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

Deadline for manuscript submissions: closed (30 May 2020) | Viewed by 63733

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Prof. Dr. Felix Lopez Figueroa

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Department of Ecology and Geology, Faculty of Sciences, University of Málaga, E-29071 Málaga, Spain
Interests: algal photobiology; antioxidants; cosmeceutics; integrated multitrophic aquaculture; UV-photoprotectors

Special Issue Information

Dear Colleagues,

In the last 10 years, a great number of publications (both regular papers and reviews) have been published on the interesting molecules of mycosporine-like amino acid. They have been detected in cyanobacteria, microalgae, macroalgae, and marine animals (by ingestion). Despite significant advances in the research of MAAs, current overviews in the recent publications involving MAA research still need reporting. The aim of this Special Issue is to join as an interdisciplinary approach, the photochemical and photobiological aspects, with emphasis on the bioactive properties, such as UV photoprotectors, antioxidant, immunostimulant, growth factor, DNA protection, inhibition of collagenase, elastase and hyaluronidase, and anti-photoaging, among others, and its potential use as nutracosmeceutic molecules (i.e., oral and topic photoprotector).

I cordially invite researchers to contribute to this Special Issue by submitting original research articles and review papers.

Prof. Dr. Felix Lopez Figueroa
Guest Editor

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Keywords

Isolation and structure elucidation of MAAs
Identification and regulation of biosynthetic genes of MAAs
Excited state properties, photo, and thermostability of MAAs
MAAs in cyanobacteria, microalgae, and macroalgae
MAAs in marine animals: pharmacological applications
Antioxidant capacity of MAAs
Immunological properties of MAAs
Anti-photoaging capacity and skin photoprotection
MAAs like substances produced by chemical synthesis
MAAs in cosmeceutic products

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Published Papers (10 papers)

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Research

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26 pages, 2014 KiB

Open AccessArticle

Cyanobacteria and Red Macroalgae as Potential Sources of Antioxidants and UV Radiation-Absorbing Compounds for Cosmeceutical Applications

by Julia Vega, José Bonomi-Barufi, Juan Luis Gómez-Pinchetti and Félix L. Figueroa

Mar. Drugs 2020, 18(12), 659; https://doi.org/10.3390/md18120659 - 21 Dec 2020

Cited by 60 | Viewed by 7849

Abstract

In recent years, research on natural products has gained considerable attention, particularly in the cosmetic industry, which is looking for new bio-active and biodegradable molecules. In this study, cosmetic properties of cyanobacteria and red macroalgae were analyzed. The extractions were conducted in different solvents (water, ethanol and two combinations of water:ethanol). The main molecules with antioxidant and photoprotective capacity were mycosporine-like amino acids (MAAs), scytonemin and phenolic compounds. The highest contents of scytonemin (only present in cyanobacteria) were observed in Scytonema sp. (BEA 1603B) and Lyngbya sp. (BEA 1328B). The highest concentrations of MAAs were found in the red macroalgae Porphyra umbilicalis, Gelidium corneum and Osmundea pinnatifida and in the cyanobacterium Lyngbya sp. Scytonema sp. was the unique species that presented an MAA with maximum absorption in the UV-B band, being identified as mycosporine-glutaminol for the first time in this species. The highest content of polyphenols was observed in Scytonema sp. and P. umbilicalis. Water was the best extraction solvent for MAAs and phenols, whereas scytonemin was better extracted in a less polar solvent such as ethanol:_dH₂O (4:1). Cyanobacterium extracts presented higher antioxidant activity than those of red macroalgae. Positive correlations of antioxidant activity with different molecules, especially polyphenols, biliproteins and MAAs, were observed. Hydroethanolic extracts of some species incorporated in creams showed an increase in the photoprotection capacity in comparison with the base cream. Extracts of these organisms could be used as natural photoprotectors improving the diversity of sunscreens. The combination of different extracts enriched in scytonemin and MAAs could be useful to design broad-band natural UV-screen cosmeceutical products. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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19 pages, 3025 KiB

Open AccessArticle

Efficient Extraction and Antioxidant Capacity of Mycosporine-Like Amino Acids from Red Alga Dulse Palmaria palmata in Japan

by Yuki Nishida, Yuya Kumagai, Shunta Michiba, Hajime Yasui and Hideki Kishimura

Mar. Drugs 2020, 18(10), 502; https://doi.org/10.3390/md18100502 - 30 Sep 2020

Cited by 46 | Viewed by 8592

Abstract

Mycosporine-like amino acids (MAAs) are the ultraviolet (UV)-absorbable compounds, which are naturally produced by cyanobacteria and algae. Not only these algae but also marine organisms utilize MAAs to protect their DNA from UV-induced damage. On the other hand, the content of MAAs in algae was changed by the environmental condition and season. In addition to the UV-protected function, the antioxidant capacity of MAAs can apply to the cosmetic sunscreen materials and anti-cancer for human health. In this study, we developed the efficient extraction method of MAAs from red alga dulse in Usujiri (Hokkaido, Japan) and investigated the monthly variation. We also evaluated the antioxidant capacity. We employed the successive extraction method of water and then methanol extraction. Spectrophotometric and HPLC analyses revealed that the yield of MAAs by 6 h water extraction was the highest among the tested conditions, and the content of MAAs in the sample of February was the most (6.930 µmol g⁻¹ dry weight) among the sample from January to May in 2019. Antioxidant capacity of MAAs such as crude MAAs, the purified palythine and porphyra-334 were determined by 2,2’-azinobis(3-ethylbenzothiazoline 6-sulfonic acid) (ABTS) radical scavenging and ferrous reducing power assays in various pH conditions, showing that the highest scavenging activity and reducing power were found at alkaline condition (pH 8.0). Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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17 pages, 1821 KiB

Open AccessArticle

Seasonal Variation of Mycosporine-Like Amino Acids in Three Subantarctic Red Seaweeds

by Jocelyn Jofre, Paula S. M. Celis-Plá, Félix L. Figueroa and Nelso P. Navarro

Mar. Drugs 2020, 18(2), 75; https://doi.org/10.3390/md18020075 - 24 Jan 2020

Cited by 27 | Viewed by 4690

Abstract

UV-absorbing compounds, such as mycosporine-like amino acids (MAAs), are a group of secondary metabolites present in many marine species, including red seaweeds. In these organisms, the content and proportion of the composition of MAAs vary, depending on the species and several environmental factors. Its high cosmetic interest calls for research on the content and composition of MAAs, as well as the dynamics of MAAs accumulation in seaweeds from different latitudes. Therefore, this study aimed to survey the content of UV-absorbing MAAs in three Subantarctic red seaweeds during a seasonal cycle. Using spectrophotometric and HPLC techniques, the content and composition of MAAs of intertidal Iridaea tuberculosa, Nothogenia fastigiate, and Corallina officinalis were assessed. Some samples were also analyzed using high-resolution mass spectrometry coupled with HPLC-ESI-MS in order to identify more precisely the MAA composition. I. tuberculosa exhibited the highest MAA values (above 1 mg g⁻¹ of dried mass weight), while C. officinalis showed values not exceeding 0.4 mg g⁻¹. Porphyra-334 was the main component in N. fastigiata, whereas I. tuberculosa and C. officinalis exhibited a high content of palythine. Both content and composition of MAAs varied seasonally, with high concentration recorded in different seasons, depending on the species, i.e., winter (I. tuberculosa), spring (N. fastigiata), and summer (C. officinalis). HPLC-ESI-MS allowed us to identify seven different MAAs. Two were recorded for the first time in seaweeds from Subantarctic areas (mycosporine-glutamic acid and palythine-serine), and we also recorded an eighth UV-absorbing compound which remains unidentified. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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16 pages, 2365 KiB

Open AccessArticle

Absolute Configuration of Mycosporine-Like Amino Acids, Their Wound Healing Properties and In Vitro Anti-Aging Effects

by Maria Orfanoudaki, Anja Hartmann, Mostafa Alilou, Thomas Gelbrich, Patricia Planchenault, Séverine Derbré, Andreas Schinkovitz, Pascal Richomme, Andreas Hensel and Markus Ganzera

Mar. Drugs 2020, 18(1), 35; https://doi.org/10.3390/md18010035 - 31 Dec 2019

Cited by 36 | Viewed by 4971

Abstract

Mycosporine-like amino acids (MAAs) are water-soluble metabolites, reported to exhibit strong UV-absorbing properties. They have been found in a wide range of marine organisms, especially those that are exposed to extreme levels of sunlight, to protect them against solar radiation. In the present study, the absolute configuration of 14 mycosporine-like-amino acids was determined by combining the results of electronic circular dichroism (ECD) experiments and that of advanced Marfey’s method using LC-MS. The crystal structure of a shinorine hydrate was determined from single crystal X-ray diffraction data and its absolute configuration was established from anomalous-dispersion effects. Furthermore, the anti-aging and wound-healing properties of these metabolites were evaluated in three different assays namely the inhibition of collagenase, inhibition of advanced glycation end products (AGEs) and wound healing assay (scratch assay). Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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14 pages, 2263 KiB

Open AccessArticle

Quantitative and Qualitative HPLC Analysis of Mycosporine-Like Amino Acids Extracted in Distilled Water for Cosmetical Uses in Four Rhodophyta

by Patricia Chaves-Peña, Francisca de la Coba, Felix L. Figueroa and Nathalie Korbee

Mar. Drugs 2020, 18(1), 27; https://doi.org/10.3390/md18010027 - 28 Dec 2019

Cited by 33 | Viewed by 5330

Abstract

Mycosporine-like amino acids (MAAs) have gained considerable attention as highly active photoprotective candidates for human sunscreens. However, more studies are necessary to evaluate the extraction efficiencies of these metabolites in cosmetic compatible solvents, as well as, their subsequent HPLC analysis. In the present study, MAA extraction using distilled water and 20% aqueous methanol in four Rhodophyta was investigated. Different re-dissolution solvents and a C8 and C18 columns were tested for the HPLC analysis. Porphyra-334, shinorine, palythine, palythine-serine, asterina-330, and palythinol were identified by HPLC/ESI-MS. The separation of these MAAs were improved employing the C8-column, and using methanol as re-dissolution solvent. Regarding total MAAs concentrations, no differences between the two solvents were found. The highest MAA amounts were observed injecting them directly in the HPLC. According to these results, distilled water could be an excellent extraction solvent for MAAs. Nevertheless, the re-dissolution in pure methanol after dryness would be the best option for the qualitative analysis of the most common MAAs in these red algae. Our results entail important implications regarding the use of red macroalgae as promising candidates as environment-friendly sources of natural sunscreens. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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15 pages, 860 KiB

Open AccessFeature PaperArticle

Bostrychines A–F, Six Novel Mycosporine-Like Amino-Acids and a Novel Betaine from the Red Alga Bostrychia scorpioides

by Maria Orfanoudaki, Anja Hartmann, Helena Miladinovic, Hieu Nguyen Ngoc, Ulf Karsten and Markus Ganzera

Mar. Drugs 2019, 17(6), 356; https://doi.org/10.3390/md17060356 - 14 Jun 2019

Cited by 29 | Viewed by 5312

Abstract

Various red algae have repeatedly been reported to produce a variety of UV-absorbing mycosporine-like amino acids (MAAs), compounds that are well-known as natural sun-screens, as well as a plethora of betaines, metabolites which contribute to the osmotic balance under salt stress. Among other Rhodophyta, Bostrychia scorpioides, which is thriving as epiphyte on salt marsh plants in Europe and hence experiences extreme environmental conditions such as desiccation, UV-stress and osmotic stress, has barely been investigated for its secondary metabolites. In the present study, seven mycosporine like-amino acids and two betaines were isolated from Bostrychia scorpioides using various chromatographic techniques. Their structures were confirmed by Nuclear Magnetic Resonance (NMR) spectroscopy and High Resolution Mass Spectrometry (HRMS). Six MAAs and one betaine were chemically characterized as new natural products. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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Review

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14 pages, 3931 KiB

Open AccessReview

Mycosporine-Like Amino Acids (MAAs) in Zooplankton

by Samuel Hylander

Mar. Drugs 2020, 18(2), 72; https://doi.org/10.3390/md18020072 - 23 Jan 2020

Cited by 15 | Viewed by 4076

Abstract

Organisms have different adaptations to avoid damage from ultraviolet radiation and one such adaptation is the accumulation of mycosporine-like amino acids (MAAs). These compounds are common in aquatic taxa but a comprehensive review is lacking on their distribution and function in zooplankton. This paper shows that zooplankton MAA concentrations range from non-detectable to ~13 µg mgDW⁻¹. Copepods, rotifers, and krill display a large range of concentrations, whereas cladocerans generally do not contain MAAs. The proposed mechanisms to gain MAAs are via ingestion of MAA-rich food or via symbiotic bacteria providing zooplankton with MAAs. Exposure to UV-radiation increases the concentrations in zooplankton both via increasing MAA concentrations in the phytoplankton food and due to active accumulation. Concentrations are generally low during winter and higher in summer and females seem to deposit MAAs in their eggs. The concentrations of MAAs in zooplankton tend to increase with altitude but only up to a certain altitude suggesting some limitation for the uptake. Shallow and UV-transparent systems tend to have copepods with higher concentrations of MAAs but this has only been shown in a few species. A high MAA concentration has also been shown to lead to lower UV-induced mortality and an overall increased fitness. While there is a lot of information on MAAs in zooplankton we still lack understanding of the potential costs and constraints for accumulation. There is also scarce information in some taxa such as rotifers as well as from systems in tropical, sub(polar) areas as well as in marine systems in general. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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23 pages, 4571 KiB

Open AccessReview

Distribution, Contents, and Types of Mycosporine-Like Amino Acids (MAAs) in Marine Macroalgae and a Database for MAAs Based on These Characteristics

by Yingying Sun, Naisheng Zhang, Jing Zhou, Shasha Dong, Xin Zhang, Lei Guo and Ganlin Guo

Mar. Drugs 2020, 18(1), 43; https://doi.org/10.3390/md18010043 - 7 Jan 2020

Cited by 51 | Viewed by 7225

Abstract

Mycosporine-like amino acids (MAAs), maximally absorbed in the wavelength region of 310–360 nm, are widely distributed in algae, phytoplankton and microorganisms, as a class of possible multi-functional compounds. In this work, based on the Web of Science, Springer, Google Scholar, and China national knowledge infrastructure (CNKI), we have summarized and analyzed the studies related to MAAs in marine macroalgae over the past 30 years (1990–2019), mainly focused on MAAs distribution, contents, and types. It was confirmed that 572 species marine macroalgae contained MAAs, namely in 45 species of Chlorophytes, 41 species of Phaeophytes, and 486 species of Rhodophytes, and they respectively belonged to 28 orders. On this basis, we established an open online database to quickly retrieve MAAs in 501 species of marine macroalgae. Furthermore, research concerning MAAs in marine macroalgae were analyzed using CiteSpace. It could easily be seen that the preparation and purification of MAAs in marine macroalgae have not been intensively studied during the past 10 years, and therefore it is necessary to strengthen the research in the preparation and purification of MAA purified standards from marine macroalgae in the future. We agreed that this process is not only interesting, but important due to the potential use of MAAs as food and cosmetics, as well as within the medicine industry. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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17 pages, 1567 KiB

Open AccessReview

Mycosporine-Like Amino Acids: Making the Foundation for Organic Personalised Sunscreens

by Nedeljka N. Rosic

Mar. Drugs 2019, 17(11), 638; https://doi.org/10.3390/md17110638 - 12 Nov 2019

Cited by 82 | Viewed by 9287

Abstract

The surface of the Earth is exposed to harmful ultraviolet radiation (UVR: 280–400 nm). Prolonged skin exposure to UVR results in DNA damage through oxidative stress due to the production of reactive oxygen species (ROS). Mycosporine-like amino acids (MAAs) are UV-absorbing compounds, found in many marine and freshwater organisms that have been of interest in use for skin protection. MAAs are involved in photoprotection from damaging UVR thanks to their ability to absorb light in both the UV-A (315–400 nm) and UV-B (280–315 nm) range without producing free radicals. In addition, by scavenging ROS, MAAs play an antioxidant role and suppress singlet oxygen-induced damage. Currently, there are over 30 different MAAs found in nature and they are characterised by different antioxidative and UV-absorbing capacities. Depending on the environmental conditions and UV level, up- or downregulation of genes from the MAA biosynthetic pathway results in seasonal fluctuation of the MAA content in aquatic species. This review will provide a summary of the MAA antioxidative and UV-absorbing features, including the genes involved in the MAA biosynthesis. Specifically, regulatory mechanisms involved in MAAs pathways will be evaluated for controlled MAA synthesis, advancing the potential use of MAAs in human skin protection. Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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Other

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7 pages, 246 KiB

Open AccessCommentary

Mycosporine-Like Amino Acids from Marine Resource

by Félix L. Figueroa

Mar. Drugs 2021, 19(1), 18; https://doi.org/10.3390/md19010018 - 4 Jan 2021

Cited by 26 | Viewed by 4579

Abstract

In the last 10 years, a great number of publications (both regular papers and reviews) have been published on the interesting molecules—mycosporine-like amino acids (MAAs). Despite significant advances in the research of MAAs, current overviews in the recent publications involving MAA research still need reporting. The aim of this Special Issue is to join, as an interdisciplinary approach, the photochemical and photobiological aspects, with emphasis on new natural resources to obtain both algae and zooplankton MAAs, advances in methodology of extraction and chemical identification of new MAAs. Finally, this Special Issue reviews the bioactivities of MAAs including UVR screen, antioxidant, immunostimulant, growth factor, DNA protection, inhibition of collagenase, elastase and hyaluronidase, and anti-photoaging, among others, and their potential use as nutracosmeceutic molecules (i.e., oral and topic photoprotector). Full article

(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)

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