Marine Drugs

11 pages, 1500 KiB

Open AccessArticle

Integration of the Exogenous Tuning of Thraustochytrid Fermentation and Sulfur Polymerization of Single-Cell Oil for Developing Plant-like Oils

by Adarsha Gupta, Max J. H. Worthington, Justin M. Chalker and Munish Puri

Mar. Drugs 2022, 20(10), 655; https://doi.org/10.3390/md20100655 - 21 Oct 2022

Cited by 1 | Viewed by 1598

Abstract

In this study, we have demonstrated a bioprocessing approach encompassing the exogenous addition of low-molecular-weight compounds to tune the fatty acid (FA) profile in a novel thraustochytrid strain to produce desirable FAs. Maximum lipid recovery (38%, dry wt. biomass) was obtained at 1% [...] Read more.

In this study, we have demonstrated a bioprocessing approach encompassing the exogenous addition of low-molecular-weight compounds to tune the fatty acid (FA) profile in a novel thraustochytrid strain to produce desirable FAs. Maximum lipid recovery (38%, dry wt. biomass) was obtained at 1% Tween 80 and 0.25 mg/L of Vitamin B12. The transesterified lipid showed palmitic acid (C16, 35.7% TFA), stearic acid (C18, 2.1% TFA), and oleic acid (C18:1, 18.7% TFA) as the main components of total FAs, which are mainly present in plant oils. Strikingly, D-limonene addition in the fermentation medium repressed the production of polyunsaturated fatty acid (PUFAs). Sulfur-polymerization-guided lipid separation revealed the presence of saturated (SFAs, 53% TFA) and monounsaturated fatty acids (MUFAs, 46.6% TFA) in thraustochytrid oil that mimics plant-oil-like FA profiles. This work is industrially valuable and advocates the use of sulfur polymerization for preparation of plant-like oils through tuneable thraustochytrid lipids. Full article

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32 pages, 2306 KiB

Open AccessReview

Marine Biological Macromolecules and Chemically Modified Macromolecules; Potential Anticoagulants

by Pathum Chandika, Pipuni Tennakoon, Tae-Hee Kim, Se-Chang Kim, Jae-Young Je, Jae-Il Kim, Bonggi Lee, BoMi Ryu, Hyun Wook Kang, Hyun-Woo Kim, Young-Mog Kim, Chang Su Kim, Il-Whan Choi, Won Sun Park, Myunggi Yi and Won-Kyo Jung

Mar. Drugs 2022, 20(10), 654; https://doi.org/10.3390/md20100654 - 21 Oct 2022

Cited by 4 | Viewed by 2384

Abstract

Coagulation is a potential defense mechanism that involves activating a series of zymogens to convert soluble fibrinogen to insoluble fibrin clots to prevent bleeding and hemorrhagic complications. To prevent the extra formation and diffusion of clots, the counterbalance inhibitory mechanism is activated at [...] Read more.

Coagulation is a potential defense mechanism that involves activating a series of zymogens to convert soluble fibrinogen to insoluble fibrin clots to prevent bleeding and hemorrhagic complications. To prevent the extra formation and diffusion of clots, the counterbalance inhibitory mechanism is activated at levels of the coagulation pathway. Contrariwise, this system can evade normal control due to either inherited or acquired defects or aging which leads to unusual clots formation. The abnormal formations and deposition of excess fibrin trigger serious arterial and cardiovascular diseases. Although heparin and heparin-based anticoagulants are a widely prescribed class of anticoagulants, the clinical use of heparin has limitations due to the unpredictable anticoagulation, risk of bleeding, and other complications. Hence, significant interest has been established over the years to investigate alternative therapeutic anticoagulants from natural sources, especially from marine sources with good safety and potency due to their unique chemical structure and biological activity. This review summarizes the coagulation cascade and potential macromolecular anticoagulants derived from marine flora and fauna. Full article

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15 pages, 5143 KiB

Open AccessArticle

Branched Chondroitin Sulfate Oligosaccharides Derived from the Sea Cucumber Acaudina molpadioides Stimulate Neurite Outgrowth

by Weili Wang, Hui Mao, Sujuan Li, Longlong Zhang, Lian Yang, Ronghua Yin and Jinhua Zhao

Mar. Drugs 2022, 20(10), 653; https://doi.org/10.3390/md20100653 - 21 Oct 2022

Cited by 3 | Viewed by 1418

Abstract

Fucosylated chondroitin sulfate (FCS) from the sea cucumber Acaudina molpadioides (FCS_Am) is the first one that was reported to be branched by disaccharide GalNAc-(α1,2)-Fuc_3S4S (15%) and sulfated Fuc (85%). Here, four size-homogenous fractions, and seven oligosaccharides, were separated from its [...] Read more.

Fucosylated chondroitin sulfate (FCS) from the sea cucumber Acaudina molpadioides (FCS_Am) is the first one that was reported to be branched by disaccharide GalNAc-(α1,2)-Fuc_3S4S (15%) and sulfated Fuc (85%). Here, four size-homogenous fractions, and seven oligosaccharides, were separated from its β-eliminative depolymerized products. Detailed NMR spectroscopic and MS analyses revealed the oligomers as hexa-, hepta-, octa-, and nonasaccharide, which further confirmed the precise structure of native FCS_Am: it was composed of the CS-E-like backbone with a full content of sulfation at O-4 and O-6 of GalNAc in the disaccharide repeating unit, and the branches consisting of sulfated fucose (Fuc_4S and Fuc_2S4S) and heterodisaccharide [GalNAc-(α1,2)-Fuc_3S4S]. Pharmacologically, FCS_Am and its depolymerized derivatives, including fractions and oligosaccharides, showed potent neurite outgrowth-promoting activity in a chain length-dependent manner. A comparison of analyses among oligosaccharides revealed that the sulfate pattern of the Fuc branches, instead of the heterodisaccharide, could affect the promotion intensity. Fuc_2S4S and the saccharide length endowed the neurite outgrowth stimulation activity most. Full article

(This article belongs to the Special Issue Bioactive Compounds from Sea Cucumbers)

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17 pages, 6255 KiB

Open AccessArticle

Bromoditerpenes from the Red Seaweed Sphaerococcus coronopifolius as Potential Cytotoxic Agents and Proteasome Inhibitors and Related Mechanisms of Action

by Celso Alves, Joana Silva, Susete Pintéus, Romina A. Guedes, Rita C. Guedes, Rebeca Alvariño, Rafaela Freitas, Márcia I. Goettert, Helena Gaspar, Amparo Alfonso, Maria C. Alpoím, Luis M. Botana and Rui Pedrosa

Mar. Drugs 2022, 20(10), 652; https://doi.org/10.3390/md20100652 - 20 Oct 2022

Cited by 2 | Viewed by 2062

Abstract

Seaweeds are a great source of compounds with cytotoxic properties with the potential to be used as anticancer agents. This study evaluated the cytotoxic and proteasome inhibitory activities of 12R-hydroxy-bromosphaerol, 12S-hydroxy-bromosphaerol, and bromosphaerol isolated from Sphaerococcus coronopifolius. The [...] Read more.

Seaweeds are a great source of compounds with cytotoxic properties with the potential to be used as anticancer agents. This study evaluated the cytotoxic and proteasome inhibitory activities of 12R-hydroxy-bromosphaerol, 12S-hydroxy-bromosphaerol, and bromosphaerol isolated from Sphaerococcus coronopifolius. The cytotoxicity was evaluated on malignant cell lines (A549, CACO-2, HCT-15, MCF-7, NCI-H226, PC-3, SH-SY5Y, and SK-MEL-28) using the MTT and LDH assays. The ability of compounds to stimulate the production of hydrogen peroxide (H₂O₂) and to induce mitochondrial dysfunction, the externalization of phosphatidylserine, Caspase-9 activity, and changes in nuclear morphology was also studied on MCF-7 cells. The ability to induce DNA damage was also studied on L929 fibroblasts. The proteasome inhibitory activity was estimated through molecular docking studies. The compounds exhibited IC₅₀ values between 15.35 and 53.34 µM. 12R-hydroxy-bromosphaerol and 12S-hydroxy-bromosphaerol increased the H₂O₂ levels on MCF-7 cells, and bromosphaerol induced DNA damage on fibroblasts. All compounds promoted a depolarization of mitochondrial membrane potential, Caspase-9 activity, and nuclear condensation and fragmentation. The compounds have been shown to interact with the chymotrypsin-like catalytic site through molecular docking studies; however, only 12S-hydroxy-bromosphaerol evidenced interaction with ALA20 and SER169, key residues of the proteasome catalytic mechanism. Further studies should be outlined to deeply characterize and understand the potential of those bromoditerpenes for anticancer therapeutics. Full article

(This article belongs to the Special Issue Marine Natural Products as Anticancer Agents 2.0)

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17 pages, 3531 KiB

Open AccessArticle

The Antimicrobial Peptide LJ-hep2 from Lateolabrax japonicus Exerting Activities against Multiple Pathogenic Bacteria and Immune Protection In Vivo

by Ruihao Gong, Zhe An, Weibin Zhang, Fangyi Chen and Ke-Jian Wang

Mar. Drugs 2022, 20(10), 651; https://doi.org/10.3390/md20100651 - 20 Oct 2022

Cited by 4 | Viewed by 1869

Abstract

Hepcidin is widely present in many kinds of fish and is an important innate immune factor. A variety of HAMP2-type hepcidins have strong antimicrobial activity and immunomodulatory functions and are expected to be developed as substitutes for antibiotics. In this study, the antimicrobial [...] Read more.

Hepcidin is widely present in many kinds of fish and is an important innate immune factor. A variety of HAMP2-type hepcidins have strong antimicrobial activity and immunomodulatory functions and are expected to be developed as substitutes for antibiotics. In this study, the antimicrobial activity of Hepc2 from Japanese seabass (Lateolabrax japonicus) (designated as LJ-hep2) was investigated using its recombinant precursor protein (rLJ-hep2) expressed in Pichia pastoris and a chemically synthesized mature peptide (LJ-hep2_(66–86)). The results showed that both rLJ-hep2 and synthetic LJ-hep2_(66–86) displayed broad antimicrobial spectrum with potent activity against gram-negative and gram-positive bacteria, and fungi. Especially, LJ-hep2_(66–86) had stronger antimicrobial activity and exhibited potent activity against several clinically isolated multidrug-resistant bacteria, including Acinetobacter baumannii, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae and Enterococcus faecium. Moreover, LJ-hep2_(66–86) exerted rapid bactericidal kinetic (killed tested bacteria within 2 h), induced significant morphological changes and promoted agglutination of E. coli, P. aeruginosa and Aeromonas hydrophila. The activity of LJ-hep2_(66–86) against E. coli, P. aeruginosa and A. hydrophila was stable and remained active when heated for 30 min. In addition, LJ-hep2_(66–86) exhibited no cytotoxicity to the mammalian cell line HEK293T and fish cell lines (EPC and ZF4). In vivo study showed that LJ-hep2_(66–86) could improve the survival rate of marine medaka (Oryzias melastigma) by about 40% under the challenge of A. hydrophila, indicating its immunoprotective function. Taken together, both rLJ-hep2 and LJ-hep2_(66–86) have good prospects to be used as potential antimicrobial agents in aquaculture and medicine in the future. Full article

(This article belongs to the Special Issue Marine Bioactive Peptides: Structure, Function, and Therapeutic Potential - III)

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23 pages, 6897 KiB

Open AccessArticle

Two Laminaria japonica Fermentation Broths Alleviate Oxidative Stress and Inflammatory Response Caused by UVB Damage: Photoprotective and Reparative Effects

by Qianru Sun, Jiaxuan Fang, Ziwen Wang, Zixin Song, Jiman Geng, Dongdong Wang, Changtao Wang and Meng Li

Mar. Drugs 2022, 20(10), 650; https://doi.org/10.3390/md20100650 - 20 Oct 2022

Cited by 5 | Viewed by 2074

Abstract

UVB radiation can induce oxidative stress and inflammatory response in human epidermal cells. We establish a UVB-induced damage model of human immortalized epidermal keratinocytes (HaCaT) to explore the protective and reparative effects of Laminaria japonica on UVB-damaged epidermal inflammation after fermentation by white [...] Read more.

UVB radiation can induce oxidative stress and inflammatory response in human epidermal cells. We establish a UVB-induced damage model of human immortalized epidermal keratinocytes (HaCaT) to explore the protective and reparative effects of Laminaria japonica on UVB-damaged epidermal inflammation after fermentation by white Ganoderma lucidum (Curtis) P. Karst and Saccharomyces cerevisiae. Compared with unfermented Laminaria japonica, fermented Laminaria japonica possesses stronger in vitro free radical scavenging ability. Laminaria japonica white Ganoderma lucidum fermentation broth (LJ-G) and Laminaria japonica rice wine yeast fermentation broth (LJ-Y) can more effectively remove excess reactive oxygen species (ROS) in cells and increase the content of the intracellular antioxidant enzymes heme oxygenase-1 (HO-1) and NAD(P)H quinone oxidoreductase 1 (NQO-1). In addition, fermented Laminaria japonica effectively reduces the content of pro-inflammatory factors ILs, TNF-α and MMP-9 secreted by cells. The molecular research results show that fermented Laminaria japonica activates the Nrf2 signaling pathway, increases the synthesis of antioxidant enzymes, inhibits the gene expression levels of pro-inflammatory factors, and alleviates cellular oxidative stress and inflammatory response caused by UVB radiation. Based on the above results, we conclude that fermented Laminaria japonica has stronger antioxidant and anti-inflammatory activity than unfermented Laminaria japonica, possesses good safety, and can be developed and used as a functional inflammation reliever. Fermented Laminaria japonica polysaccharide has a more slender morphological structure and more rockulose, with better moisturizing and rheological properties. Full article

(This article belongs to the Special Issue Marine Bioactive Compounds against Oxidative Stress and Inflammation)

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11 pages, 1987 KiB

Open AccessArticle

Structural Investigation of Aaptourinamine by a Novel Module-Assembly-Based Calculation

by Xing Shi, Zhihui Wu, Tianyun Jin, Cili Wang and Pinglin Li

Mar. Drugs 2022, 20(10), 649; https://doi.org/10.3390/md20100649 - 20 Oct 2022

Viewed by 1502

Abstract

Natural products have various and complicated structures, which is still a challenge for elucidating these compounds, especially for those lacking two-dimensional nuclear magnetic resonance (2D NMR) correlations mainly caused by high C/H ratios or proton-deficient and multiple heteroatoms through the conventional structural analytical [...] Read more.

Natural products have various and complicated structures, which is still a challenge for elucidating these compounds, especially for those lacking two-dimensional nuclear magnetic resonance (2D NMR) correlations mainly caused by high C/H ratios or proton-deficient and multiple heteroatoms through the conventional structural analytical methods. We reported a novel module-assembly calculation method named Dooerafa, which included constructing the meta-structures by a grafting method based on the crucial and the limited 2D NMR correlations, ring-contraction strategy based on mechanic force field and quantum chemical theory, and self-assemble calculation in Python programming for shaping up the structural candidates along with DFT-GIAO calculation. This new method, verified by a known alkaloid spiroreticulatine with the structure determined by X-ray diffraction, was performed for the structural elucidation of aaptourinamine isolated from marine sponge Aaptos suberitoides, showing us a brand new scaffold of imidazo [4,5,1-ij]pyrrolo [3,2-f]quinolin-7(8H)-one, which has a biosynthetic relationship with the bioactive and structurally unique aaptamine alkaloid. Full article

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16 pages, 1957 KiB

Open AccessArticle

Meridianins Inhibit GSK3β In Vivo and Improve Behavioral Alterations Induced by Chronic Stress

by Anna Sancho-Balsells, Esther García-García, Francesca Flotta, Wanqi Chen, Jordi Alberch, Manuel J. Rodríguez, Conxita Avila and Albert Giralt

Mar. Drugs 2022, 20(10), 648; https://doi.org/10.3390/md20100648 - 19 Oct 2022

Cited by 1 | Viewed by 1998

Abstract

Major depression disorder (MDD) is a severe mental alteration with a multifactorial origin, and chronic stress is one of the most relevant environmental risk factors associated with MDD. Although there exist some therapeutical options, 30% of patients are still resistant to any type [...] Read more.

Major depression disorder (MDD) is a severe mental alteration with a multifactorial origin, and chronic stress is one of the most relevant environmental risk factors associated with MDD. Although there exist some therapeutical options, 30% of patients are still resistant to any type of treatment. GSK3β inhibitors are considered very promising therapeutic tools to counteract stress-related affectations. However, they are often associated with excessive off-target effects and undesired secondary alterations. Meridianins are alkaloids with an indole framework linked to an aminopyrimidine ring from Antarctic marine ascidians. Meridianins could overcome several of the aforementioned limitations since we previously demonstrated that they can inhibit GSK3β activity without the associated neurotoxic or off-target effects in rodents. Here, we show that meridianins delivered into the lateral ventricle inhibited GSK3β in several brain regions involved with stress-related symptoms. We also observed changes in major signaling pathways in the prefrontal cortex (Akt and PKA) and hippocampus (PKC and GluR1). Moreover, meridianins increased synaptic activity, specifically in the CA1 but not in the CA3 or other hippocampal subfields. Finally, we chronically treated the mice subjected to an unpredictable mild chronic stress (CUMS) paradigm with meridianins. Our results showed improvements produced by meridianins in behavioral alterations provoked by CUMS. In conclusion, meridianins could be of therapeutic interest to patients with stress-related disorders such as MDD. Full article

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

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14 pages, 2901 KiB

Open AccessArticle

Manzamine-A Alters In Vitro Calvarial Osteoblast Function

by Samantha Hardy, Yeun-Mun Choo, Mark Hamann and James Cray

Mar. Drugs 2022, 20(10), 647; https://doi.org/10.3390/md20100647 - 19 Oct 2022

Cited by 2 | Viewed by 1972

Abstract

Manzamine-A is a marine-derived alkaloid which has anti-viral and anti-proliferative properties and is currently being investigated for its efficacy in the treatment of certain viruses (malaria, herpes, HIV-1) and cancers (breast, cervical, colorectal). Manzamine-A has been found to exert effects via modulation of [...] Read more.

Manzamine-A is a marine-derived alkaloid which has anti-viral and anti-proliferative properties and is currently being investigated for its efficacy in the treatment of certain viruses (malaria, herpes, HIV-1) and cancers (breast, cervical, colorectal). Manzamine-A has been found to exert effects via modulation of SIX1 gene expression, a gene critical to craniofacial development via the WNT, NOTCH, and PI3K/AKT pathways. To date little work has focused on Manzamine-A and how its use may affect bone. We hypothesize that Manzamine-A, through SIX1, alters bone cell activity. Here, we assessed the effects of Manzamine-A on cells that are responsible for the generation of bone, pre-osteoblasts and osteoblasts. PCR, qrtPCR, MTS cell viability, Caspase 3/7, and functional assays were used to test the effects of Manzamine-A on these cells. Our data suggests Six1 is highly expressed in osteoblasts and their progenitors. Further, osteoblast progenitors and osteoblasts exhibit great sensitivity to Manzamine-A treatment exhibited by a significant decrease in cell viability, increase in cellular apoptosis, and decrease in alkaline phosphatase activity. In silico binding experiment showed that manzamine A potential as an inhibitor of cell proliferation and survival proteins, i.e., Iκb, JAK2, AKT, PKC, FAK, and Bcl-2. Overall, our data suggests Manzamine-A may have great effects on bone health overall and may disrupt skeletal development, homeostasis, and repair. Full article

(This article belongs to the Special Issue Marine Bioactive Compounds on Osteoporosis and Related Bone Diseases)

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13 pages, 2516 KiB

Open AccessArticle

Preparation, Anticoagulant and Antioxidant Properties of Glucosamine-Heparin Salt

by Qin Miao, Qing Li, Wenqiang Tan, Yingqi Mi, Bing Ma, Jingjing Zhang and Zhanyong Guo

Mar. Drugs 2022, 20(10), 646; https://doi.org/10.3390/md20100646 - 18 Oct 2022

Cited by 1 | Viewed by 1472

Abstract

Excessive inorganic ions in vivo may lead to electrolyte disorders and induce damage to the human body. Therefore, preparation of enhanced bioactivity compounds, composed of activated organic cations and organic anions, is of great interest among researchers. In this work, glucosamine-heparin salt (GHS) [...] Read more.

Excessive inorganic ions in vivo may lead to electrolyte disorders and induce damage to the human body. Therefore, preparation of enhanced bioactivity compounds, composed of activated organic cations and organic anions, is of great interest among researchers. In this work, glucosamine-heparin salt (GHS) was primarily synthesized with positively charged glucosamine hydrochloride (GAH) and negatively charged heparin sodium (Heps) by ion exchange method. Then, the detailed structural information of the GHS was characterized by FTIR, ¹H NMR spectroscopy and ICP-MS. In addition, its anticoagulant potency and antioxidant properties were evaluated, respectively. The results demonstrated that GHS salt achieved enhanced antioxidant activities, including 98.78% of O₂•⁻ radical scavenging activity, 91.23% of •OH radical scavenging rate and 66.49% of DPPH radical scavenging capacity at 1.6 mg/mL, severally. Meanwhile, anticoagulant potency (ATTP) of GHS strengthened from 153.10 ± 17.14 to 180.03 ± 6.02 at 0.75 μmol/L. Thus, introducing cationic glucosamine residues into GHS could improve its anticoagulant activity. The findings suggest that GHS product with a small amount of inorganic ions can greatly abate the prime cost of antioxidants and anticoagulants, and has significant economic benefits and practical significance. Full article

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15 pages, 3049 KiB

Open AccessArticle

Astaxanthin Protection against Neuronal Excitotoxicity via Glutamate Receptor Inhibition and Improvement of Mitochondrial Function

by Swapna Kannothum Kandy, Madhura Milind Nimonkar, Suravi Sasmita Dash, Bhupesh Mehta and Yogananda S. Markandeya

Mar. Drugs 2022, 20(10), 645; https://doi.org/10.3390/md20100645 - 18 Oct 2022

Cited by 7 | Viewed by 2889

Abstract

Excitotoxicity is known to associate with neurodegenerative diseases, such as Alzheimer’s disease, Parkinson’s disease, Amyotrophic lateral sclerosis and Huntington’s disease, as well as aging, stroke, trauma, ischemia and epilepsy. Excessive release of glutamate, overactivation of glutamate receptors, calcium overload, mitochondrial dysfunction and excessive [...] Read more.

Excitotoxicity is known to associate with neurodegenerative diseases, such as Alzheimer’s disease, Parkinson’s disease, Amyotrophic lateral sclerosis and Huntington’s disease, as well as aging, stroke, trauma, ischemia and epilepsy. Excessive release of glutamate, overactivation of glutamate receptors, calcium overload, mitochondrial dysfunction and excessive reactive oxygen species (ROS) formation are a few of the suggested key mechanisms. Astaxanthin (AST), a carotenoid, is known to act as an antioxidant and protect neurons from excitotoxic injuries. However, the exact molecular mechanism of AST neuroprotection is not clear. Thus, in this study, we investigated the role of AST in neuroprotection in excitotoxicity. We utilized primary cortical neuronal culture and live cell fluorescence imaging for the study. Our results suggest that AST prevents neuronal death, reduces ROS formation and decreases the abnormal mitochondrial membrane depolarization induced by excitotoxic glutamate insult. Additionally, AST modulates intracellular calcium levels by inhibiting peak and irreversible secondary sustained calcium levels in neurons. Furthermore, AST regulates the ionotropic glutamate subtype receptors NMDA, AMPA, KA and mitochondrial calcium. Moreover, AST decreases NMDA and AMPA receptor protein expression levels, while KA remains unaffected. Overall, our results indicate that AST protects neurons from excitotoxic neuronal injury by regulating ionotropic glutamate receptors, cytosolic secondary calcium rise and mitochondrial calcium buffering. Hence, AST could be a promising therapeutic agent against excitotoxic insults in neurodegenerative diseases. Full article

(This article belongs to the Topic Safety and Toxicological Risks of Medicinal Plants and Natural Products: Mechanistic Insights)

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15 pages, 2270 KiB

Open AccessArticle

Exogenous Arachidonic Acid Affects Fucoxanthin Biosynthesis and Photoprotection in Phaeodactylum tricornutum

by Shuaiqi Zhu, Song Bin, Wenda Wang, Shan Lu and Wenqiang Yang

Mar. Drugs 2022, 20(10), 644; https://doi.org/10.3390/md20100644 - 17 Oct 2022

Viewed by 1597

Abstract

Fucoxanthin is an oxygenated carotenoid component that has been reported to play important roles in anti-oxidation, anti-obesity and anti-cancer in the human body. Fucoxanthin-chlorophyll protein (FCP) complexes participate in light harvesting and photoprotection in diatom. In order to better understand the change of [...] Read more.

Fucoxanthin is an oxygenated carotenoid component that has been reported to play important roles in anti-oxidation, anti-obesity and anti-cancer in the human body. Fucoxanthin-chlorophyll protein (FCP) complexes participate in light harvesting and photoprotection in diatom. In order to better understand the change of fucoxanthin content and its role in photoprotection, the growth, fucoxanthin biosynthesis and photosynthetic phenotypes were studied in the diatom Phaeodactylum tricornutum under the treatment of exogenous arachidonic acid (AA). Our results demonstrated that even low concentration of AA at 0.1 mg/L strongly induced fucoxanthin accumulation in algal cells to a maximum of 1.1 mg/g dry weight (DW), which was 36.6% higher than that in the untreated ones. By principal component analysis (PCA), we also identified a close correlation between fucoxanthin accumulation and the expression of genes involved in fucoxanthin biosynthesis, especially phytoene synthase (PSY), suggesting that AA change the metabolism of fucoxanthin by inducing carotenoid metabolic enzymes at the transcriptional level. Furthermore, we found that the exogenous application of AA affected non-photochemical quenching (NPQ) and photoinhibition, which resulted from the changed diadinoxanthin (DD) and diatoxanthin (DT) cycle, and thus played an important role in photoprotection. Full article

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

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24 pages, 665 KiB

Open AccessReview

Antimicrobial Secondary Metabolites from the Mangrove Plants of Asia and the Pacific

by Mazdida Sulaiman, Veeranoot Nissapatorn, Mohammed Rahmatullah, Alok K. Paul, Mogana Rajagopal, Nor Azizun Rusdi, Jaya Seelan Sathya Seelan, Monica Suleiman, Zainul Amiruddin Zakaria and Christophe Wiart

Mar. Drugs 2022, 20(10), 643; https://doi.org/10.3390/md20100643 - 15 Oct 2022

Cited by 6 | Viewed by 3601

Abstract

Microbes such as the White Spot Syndrome Virus account for severe losses in the shrimp farming industry globally. This review examines the literature on the mangrove plants of Asia and the Pacific with antibacterial, antifungal, or antiviral activities. All of the available data [...] Read more.

Microbes such as the White Spot Syndrome Virus account for severe losses in the shrimp farming industry globally. This review examines the literature on the mangrove plants of Asia and the Pacific with antibacterial, antifungal, or antiviral activities. All of the available data published on this subject were collected from Google Scholar, PubMed, Science Direct, Web of Science, ChemSpider, PubChem, and a library search from 1968 to 2022. Out of about 286 plant species, 119 exhibited antimicrobial effects, and a total of 114 antimicrobial natural products have been identified including 12 with MIC values below 1 µg/mL. Most of these plants are medicinal. The mangrove plants of Asia and the Pacific yield secondary metabolites with the potential to mitigate infectious diseases in shrimp aquaculture. Full article

(This article belongs to the Special Issue Bio-Active Products from Mangrove Ecosystems)

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32 pages, 9725 KiB

Open AccessEditor’s ChoiceReview

The Tetrahydrofuran Motif in Marine Lipids and Terpenes

by Paula González-Andrés, Laura Fernández-Peña, Carlos Díez-Poza and Asunción Barbero

Mar. Drugs 2022, 20(10), 642; https://doi.org/10.3390/md20100642 - 15 Oct 2022

Cited by 9 | Viewed by 2686

Abstract

Heterocycles are particularly common moieties within marine natural products. Specifically, tetrahydrofuranyl rings are present in a variety of compounds which present complex structures and interesting biological activities. Focusing on terpenoids, a high number of tetrahydrofuran-containing metabolites have been isolated during the last decades. [...] Read more.

Heterocycles are particularly common moieties within marine natural products. Specifically, tetrahydrofuranyl rings are present in a variety of compounds which present complex structures and interesting biological activities. Focusing on terpenoids, a high number of tetrahydrofuran-containing metabolites have been isolated during the last decades. They show promising biological activities, making them potential leads for novel antibiotics, antikinetoplastid drugs, amoebicidal substances, or anticancer drugs. Thus, they have attracted the attention of the synthetics community and numerous approaches to their total syntheses have appeared. Here, we offer the reader an overview of marine-derived terpenoids and related compounds, their isolation, structure determination, and a special focus on their total syntheses and biological profiles. Full article

(This article belongs to the Special Issue Heterocyclic Compounds from Marine Organisms)

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16 pages, 1135 KiB

Open AccessArticle

New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish Ceramaster patagonicus

by Timofey V. Malyarenko, Viktor M. Zakharenko, Alla A. Kicha, Alexandra S. Kuzmich, Olesya S. Malyarenko, Anatoly I. Kalinovsky, Roman S. Popov, Vasily I. Svetashev and Natalia V. Ivanchina

Mar. Drugs 2022, 20(10), 641; https://doi.org/10.3390/md20100641 - 14 Oct 2022

Cited by 2 | Viewed by 2057

Abstract

Three new ceramides (1–3) and three new cerebrosides (4, 8, and 9), along with three previously known cerebrosides (ophidiocerebrosides C (5), D (6), and CE-3-2 (7)), were isolated from [...] Read more.

Three new ceramides (1–3) and three new cerebrosides (4, 8, and 9), along with three previously known cerebrosides (ophidiocerebrosides C (5), D (6), and CE-3-2 (7)), were isolated from a deep-sea starfish species, the orange cookie starfish Ceramaster patagonicus. The structures of 1−4, 8, and 9 were determined by the NMR and ESIMS techniques and also through chemical transformations. Ceramides 1–3 contain iso-C₂₁ or C₂₃ Δ⁹-phytosphingosine as a long-chain base and have C₁₆ or C₁₇ (2R)-2-hydroxy-fatty acids of the normal type. Cerebroside 4 contains C₂₂ Δ⁹-sphingosine anteiso-type as a long-chain base and (2R)-2-hydroxyheptadecanoic acid of the normal type, while compounds 8 and 9 contain saturated C-17 phytosphingosine anteiso-type as a long-chain base and differ from each other in the length of the polymethylene chain of (2R)-2-hydroxy-fatty acids of the normal type: C₂₃ in 8 and C₂₄ in 9. All the new cerebrosides (4, 8, and 9) have β-D-glucopyranose as a monosaccharide residue. The composition of neutral sphingolipids from C. patagonicus was described for the first time. The investigated compounds 1–3, 5–7, and 9 exhibit slight to moderate cytotoxic activity against human cancer cells (HT-29, SK-MEL-28, and MDA-MB-231) and normal embryonic kidney cells HEK293. Compounds 2, 5, and 6 at a concentration of 20 µM inhibit colony formation of MDA-MB-231 cells by 68%, 54%, and 68%, respectively. The colony-inhibiting activity of compounds 2, 5, and 6 is comparable to the effect of doxorubicin, which reduces the number of colonies by 70% at the same concentration. 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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36 pages, 5236 KiB

Open AccessReview

Towards Sustainable Medicinal Resources through Marine Soft Coral Aquaculture: Insights into the Chemical Diversity and the Biological Potential

by Ngoc Bao An Nguyen, Lo-Yun Chen, Mohamed El-Shazly, Bo-Rong Peng, Jui-Hsin Su, Ho-Cheng Wu, I-Ta Lee and Kuei-Hung Lai

Mar. Drugs 2022, 20(10), 640; https://doi.org/10.3390/md20100640 - 14 Oct 2022

Cited by 8 | Viewed by 2304

Abstract

In recent decades, aquaculture techniques for soft corals have made remarkable progress in terms of conditions and productivity. Researchers have been able to obtain larger quantities of soft corals, thus larger quantities of biologically active metabolites, allowing them to study their biological activity [...] Read more.

In recent decades, aquaculture techniques for soft corals have made remarkable progress in terms of conditions and productivity. Researchers have been able to obtain larger quantities of soft corals, thus larger quantities of biologically active metabolites, allowing them to study their biological activity in many pharmacological assays and even produce sufficient quantities for clinical trials. In this review, we summarize 201 secondary metabolites that have been identified from cultured soft corals in the era from 2002 to September 2022. Various types of diterpenes (eunicellins, cembranes, spatanes, norcembranes, briaranes, and aquarianes), as well as biscembranes, sterols, and quinones were discovered and subjected to bioactivity investigations in 53 different studies. We also introduce a more in-depth discussion of the potential biological effects (anti-cancer, anti-inflammatory, and anti-microbial) and the mechanisms of action of the identified secondary metabolites. We hope this review will shed light on the untapped potential applications of aquaculture to produce valuable secondary metabolites to tackle current and emerging health conditions. Full article

(This article belongs to the Special Issue Soft Corals (Octocorallia) Are Marine Bio-Resources towards Biotechnology and Medical Applications)

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22 pages, 4010 KiB

Open AccessArticle

Anti-Inflammatory and Antioxidant Properties of Malapterurus electricus Skin Fish Methanolic Extract in Arthritic Rats: Therapeutic and Protective Effects

by Abeer H. Elmaidomy, Esraa M. Mohamed, Hanan F. Aly, Eman A. Younis, Shams Gamal Eldin Shams, Faisal H. Altemani, Mubarak A. Alzubaidi, Mohammed Almaghrabi, Adnan Al Harbi, Faisal Alsenani, Ahmed M. Sayed and Usama Ramadan Abdelmohsen

Mar. Drugs 2022, 20(10), 639; https://doi.org/10.3390/md20100639 - 14 Oct 2022

Cited by 6 | Viewed by 2337

Abstract

The protective and therapeutic anti-inflammatory and antioxidant potency of Malapterurus electricus (F. Malapteruridae) skin fish methanolic extract (FE) (300 mg/kg.b.wt/day for 7 days, orally) was tested in monosodium urate(MSU)-induced arthritic Wistar albino male rats’ joints. Serum uric acid, TNF-α, IL-1β, NF-𝜅B, MDA, GSH, [...] Read more.

The protective and therapeutic anti-inflammatory and antioxidant potency of Malapterurus electricus (F. Malapteruridae) skin fish methanolic extract (FE) (300 mg/kg.b.wt/day for 7 days, orally) was tested in monosodium urate(MSU)-induced arthritic Wistar albino male rats’ joints. Serum uric acid, TNF-α, IL-1β, NF-𝜅B, MDA, GSH, catalase, SOD, and glutathione reductase levels were all measured. According to the findings, FE significantly reduced uric acid levels and ankle swelling in both protective and therapeutic groups. Furthermore, it has anti-inflammatory effects by downregulating inflammatory cytokines, primarily through decreased oxidative stress and increased antioxidant status. All the aforementioned lesions were significantly improved in protected and treated rats with FE, according to histopathological findings. iNOS immunostaining revealed that protected and treated arthritic rats with FE had weak positive immune-reactive cells. Phytochemical analysis revealed that FE was high in fatty and amino acids. The most abundant compounds were vaccenic (24.52%), 9-octadecenoic (11.66%), palmitic (34.66%), stearic acids (14.63%), glycine (0.813 mg/100 mg), and alanine (1.645 mg/100 mg). Extensive molecular modelling and dynamics simulation experiments revealed that compound 4 has the potential to target and inhibit COX isoforms with a higher affinity for COX-2. As a result, we contend that FE could be a promising protective and therapeutic option for arthritis, aiding in the prevention and progression of this chronic inflammatory disease. Full article

(This article belongs to the Special Issue Discovery of New Marine Natural Products using Omics approaches)

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10 pages, 620 KiB

Open AccessCommentary

Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum

by Anatolii I. Usov, Maria I. Bilan, Nadezhda E. Ustyuzhanina and Nikolay E. Nifantiev

Mar. Drugs 2022, 20(10), 638; https://doi.org/10.3390/md20100638 - 13 Oct 2022

Cited by 12 | Viewed by 2356

Abstract

Preparations of sulfated polysaccharides obtained from brown algae are known as fucoidans. These biopolymers have attracted considerable attention due to many biological activities which may find practical applications. Two Atlantic representatives of Phaeophyceae, namely, Fucus vesiculosus and Ascophyllum nodosum, belonging to the [...] Read more.

Preparations of sulfated polysaccharides obtained from brown algae are known as fucoidans. These biopolymers have attracted considerable attention due to many biological activities which may find practical applications. Two Atlantic representatives of Phaeophyceae, namely, Fucus vesiculosus and Ascophyllum nodosum, belonging to the same order Fucales, are popular sources of commercial fucoidans, which often regarded as very similar in chemical composition and biological actions. Nevertheless, these two fucoidan preparations are polysaccharide mixtures which differ considerably in amount and chemical nature of components, and hence, this circumstance should be taken into account in the investigation of their biological properties and structure–activity relationships. In spite of these differences, fractions with carefully characterized structures prepared from both fucoidans may have valuable applications in drug development. 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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17 pages, 2576 KiB

Open AccessFeature PaperEditor’s ChoiceArticle

An Aminopyrimidone and Aminoimidazoles Alkaloids from the Rodrigues Calcareous Marine Sponge Ernsta naturalis

by Pierre-Eric Campos, Gaëtan Herbette, Laetitia Fougère, Patricia Clerc, Florent Tintillier, Nicole J. de Voogd, Géraldine Le Goff, Jamal Ouazzani and Anne Gauvin-Bialecki

Mar. Drugs 2022, 20(10), 637; https://doi.org/10.3390/md20100637 - 13 Oct 2022

Cited by 2 | Viewed by 2121

Abstract

A chemical study of the CH₂Cl₂−MeOH (1:1) extract from the sponge Ernsta naturalis collected in Rodrigues (Mauritius) based on a molecular networking dereplication strategy highlighted one novel aminopyrimidone alkaloid compound, ernstine A (1), seven new aminoimidazole alkaloid [...] Read more.

A chemical study of the CH₂Cl₂−MeOH (1:1) extract from the sponge Ernsta naturalis collected in Rodrigues (Mauritius) based on a molecular networking dereplication strategy highlighted one novel aminopyrimidone alkaloid compound, ernstine A (1), seven new aminoimidazole alkaloid compounds, phorbatopsins D–E (2, 3), calcaridine C (4), naamines H–I (5, 7), naamidines J–K (6, 8), along with the known thymidine (9). Their structures were established by spectroscopic analysis (1D and 2D NMR spectra and HRESIMS data). To improve the investigation of this unstudied calcareous marine sponge, a metabolomic study by molecular networking was conducted. The isolated molecules are distributed in two clusters of interest. Naamine and naamidine derivatives are grouped together with ernstine in the first cluster of twenty-three molecules. Phorbatopsin derivatives and calcaridine C are grouped together in a cluster of twenty-one molecules. Interpretation of the MS/MS spectra of other compounds of these clusters with structural features close to the isolated ones allowed us to propose a structural hypothesis for 16 compounds, 5 known and 11 potentially new. Full article

(This article belongs to the Special Issue Heterocyclic Compounds from Marine Organisms)

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1 pages, 168 KiB

Open AccessCorrection

Correction: Haque et al. Marine Natural Products in Clinical Use. Mar. Drugs 2022, 20, 528

by Neshatul Haque, Sana Parveen, Tingting Tang, Jiaen Wei and Zunnan Huang

Mar. Drugs 2022, 20(10), 636; https://doi.org/10.3390/md20100636 - 13 Oct 2022

Cited by 5 | Viewed by 1234

Abstract

The authors would like to make corrections to a recently published paper [...] Full article

14 pages, 1235 KiB

Open AccessArticle

Isolation, Synthesis and Absolute Configuration of the Pericharaxins A and B, Epimeric Hydroxy-Polyene Glycerol Ethers from the Calcarean Sponge Pericharax heteroraphis

by Capucine Jourdain de Muizon, Céline Moriou, Sylvain Petek, Merrick Ekins, Marthe Rousseau and Ali Al Mourabit

Mar. Drugs 2022, 20(10), 635; https://doi.org/10.3390/md20100635 - 11 Oct 2022

Cited by 1 | Viewed by 1826

Abstract

Naturally occurring epimeric hydroxy-polyene glycerol ether pericharaxins A (1a) and B (1b) were isolated from the calcarean sponge Pericharax heteroraphis. The structural and stereochemical characterization of both diastereoisomers were established on the basis of spectroscopic data analysis and [...] Read more.

Naturally occurring epimeric hydroxy-polyene glycerol ether pericharaxins A (1a) and B (1b) were isolated from the calcarean sponge Pericharax heteroraphis. The structural and stereochemical characterization of both diastereoisomers were established on the basis of spectroscopic data analysis and total synthesis in seven steps. The mixture of pericharaxins A (1a) and B (1b) was proven to be epimeric by chiral-phase HPLC analysis of both synthetic and natural samples. Further separation of the epimers and application of Mosher’s method to the synthetic compounds allowed unequivocal absolute configuration assignment. While natural products and the synthetic intermediates were shown to be non-cytotoxic on the HCT116 cell line, the endochondral differentiation activity using human type X collagen transcription activity in ATDC5 cells is interesting. Full article

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26 pages, 2731 KiB

Open AccessArticle

Marine Biotoxins in Whole and Processed Scallops from the Argentine Sea

by Alejandra B. Goya, Danial Baqer, Ryan P. Alexander, Patrycja Stubbs, Karl Dean, Adam M. Lewis, Lewis Coates, Benjamin H. Maskrey and Andrew D. Turner

Mar. Drugs 2022, 20(10), 634; https://doi.org/10.3390/md20100634 - 10 Oct 2022

Cited by 2 | Viewed by 1965

Abstract

Harmful algal blooms are an increasing worldwide threat to the seafood industry and human health as a consequence of the natural production of biotoxins that can accumulate in shellfish. In the Argentine Sea, this has been identified as an issue for the offshore [...] Read more.

Harmful algal blooms are an increasing worldwide threat to the seafood industry and human health as a consequence of the natural production of biotoxins that can accumulate in shellfish. In the Argentine Sea, this has been identified as an issue for the offshore fisheries of Patagonian scallops (Zygochlamys patagonica), leading to potentially harmful effects on consumers. Here we assess spatial and temporal patterns in marine biotoxin concentrations in Patagonian scallops harvested in Argentinian waters between 2012–2017, based on analyses for paralytic shellfish toxins, lipophilic toxins, and amnesic shellfish toxins. There was no evidence for concentrations of lipophilic or amnesic toxins above regulatory acceptance thresholds, with trace concentrations of pectenotoxin 2, azaspiracid 2 and okadaic acid group toxins confirmed. Conversely, paralytic shellfish toxins were quantified in some scallops. Gonyautoxins 1 and 2 dominated the unusual toxin profiles (91%) in terms of saxitoxin equivalents with maximum concentrations reaching 3985 µg STX eq/kg and with changes in profiles linked in part to seasonal changes. Total toxin concentrations were compared between samples of the adductor muscle and whole tissue, with results showing the absence of toxins in the adductor muscle confirming toxin accumulation in the digestive tracts of the scallops and the absence of a human health threat following the processing of scallop adductor meat. These findings highlight that paralytic shellfish toxins with an unusual toxin profile can occur in relatively high concentrations in whole Patagonian scallops in specific regions and during particular time periods, also showing that the processing of scallops on board factory ships to obtain frozen adductor muscle is an effective management process that minimizes the risk of poisonings from final products destined for human consumption. Full article

(This article belongs to the Section Marine Toxins)

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14 pages, 2080 KiB

Open AccessArticle

An In Vivo Study to Evaluate the Efficacy of Blue Shark (Prionace glauca) Cartilage Collagen as a Cosmetic

by Wen-Chien Lu, Chien-Shan Chiu, Yung-Jia Chan, Tian-Pin Guo, Ching-Chin Lin, Po-Chun Wang, Po-Yu Lin, Amanda Tresiliana Mulio and Po-Hsien Li

Mar. Drugs 2022, 20(10), 633; https://doi.org/10.3390/md20100633 - 05 Oct 2022

Cited by 7 | Viewed by 2458

Abstract

The “blue shark”, Prionace glauca (class: Chondrichthyes), is a pelagic shark species commonly found in tropical and temperate oceans. This shark is mainly sold in Asian countries as food and as traditional Chinese medicine. According to the Red List of the International Union [...] Read more.

The “blue shark”, Prionace glauca (class: Chondrichthyes), is a pelagic shark species commonly found in tropical and temperate oceans. This shark is mainly sold in Asian countries as food and as traditional Chinese medicine. According to the Red List of the International Union for the Conservation of Nature, P. glauca is classified as low-risk to near endangered. P. glauca cartilage contains collagen type II, which makes it suitable as a bioactive ingredient in cosmeceutical products. This study evaluated the effects of a gel containing various concentrations (0.125–5%) of lyophilized hydrolyzed P. glauca cartilage on the human inner wrist skin compared to a placebo (base). A skin properties evaluation test was conducted before and after applying various concentrations (0.125–5%) of the P. glauca cartilage gel for 10 and 20 min on the inner wrists of participants using a skin analyzer that determined the moisture level, oil level, texture level, complexion level, and the 3D level. Adding lyophilized hydrolyzed shark cartilage (LHSC) significantly improved the moisture, texture, and complexion of the skin while controlling oil and providing a wrinkle-smoothing effect. The result indicated that LHSC formulations were prepared at different concentrations, and they had significantly enhanced effects on skin hydration and elasticity (texture) and the smoothing of wrinkles (3D level). The LHSC also effectively controlled oil secretion and the complexion. Full article

(This article belongs to the Special Issue Collagen and Bioactives from Marine By-Products)

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28 pages, 2127 KiB

Open AccessArticle

Total Synthesis and Biological Evaluation of Modified Ilamycin Derivatives

by Jennifer Greve, Axel Mogk and Uli Kazmaier

Mar. Drugs 2022, 20(10), 632; https://doi.org/10.3390/md20100632 - 03 Oct 2022

Cited by 6 | Viewed by 1772

Abstract

Ilamycins/rufomycins are marine cycloheptapeptides containing unusual amino acids. Produced by Streptomyces sp., these compounds show potent activity against a range of mycobacteria, including multidrug-resistant strains of Mycobacterium tuberculosis. The cyclic peptides target the AAA+ protein ClpC1 that, together with the peptidases ClpP1/ClpP2, [...] Read more.

Ilamycins/rufomycins are marine cycloheptapeptides containing unusual amino acids. Produced by Streptomyces sp., these compounds show potent activity against a range of mycobacteria, including multidrug-resistant strains of Mycobacterium tuberculosis. The cyclic peptides target the AAA+ protein ClpC1 that, together with the peptidases ClpP1/ClpP2, forms an essential ATP-driven protease. Derivatives of the ilamycins with a simplified tryptophane unit are synthesized in a straightforward manner. The ilamycin derivative 26 with a cyclic hemiaminal structure is active in the nM-range against several mycobacterial strains and shows no significant cytotoxicity. In contrast, derivative 27, with a glutamic acid at this position, is significantly less active, with MICs in the mid µM-range. Detailed investigations of the mode of action of 26 indicate that 26 deregulates ClpC1 activity and strongly enhances ClpC1-WT ATPase activity. The consequences of 26 on ClpC1 proteolytic activities were substrate-specific, suggesting dual effects of 26 on ClpC1-WT function. The positive effect relates to ClpC1-WT ATPase activation, and the negative to competition with substrates for binding to the ClpC1 NTD. Full article

(This article belongs to the Special Issue Chemical Modification and Structural Elucidation of Marine Natural Products)

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14 pages, 2582 KiB

Open AccessArticle

In Vivo Anticoagulant and Antithrombic Activity of Depolymerized Glycosaminoglycan from Apostichopus japonicus and Dynamic Effect–Exposure Relationship in Rat Plasma

by Han Wang, Dandan He, Linlin Duan, Lv Lv, Qun Gao, Yuanhong Wang, Shuang Yang and Zhihua Lv

Mar. Drugs 2022, 20(10), 631; https://doi.org/10.3390/md20100631 - 02 Oct 2022

Cited by 2 | Viewed by 2137

Abstract

Glycosaminoglycan from Apostichopus japonicus (AHG) and its depolymerized fragments (DAHGs) are anticoagulant fucosylated chondroitin sulfate. The aim of this study was to further evaluate the anticoagulant and antithrombic activity of AHG and DAHGs, as well as reveal the dynamic relationship between exposure and [...] Read more.

Glycosaminoglycan from Apostichopus japonicus (AHG) and its depolymerized fragments (DAHGs) are anticoagulant fucosylated chondroitin sulfate. The aim of this study was to further evaluate the anticoagulant and antithrombic activity of AHG and DAHGs, as well as reveal the dynamic relationship between exposure and effect in vivo. The results demonstrated that AHG100 (Mw~100 kDa), DAHG50 (Mw~50 kDa), and DAHG10 (Mw~10 kDa) exhibited potent anticoagulant activity by inhibiting intrinsic factor Xase complex (FXase) as well as antithrombin-dependent factor IIa (FIIa) and factor Xa (FXa). These glycosaminoglycans markedly prevented thrombosis formation and thrombin-induced platelet aggregation in a dose- and molecular weight-dependent manner in vitro and in vivo. The further bleeding time measurement indicated that DAHG10 exhibited obviously lower hemorrhage risks than native AHG100. Following oral administration, DAHG10 could be absorbed into blood, further dose-dependently prolonging activated partial thromboplastin time (APTT) and thrombin time (TT) as well as inhibiting FXa and FIIa partially through FXase. Anticoagulant activity was positively associated with plasma concentration following oral administration of DAHG10. Our study proposed a new point of view to understand the correlation between effects and exposure of fucosylated chondroitin sulfate as an effective and safe oral antithrombotic agent. Full article

(This article belongs to the Collection Marine Polysaccharides)

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16 pages, 4339 KiB

Open AccessArticle

Molecular Network Guided Cataloging of the Secondary Metabolome of Selected Egyptian Red Sea Soft Corals

by Nesrine M. Hegazi, Tarik A. Mohamed, Hamada H. Saad, Montaser A. Al-Hammady, Taha A. Hussien, Mohamed-Elamir F. Hegazy and Harald Gross

Mar. Drugs 2022, 20(10), 630; https://doi.org/10.3390/md20100630 - 01 Oct 2022

Cited by 3 | Viewed by 2180

Abstract

Soft corals are recognized as an abundant source of diverse secondary metabolites with unique chemical features and physiologic capabilities. However, the discovery of these metabolites is usually hindered by the traditional protocol which requires a large quantity of living tissue for isolation and [...] Read more.

Soft corals are recognized as an abundant source of diverse secondary metabolites with unique chemical features and physiologic capabilities. However, the discovery of these metabolites is usually hindered by the traditional protocol which requires a large quantity of living tissue for isolation and spectroscopic investigations. In order to overcome this problem, untargeted metabolomics protocols have been developed. The latter have been applied here to study the chemodiversity of common Egyptian soft coral species, using only minute amounts of coral biomass. Spectral similarity networks, based on high-resolution tandem mass spectrometry data, were employed to explore and highlight the metabolic biodiversity of nine Egyptian soft coral species. Species-specific metabolites were highlighted for future prioritization of soft coral species for MS-guided chemical investigation. Overall, 79 metabolites were tentatively assigned, encompassing diterpenes, sesquiterpenes, and sterols. Simultaneously, the methodology assisted in shedding light on newly-overlooked chemical diversity with potential undescribed scaffolds. For instance, glycosylated fatty acids, nitrogenated aromatic compounds, and polyketides were proposed in Sinularia leptoclados, while alkaloidal terpenes and N-acyl amino acids were proposed in both Sarcophyton roseum and Sarcophyton acutum. Full article

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17 pages, 2617 KiB

Open AccessArticle

A Comparative Study of the Anti-Obesity Effects of Dietary Sea Cucumber Saponins and Energy Restriction in Response to Weight Loss and Weight Regain in Mice

by Lu Wen, Rong Li, Ying-Cai Zhao, Jin-Yue Yang, Xiao-Yue Li, Chang-Hu Xue, Tian-Tian Zhang and Yu-Ming Wang

Mar. Drugs 2022, 20(10), 629; https://doi.org/10.3390/md20100629 - 01 Oct 2022

Cited by 2 | Viewed by 2043

Abstract

Dietary supplementation of sea cucumber saponins and calorie restriction have been proved to be effective in alleviating obesity, but the differences of anti-obesity effects between sea cucumber saponins and energy restriction during weight loss and weight regain are still unknown. In the present [...] Read more.

Dietary supplementation of sea cucumber saponins and calorie restriction have been proved to be effective in alleviating obesity, but the differences of anti-obesity effects between sea cucumber saponins and energy restriction during weight loss and weight regain are still unknown. In the present study, high-fat-induced obesity mice were randomly divided into three groups, including a high-fat diet group (HF), an energy restriction by 40% group (HF-L), and a sea cucumber saponins group (HF-S), to compare the effects of dietary sea cucumber saponins and energy restriction on the weight, glucose, and lipid metabolism of obese mice during weight loss and weight regain. The results showed that dietary 0.06% sea cucumber saponins and limiting energy intake by 40% had the same weight loss effect. Interestingly, sea cucumber saponins could alleviate impaired glucose tolerance and insulin resistance caused by obesity. In addition, the inhibited SREBP-1c mediated lipogenesis might lead to the alleviation of weight regain after resuming the high-fat diet even when sea cucumber saponins were no longer supplemented. In contrast, limiting energy intake tended to promote lipid synthesis in the liver and white adipose tissue after restoring a high-fat diet, and inflammation was also induced. The findings indicated that sea cucumber saponins could replace calorie restriction to prevent obesity and might be used as a functional food or drug to resist obesity and related diseases caused by obesity. Full article

(This article belongs to the Special Issue Commemorating the Launch of the Section “Marine-Derived Ingredients for Drugs, Cosmeceuticals and Nutraceuticals”)

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18 pages, 6831 KiB

Open AccessArticle

Network Pharmacological Analysis of the Red Sea Sponge Hyrtios erectus Extract to Reveal Anticancer Efficacy of Corresponding Loaded Niosomes

by Heba A. Abou-Taleb, Ahmed M. Sayed, Hesham Refaat, Faisal Alsenani, Eman Alaaeldin, Fatma A. Mokhtar, Usama Ramadan Abdelmohsen and Nourhan Hisham Shady

Mar. Drugs 2022, 20(10), 628; https://doi.org/10.3390/md20100628 - 01 Oct 2022

Cited by 6 | Viewed by 2174

Abstract

In this study, the LC-HRMS-assisted chemical profiling of Hyrtios erectus sponge led to the annotation of eleven major compounds (1–11). H. erectus-derived crude extract (HE) was tested in vitro for its antiproliferative activity against three human cancer cell [...] Read more.

In this study, the LC-HRMS-assisted chemical profiling of Hyrtios erectus sponge led to the annotation of eleven major compounds (1–11). H. erectus-derived crude extract (HE) was tested in vitro for its antiproliferative activity against three human cancer cell lines, Hep-G2 (human liver cancer cell line), MCF-7 (breast cancer cell line), and Caco-2 (colon cancer cell line), before and after encapsulation within niosomes. Hyrtios erectus extract showed moderate in vitro antiproliferative activities towards the studied cell lines with IC₅₀ values 18.5 ± 0.08, 15.2 ± 0.11, and 13.4 ± 0.12, respectively. The formulated extract-containing niosomes (size 142.3 ± 10.3 nm, PDI 0.279, and zeta potential 22.8 ± 1.6) increased the in vitro antiproliferative activity of the entrapped extract significantly (IC₅₀ 8.5 ± 0.04, 4.1 ± 0.07, and 3.4 ± 0.05, respectively). A subsequent computational chemical study was performed to build a sponge–metabolite–targets–cancer diseases network, by focusing on targets that possess anticancer activity toward the three cancer types: breast, colon, and liver. Pubchem, BindingDB, and DisGenet databases were used to build the network. Shinygo and KEGG databases in addition to FunRich software were used for gene ontology and functional analysis. The computational analysis linked the metabolites to 200 genes among which 147 genes related to cancer and only 64 genes are intersected in the three cancer types. The study proved that the co-occurrence of compounds 1, 2, 3, 7, 8, and 10 are the most probable compounds possessing cytotoxic activity due to large number of connections to the intersected cytotoxic genes with edges range from 9-14. The targets possess the anticancer effect through Pathways in cancer, Endocrine resistance and Proteoglycans in cancer as mentioned by KEGG and ShinyGo 7.1 databases. This study introduces niosomes as a promising strategy to promote the cytotoxic potential of H. erectus extract. Full article

(This article belongs to the Special Issue Marine Compounds and Research of the Middle East)

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20 pages, 6016 KiB

Open AccessArticle

Therapeutic Potential of Microalgae-Derived Bioactive Metabolites Is Influenced by Different Large-Scale Culture Strategies

by Jezabel Garcia-Parra, Claudio Fuentes-Grünewald and Deyarina Gonzalez

Mar. Drugs 2022, 20(10), 627; https://doi.org/10.3390/md20100627 - 30 Sep 2022

Cited by 2 | Viewed by 2388

Abstract

Microalgae have been identified as one of the most promising sources of novel bioactive compounds for biomedical applications, the food industry, and cosmetics. In the last decade, several biotechnological developments have facilitated the identification of a growing number of compounds as well as [...] Read more.

Microalgae have been identified as one of the most promising sources of novel bioactive compounds for biomedical applications, the food industry, and cosmetics. In the last decade, several biotechnological developments have facilitated the identification of a growing number of compounds as well as the study of optimal microalgae culture conditions for the production of biomass enriched in specific molecules of interest. In this study, two common commercial marine microalgae (Nannochloropsis oculata and Porphyridium purpureum) were cultured in standard and nutrient-stressed conditions and the obtained biomass extracts were assessed for their potential to inhibit cancer cell proliferation and migration as well as their antioxidant activity. Results from viability in 2D and 3D cancer cell models showed an enhancement of the antitumour activity of P. purpureum in the 3D model compared to 2D, together with a greater capacity to reduce the migration capacity of cancer cells with the biomass from nutrient-stressed conditions, whereas the antioxidant activity of N. oculata decreased when exposed to nutrient-stressed conditions. To date, this is one of the few studies that proves that controlled changes in large-scale culturing conditions such as nutrient depletion have a relevant impact in the bioactivity of the biomass on cancer cells. Full article

(This article belongs to the Special Issue Development and Application of Marine-Derived Anti-cancer Agents)

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25 pages, 7801 KiB

Open AccessArticle

Bioactive Peptides from Skipjack Tuna Cardiac Arterial Bulbs: Preparation, Identification, Antioxidant Activity, and Stability against Thermal, pH, and Simulated Gastrointestinal Digestion Treatments

by Wei-Wei Cai, Xiao-Meng Hu, Yu-Mei Wang, Chang-Feng Chi and Bin Wang

Mar. Drugs 2022, 20(10), 626; https://doi.org/10.3390/md20100626 - 30 Sep 2022

Cited by 41 | Viewed by 5622

Abstract

Cardiac arterial bulbs of Skipjack tuna (Katsuwonus pelamis) are rich in elastin, and its hydrolysates are high quality raw materials for daily cosmetics. In order to effectively utilizing Skipjack tuna processing byproducts-cardiac arterial bulbs and to prepare peptides with high antioxidant [...] Read more.

Cardiac arterial bulbs of Skipjack tuna (Katsuwonus pelamis) are rich in elastin, and its hydrolysates are high quality raw materials for daily cosmetics. In order to effectively utilizing Skipjack tuna processing byproducts-cardiac arterial bulbs and to prepare peptides with high antioxidant activity, pepsin was selected from six proteases for hydrolyzing proteins, and the best hydrolysis conditions of pepsin were optimized. Using ultrafiltration and chromatographic methods, eleven antioxidant peptides were purified from protein hydrolysate of tuna cardiac arterial bulbs. Four tripeptides (QGD, PKK, GPQ and GLN) were identified as well as seven pentapeptides (GEQSN, GEEGD, YEGGD, GEGER, GEGQR, GPGLM and GDRGD). Three out of them, namely the tripeptide PKK and the pentapeptides YEGGD and GPGLM exhibited the highest radical scavenging activities on 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl, 2,2′-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and superoxide anion assays. They also showed to protect plasmid DNA and HepG2 cells against H₂O₂-induced oxidative stress. Furthermore, they exhibited high stability under temperature ranged from 20-100 °C, pH values ranged from 3-11, and they simulated gastrointestinal digestion for 240 min. These results suggest that the prepared eleven antioxidant peptides from cardiac arterial bulbs, especially the three peptides PKK, YEGGD, and GPGLM, could serve as promising candidates in health-promoting products due to their high antioxidant activity and their stability. Full article

(This article belongs to the Special Issue Marine Linear Peptides: Isolation, Structure, Biological Properties, Synthesis, Biosynthesis, and Current Advances in Therapeutics)

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Mar. Drugs, Volume 20, Issue 10 (October 2022) – 69 articles

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