

Asthma is a persistent inflammatory disease of the bronchi characterized by oxidative stress, airway remodeling, and inflammation. Echinochrome (Ech) is a dark-red pigment with antioxidant and anti-inflammatory activities. In this research, we aimed to investigate the effects of Ech against asthma-induced inflammation, oxidative [...] Read more.

Asthma is a persistent inflammatory disease of the bronchi characterized by oxidative stress, airway remodeling, and inflammation. Echinochrome (Ech) is a dark-red pigment with antioxidant and anti-inflammatory activities. In this research, we aimed to investigate the effects of Ech against asthma-induced inflammation, oxidative stress, and histopathological alterations in the spleen, liver, and kidney in mice. Mice were divided into four groups (n = 8 for each): control, asthmatic, and asthmatic mice treated intraperitoneally with 0.1 and 1 mg/kg of Ech. In vitro, findings confirmed the antioxidant and anti-inflammatory activities of Ech. Ech showed antiasthmatic effects by lowering the serum levels of immunoglobulin E (IgE), interleukin 4 (IL-4), and interleukin 1β (IL-1β). It attenuated oxidative stress by lowering malondialdehyde (MDA) and nitric oxide (NO) contents and increasing reduced glutathione (GSH), superoxide dismutase (SOD), glutathione-s-transferase (GST), and catalase (CAT) in the liver, spleen, and kidney. Moreover, it protected asthma-induced kidney and liver functions by increasing total protein and albumin and decreasing aspartate aminotransferase (AST), alanine aminotransferase (ALT), creatinine, urea, and uric acid levels. Additionally, it ameliorated histopathological abnormalities in the lung, liver, spleen, and kidney. Additionally, molecular docking studies were used to examine the interactions between Ech and Kelch-like ECH-associated protein 1 (Keap1). PCR and Western blot analyses confirmed the association of Ech with Keap1 and, consequently, the regulatory role of Ech in the Keap1-(nuclear factor erythroid 2-related factor 2) Nrf2 signaling pathway in the liver, spleen, and kidney. According to our findings, Ech prevented asthma and its complications in the spleen, liver, and kidney. Inhibition of inflammation and oxidative stress are two of echinochrome’s therapeutic actions in managing asthma by modulating the Keap1/Nrf2 signaling pathway. Full article

(This article belongs to the Special Issue Pharmacological Potential of Marine Natural Products)

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17 pages, 5244 KiB

Open AccessArticle

Arctic Sea Ice Microalga Chlamydomonas latifrons KNF0041: Identification and Statistical Optimization of Medium for Enhanced Biomass and Omega-3/Omega-6

by Hyunsik Chae, Sanghee Kim, Han-Gu Choi, Ji Hee Kim, Se Jong Han and Eun Jae Kim

Mar. Drugs 2023, 21(8), 454; https://doi.org/10.3390/md21080454 - 17 Aug 2023

Viewed by 1510

Abstract

Polar microorganisms produce biologically active compounds that enable them to survive in harsh environments. These compounds have potential biomedical applications. The green microalga Chlamydomonas latifrons KNF0041, isolated from Arctic sea ice, has been found to produce polyunsaturated fatty acids (PUFAs), including omega-3 and [...] Read more.

Polar microorganisms produce biologically active compounds that enable them to survive in harsh environments. These compounds have potential biomedical applications. The green microalga Chlamydomonas latifrons KNF0041, isolated from Arctic sea ice, has been found to produce polyunsaturated fatty acids (PUFAs), including omega-3 and omega-6, which have antioxidant properties. To improve the biomass production of strain KNF0041, statistical methods such as the Plackett–Burman design, Box–Behnken design, and response surface methodology (RSM) were utilized for medium optimization. The optimized medium was designed with increased potassium phosphate content and reduced acetic acid (AcOH) content. The use of the optimized medium resulted in an increase in the cell number as biomass of strain KNF0041 by 34.18% and the omega-3 and omega-6 fatty acid (FA) content by 10.04% and 58.29%, respectively, compared to that in normal TAP medium, which is known as the growth medium for Chlamydomonas culture. In this study, Chlamydomonas latifrons was discovered for the first time in the polar region and identified using morphology and molecular phylogenetic analyses, the secondary structures of the internal transcribed spacers, and optimized culture conditions. The results of this study provide an efficient method for the application of polar microalgae for the production of bioactive compounds. Full article

(This article belongs to the Special Issue Advances in Algal Biotechnology)

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10 pages, 927 KiB

Open AccessArticle

Trichoderols B-G, Six New Lipids from the Marine Algicolous Fungus Trichoderma sp. Z43

by Zhen-Zhen Shi, Xiu-Li Yin and Nai-Yun Ji

Mar. Drugs 2023, 21(8), 453; https://doi.org/10.3390/md21080453 - 17 Aug 2023

Cited by 1 | Viewed by 1439

Abstract

Six new lipids, trichoderols B-G (1–6), along with a known one, triharzianin B (7), were isolated from the culture of Trichoderma sp. Z43 obtained from the surface of the marine brown alga Dictyopteris divaricata. Their structures [...] Read more.

Six new lipids, trichoderols B-G (1–6), along with a known one, triharzianin B (7), were isolated from the culture of Trichoderma sp. Z43 obtained from the surface of the marine brown alga Dictyopteris divaricata. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1–7 were assayed for inhibiting the growth of three phytopathogenic fungi (Fusarium graminearum, Gaeumannomyces graminis, and Glomerella cingulata), four marine phytoplankton species (Amphidinium carterae, Heterocapsa circularisquama, Heterosigma akashiwo, and Prorocentrum donghaiense), and one marine zooplankton (Artemia salina). Compounds 1, 4, and 7 exhibited weak antifungal activities against three phytopathogenic fungi tested with MIC ≥ 64 μg/mL. All compounds displayed moderate antimicroalgal activity with IC₅₀ ≥ 15 μg/mL and low toxicity to the brine shrimp Artemia salina. Full article

(This article belongs to the Special Issue A Theme Issue Honoring Professor Peter Proksch's 70th Birthday: Bioactive Compounds from the Ocean)

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5 pages, 242 KiB

Open AccessEditorial

Marine Drug Discovery through Computer-Aided Approaches

by Susana P. Gaudêncio and Florbela Pereira

Mar. Drugs 2023, 21(8), 452; https://doi.org/10.3390/md21080452 - 17 Aug 2023

Cited by 1 | Viewed by 1666

Abstract

Besides the importance of our oceans as oxygen factories, food providers, shipping pathways, and tourism enablers, oceans hide an unprecedented wealth of opportunities [...] Full article

(This article belongs to the Special Issue Marine Drug Discovery through Computer-Aided Approaches)

26 pages, 2957 KiB

Open AccessReview

Marine-Derived Components: Can They Be a Potential Therapeutic Approach to Parkinson’s Disease?

by Joana Silva, Celso Alves, Francisca Soledade, Alice Martins, Susete Pinteus, Helena Gaspar, Amparo Alfonso and Rui Pedrosa

Mar. Drugs 2023, 21(8), 451; https://doi.org/10.3390/md21080451 - 16 Aug 2023

Cited by 6 | Viewed by 2589

Abstract

The increase in the life expectancy average has led to a growing elderly population, thus leading to a prevalence of neurodegenerative disorders, such as Parkinson’s disease (PD). PD is the second most common neurodegenerative disorder and is characterized by a progressive degeneration of [...] Read more.

The increase in the life expectancy average has led to a growing elderly population, thus leading to a prevalence of neurodegenerative disorders, such as Parkinson’s disease (PD). PD is the second most common neurodegenerative disorder and is characterized by a progressive degeneration of the dopaminergic neurons in the substantia nigra pars compacta (SNpc). The marine environment has proven to be a source of unique and diverse chemical structures with great therapeutic potential to be used in the treatment of several pathologies, including neurodegenerative impairments. This review is focused on compounds isolated from marine organisms with neuroprotective activities on in vitro and in vivo models based on their chemical structures, taxonomy, neuroprotective effects, and their possible mechanism of action in PD. About 60 compounds isolated from marine bacteria, fungi, mollusk, sea cucumber, seaweed, soft coral, sponge, and starfish with neuroprotective potential on PD therapy are reported. Peptides, alkaloids, quinones, terpenes, polysaccharides, polyphenols, lipids, pigments, and mycotoxins were isolated from those marine organisms. They can act in several PD hallmarks, reducing oxidative stress, preventing mitochondrial dysfunction, α-synuclein aggregation, and blocking inflammatory pathways through the inhibition translocation of NF-kB factor, reduction of human tumor necrosis factor α (TNF-α), and interleukin-6 (IL-6). This review gathers the marine natural products that have shown pharmacological activities acting on targets belonging to different intracellular signaling pathways related to PD development, which should be considered for future pre-clinical studies. Full article

(This article belongs to the Special Issue Neuroprotective Effects of Marine Natural Products 2022)

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21 pages, 2439 KiB

Open AccessArticle

Growth Behavior, Biomass Composition and Fatty Acid Methyl Esters (FAMEs) Production Potential of Chlamydomonas reinhardtii, and Chlorella vulgaris Cultures

by Itzel Y. López-Pacheco, Victoria Guadalupe Ayala-Moreno, Catherinne Arlette Mejia-Melara, José Rodríguez-Rodríguez, Sara P. Cuellar-Bermudez, Reyna Berenice González-González, Karina G. Coronado-Apodaca, Leonardo I. Farfan-Cabrera, Georgia María González-Meza, Hafiz M. N. Iqbal and Roberto Parra-Saldívar

Mar. Drugs 2023, 21(8), 450; https://doi.org/10.3390/md21080450 - 15 Aug 2023

Cited by 6 | Viewed by 2790

Abstract

The production of biomolecules by microalgae has a wide range of applications in the development of various materials and products, such as biodiesel, food supplements, and cosmetics. Microalgae biomass can be produced using waste and in a smaller space than other types of [...] Read more.

The production of biomolecules by microalgae has a wide range of applications in the development of various materials and products, such as biodiesel, food supplements, and cosmetics. Microalgae biomass can be produced using waste and in a smaller space than other types of crops (e.g., soja, corn), which shows microalgae’s great potential as a source of biomass. Among the produced biomolecules of greatest interest are carbohydrates, proteins, lipids, and fatty acids. In this study, the production of these biomolecules was determined in two strains of microalgae (Chlamydomonas reinhardtii and Chlorella vulgaris) when exposed to different concentrations of nitrogen, phosphorus, and sulfur. Results show a significant microalgal growth (3.69 g L⁻¹) and carbohydrates (163 mg g⁻¹) increase in C. reinhardtii under low nitrogen concentration. Also, higher lipids content was produced under low sulfur concentration (246 mg g⁻¹). It was observed that sulfur variation could affect in a negative way proteins production in C. reinhardtii culture. In the case of C. vulgaris, a higher biomass production was obtained in the standard culture medium (1.37 g L⁻¹), and under a low-phosphorus condition, C. vulgaris produced a higher lipids concentration (248 mg g⁻¹). It was observed that a low concentration of nitrogen had a better effect on the accumulation of fatty acid methyl esters (FAMEs) (C16-C18) in both microalgae. These results lead us to visualize the effects that the variation in macronutrients can have on the growth of microalgae and their possible utility for the production of microalgae-based subproducts. Full article

(This article belongs to the Special Issue Fatty Acids from Marine Organisms)

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13 pages, 1588 KiB

Open AccessFeature PaperEditor’s ChoiceArticle

MariClus: Your One-Stop Platform for Information on Marine Natural Products, Their Gene Clusters and Producing Organisms

by Cedric Hermans, Maarten Lieven De Mol, Marieke Mispelaere, Anne-Sofie De Rop, Jeltien Rombaut, Tesneem Nusayr, Rebecca Creamer, Sofie L. De Maeseneire, Wim K. Soetaert and Paco Hulpiau

Mar. Drugs 2023, 21(8), 449; https://doi.org/10.3390/md21080449 - 15 Aug 2023

Viewed by 3683

Abstract

Background: The marine environment hosts the vast majority of living species and marine microbes that produce natural products with great potential in providing lead compounds for drug development. With over 70% of Earth’s surface covered in water and the high interaction rate associated [...] Read more.

Background: The marine environment hosts the vast majority of living species and marine microbes that produce natural products with great potential in providing lead compounds for drug development. With over 70% of Earth’s surface covered in water and the high interaction rate associated with liquid environments, this has resulted in many marine natural product discoveries. Our improved understanding of the biosynthesis of these molecules, encoded by gene clusters, along with increased genomic information will aid us in uncovering even more novel compounds. Results: We introduce MariClus (https://www.mariclus.com), an online user-friendly platform for mining and visualizing marine gene clusters. The first version contains information on clusters and the predicted molecules for over 500 marine-related prokaryotes. The user-friendly interface allows scientists to easily search by species, cluster type or molecule and visualize the information in table format or graphical representation. Conclusions: This new online portal simplifies the exploration and comparison of gene clusters in marine species for scientists and assists in characterizing the bioactive molecules they produce. MariClus integrates data from public sources, like GenBank, MIBiG and PubChem, with genome mining results from antiSMASH. This allows users to access and analyze various aspects of marine natural product biosynthesis and diversity. Full article

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25 pages, 4624 KiB

Open AccessArticle

Proteomic and Transcriptomic Analyses to Decipher the Chitinolytic Response of Jeongeupia spp.

by Nathanael D. Arnold, Daniel Garbe and Thomas B. Brück

Mar. Drugs 2023, 21(8), 448; https://doi.org/10.3390/md21080448 - 15 Aug 2023

Cited by 2 | Viewed by 1722

Abstract

In nature, chitin, the most abundant marine biopolymer, does not accumulate due to the action of chitinolytic organisms, whose saccharification systems provide instructional blueprints for effective chitin conversion. Therefore, discovery and deconstruction of chitinolytic machineries and associated enzyme systems are essential for the [...] Read more.

In nature, chitin, the most abundant marine biopolymer, does not accumulate due to the action of chitinolytic organisms, whose saccharification systems provide instructional blueprints for effective chitin conversion. Therefore, discovery and deconstruction of chitinolytic machineries and associated enzyme systems are essential for the advancement of biotechnological chitin valorization. Through combined investigation of the chitin-induced secretome with differential proteomic and transcriptomic analyses, a holistic system biology approach has been applied to unravel the chitin response mechanisms in the Gram-negative Jeongeupia wiesaeckerbachi. Hereby, the majority of the genome-encoded chitinolytic machinery, consisting of various glycoside hydrolases and a lytic polysaccharide monooxygenase, could be detected extracellularly. Intracellular proteomics revealed a distinct translation pattern with significant upregulation of glucosamine transport, metabolism, and chemotaxis-associated proteins. While the differential transcriptomic results suggested the overall recruitment of more genes during chitin metabolism compared to that of glucose, the detected protein-mRNA correlation was low. As one of the first studies of its kind, the involvement of over 350 unique enzymes and 570 unique genes in the catabolic chitin response of a Gram-negative bacterium could be identified through a three-way systems biology approach. Based on the cumulative data, a holistic model for the chitinolytic machinery of Jeongeupia spp. is proposed. Full article

(This article belongs to the Special Issue Collagen and Chitin from Marine Resources and Their Interdisciplinary Applications)

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15 pages, 4393 KiB

Open AccessArticle

Anti-Atopic Dermatitis Activity of Epi-Oxyzoanthamine Isolated from Zoanthid

by Chieh-Chen Huang, Yuan-Hsin Lo, Yu-Jou Hsu, Yuan-Bin Cheng, Chia-Chi Kung, Cher-Wei Liang, Der-Chen Chang, Kang-Ling Wang and Chi-Feng Hung

Mar. Drugs 2023, 21(8), 447; https://doi.org/10.3390/md21080447 - 12 Aug 2023

Cited by 2 | Viewed by 2292

Abstract

Atopic dermatitis (AD, eczema) is a condition that causes dry, itchy, and inflamed skin and occurs most frequently in children but also affects adults. However, common clinical treatments provide limited relief and have some side effects. Therefore, there is a need to develop [...] Read more.

Atopic dermatitis (AD, eczema) is a condition that causes dry, itchy, and inflamed skin and occurs most frequently in children but also affects adults. However, common clinical treatments provide limited relief and have some side effects. Therefore, there is a need to develop new effective therapies to treat AD. Epi-oxyzoanthamine is a small molecule alkaloid isolated from Formosan zoanthid. Relevant studies have shown that zoanthamine alkaloids have many pharmacological and biological activities, including anti-lymphangiogenic functions. However, there are no studies on the use of epi-oxyzoanthamine on the skin. In this paper, epi-oxyzoanthamine has been shown to have potential in the treatment of atopic dermatitis. Through in vitro studies, it was found that epi-oxyzoanthamine inhibited the expression of cytokines in TNF-α/IFN-γ-stimulated human keratinocyte (HaCaT) cells, and it reduced the phosphorylation of MAPK and the NF-κB signaling pathway. Atopic dermatitis-like skin inflammation was induced in a mouse model using 2,4-dinitrochlorobenzene (DNCB) in vivo. The results showed that epi-oxyzoanthamine significantly decreased skin barrier damage, scratching responses, and epidermal hyperplasia induced by DNCB. It significantly reduced transepidermal water loss (TEWL), erythema, ear thickness, and spleen weight, while also increasing surface skin hydration. These results indicate that epi-oxyzoanthamine from zoanthid has good potential as an alternative medicine for treating atopic dermatitis or other skin-related inflammatory diseases. Full article

(This article belongs to the Special Issue Pharmacological Potential of Marine Natural Products)

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13 pages, 2768 KiB

Open AccessArticle

Petrosamine Revisited. Experimental and Computational Investigation of Solvatochromism, Tautomerism and Free Energy Landscapes of a Pyridoacridinium Quaternary Salt

by Christopher J. Gartshore, Xiao Wang, Yongxuan Su and Tadeusz F. Molinski

Mar. Drugs 2023, 21(8), 446; https://doi.org/10.3390/md21080446 - 11 Aug 2023

Cited by 1 | Viewed by 1468

Abstract

Petrosamine (1)—a colored pyridoacridine alkaloid from the Belizean sponge, Petrosia sp., that is also a potent inhibitor of acetylcholine esterase (AChE)—was investigated by spectroscopic and computational methods. Analysis of the petrosamine-free energy landscapes, pK_a and tautomerism, revealed an accurate [...] Read more.

Petrosamine (1)—a colored pyridoacridine alkaloid from the Belizean sponge, Petrosia sp., that is also a potent inhibitor of acetylcholine esterase (AChE)—was investigated by spectroscopic and computational methods. Analysis of the petrosamine-free energy landscapes, pK_a and tautomerism, revealed an accurate electronic depiction of the molecular structure of 1 as the di-keto form, with a net charge of q = +1, rather than a dication (q = +2) under ambient conditions of isolation-purification. The pronounced solvatochromism (UV-vis) reported for 1, and related analogs were investigated in detail and is best explained by charge delocalization and stabilization of the ground state (HOMO) of 1 rather than an equilibrium of competing tautomers. Refinement of the molecular structure 1 by QM methods complements published computational docking studies to define the contact points in the enzyme active site that may improve the design of new AChE inhibitors based on the pyridoacridine alkaloid molecular skeleton. Full article

(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)

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23 pages, 1221 KiB

Open AccessReview

Overview and Challenges of Large-Scale Cultivation of Photosynthetic Microalgae and Cyanobacteria

by Lucie Novoveská, Søren Laurentius Nielsen, Orhan Tufan Eroldoğan, Berat Zeki Haznedaroglu, Baruch Rinkevich, Stefano Fazi, Johan Robbens, Marlen Vasquez and Hjörleifur Einarsson

Mar. Drugs 2023, 21(8), 445; https://doi.org/10.3390/md21080445 - 10 Aug 2023

Cited by 41 | Viewed by 8431

Abstract

Microalgae and cyanobacteria are diverse groups of organisms with great potential to benefit societies across the world. These organisms are currently used in food, feed, pharmaceutical and cosmetic industries. In addition, a variety of novel compounds are being isolated. Commercial production of photosynthetic [...] Read more.

Microalgae and cyanobacteria are diverse groups of organisms with great potential to benefit societies across the world. These organisms are currently used in food, feed, pharmaceutical and cosmetic industries. In addition, a variety of novel compounds are being isolated. Commercial production of photosynthetic microalgae and cyanobacteria requires cultivation on a large scale with high throughput. However, scaling up production from lab-based systems to large-scale systems is a complex and potentially costly endeavor. In this review, we summarise all aspects of large-scale cultivation, including aims of cultivation, species selection, types of cultivation (ponds, photobioreactors, and biofilms), water and nutrient sources, temperature, light and mixing, monitoring, contamination, harvesting strategies, and potential environmental risks. Importantly, we also present practical recommendations and discuss challenges of profitable large-scale systems associated with economical design, effective operation and maintenance, automation, and shortage of experienced phycologists. Full article

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22 pages, 5235 KiB

Open AccessArticle

Bioactivity Screening and Genomic Analysis Reveals Deep-Sea Fish Microbiome Isolates as Sources of Novel Antimicrobials

by Shona Uniacke-Lowe, Fergus W. J. Collins, Colin Hill and R. Paul Ross

Mar. Drugs 2023, 21(8), 444; https://doi.org/10.3390/md21080444 - 7 Aug 2023

Cited by 8 | Viewed by 2494

Abstract

With the increase in antimicrobial resistance and the subsequent demand for novel therapeutics, the deep-sea fish microbiome can be a relatively untapped source of antimicrobials, including bacteriocins. Previously, bacterial isolates were recovered from the gut of deep-sea fish sampled from the Atlantic Ocean.In [...] Read more.

With the increase in antimicrobial resistance and the subsequent demand for novel therapeutics, the deep-sea fish microbiome can be a relatively untapped source of antimicrobials, including bacteriocins. Previously, bacterial isolates were recovered from the gut of deep-sea fish sampled from the Atlantic Ocean.In this study, we used in vitro methods to screen a subset of these isolates for antimicrobial activity, and subsequently mined genomic DNA from isolates of interest for bacteriocin and other antimicrobial metabolite genes. We observed antimicrobial activity against foodborne pathogens, including Staphylococcus aureus, Listeria monocytogenes, Enterococcus faecalis and Micrococcus luteus. In total, 147 candidate biosynthetic gene clusters were identified in the genomic sequences, including 35 bacteriocin/RiPP-like clusters. Other bioactive metabolite genes detected included non-ribosomal peptide synthases (NRPS), polyketide synthases (PKS; Types 1 and 3), beta-lactones and terpenes. Moreover, four unique bacteriocin gene clusters were annotated and shown to encode novel peptides: a class IIc bacteriocin, two class IId bacteriocins and a class I lanthipeptide (LanM subgroup). Our dual in vitro and in silico approach allowed for a more comprehensive understanding of the bacteriocinogenic potential of these deep-sea isolates and an insight into the antimicrobial molecules that they may produce. Full article

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21 pages, 3770 KiB

Open AccessArticle

New Phocoenamicin and Maklamicin Analogues from Cultures of Three Marine-Derived Micromonospora Strains

by Maria Kokkini, Daniel Oves-Costales, Pilar Sánchez, Ángeles Melguizo, Thomas A. Mackenzie, Mercedes Pérez-Bonilla, Jesús Martín, Arianna Giusti, Peter de Witte, Francisca Vicente, Olga Genilloud and Fernando Reyes

Mar. Drugs 2023, 21(8), 443; https://doi.org/10.3390/md21080443 - 7 Aug 2023

Cited by 1 | Viewed by 1860

Abstract

Antimicrobial resistance can be considered a hidden global pandemic and research must be reinforced for the discovery of new antibiotics. The spirotetronate class of polyketides, with more than 100 bioactive compounds described to date, has recently grown with the discovery of phocoenamicins, compounds [...] Read more.

Antimicrobial resistance can be considered a hidden global pandemic and research must be reinforced for the discovery of new antibiotics. The spirotetronate class of polyketides, with more than 100 bioactive compounds described to date, has recently grown with the discovery of phocoenamicins, compounds displaying different antibiotic activities. Three marine Micromonospora strains (CA-214671, CA-214658 and CA-218877), identified as phocoenamicins producers, were chosen to scale up their production and LC/HRMS analyses proved that EtOAc extracts from their culture broths produce several structurally related compounds not disclosed before. Herein, we report the production, isolation and structural elucidation of two new phocoenamicins, phocoenamicins D and E (1–2), along with the known phocoenamicin, phocoenamicins B and C (3–5), as well as maklamicin (7) and maklamicin B (6), the latter being reported for the first time as a natural product. All the isolated compounds were tested against various human pathogens and revealed diverse strong to negligible activity against methicillin-resistant Staphylococcus aureus, Mycobacterium tuberculosis H37Ra, Enterococcus faecium and Enterococcus faecalis. Their cell viability was also evaluated against the human liver adenocarcinoma cell line (Hep G2), demonstrating weak or no cytotoxicity. Lastly, the safety of the major compounds obtained, phocoenamicin (3), phocoenamicin B (4) and maklamicin (7), was tested against zebrafish eleuthero embryos and all of them displayed no toxicity up to a concentration of 25 μM. Full article

(This article belongs to the Section Marine Pharmacology)

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10 pages, 1389 KiB

Open AccessArticle

New Sorbicillinoids from the Mangrove Endophytic Fungus Trichoderma reesei SCNU-F0042

by Jialin Li, Tao Chen, Jianchen Yu, Hao Jia, Chen Chen and Yuhua Long

Mar. Drugs 2023, 21(8), 442; https://doi.org/10.3390/md21080442 - 5 Aug 2023

Cited by 3 | Viewed by 1862

Abstract

Three new dimeric sorbicillinoids (1–3) and one new 3,4,6-trisubstituted α-pyrone (5), along with seven analogues (4 and 6–11), were isolated from the mangrove endophytic fungus Trichoderma reesei SCNU-F0042 under the guidance of molecular [...] Read more.

Three new dimeric sorbicillinoids (1–3) and one new 3,4,6-trisubstituted α-pyrone (5), along with seven analogues (4 and 6–11), were isolated from the mangrove endophytic fungus Trichoderma reesei SCNU-F0042 under the guidance of molecular networking approach. Their chemical structures were established by 1D and 2D NMR HR-ESI-MS and ECD analysis. In a bioassay, compound 2 exhibited moderate SARS-CoV-2 inhibitory activity with an EC₅₀ value of 29.0 μM. Full article

(This article belongs to the Special Issue Pharmacological Potential of Marine Natural Products)

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53 pages, 4206 KiB

Open AccessReview

Secondary Metabolites, Biological Activities, and Industrial and Biotechnological Importance of Aspergillus sydowii

by Sabrin R. M. Ibrahim, Shaimaa G. A. Mohamed, Baiaan H. Alsaadi, Maryam M. Althubyani, Zainab I. Awari, Hazem G. A. Hussein, Abrar A. Aljohani, Jumanah Faisal Albasri, Salha Atiah Faraj and Gamal A. Mohamed

Mar. Drugs 2023, 21(8), 441; https://doi.org/10.3390/md21080441 - 5 Aug 2023

Cited by 12 | Viewed by 2919

Abstract

Marine-derived fungi are renowned as a source of astonishingly significant and synthetically appealing metabolites that are proven as new lead chemicals for chemical, pharmaceutical, and agricultural fields. Aspergillus sydowii is a saprotrophic, ubiquitous, and halophilic fungus that is commonly found in different marine [...] Read more.

Marine-derived fungi are renowned as a source of astonishingly significant and synthetically appealing metabolites that are proven as new lead chemicals for chemical, pharmaceutical, and agricultural fields. Aspergillus sydowii is a saprotrophic, ubiquitous, and halophilic fungus that is commonly found in different marine ecosystems. This fungus can cause aspergillosis in sea fan corals leading to sea fan mortality with subsequent changes in coral community structure. Interestingly, A. sydowi is a prolific source of distinct and structurally varied metabolites such as alkaloids, xanthones, terpenes, anthraquinones, sterols, diphenyl ethers, pyrones, cyclopentenones, and polyketides with a range of bioactivities. A. sydowii has capacity to produce various enzymes with marked industrial and biotechnological potential, including α-amylases, lipases, xylanases, cellulases, keratinases, and tannases. Also, this fungus has the capacity for bioremediation as well as the biocatalysis of various chemical reactions. The current work aimed at focusing on the bright side of this fungus. In this review, published studies on isolated metabolites from A. sydowii, including their structures, biological functions, and biosynthesis, as well as the biotechnological and industrial significance of this fungus, were highlighted. More than 245 compounds were described in the current review with 134 references published within the period from 1975 to June 2023. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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27 pages, 5998 KiB

Open AccessReview

Microalgae: A Promising Source of Bioactive Phycobiliproteins

by Latifa Tounsi, Hajer Ben Hlima, Faiez Hentati, Ons Hentati, Hana Derbel, Philippe Michaud and Slim Abdelkafi

Mar. Drugs 2023, 21(8), 440; https://doi.org/10.3390/md21080440 - 4 Aug 2023

Cited by 19 | Viewed by 3298

Abstract

Phycobiliproteins are photosynthetic light-harvesting pigments isolated from microalgae with fluorescent, colorimetric and biological properties, making them a potential commodity in the pharmaceutical, cosmetic and food industries. Hence, improving their metabolic yield is of great interest. In this regard, the present review aimed, first, [...] Read more.

Phycobiliproteins are photosynthetic light-harvesting pigments isolated from microalgae with fluorescent, colorimetric and biological properties, making them a potential commodity in the pharmaceutical, cosmetic and food industries. Hence, improving their metabolic yield is of great interest. In this regard, the present review aimed, first, to provide a detailed and thorough overview of the optimization of culture media elements, as well as various physical parameters, to improve the large-scale manufacturing of such bioactive molecules. The second section of the review offers systematic, deep and detailed data about the current main features of phycobiliproteins. In the ultimate section, the health and nutritional claims related to these bioactive pigments, explaining their noticeable potential for biotechnological uses in various fields, are examined. Full article

(This article belongs to the Special Issue Functional Foods from Marine Microalgae)

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34 pages, 3975 KiB

Open AccessReview

Review of Marine Cyanobacteria and the Aspects Related to Their Roles: Chemical, Biological Properties, Nitrogen Fixation and Climate Change

by Hesham R. El-Seedi, Mohamed F. El-Mallah, Nermeen Yosri, Muaaz Alajlani, Chao Zhao, Muhammad A. Mehmood, Ming Du, Hammad Ullah, Maria Daglia, Zhiming Guo, Shaden A. M. Khalifa and Qiyang Shou

Mar. Drugs 2023, 21(8), 439; https://doi.org/10.3390/md21080439 - 3 Aug 2023

Cited by 6 | Viewed by 5617

Abstract

Marine cyanobacteria are an ancient group of photosynthetic microbes dating back to 3.5 million years ago. They are prolific producers of bioactive secondary metabolites. Over millions of years, natural selection has optimized their metabolites to possess activities impacting various biological targets. This paper [...] Read more.

Marine cyanobacteria are an ancient group of photosynthetic microbes dating back to 3.5 million years ago. They are prolific producers of bioactive secondary metabolites. Over millions of years, natural selection has optimized their metabolites to possess activities impacting various biological targets. This paper discusses the historical and existential records of cyanobacteria, and their role in understanding the evolution of marine cyanobacteria through the ages. Recent advancements have focused on isolating and screening bioactive compounds and their respective medicinal properties, and we also discuss chemical property space and clinical trials, where compounds with potential pharmacological effects, such as cytotoxicity, anticancer, and antiparasitic properties, are highlighted. The data have shown that about 43% of the compounds investigated have cytotoxic effects, and around 8% have anti-trypanosome activity. We discussed the role of different marine cyanobacteria groups in fixing nitrogen percentages on Earth and their outcomes in fish productivity by entering food webs and enhancing productivity in different agricultural and ecological fields. The role of marine cyanobacteria in the carbon cycle and their outcomes in improving the efficiency of photosynthetic CO₂ fixation in the chloroplasts of crop plants, thus enhancing the crop plant’s yield, was highlighted. Ultimately, climate changes have a significant impact on marine cyanobacteria where the temperature rises, and CO₂ improves the cyanobacterial nitrogen fixation. Full article

(This article belongs to the Special Issue Bioactive Product from Marine Cyanobacteria)

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18 pages, 7007 KiB

Open AccessFeature PaperArticle

Drug Delivery through Epidermal Tissue Cells by Functionalized Biosilica from Diatom Microalgae

by Danilo Vona, Annarita Flemma, Francesca Piccapane, Pietro Cotugno, Stefania Roberta Cicco, Vincenza Armenise, Cesar Vicente-Garcia, Maria Michela Giangregorio, Giuseppe Procino and Roberta Ragni

Mar. Drugs 2023, 21(8), 438; https://doi.org/10.3390/md21080438 - 3 Aug 2023

Cited by 7 | Viewed by 2573

Abstract

Diatom microalgae are a natural source of fossil biosilica shells, namely the diatomaceous earth (DE), abundantly available at low cost. High surface area, mesoporosity and biocompatibility, as well as the availability of a variety of approaches for surface chemical modification, make DE highly [...] Read more.

Diatom microalgae are a natural source of fossil biosilica shells, namely the diatomaceous earth (DE), abundantly available at low cost. High surface area, mesoporosity and biocompatibility, as well as the availability of a variety of approaches for surface chemical modification, make DE highly profitable as a nanostructured material for drug delivery applications. Despite this, the studies reported so far in the literature are generally limited to the development of biohybrid systems for drug delivery by oral or parenteral administration. Here we demonstrate the suitability of diatomaceous earth properly functionalized on the surface with n-octyl chains as an efficient system for local drug delivery to skin tissues. Naproxen was selected as a non-steroidal anti-inflammatory model drug for experiments performed both in vitro by immersion of the drug-loaded DE in an artificial sweat solution and, for the first time, by trans-epidermal drug permeation through a 3D-organotypic tissue that better mimics the in vivo permeation mechanism of drugs in human skin tissues. Octyl chains were demonstrated to both favour the DE adhesion onto porcine skin tissues and to control the gradual release and the trans-epidermal permeation of Naproxen within 24 h of the beginning of experiments. The evidence of the viability of human epithelial cells after permeation of the drug released from diatomaceous earth, also confirmed the biocompatibility with human skin of both Naproxen and mesoporous biosilica from diatom microalgae, disclosing promising applications of these drug-delivery systems for therapies of skin diseases. Full article

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18 pages, 7511 KiB

Open AccessArticle

Surf Redfish-Based ZnO-NPs and Their Biological Activity with Reference to Their Non-Target Toxicity

by Ahmed I. Hasaballah, Hussein A. El-Naggar, Ibrahim E. Abd-El Rahman, Fatimah Al-Otibi, Reham M. Alahmadi, Othman F. Abdelzaher, Mohamed H. Kalaba, Basma H. Amin, Mohamed M. Mabrouk, Ahmed G. A. Gewida, Marwa F. Abd El-Kader and Mostafa A. Elbahnasawy

Mar. Drugs 2023, 21(8), 437; https://doi.org/10.3390/md21080437 - 2 Aug 2023

Cited by 3 | Viewed by 1761

Abstract

The marine environment is a rich source of bioactive compounds. Therefore, the sea cucumber was isolated from the Red Sea at the Al-Ain Al-Sokhna coast and it was identified as surf redfish (Actinopyga mauritiana). The aqueous extract of the surf redfish [...] Read more.

The marine environment is a rich source of bioactive compounds. Therefore, the sea cucumber was isolated from the Red Sea at the Al-Ain Al-Sokhna coast and it was identified as surf redfish (Actinopyga mauritiana). The aqueous extract of the surf redfish was utilized as an ecofriendly, novel and sustainable approach to fabricate zinc oxide nanoparticles (ZnO-NPs). The biosynthesized ZnO-NPs were physico-chemically characterized and evaluated for their possible antibacterial and insecticidal activities. Additionally, their safety in the non-target organism model (Nile tilapia fish) was also investigated. ZnO-NPs were spherical with an average size of 24.69 ± 11.61 nm and had a peak at 350 nm as shown by TEM and UV-Vis, respectively. XRD analysis indicated a crystalline phase of ZnO-NPs with an average size of 21.7 nm. The FTIR pattern showed biological residues from the surf redfish extract, highlighting their potential role in the biosynthesis process. DLS indicated a negative zeta potential (−19.2 mV) of the ZnO-NPs which is a good preliminary indicator for their stability. ZnO-NPs showed larvicidal activity against mosquito Culex pipiens (LC₅₀ = 15.412 ppm and LC₉₀ = 52.745 ppm) and a potent adulticidal effect to the housefly Musca domestica (LD₅₀ = 21.132 ppm and LD₉₀ = 84.930 ppm). Tested concentrations of ZnO-NPs showed strong activity against the 3rd larval instar. Topical assays revealed dose-dependent adulticidal activity against M. domestica after 24 h of treatment with ZnO-NPs. ZnO-NPs presented a wide antibacterial activity against two fish-pathogen bacteria, Pseudomonas aeruginosa and Aeromonas hydrophila. Histopathological and hematological investigations of the non-target organism, Nile tilapia fish exposed to 75–600 ppm ZnO-NPs provide dose-dependent impacts. Overall, data highlighted the potential applications of surf redfish-mediated ZnO-NPs as an effective and safe way to control mosquitoes, houseflies and fish pathogenic bacteria. Full article

(This article belongs to the Special Issue Perspectives for the Development of New Multitarget Marine Drugs)

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22 pages, 17883 KiB

Open AccessArticle

From Threat to Opportunity: Harnessing the Invasive Carpobrotus edulis (L.) N.E.Br for Nutritional and Phytotherapeutic Valorization Amid Seasonal and Spatial Variability

by Catarina Guerreiro Pereira, Nuno R. Neng and Luísa Custódio

Mar. Drugs 2023, 21(8), 436; https://doi.org/10.3390/md21080436 - 1 Aug 2023

Cited by 4 | Viewed by 1544

Abstract

Carpobrotus edulis (L.) N.E.Br. (Hottentot-fig) is a problematic invasive species found in coastal areas worldwide. Mechanical removal is a common control method, leaving the removed biomass available as a possible source of natural phytochemicals with prospective commercial applications. While the Hottentot-fig’s vegetative organs [...] Read more.

Carpobrotus edulis (L.) N.E.Br. (Hottentot-fig) is a problematic invasive species found in coastal areas worldwide. Mechanical removal is a common control method, leaving the removed biomass available as a possible source of natural phytochemicals with prospective commercial applications. While the Hottentot-fig’s vegetative organs have been studied previously, this work establishes for the first time a seasonal and spatial comparative analysis of its nutritional, chemical, and bioactivity profiles (in three locations over four seasons). Proximate and mineral contents were assessed, along with its phenolic composition and in vitro antioxidant and anti-inflammatory properties. Hottentot-fig’s biomass offered a good supply of nutrients, mainly carbohydrates, proteins, and minerals, with a tendency for higher concentrations of the most relevant minerals and proteins in autumn and winter, and in plants from sites A (Ria de Alvor lagoon) and B (Ancão beach). The extracts were rich in polyphenolics, with higher levels in spring and summer, especially for luteolin-7-O-glucoside and salicylic and coumaric acids. The extracts were also effective antioxidants, with stronger radical scavenging activities in spring and summer, along with anti-inflammatory properties. Our results suggest that the usually discarded plant material of this invasive halophyte could be valuable as a source of natural products with potential biotechnological applications in the food and nutraceutical industries. Full article

(This article belongs to the Section Marine Chemoecology for Drug Discovery)

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23 pages, 3670 KiB

Open AccessArticle

Five Years Monitoring the Emergence of Unregulated Toxins in Shellfish in France (EMERGTOX 2018–2022)

by Zouher Amzil, Amélie Derrien, Aouregan Terre Terrillon, Véronique Savar, Thomas Bertin, Marion Peyrat, Audrey Duval, Korian Lhaute, Nathalie Arnich, Vincent Hort and Marina Nicolas

Mar. Drugs 2023, 21(8), 435; https://doi.org/10.3390/md21080435 - 31 Jul 2023

Cited by 11 | Viewed by 2376

Abstract

Shellfish accumulate microalgal toxins, which can make them unsafe for human consumption. In France, in accordance with EU regulations, three groups of marine toxins are currently under official monitoring: lipophilic toxins, saxitoxins, and domoic acid. Other unregulated toxin groups are also present in [...] Read more.

Shellfish accumulate microalgal toxins, which can make them unsafe for human consumption. In France, in accordance with EU regulations, three groups of marine toxins are currently under official monitoring: lipophilic toxins, saxitoxins, and domoic acid. Other unregulated toxin groups are also present in European shellfish, including emerging lipophilic and hydrophilic marine toxins (e.g., pinnatoxins, brevetoxins) and the neurotoxin β-N-methylamino-L-alanine (BMAA). To acquire data on emerging toxins in France, the monitoring program EMERGTOX was set up along the French coasts in 2018. Three new broad-spectrum LC-MS/MS methods were developed to quantify regulated and unregulated lipophilic and hydrophilic toxins and the BMAA group in shellfish (bivalve mollusks and gastropods). A single-laboratory validation of each of these methods was performed. Additionally, these specific, reliable, and sensitive operating procedures allowed the detection of groups of EU unregulated toxins in shellfish samples from French coasts: spirolides (SPX-13-DesMeC, SPX-DesMeD), pinnatoxins (PnTX-G, PnTX-A), gymnodimines (GYM-A), brevetoxins (BTX-2, BTX-3), microcystins (dmMC-RR, MC-RR), anatoxin, cylindrospermopsin and BMAA/DAB. Here, we present essentially the results of the unregulated toxins obtained from the French EMERGTOX monitoring plan during the past five years (2018–2022). Based on our findings, we outline future needs for monitoring to protect consumers from emerging unregulated toxins. Full article

(This article belongs to the Special Issue Emerging Toxins Accumulation in Shellfish)

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13 pages, 3601 KiB

Open AccessArticle

Anti-Protozoan Activities of Polar Fish-Derived Polyalanine Synthetic Peptides

by Ellynes Amancio Correia Nunes, Maria Cláudia da Silva, Marlon Henrique Cardoso, Sergio Leandro Espíndola Preza, Lucas Silva de Oliveira, Breno Emanuel Farias Frihling, Sébastien Olivier Charneau, Philippe Grellier, Octávio Luiz Franco and Ludovico Migliolo

Mar. Drugs 2023, 21(8), 434; https://doi.org/10.3390/md21080434 - 31 Jul 2023

Cited by 1 | Viewed by 1688

Abstract

Chagas disease, sleeping sickness and malaria are infectious diseases caused by protozoan parasites that kill millions of people worldwide. Here, we performed in vitro assays of Pa-MAP, Pa-MAP1.9, and Pa-MAP2 synthetic polyalanine peptides derived from the polar fish Pleuronectes americanus toward [...] Read more.

Chagas disease, sleeping sickness and malaria are infectious diseases caused by protozoan parasites that kill millions of people worldwide. Here, we performed in vitro assays of Pa-MAP, Pa-MAP1.9, and Pa-MAP2 synthetic polyalanine peptides derived from the polar fish Pleuronectes americanus toward Trypanosoma cruzi, T. brucei gambiense and Plasmodium falciparum activities. We demonstrated that the peptides Pa-MAP1.9 and Pa-MAP2 were effective to inhibit T. brucei growth. In addition, structural analyses using molecular dynamics (MD) studies showed that Pa-MAP2 penetrates deeper into the membrane and interacts more with phospholipids than Pa-MAP1.9, corroborating the previous in vitro results showing that Pa-MAP1.9 acts within the cell, while Pa-MAP2 acts via membrane lysis. In conclusion, polyalanine Pa-MAP1.9 and Pa-MAP2 presented activity against bloodstream forms of T. b. gambiense, thus encouraging further studies on the application of these peptides as a treatment for sleeping sickness. Full article

(This article belongs to the Special Issue Marine Drugs Research in Brazil)

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12 pages, 2073 KiB

Open AccessArticle

Astaxanthin: A Marine Drug That Ameliorates Cerebrovascular-Damage-Associated Alzheimer’s Disease in a Zebrafish Model via the Inhibition of Matrix Metalloprotease-13

by Nallupillai Paramakrishnan, Khian Giap Lim, Yamunna Paramaswaran, Nemat Ali, Mohammad Waseem, Gamal A. Shazly, Yousef A. Bin Jardan and Arunachalam Muthuraman

Mar. Drugs 2023, 21(8), 433; https://doi.org/10.3390/md21080433 - 31 Jul 2023

Cited by 3 | Viewed by 2402

Abstract

Alzheimer’s disease (AD) is a major type of dementia disorder. Common cognitive changes occur as a result of cerebrovascular damage (CVD) via the disruption of matrix metalloproteinase-13 (MMP-13). In diabetic cases, the progress of vascular dementia is faster and the AD rate is [...] Read more.

Alzheimer’s disease (AD) is a major type of dementia disorder. Common cognitive changes occur as a result of cerebrovascular damage (CVD) via the disruption of matrix metalloproteinase-13 (MMP-13). In diabetic cases, the progress of vascular dementia is faster and the AD rate is higher. Patients with type 2 diabetes are known to have a higher risk of the factor for AD progression. Hence, this study is designed to investigate the role of astaxanthin (AST) in CVD-associated AD in zebrafish via the inhibition of MMP-13 activity. CVD was developed through the intraperitoneal and intracerebral injection of streptozotocin (STZ). The AST (10 and 20 mg/L), donepezil (1 mg/L), and MMP-13 inhibitor (i.e., CL-82198; 10 μM) were exposed for 21 consecutive days in CVD animals. The cognitive changes in zebrafish were evaluated through light and dark chamber tests, a color recognition test, and a T-maze test. The biomarkers of AD pathology were assessed via the estimation of the cerebral extravasation of Evans blue, tissue nitrite, amyloid beta-peptide aggregation, MMP-13 activity, and acetylcholinesterase activity. The results revealed that exposure to AST leads to ameliorative behavioral and biochemical changes. Hence, AST can be used for the management of AD due to its multi-targeted actions, including MMP-13 inhibition. Full article

(This article belongs to the Special Issue Marine Compounds as Anti-Alzheimer's Agent)

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22 pages, 22977 KiB

Open AccessArticle

Evaluation of Toxicity Equivalency Factors of Tetrodotoxin Analogues with a Neuro-2a Cell-Based Assay and Application to Puffer Fish from Greece

by Mounira Alkassar, Andres Sanchez-Henao, Jaume Reverté, Lourdes Barreiro, Maria Rambla-Alegre, Sandra Leonardo, Manolis Mandalakis, Panagiota Peristeraki, Jorge Diogène and Mònica Campàs

Mar. Drugs 2023, 21(8), 432; https://doi.org/10.3390/md21080432 - 29 Jul 2023

Cited by 10 | Viewed by 2778

Abstract

Tetrodotoxin (TTX) is a potent marine neurotoxin involved in poisoning cases, especially through the consumption of puffer fish. Knowledge of the toxicity equivalency factors (TEFs) of TTX analogues is crucial in monitoring programs to estimate the toxicity of samples analyzed with instrumental analysis [...] Read more.

Tetrodotoxin (TTX) is a potent marine neurotoxin involved in poisoning cases, especially through the consumption of puffer fish. Knowledge of the toxicity equivalency factors (TEFs) of TTX analogues is crucial in monitoring programs to estimate the toxicity of samples analyzed with instrumental analysis methods. In this work, TTX analogues were isolated from the liver of a Lagocephalus sceleratus individual caught on South Crete coasts. A cell-based assay (CBA) for TTXs was optimized and applied to the establishment of the TEFs of 5,11-dideoxyTTX, 11-norTTX-6(S)-ol, 11-deoxyTTX and 5,6,11-trideoxyTTX. Results showed that all TTX analogues were less toxic than the parent TTX, their TEFs being in the range of 0.75–0.011. Then, different tissues of three Lagocephalus sceleratus individuals were analyzed with CBA and liquid chromatography-tandem mass spectrometry (LC-MS/MS). The obtained TEFs were applied to the TTX analogues’ concentrations obtained by LC-MS/MS analysis, providing an indication of the overall toxicity of the sample. Information about the TEFs of TTX analogues is valuable for food safety control, allowing the estimation of the risk of fish products to consumers. Full article

(This article belongs to the Section Marine Toxins)

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23 pages, 6282 KiB

Open AccessArticle

Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus

by Olesya I. Zhuravleva, Ekaterina A. Chingizova, Galina K. Oleinikova, Sofya S. Starnovskaya, Alexandr S. Antonov, Natalia N. Kirichuk, Alexander S. Menshov, Roman S. Popov, Natalya Yu. Kim, Dmitrii V. Berdyshev, Artur R. Chingizov, Alexandra S. Kuzmich, Irina V. Guzhova, Anton N. Yurchenko and Ekaterina A. Yurchenko

Mar. Drugs 2023, 21(8), 431; https://doi.org/10.3390/md21080431 - 29 Jul 2023

Cited by 5 | Viewed by 1904

Abstract

New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated [...] Read more.

New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds 1–4 and 6–13 showed a significant antimicrobial effects against Staphylococcus aureus growth, and acruciquinone A (1), dendryol B (4), coniothyrinone B (7), and ω-hydroxypachybasin (9) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding 4, inhibited urease activity. We studied the effects of anthraquinones 1, 4, 7, and 9 and coniothyrinone D (6) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with S. aureus. Anthraquinones significantly reduce the negative impact of S. aureus on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (1) revealed the most pronounced effect. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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20 pages, 4452 KiB

Open AccessArticle

Enhanced In Vitro Anti-Photoaging Effect of Degraded Seaweed Polysaccharides by UV/H₂O₂ Treatment

by Wanzi Yao, Jiayu Yong, Bingxue Lv, Siyu Guo, Lijun You, Peter Chi-Keung Cheung and Viktoryia I. Kulikouskaya

Mar. Drugs 2023, 21(8), 430; https://doi.org/10.3390/md21080430 - 29 Jul 2023

Cited by 8 | Viewed by 2044

Abstract

The high molecular weight and poor solubility of seaweed polysaccharides have limited their function and application. In this study, ultraviolet/hydrogen peroxide (UV/H₂O₂) treatment was used to prepare low-molecular-weight seaweed polysaccharides from Sargassum fusiforme. The effects of UV/H₂ [...] Read more.

The high molecular weight and poor solubility of seaweed polysaccharides have limited their function and application. In this study, ultraviolet/hydrogen peroxide (UV/H₂O₂) treatment was used to prepare low-molecular-weight seaweed polysaccharides from Sargassum fusiforme. The effects of UV/H₂O₂ treatment on the physicochemical properties and anti-photoaging activity of S. fusiforme polysaccharides were studied. UV/H₂O₂ treatment effectively degraded polysaccharides from S. fusiforme (DSFPs), reducing their molecular weight from 271 kDa to 26 kDa after 2 h treatment. The treatment did not affect the functional groups in DSFPs but changed their molar percentage of monosaccharide composition and morphology. The effects of the treatment on the anti-photoaging function of S. fusiforme polysaccharides were investigated using human epidermal HaCaT cells in vitro. DFSPs significantly improved the cell viability and hydroxyproline secretion of UVB-irradiated HaCaT cells. In particular, DSFP-45 obtained from UV/H₂O₂ treatment for 45 min showed the best anti-photoaging effect. Moreover, DSFP-45 significantly increased the content and expression of collagen I and decreased those of pro-inflammatory cytokines, including interleukin-1β, interleukin-6, and tumor necrosis factor-α. Thus, UV/H₂O₂ treatment could effectively improve the anti-photoaging activity of S. fusiforme polysaccharides. These results provide some insights for developing novel and efficient anti-photoaging drugs or functional foods from seaweed polysaccharides. Full article

(This article belongs to the Section Structural Studies on Marine Natural Products)

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20 pages, 2551 KiB

Open AccessArticle

Exploration of Vulcanodinium rugosum Toxins and their Metabolism Products in Mussels from the Ingril Lagoon Hotspot in France

by Vincent Hort, Isabel Bastardo-Fernández and Marina Nicolas

Mar. Drugs 2023, 21(8), 429; https://doi.org/10.3390/md21080429 - 29 Jul 2023

Cited by 2 | Viewed by 3176

Abstract

Over the year 2018, we assessed toxin contamination of shellfish collected on a monthly basis in Ingril Lagoon, France, a site known as a hotspot for Vulcanodinium rugosum growth. This short time-series study gave an overview of the presence and seasonal variability of [...] Read more.

Over the year 2018, we assessed toxin contamination of shellfish collected on a monthly basis in Ingril Lagoon, France, a site known as a hotspot for Vulcanodinium rugosum growth. This short time-series study gave an overview of the presence and seasonal variability of pinnatoxins, pteriatoxins, portimines and kabirimine, all associated with V. rugosum, in shellfish. Suspect screening and targeted analysis approaches were implemented by means of liquid chromatography coupled to both low- and high-resolution mass spectrometry. We detected pinnatoxin-A and pinnatoxin-G throughout the year, with maximum levels for each one observed in June (6.7 µg/kg for pinnatoxin-A; 467.5 µg/kg for pinnatoxin-G), whereas portimine-A was detected between May and September (maximum level = 75.6 µg/kg). One of the main findings was the identification of a series of fatty acid esters of pinnatoxin-G (n = 13) although the levels detected were low. The profile was dominated by the palmitic acid conjugation of pinnatoxin-G. The other 12 fatty acid esters had not been reported in European shellfish to date. In addition, after thorough investigations, two compounds were detected, with one being probably identified as portimine-B, and the other one putatively attributed to pteriatoxins. If available, reference materials would have ensured full identification. Monitoring of these V. rugosum emerging toxins and their biotransformation products will contribute towards filling the data gaps pointed out in risk assessments and in particular the need for more contamination data for shellfish. Full article

(This article belongs to the Special Issue Emerging Toxins Accumulation in Shellfish)

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Mar. Drugs, Volume 21, Issue 8 (August 2023) – 38 articles

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