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15 pages, 1877 KiB

Open AccessArticle

Water-Soluble Saccharina latissima Polysaccharides and Relation of Their Structural Characteristics with In Vitro Immunostimulatory and Hypocholesterolemic Activities

by Ana S. P. Moreira, Diana Gaspar, Sónia S. Ferreira, Alexandra Correia, Manuel Vilanova, Marie-Mathilde Perrineau, Philip D. Kerrison, Claire M. M. Gachon, Maria Rosário Domingues, Manuel A. Coimbra, Filipe M. Coreta-Gomes and Cláudia Nunes

Mar. Drugs 2023, 21(3), 183; https://doi.org/10.3390/md21030183 - 16 Mar 2023

Cited by 7 | Viewed by 2078

Abstract

Brown macroalgae are an important source of polysaccharides, mainly fucose-containing sulphated polysaccharides (FCSPs), associated with several biological activities. However, the structural diversity and structure–function relationships for their bioactivities are still undisclosed. Thus, the aim of this work was to characterize the chemical structure [...] Read more.

Brown macroalgae are an important source of polysaccharides, mainly fucose-containing sulphated polysaccharides (FCSPs), associated with several biological activities. However, the structural diversity and structure–function relationships for their bioactivities are still undisclosed. Thus, the aim of this work was to characterize the chemical structure of water-soluble Saccharina latissima polysaccharides and evaluate their immunostimulatory and hypocholesterolemic activities, helping to pinpoint a structure–activity relationship. Alginate, laminarans (F1, neutral glucose-rich polysaccharides), and two fractions (F2 and F3) of FCSPs (negatively charged) were studied. Whereas F2 is rich in uronic acids (45 mol%) and fucose (29 mol%), F3 is rich in fucose (59 mol%) and galactose (21 mol%). These two fractions of FCSPs showed immunostimulatory activity on B lymphocytes, which could be associated with the presence of sulphate groups. Only F2 exhibited a significant effect in reductions in in vitro cholesterol’s bioaccessibility attributed to the sequestration of bile salts. Therefore, S. latissima FCSPs were shown to have potential as immunostimulatory and hypocholesterolemic functional ingredients, where their content in uronic acids and sulphation seem to be relevant for the bioactive and healthy properties. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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12 pages, 2145 KiB

Open AccessArticle

Isolation, Characterization and Immunomodulatory Activity Evaluation of Chrysolaminarin from the Filamentous Microalga Tribonema aequale

by Feifei Wang, Rundong Yang, Yuhao Guo and Chengwu Zhang

Mar. Drugs 2023, 21(1), 13; https://doi.org/10.3390/md21010013 - 24 Dec 2022

Cited by 3 | Viewed by 1324

Abstract

The aim of this study is to investigate the differences in the accumulation capacity of chrysolaminarin among six Tribonema species and to isolate this polysaccharide for immunomodulatory activity evaluation. The results showed that T. aequale was the most productive strain with the highest [...] Read more.

The aim of this study is to investigate the differences in the accumulation capacity of chrysolaminarin among six Tribonema species and to isolate this polysaccharide for immunomodulatory activity evaluation. The results showed that T. aequale was the most productive strain with the highest content and productivity of chrysolaminarin, which were 17.20% (% of dry weight) and 50.91 mg/L/d, respectively. Chrysolaminarin was then extracted and isolated from this alga, and its monosaccharide composition was mainly composed of a glucose (61.39%), linked by β-D-(1→3) (main chain) and β-D-(1→6) (branch chain) glycosidic bonds, with a molecular weight of less than 6 kDa. In vitro immunomodulatory assays showed that it could activate RAW264.7 cells at a certain concentration (1000 μg/mL), as evidenced by the increased phagocytic activity and upregulated mRNA expression levels of IL-1β, IL6, TNF-α and Nos2. Moreover, Western blot revealed that this polysaccharide stimulated the phosphorylation of p-65, p-38 and JNK in NF-κB and MAPK signaling pathways. Overall, these findings provide a reference for the further development and utilization of algae-based chrysolaminarin, while also offering an in-depth understanding of the immunoregulatory mechanism. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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16 pages, 3301 KiB

Open AccessArticle

Ethyl Acetate Extract of Marine Algae, Halymenia durvillei, Provides Photoprotection against UV-Exposure in L929 and HaCaT Cells

by Pichnaree Kraokaew, Preeyanuch Manohong, Prachayaporn Prasertsuksri, Prapaporn Jattujan, Nakhon Niamnont, Montakan Tamtin, Prasert Sobhon and Krai Meemon

Mar. Drugs 2022, 20(11), 707; https://doi.org/10.3390/md20110707 - 11 Nov 2022

Cited by 3 | Viewed by 2565

Abstract

Halymenia durvillei is a red alga distributed along the coasts of Southeast Asian countries including Thailand. Previous studies have shown that an ethyl acetate fraction of H. durvillei (HDEA), containing major compounds including n-hexadecanoic acid, 2-butyl-5-hexyloctahydro-1H-indene, 3-(hydroxyacetyl) indole and indole-3-carboxylic acid, possesses high [...] Read more.

Halymenia durvillei is a red alga distributed along the coasts of Southeast Asian countries including Thailand. Previous studies have shown that an ethyl acetate fraction of H. durvillei (HDEA), containing major compounds including n-hexadecanoic acid, 2-butyl-5-hexyloctahydro-1H-indene, 3-(hydroxyacetyl) indole and indole-3-carboxylic acid, possesses high antioxidant and anti-lung cancer activities. The present study demonstrated that HDEA could protect mouse skin fibroblasts (L929) and human immortalized keratinocytes (HaCaT) against photoaging due to ultraviolet A and B (UVA and UVB) by reducing intracellular reactive oxygen species (ROS) and expressions of matrix metalloproteinases (MMP1 and MMP3), as well as increasing Nrf2 nuclear translocation, upregulations of mRNA transcripts of antioxidant enzymes, including superoxide dismutase (SOD), heme oxygenase (HMOX) and glutathione S-transferase pi1 (GSTP1), and procollagen synthesis. The results indicate that HDEA has the potential to protect skin cells from UV irradiation through the activation of the Nrf2 pathway, which leads to decreasing intracellular ROS and MMP production, along with the restoration of skin collagen. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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15 pages, 932 KiB

Open AccessArticle

Comparative Study of the Pharmacological Properties of Luteolin and Its 7,3′-Disulfate

by Emma P. Kozlovskaya, Aleksandr M. Popov, Olga N. Styshova, Aleksey I. Vakhrushev, Tatyana A. Rutckova, Anna B. Podvolotskaya and Ludmila A. Tekutyeva

Mar. Drugs 2022, 20(7), 426; https://doi.org/10.3390/md20070426 - 28 Jun 2022

Cited by 2 | Viewed by 1746

Abstract

The global spread of the metabolic syndrome, oncological and viral diseases forces researchers to pay increased attention to the secondary metabolites of marine hydrobionts, which often have a high therapeutic potential in the treatment of these pathologies and are effective components of functional [...] Read more.

The global spread of the metabolic syndrome, oncological and viral diseases forces researchers to pay increased attention to the secondary metabolites of marine hydrobionts, which often have a high therapeutic potential in the treatment of these pathologies and are effective components of functional food. The flavone luteolin (LT), as one of the most widely distributed and studied plant metabolites, is distinguished by a diverse spectrum of biological activity and a pleiotropic nature of the mechanism of action at the molecular, cellular and organismal levels. However, there is still practically no information on the spectrum of biological activity of its sulfated derivatives, which are widely represented in seagrasses of the genus Zostera. In the present work, a comparative study of the pharmacological properties of LT and its 7,3′-disulfate was carried out with a brief analysis of the special role of sulfation in the pharmacological activity of flavonoids. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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14 pages, 16397 KiB

Open AccessArticle

In Silico Virtual Screening of Marine Aldehyde Derivatives from Seaweeds against SARS-CoV-2

by Nalae Kang, Seong-Yeong Heo, Seon-Heui Cha, Ginnae Ahn and Soo-Jin Heo

Mar. Drugs 2022, 20(6), 399; https://doi.org/10.3390/md20060399 - 16 Jun 2022

Cited by 7 | Viewed by 2295

Abstract

Coronavirus disease 2019, caused by the outbreak of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), is an ongoing global pandemic that poses an unprecedented threat to the global economy and human health. Several potent inhibitors targeting SARS-CoV-2 have been published; however, most of [...] Read more.

Coronavirus disease 2019, caused by the outbreak of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), is an ongoing global pandemic that poses an unprecedented threat to the global economy and human health. Several potent inhibitors targeting SARS-CoV-2 have been published; however, most of them have failed in clinical trials. This study aimed to assess the therapeutic compounds among aldehyde derivatives from seaweeds as potential SARS-CoV-2 inhibitors using a computer simulation protocol. The absorption, distribution, metabolism, excretion, and toxicity (ADME/Tox) properties of the compounds were analyzed using a machine learning algorithm, and the docking simulation of these compounds to the 3C-like protease (Protein Data Bank (PDB) ID: 6LU7) was analyzed using a molecular docking protocol based on the CHARMm algorithm. These compounds exhibited good drug-like properties following the Lipinski and Veber rules. Among the marine aldehyde derivatives, 4-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, and 5-bromoprotocatechualdehyde were predicted to have good absorption and solubility levels and non-hepatotoxicity in the ADME/Tox prediction. 3-hydroxybenzaldehyde and 3,4-dihydroxybenzaldehyde were predicted to be non-toxic in TOPKAT prediction. In addition, 3,4-dihydroxybenzaldehyde was predicted to exhibit interactions with the 3C-like protease, with binding energies of −71.9725 kcal/mol. The computational analyses indicated that 3,4-dihydroxybenzaldehyde could be regarded as potential a SARS-CoV-2 inhibitor. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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10 pages, 1292 KiB

Open AccessArticle

Mitigative Effects of PFF-A Isolated from Ecklonia cava on Pigmentation in a Zebrafish Model and Melanogenesis in B16F10 Cells

by Jun-Geon Je, Yunfei Jiang, Jun-Ho Heo, Xining Li, You-Jin Jeon and Bo-Mi Ryu

Mar. Drugs 2022, 20(2), 123; https://doi.org/10.3390/md20020123 - 04 Feb 2022

Cited by 3 | Viewed by 2368

Abstract

Melanin synthesis is a defense mechanism that prevents skin damage, but excessive accumulation of melanin occurs in the skin in various reactions such as pigmentation, lentigines, and freckles. Although anti-melanogenic effects have been demonstrated for various naturally occurring marine products that inhibit and [...] Read more.

Melanin synthesis is a defense mechanism that prevents skin damage, but excessive accumulation of melanin occurs in the skin in various reactions such as pigmentation, lentigines, and freckles. Although anti-melanogenic effects have been demonstrated for various naturally occurring marine products that inhibit and control tyrosinase activity, most studies have not been extended to in vivo applications. Phlorofucofuroeckol-A (PFF-A, 12.5–100 µM) isolated from Ecklonia cava has previously been shown to have tyrosinase-mitigative effects in B16F10 cells, but it has not been evaluated in an in vivo model, and its underlying mechanism for anti-melanogenic effects has not been studied. In the present study, we evaluated the safety and efficacy of PFF-A for anti-melanogenic effects in an in vivo model. We selected low doses of PFF-A (1.5–15 nM) and investigated their mitigative effects on pigmentation stimulated by α-MSH in vivo and their related-mechanism in an in vitro model. The findings suggest that low-dose PFF-A derived from E. cava suppresses pigmentation in vivo and melanogenesis in vitro. Therefore, this study presents the possibility that PFF-A could be utilized as a new anti-melanogenic agent in the cosmeceutical industries. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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18 pages, 1883 KiB

Open AccessArticle

Bioprospecting of Less-Polar Fractions of Ericaria crinita and Ericaria amentacea: Developmental Toxicity and Antioxidant Activity

by Sanja Radman, Lara Čižmek, Sanja Babić, Ana-Marija Cikoš, Rozelindra Čož-Rakovac, Stela Jokić and Igor Jerković

Mar. Drugs 2022, 20(1), 57; https://doi.org/10.3390/md20010057 - 06 Jan 2022

Cited by 20 | Viewed by 2606

Abstract

Ericaria crinita and Ericaria amentacea from the Adriatic Sea (Croatia) were investigated with respect to the presence of less-polar compounds for the first time after fractionation by solid-phase extraction (SPE). The composition of less-polar fractions of freeze-dried E. crinita (FdEc) and E. amentacea [...] Read more.

Ericaria crinita and Ericaria amentacea from the Adriatic Sea (Croatia) were investigated with respect to the presence of less-polar compounds for the first time after fractionation by solid-phase extraction (SPE). The composition of less-polar fractions of freeze-dried E. crinita (FdEc) and E. amentacea (FdEa) were analyzed by high-performance liquid chromatography–high-resolution mass spectrometry with electrospray ionization (UHPLC-ESI-HRMS). The major identified compounds were: amides of higher aliphatic acids (palmitoleamide, linoleamide, palmitamide, oleamide and erucamide) and related compounds, carotenoid (fucoxanthin), chlorophyll derivatives (pheophytin a and b and their derivatives) and higher terpenes (loliolide, isoamijiol with its oxidation product), β-stigmasterol and (3β,6α)-14-methylergosta-8,24(28)-diene-3,6-diol). The toxic effects observed on the less-polar fractions obtained from Ericaria species on zebrafish Danio rerio embryos could be associated with the high abundance of all five detected amides. The antioxidant activity of the fractions was evaluated by means of five independent assays, including the reduction of the radical cation (ABTS), the oxygen radical absorbance capacity (ORAC), ferric-reducing antioxidant power (FRAP), the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) assay and the Folin–Ciocalteu method. A higher antioxidant activity of E. amentacea in comparison to that of the E. crinita fractions was found with IC₅₀ concentrations of 0.072 and 1.177 mg/mL, respectively. The correlation between the activity and the chemical composition revealed that the synergistic effect of different compounds impacted their antioxidant response. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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Review

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32 pages, 761 KiB

Open AccessEditor’s ChoiceReview

Applications of Antioxidant Secondary Metabolites of Sargassum spp.

by Marcelo D. Catarino, Rita Silva-Reis, Amina Chouh, Sónia Silva, Susana S. Braga, Artur M. S. Silva and Susana M. Cardoso

Mar. Drugs 2023, 21(3), 172; https://doi.org/10.3390/md21030172 - 09 Mar 2023

Cited by 8 | Viewed by 6171

Abstract

Sargassum is one of the largest and most diverse genus of brown seaweeds, comprising of around 400 taxonomically accepted species. Many species of this genus have long been a part of human culture with applications as food, feed, and remedies in folk medicine. [...] Read more.

Sargassum is one of the largest and most diverse genus of brown seaweeds, comprising of around 400 taxonomically accepted species. Many species of this genus have long been a part of human culture with applications as food, feed, and remedies in folk medicine. Apart from their high nutritional value, these seaweeds are also a well-known reservoir of natural antioxidant compounds of great interest, including polyphenols, carotenoids, meroterpenoids, phytosterols, and several others. Such compounds provide a valuable contribution to innovation that can translate, for instance, into the development of new ingredients for preventing product deterioration, particularly in food products, cosmetics or biostimulants to boost crops production and tolerance to abiotic stress. This manuscript revises the chemical composition of Sargassum seaweeds, highlighting their antioxidant secondary metabolites, their mechanism of action, and multiple applications in fields, including agriculture, food, and health. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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26 pages, 1278 KiB

Open AccessReview

Seaweed as a Natural Source against Phytopathogenic Bacteria

by Tânia F. L. Vicente, Carina Félix, Rafael Félix, Patrícia Valentão and Marco F. L. Lemos

Mar. Drugs 2023, 21(1), 23; https://doi.org/10.3390/md21010023 - 28 Dec 2022

Cited by 7 | Viewed by 4722

Abstract

Plant bacterial pathogens can be devastating and compromise entire crops of fruit and vegetables worldwide. The consequences of bacterial plant infections represent not only relevant economical losses, but also the reduction of food availability. Synthetic bactericides have been the most used tool to [...] Read more.

Plant bacterial pathogens can be devastating and compromise entire crops of fruit and vegetables worldwide. The consequences of bacterial plant infections represent not only relevant economical losses, but also the reduction of food availability. Synthetic bactericides have been the most used tool to control bacterial diseases, representing an expensive investment for the producers, since cyclic applications are usually necessary, and are a potential threat to the environment. The development of greener methodologies is of paramount importance, and some options are already available in the market, usually related to genetic manipulation or plant community modulation, as in the case of biocontrol. Seaweeds are one of the richest sources of bioactive compounds, already being used in different industries such as cosmetics, food, medicine, pharmaceutical investigation, and agriculture, among others. They also arise as an eco-friendly alternative to synthetic bactericides. Several studies have already demonstrated their inhibitory activity over relevant bacterial phytopathogens, some of these compounds are known for their eliciting ability to trigger priming defense mechanisms. The present work aims to gather the available information regarding seaweed extracts/compounds with antibacterial activity and eliciting potential to control bacterial phytopathogens, highlighting the extracts from brown algae with protective properties against microbial attack. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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22 pages, 1658 KiB

Open AccessReview

Macroalgae Specialized Metabolites: Evidence for Their Anti-Inflammatory Health Benefits

by Djenisa H. A. Rocha, Diana C. G. A. Pinto and Artur M. S. Silva

Mar. Drugs 2022, 20(12), 789; https://doi.org/10.3390/md20120789 - 19 Dec 2022

Cited by 11 | Viewed by 2010

Abstract

Inflammation is an organism’s response to chemical or physical injury. It is split into acute and chronic inflammation and is the last, most significant cause of death worldwide. Nowadays, according to the World Health Organization (WHO), the greatest threat to human health is [...] Read more.

Inflammation is an organism’s response to chemical or physical injury. It is split into acute and chronic inflammation and is the last, most significant cause of death worldwide. Nowadays, according to the World Health Organization (WHO), the greatest threat to human health is chronic disease. Worldwide, three out of five people die from chronic inflammatory diseases such as stroke, chronic respiratory diseases, heart disorders, and cancer. Nowadays, anti-inflammatory drugs (steroidal and non-steroidal, enzyme inhibitors that are essential in the inflammatory process, and receptor antagonists, among others) have been considered as promising treatments to be explored. However, there remains a significant proportion of patients who show poor or incomplete responses to these treatments or experience associated severe side effects. Seaweeds represent a valuable resource of bioactive compounds associated with anti-inflammatory effects and offer great potential for the development of new anti-inflammatory drugs. This review presents an overview of specialized metabolites isolated from seaweeds with in situ and in vivo anti-inflammatory properties. Phlorotannins, carotenoids, sterols, alkaloids, and polyunsaturated fatty acids present significant anti-inflammatory effects given that some of them are involved directly or indirectly in several inflammatory pathways. The majority of the isolated compounds inhibit the pro-inflammatory mediators/cytokines. Studies have suggested an excellent selectivity of chromene nucleus towards inducible pro-inflammatory COX-2 than its constitutive isoform COX-1. Additional research is needed to understand the mechanisms of action of seaweed’s compounds in inflammation, given the production of sustainable and healthier anti-inflammatory agents. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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35 pages, 2610 KiB

Open AccessReview

A Systematic Review on Marine Algae-Derived Fucoxanthin: An Update of Pharmacological Insights

by Md. Mohibbullah, Md. Nazmul Haque, Abdullah Al Mamun Sohag, Md. Tahmeed Hossain, Md. Sarwar Zahan, Md. Jamal Uddin, Md. Abdul Hannan, Il Soo Moon and Jae-Suk Choi

Mar. Drugs 2022, 20(5), 279; https://doi.org/10.3390/md20050279 - 22 Apr 2022

Cited by 31 | Viewed by 4507

Abstract

Fucoxanthin, belonging to the xanthophyll class of carotenoids, is a natural antioxidant pigment of marine algae, including brown macroalgae and diatoms. It represents 10% of the total carotenoids in nature. The plethora of scientific evidence supports the potential benefits of nutraceutical and pharmaceutical [...] Read more.

Fucoxanthin, belonging to the xanthophyll class of carotenoids, is a natural antioxidant pigment of marine algae, including brown macroalgae and diatoms. It represents 10% of the total carotenoids in nature. The plethora of scientific evidence supports the potential benefits of nutraceutical and pharmaceutical uses of fucoxanthin for boosting human health and disease management. Due to its unique chemical structure and action as a single compound with multi-targets of health effects, it has attracted mounting attention from the scientific community, resulting in an escalated number of scientific publications from January 2017 to February 2022. Fucoxanthin has remained the most popular option for anti-cancer and anti-tumor activity, followed by protection against inflammatory, oxidative stress-related, nervous system, obesity, hepatic, diabetic, kidney, cardiac, skin, respiratory and microbial diseases, in a variety of model systems. Despite much pharmacological evidence from in vitro and in vivo findings, fucoxanthin in clinical research is still not satisfactory, because only one clinical study on obesity management was reported in the last five years. Additionally, pharmacokinetics, safety, toxicity, functional stability, and clinical perspective of fucoxanthin are substantially addressed. Nevertheless, fucoxanthin and its derivatives are shown to be safe, non-toxic, and readily available upon administration. This review will provide pharmacological insights into fucoxanthin, underlying the diverse molecular mechanisms of health benefits. However, it requires more activity-oriented translational research in humans before it can be used as a multi-target drug. Full article

(This article belongs to the Special Issue Seaweed Bioactive Metabolites: Health Benefits and Potential Applications)

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