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Innovative Marine Molecules: Chemistry, Biology and Analysis

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Food Chemistry".

Deadline for manuscript submissions: closed (30 November 2022) | Viewed by 18481

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Dr. Sérgio Sousa

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Centro de Biotecnologia e Química Fina (CBQF), Universidade Católica Portuguesa, 4169-005 Porto, Portugal
Interests: microalgae; lipids; marine bioactives; biotechnology; probiotics; prebiotics; microencapsulation; food science and technology; functional foods
Special Issues, Collections and Topics in MDPI journals

Dr. Ana Gomes

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Associate Professor, CBQF—Centro de Biotecnologia e Química Fina—Laboratório Associado, Universidade Católica Portuguesa, Escola Superior de Biotecnologia, Rua Diogo Botelho 1327, 4169-005 Porto, Portugal
Interests: live biotherapeutics; beneficial microorganims; probiotics; microencapsulation
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Dr. Ana P. Carvalho

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CBQF–Centro de Biotecnologia e Química Fina–Laboratório Associado, Universidade Católica Portuguesa, Escola Superior de Biotecnologia, Rua Diogo Botelho 1327, 4169-005 Porto, Portugal
Interests: by-product valorisation; green extraction processes; functional ingredients; marine bioactive lipids; microalgae; omega-3 fatty acids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Currently, the world population stands at 7.9 billion and the resources available to support the needs and feed such numbers are growing shorter. As ca. 71% of planet Earth is covered by water, 96.5% of which is contained in oceans, the marine environment is being increasingly explored to substitute, and also complement, the conventional sources of a panoply of compounds and molecules. It is also being explored as a source of innovative molecules that may be used in areas that range from food, supplements and pharmaceuticals, to cosmetics, agrofertilizers and fuel.

The diversity of compounds that can be found in marine resources is extraordinary, and recent research has focused on many different molecules, such as carbohydrates, proteins, lipids, pigments, vitamins, among others, which may be found in a multitude of organisms such as macroalgae, microalgae, fish, mollusks and crustaceans.

In light of this, the present Special Issue aims to collect and compile recent research (in the form of original research articles and reviews) within the scope of food chemistry, regarding either sources or final objectives, and in relation to innovative marine molecules in terms of their chemical and biological natures as well as their analysis.

Dr. Sérgio Sousa
Prof. Dr. Ana Gomes
Dr. Ana P. Carvalho
Guest Editors

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

food (product)
marine molecules
chemical structure
isolation
purification
characterization
bioactivity
mechanism of action
analysis methods

Related Special Issue

Innovative Marine Molecules: Chemistry, Biology and Analysis (Volume II) in Molecules

Published Papers (9 papers)

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Research

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23 pages, 5507 KiB

Open AccessArticle

Towards Developing Novel Prostate Cancer Recurrence Suppressors: Acute Toxicity of Pseurotin A, an Orally Active PCSK9 Axis-Targeting Small-Molecule in Swiss Albino Mice

by Oliver C. McGehee, Hassan Y. Ebrahim, Ashkan H. Rad, Khaldoun S. Abdelwahed, Ethar A. Mudhish, Judy A. King, Iman E. Helal, Sharon A. Meyer and Khalid A. El Sayed

Molecules 2023, 28(3), 1460; https://doi.org/10.3390/molecules28031460 - 02 Feb 2023

Cited by 2 | Viewed by 2132

Abstract

The proprotein convertase subtilisin kexin type 9 (PCSK9) emerged as a molecular target of great interest for the management of cardiovascular disorders due to its ability to reduce low density lipoprotein (LDL) cholesterol by binding and targeting at LDLR for lysosomal degradation in cells. Preliminary studies revealed that pseurotin A (PsA), a spiro-heterocyclic γ-lactam alkaloid from several marine and terrestrial Aspergillus and Penicillium species, has the ability to dually suppress the PCSK9 expression and protein–protein interaction (PPI) with LDLR, resulting in an anti-hypercholesterolemic effect and modulating the oncogenic role of PCSK9 axis in breast and prostate cancers progression and recurrence. Thus, a preliminary assessment of the PsA acute toxicity represents the steppingstone to develop PsA as a novel orally active PCSK9 axis modulating cancer recurrence inhibitor. PsA studies for in vitro toxicity on RWPE-1 and CCD 841 CoN human non-tumorigenic prostate and colon cells, respectively, indicated a cellular death shown at a 10-fold level of its reported anticancer activity. Moreover, a Western blot analysis revealed a significant downregulation of the pro-survival marker Bcl-2, along with the upregulation of the proapoptotic Bax and caspases 3/7, suggesting PsA-mediated induction of cell apoptosis at very high concentrations. The Up-and-Down methodology determined the PsA LD₅₀ value of >550 mg/kg in male and female Swiss albino mice. Animals were orally administered single doses of PsA at 10, 250, and 500 mg/kg by oral gavage versus vehicle control. Mice were observed daily for 14 days with special care over the first 24 h after dosing to monitor any abnormalities in their behavioral, neuromuscular, and autonomic responses. After 14 days, the mice were euthanized, and their body and organ weights were recorded and collected. Mice plasma samples were subjected to comprehensive hematological and biochemical analyses. Collected mouse organs were histopathologically examined. No morbidity was detected following the PsA oral dosing. The 500 mg/kg female dosing group showed a 45% decrease in the body weight after 14 days but displayed no other signs of toxicity. The 250 mg/kg female dosing group had significantly increased serum levels of liver transaminases AST and ALT versus vehicle control. Moreover, a modest upregulation of apoptotic markers was observed in liver tissues of both animal sexes at 500 mg/kg dose level. However, a histopathological examination revealed no damage to the liver, kidneys, heart, brain, or lungs. While these findings suggest a possible sex-related toxicity at higher doses, the lack of histopathological injury implies that single oral doses of PsA, up to 50-fold the therapeutic dose, do not cause acute organ toxicity in mice though further studies are warranted. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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22 pages, 3145 KiB

Open AccessArticle

Antifungal Potential of Marine Organisms of the Yucatan Peninsula (Mexico) against Medically Important Candida spp.

by Dawrin Pech-Puch, Diana Grilo, Susana Eunice Calva-Pérez, Andreia Pedras, Harold Villegas-Hernández, Sergio Guillén-Hernández, Raúl Díaz-Gamboa, Mateo Forero Tunjano, Jaime Rodríguez, Oscar A. Lenis-Rojas, Carlos Jiménez and Catarina Pimentel

Molecules 2023, 28(2), 606; https://doi.org/10.3390/molecules28020606 - 06 Jan 2023

Viewed by 1552

Abstract

Invasive fungal infections represent a global health threat. They are associated with high mortality and morbidity rates, partly due to the ineffectiveness of the available antifungal agents. The rampant increase in infections recalcitrant to the current antifungals has worsened this scenario and made the discovery of new and more effective antifungals a pressing health issue. In this study, 65 extracts from marine organisms of the Yucatan Peninsula, Mexico, were screened for antifungal activity against Candida albicans and Candida glabrata, two of the most prevalent fungal species that cause nosocomial invasive fungal infections worldwide. A total of 51 sponges, 13 ascidians and 1 gorgonian were collected from the coral reef and mangrove forest in the Yucatan Peninsula (Mexico) and extracted with organic solvents. Nine crude extracts showed potent antifungal activity, of which four extracts from the sponge species Aiolochroia crassa, Amphimedon compressa, Monanchora arbuscula and Agelas citrina had promising activity against Candida spp. Bioassay-guided fractionation of the M. arbuscula extract revealed the remarkable fungicidal activity of some fractions. Analysis of the chemical composition of one of the most active fractions by UHPLC-HRMS and NMR indicated the presence of mirabilin B and penaresidin B, and their contribution to the observed antifungal activity is discussed. Overall, this work highlights marine organisms of the Yucatan Peninsula as important reservoirs of natural products with promising fungicidal activity, which may greatly advance the treatment of invasive fungal infections, especially those afflicting immunosuppressed patients. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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10 pages, 1598 KiB

Open AccessArticle

Positional Distribution of Fatty Acids in Processed Chinook Salmon Roe Lipids Determined by ¹³C Magnetic Resonance Spectroscopy (NMR)

by Senni Bunga, Mirja Kaizer Ahmmed, Alan Carne and Alaa El-Din A. Bekhit

Molecules 2023, 28(1), 454; https://doi.org/10.3390/molecules28010454 - 03 Jan 2023

Viewed by 1955

Abstract

Recently, there has been great interest in the lipidomic of marine lipids and their potential health benefits. Processing of seafood products can potentially modify the characteristics and composition of lipids. The present study investigated the effect of processing methods (salting and fermentation) on the positional distribution of fatty acids of Chinook salmon roe using ¹³C nuclear magnetic resonance spectroscopy (NMR). The NMR analysis provided information on the carbonyl atom, double bond/olefinic, glycerol backbone, aliphatic group, and chain ending methyl group regions. The obtained data showed that docosahexaenoic acid (DHA) is the main fatty acid esterified at the sn-2 position of the triacylglycerides (TAGs), while other fatty acids, such as eicosapentaenoic acid (EPA) and stearidonic acid (SDA), were randomly distributed or preferentially esterified at the sn-1 and sn-3 positions. Fermentation of salmon roe was found to enrich the level of DHA at the sn-2 position of the TAG. The processing of roe by both salt drying and fermentation did not appear to affect the proportion of EPA at the sn-2 position. This present study demonstrated that fish roe processing can enhance the proportion of DHA at the sn-2 position and potentially improve its bioavailability. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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11 pages, 1954 KiB

Open AccessArticle

Sarcoconvolutums F and G: Polyoxygenated Cembrane-Type Diterpenoids from Sarcophyton convolutum, a Red Sea Soft Coral

by Tarik A. Mohamed, Abdelsamed I. Elshamy, Mohamed H. Abd El-Razek, Asmaa M. Abdel-Tawab, Sherin K. Ali, Mohamed Aboelmagd, Midori Suenaga, Paul W. Pare, Akemi Umeyama and Mohamed-Elamir F. Hegazy

Molecules 2022, 27(18), 5835; https://doi.org/10.3390/molecules27185835 - 08 Sep 2022

Cited by 3 | Viewed by 1596

Abstract

Natural products and chemical analogues are widely used in drug discovery, notably in cancer and infectious disease pharmacotherapy. Sarcophyton convolutum (Alcyoniidae) a Red Sea–derived soft coral has been shown to be a rich source of macrocyclic diterpenes and cyclized derivatives. Two previously undescribed polyoxygenated cembrane-type diterpenoids, sarcoconvolutums F (1) and G (2), as well as four identified analogues (3–6) together with a furan derivate (7) were isolated from a solvent extract. Compounds were identified by spectroscopic techniques, including NMR, HREIMS, and CD, together with close spectral comparisons of previously published data. Sarcoconvolutum F (1) contains a rare 1-peroxid-15-hydroxy-10-ene functionality. Isolated metabolites (1–7) were screened against lung adenocarcinoma (A549), cervical cancer (HeLa) and oral cavity carcinoma (HSC-2) lines. Compound 4 exhibited an IC₅₀ 56 µM and 55 µM against A549 and HSC-2 cells, respectively. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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11 pages, 873 KiB

Open AccessArticle

Natural Products Produced in Culture by Biosynthetically Talented Salinispora arenicola Strains Isolated from Northeastern and South Pacific Marine Sediments

by David E. Williams, Kalindi D. Morgan, Doralyn S. Dalisay, Teatulohi Matainaho, Elodie Perrachon, Noemie Viller, Maïlys Delcroix, Jeanne Gauchot, Haruka Niikura, Brian O. Patrick, Katherine S. Ryan and Raymond J. Andersen

Molecules 2022, 27(11), 3569; https://doi.org/10.3390/molecules27113569 - 02 Jun 2022

Cited by 1 | Viewed by 1841

Abstract

Laboratory cultures of two ‘biosynthetically talented’ bacterial strains harvested from tropical and temperate Pacific Ocean sediment habitats were examined for the production of new natural products. Cultures of the tropical Salinispora arenicola strain RJA3005, harvested from a PNG marine sediment, produced salinorcinol (3) and salinacetamide (4), which had previously been reported as products of engineered and mutated strains of Amycolatopsis mediterranei, but had not been found before as natural products. An S. arenicola strain RJA4486, harvested from marine sediment collected in the temperate ocean waters off British Columbia, produced the new aminoquinone polyketide salinisporamine (5). Natural products 3, 4, and 5 are putative shunt products of the widely distributed rifamycin biosynthetic pathway. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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11 pages, 2709 KiB

Open AccessArticle

Cembranolides and Related Constituents from the Soft Coral Sarcophyton cinereum

by Chih-Hua Chao, Yi-Ju Chen, Chiung-Yao Huang, Fang-Rong Chang, Chang-Feng Dai and Jyh-Horng Sheu

Molecules 2022, 27(6), 1760; https://doi.org/10.3390/molecules27061760 - 08 Mar 2022

Cited by 4 | Viewed by 1582

Abstract

In an attempt to explore the bioactive metabolites of the soft coral Sarcophyton cinereum, three new cembranolides, cinerenolides A–C (1–3), and 16 known compounds were isolated and identified from the EtOAc extract. The structures of the new cembranolides were elucidated on the basis of spectroscopic analysis, and the NOE analysis of cinerenolide A (1) was performed with the assistance of the calculated lowest-energy molecular model. The relative configuration of cinerenolide C (3) was determined by the quantum chemical NMR calculation, followed by applying DP4+ analysis. In addition, the cytotoxic assays disclosed that some compounds exhibited moderate to potent activities in the proliferation of P388, DLD-1, HuCCT-1, and CCD966SK cell lines. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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15 pages, 3023 KiB

Open AccessArticle

New Carbonic Anhydrase-II Inhibitors from Marine Macro Brown Alga Dictyopteris hoytii Supported by In Silico Studies

by Kashif Rafiq, Ajmal Khan, Najeeb Ur Rehman, Sobia Ahsan Halim, Majid Khan, Liaqat Ali, Abdullah Hilal Al-Balushi, Haitham Khamis Al-Busaidi and Ahmed Al-Harrasi

Molecules 2021, 26(23), 7074; https://doi.org/10.3390/molecules26237074 - 23 Nov 2021

Cited by 7 | Viewed by 1879

Abstract

In continuation of phytochemical investigations of the methanolic extract of Dictyopteris hoytii, we have obtained twelve compounds (1–12) through column chromatography. Herein, three compounds, namely, dimethyl 2-bromoterepthalate (3), dimethyl 2,6-dibromoterepthalate (4), and (E)-3-(4-(dimethoxymethyl)phenyl) acrylic acid (5) are isolated for the first time as a natural product, while the rest of the compounds (1, 2, 6–12) are known and isolated for the first time from this source. The structures of the isolated compounds were elucidated by advanced spectroscopic 1D and 2D NMR techniques including ¹H, ¹³C, DEPT, HSQC, HMBC, COSY, NEOSY, and HR-MS and comparison with the reported literature. Furthermore, eight compounds (13–20) previously isolated by our group from the same source along with the currently isolated compounds (1–12) were screened against the CA-II enzyme. All compounds, except 6, 8, 14, and 17, were evaluated for in vitro bovine carbonic anhydrase-II (CA-II) inhibitory activity. Eventually, eleven compounds (1, 4, 5, 7, 9, 10, 12, 13, 15, 18, and 19) exhibited significant inhibitory activity against CA-II with IC₅₀ values ranging from 13.4 to 71.6 μM. Additionally, the active molecules were subjected to molecular docking studies to predict the binding behavior of those compounds. It was observed that the compounds exhibit the inhibitory potential by specifically interacting with the ZN ion present in the active site of CA-II. In addition to ZN ion, two residues (His94 and Thr199) play an important role in binding with the compounds that possess a carboxylate group in their structure. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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27 pages, 5729 KiB

Open AccessArticle

Mollusc-Derived Brominated Indoles for the Selective Inhibition of Cyclooxygenase: A Computational Expedition

by Md. Mominur Rahman, Md. Junaid, S. M. Zahid Hosen, Mohammad Mostafa, Lei Liu and Kirsten Benkendorff

Molecules 2021, 26(21), 6538; https://doi.org/10.3390/molecules26216538 - 29 Oct 2021

Cited by 4 | Viewed by 2337

Abstract

Inflammation plays an important role in different chronic diseases. Brominated indoles derived from the Australian marine mollusk Dicathais orbita (D. orbita) are of interest for their anti-inflammatory properties. This study evaluates the binding mechanism and potentiality of several brominated indoles (tyrindoxyl sulfate, tyrindoleninone, 6-bromoisatin, and 6,6′-dibromoindirubin) against inflammatory mediators cyclooxygenases-1/2 (COX-1/2) using molecular docking, followed by molecular dynamics simulation, along with physicochemical, drug-likeness, pharmacokinetic (pk), and toxicokinetic (tk) properties. Molecular docking identified that these indole compounds are anchored, with the main amino acid residues, positioned in the binding pocket of the COX-1/2, required for selective inhibition. Moreover, the molecular dynamics simulation based on root mean square deviation (RMSD), radius of gyration (Rg), solvent accessible surface area (SASA), and root mean square fluctuation (RMSF) analyses showed that these natural brominated molecules transit rapidly to a progressive constant configuration during binding with COX-1/2 and seem to accomplish a consistent dynamic behavior by maintaining conformational stability and compactness. The results were comparable to the Food and Drug Administration (FDA)-approved selective COX inhibitor, aspirin. Furthermore, the free energy of binding for the compounds assessed by molecular mechanics–Poisson–Boltzmann surface area (MM–PBSA) confirmed the binding capacity of indoles towards COX-1/2, with suitable binding energy values except for the polar precursor tyrindoxyl sulfate (with COX-1). The physicochemical and drug-likeness analysis showed zero violations of Lipinski’s rule, and the compounds are predicted to have excellent pharmacokinetic profiles. These indoles are projected to be non-mutagenic and free from hepatotoxicity, with no inhibition of human ether-a-go–go gene (hERG) I inhibitors, and the oral acute toxicity LD₅₀ in rats is predicted to be similar or lower than aspirin. Overall, this work has identified a plausible mechanism for selective COX inhibition by natural marine indoles as potential therapeutic candidates for the mitigation of inflammation. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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Review

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42 pages, 7173 KiB

Open AccessReview

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

by Carla Fernandes, Ricardo Ribeiro, Madalena Pinto and Anake Kijjoa

Molecules 2023, 28(2), 615; https://doi.org/10.3390/molecules28020615 - 07 Jan 2023

Cited by 5 | Viewed by 1960

Abstract

Cyclopeptides are considered as one of the most important classes of compounds derived from marine sources, due to their structural diversity and a myriad of their biological and pharmacological activities. Since marine-derived cyclopeptides consist of different amino acids, many of which are non-proteinogenic, they possess various stereogenic centers. In this respect, the structure elucidation of new molecular scaffolds obtained from natural sources, including marine-derived cyclopeptides, can become a very challenging task. The determination of the absolute configurations of the amino acid residues is accomplished, in most cases, by performing acidic hydrolysis, followed by analyses by liquid chromatography (LC). In a continuation with the authors’ previous publication, and to analyze the current trends, the present review covers recently published works (from January 2018 to November 2022) regarding new cyclopeptides from marine organisms, with a special focus on their biological/pharmacological activities and the absolute stereochemical assignment of the amino acid residues. Ninety-one unreported marine-derived cyclopeptides were identified during this period, most of which displayed anticancer or antimicrobial activities. Marfey’s method, which involves LC, was found to be the most frequently used for this purpose. Full article

(This article belongs to the Special Issue Innovative Marine Molecules: Chemistry, Biology and Analysis)

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