Mycosporine-2-glycine Research Articles

Mycosporine-Like Amino Acids as a Potential Inhibitor of Tyrosinase-Related Protein 1: Computational Screening, Pharmacokinetics, and Molecular Dynamics Simulation.

Melanin is the major pigment responsible for the coloring of mammalian skin, hair, and eyes to defend against ultraviolet radiation. However, excessive melanin production has resulted in numerous types of hyperpigmentation disorders. Tyrosinase-related protein 1 (TYRP1) is a transmembrane glycoprotein enzyme found in many organisms, including humans, that plays an important role in melanogenesis. Thus, controlling the enzyme activity of TYRP1 with tyrosinase inhibitors is a vital step in the treatment of hyperpigmentation problems in humans. In the present investigation, virtual screening, pharmacokinetics, drug docking, and molecular dynamics (MD) simulation were used to find the most potent drug as an inhibitor of TYRP1 to effectively treat hyperpigmentation disorder. The 3D structure of TYRP1 was retrieved from the Protein Data Bank (PDB) database (PDB ID: 5M8M) and validated by the Ramachandran plot. Pharmacokinetics and drug-likeness showed that mycosporine 2 glycine (M2G) and shinorine (SHI) were the best compounds over other ligands in the same (P-1) structural pose. However, MD simulations of the M2G showed the highest CDOCKER interaction energy (-45.182kcal/mol) and binding affinity (-65.0529kcal/mol) as compared to SHI and reference drugs. The molecular binding modes RMSD and RMSF plots have exhibited more relevance to the M2G ligand in comparison to other drug ligands. The bioactivity and ligand efficiency profiles revealed that M2G is the most effective compound as a TYRP1 inhibitor. Thus, M2G could be used as a most effective drug for developing valuable sunscreen products to cure hyperpigmentation-related diseases.

Efficient production of natural sunscreens shinorine, porphyra-334, and mycosporine-2-glycine in Saccharomyces cerevisiae

Mycosporine-like amino acids (MAAs) are promising natural sunscreens mainly produced in marine organisms. Until now, metabolic engineering efforts to produce MAAs in heterologous hosts have mainly focused on shinorine production, and the low production levels are still not suitable for industrial applications. In this study, we successfully developed Saccharomyces cerevisiae strains that can efficiently produce various disubstituted MAAs, including shinorine, porphyra-334, and mycosporine-2-glycine (M2G), which are formed by conjugating serine, threonine, and glycine to mycosporine-glycine (MG), respectively. We first generated an MG-producing strain by multiple integration of the biosynthetic genes from cyanobacteria and applying metabolic engineering strategies to increase sedoheptulose-7-phosphate pool, a substrate for MG production. Next, five mysD genes from cyanobacteria, which encode D-Ala-D-Ala ligase homologues that conjugate an amino acid to MG, were introduced into the MG-producing strain to determine the substrate preference of each MysD enzyme. MysDs from Lyngbya sp., Nostoclinckia, and Euhalothece sp. showed high specificity toward serine, threonine, and glycine, resulting in efficient production of shinorine, porphyra-334, and M2G, respectively. This is the first report on the production of porphyra-334 and M2G in S. cerevisiae. Furthermore, we identified that the substrate specificity of MysD was determined by the omega loop region of 43–45 amino acids predicted based on its structural homology to a D-Ala-D-Ala ligase from Thermus thermophilus involved in peptidoglycan biosynthesis. The substrate specificities of two MysD enzymes were interchangeable by swapping the omega loop region. Using the engineered strain expressing mysD from Lyngbya sp. or N. linckia, up to 1.53 g/L shinorine or 1.21 g/L porphyra-334 was produced by fed-batch fermentation in a 5-L bioreactor, the highest titer reported so far. These results suggest that S. cerevisiae is a promising host for industrial production of different types of MAAs, providing a sustainable and eco-friendly alternative for the development of natural sunscreens.

Global transcriptome analyses and regulatory mechanisms in Halothece sp. PCC 7418 exposed to abiotic stresses.

Halotolerant species are of interest since they occur naturally in environments with excess toxic ions. The cyanobacterium Halothece sp. PCC 7418 (hereafter referred to as Halothece) exhibits remarkable halotolerance and was used to examine stress-responsive regulatory mechanisms. The effects of five different stimuli on Halothece transcriptomes were examined using RNA sequencing. In response to diverse stresses, there were both common and stress-specific transcriptional responses. A common upregulated gene set under all stresses consisted of nine differentially expressed genes (DEGs). We also found that osmotic stress elicited the largest set of DEGs. Salt- and osmotic-responsive regulatory mechanisms shared common pathways. DEGs that were upregulated under salt stress encoded proteins involved in photosynthesis and related machineries. Furthermore, DEGs encoding two-component system (TCS) factors, transcriptional factors, scaffolds for protein-protein interactions, transporters, protein turnover factors, and lipid biosynthesis enzymes were also identified under salt stress. Notably, one-carbon (1C) metabolism factors, glycine betaine (GB) synthesis enzymes, and GB transporters were upregulated under salt stress. Metabolic analyses revealed that GB accumulated under salt stress, while mycosporine-2-glycine (M2G) accumulated under salt or osmotic stress. None of the nutrient starvations induced GB nor M2G accumulation. These results suggested that GB and M2G are two osmoprotectants that contribute to halotolerance. Based on our results, we proposed regulatory mechanisms that are crucial for halotolerance, which are coordinated with the GB, M2G, 1C, amino acid, and central carbon interlinking metabolic pathways. 1C metabolism directly fulfills the high metabolite requirements for halotolerance together with the ancillary role of several metabolic pathways.Key Points• Global transcriptome surveys together with molecular and metabolite analyses provide insights into regulatory networks that are crucial for halotolerance• Regulatory networks that are crucial for halotolerance coordinated with the two key osmoprotectants, one carbon, amino acid, and central carbon interlinking metabolic pathways• The findings have translational relevance in genomic and transcriptomic mechanisms of halotolerance.

Protective effects of mycosporine-like amino acid-containing emulsions on UV-treated mouse ear tissue from the viewpoints of antioxidation and antiglycation.

Mycosporine-like amino acids (MAAs) are promising natural antioxidative compounds with cosmetic applications for the prevention of skin aging. In this study, we evaluated the protective effects of natural resources-derived MAA-containing emulsions on mouse ear tissue exposed to UV irradiation. DBA/2CrSlc male mice were irradiated by UV light at 120mJ/cm2/day for 9 days. MAA-containing emulsions were prepared using mycosporine-2-glycine (M2G), shinorine (SHI), or porphyra-334 (P334) and applied to mice ears at a dose of 50mg/ear/day. After that, collected ear skin tissues were subjected to the observation of melanocytes, investigation for antioxidative stress markers, and measurement of advanced glycation-end products (AGEs). In addition, the antiglycative effects of MAAs were investigated in vitro. MAA-containing emulsions prepared in this study upregulated the activities of total superoxide dismutase (SOD) and catalase (CAT) in mouse ear tissue exposed to UV irradiation. Increased accumulation of copper/zinc (Cu/Zn) -SOD and/or CAT was also found in mouse ear tissue on which M2G- or P334-containing emulsion had been applied. Furthermore, P334 exhibited an antiglycative effect on elastin in vitro. Although MAA-containing emulsions have antioxidative effects as well as in vitro antiglycation, a protective effect by the accumulation of AGEs in mice ears exposed to UV was not observed. Thus, application of MAA-containing emulsions stimulated or protected the expression of antioxidant-associated proteins, thereby leading to upregulation of antioxidative activities in mouse ear skin samples tissues under UV irradiation. Additional optimization of MAA-containing emulsions, including composition, process, and dosage should be considered for further improvement of efficacy.

Expression of a stress-responsive gene cluster for mycosporine-2-glycine confers oxidative stress tolerance in Synechococcus elongatus PCC7942.

Mycosporine-like amino acids (MAAs) are a class of well-documented UV-screening compounds produced by taxonomically diverse organisms. Extensive studies revealed that a rare MAA, mycosporine-2-glycine (M2G), possesses unique biological activities and functions. M2G is not only a potent antioxidant, but also suppresses protein glycation in vitro, and production of inflammatory mediators in RAW 264.7 macrophages. The present study evaluates vital functions of M2G in a heterologous expression system. The stress-sensitive fresh water cyanobacterium Synechococcus elongatus PCC7942, carrying a M2G biosynthetic gene cluster, was generated. The M2G-expressing cells were more tolerant to H2O2-induced oxidative stress than the wild type, with a half-maximal inhibitory concentration (IC50) value of 2.3±0.06 mM. Transcriptional analysis revealed that all M2G biosynthetic genes were highly up-regulated under oxidative stress. Further, expression of vital genes in the cellular antioxidant defense system, including sodB, cat and tpxA were modulated and up-regulated. Elevated M2G was detected under oxidative stress as well as salt stress treatments. This study provides insight into the molecular and cellular effects of the M2G biosynthetic gene cluster, contributing to understanding of the mechanism behind physiological plasticity under this heterologous expression system.

Antioxidative, Anti-Inflammatory, and Anti-Aging Properties of Mycosporine-Like Amino Acids: Molecular and Cellular Mechanisms in the Protection of Skin-Aging.

Prolonged exposure to ultraviolet (UV) radiation causes photoaging of the skin and induces a number of disorders, including sunburn, fine and coarse wrinkles, and skin cancer risk. Therefore, the application of sunscreen has gained much attention to reduce the harmful effects of UV irradiation on our skin. Recently, there has been a growing demand for the replacement of chemical sunscreens with natural UV-absorbing compounds. Mycosporine-like amino acids (MAAs), promising alternative natural UV-absorbing compounds, are a group of widely distributed, low molecular-weight, water-soluble molecules that can absorb UV radiation and disperse the absorbed energy as heat, without generating reactive oxygen species (ROS). More than 30 MAAs have been characterized, from a variety of organisms. In addition to their UV-absorbing properties, there is substantial evidence that MAAs have the potential to protect against skin aging, including antioxidative activity, anti-inflammatory activity, inhibition of protein-glycation, and inhibition of collagenase activity. This review will provide an overview of MAAs, as potential anti-aging ingredients, beginning with their structure, before moving on to discuss the most recent experimental observations, including the molecular and cellular mechanisms through which MAAs might protect the skin. In particular, we focus on the potential anti-aging activity of mycosporine-2-glycine (M2G).

A Method for the Isolation and Characterization of Mycosporine-Like Amino Acids from Cyanobacteria.

This report provides a broadly applicable and cost-effective method for the purification of mycosporine-like amino acids (MAAs) from cyanobacteria. As MAAs are known to have multiple bioactivities for health and beauty, a universal isolation method of MAAs from biomass is attractive. In particular, the biomass of photosynthetic microorganisms such as cyanobacteria is of interest as a natural source of useful compound production, because of their photoautotrophic property. The method presented here is applicable for the isolation of mycosporine-2-glycine (M2G), which is a rare MAA produced in a halotolerant cyanobacterium. This method also allowed for the isolation of two of the most common MAAs, shinorine (SHI) and porphyra-334 (P334). A three-step separation process using low pressure liquid chromatography yielded purified MAAs, which were characterized by nuclear magnetic resonance (NMR) and liquid chromatography-mass spectrometry (LC/MS) analyses. The purified MAAs exhibited free radical scavenging activity in the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assay. The experimental parameters obtained in this report may allow for a scale-up of the MAA purification process for future industrial applications.

Mycosporine-2-glycine exerts anti-inflammatory and antioxidant effects in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages

Mycosporine-like amino acids (MAAs) are a group of water-soluble low-molecular-weight secondary metabolites, which are well-documented UV-screening molecules and antioxidants. We have recently demonstrated that a rare MAA, mycosporine-2-glycine (M2G), efficiently inhibited the formation of advanced glycation end-products (AGEs). Because AGEs contribute significantly to the aging process, including the pathogenesis and progression of age-related diseases, the present study further evaluated anti-inflammatory effects of M2G using an in vitro model of RAW 264.7 macrophages. We measured the inflammatory signaling molecule nitric oxide (NO) under inflammatory stimulation by lipopolysaccharide (LPS), revealing that M2G diminished LPS-induced NO production. M2G inhibited NO production approximately 2–3-fold more potently than other MAAs, including shinorine, porphyra-334, and palythine. Transcriptional analyses revealed that M2G significantly suppressed iNOS and COX-2 expression. Therefore, M2G inhibits the production of inflammatory mediators by suppressing the NF-κB pathway. Furthermore, under H2O2-induced oxidative stress, M2G down-regulated Sod1, Cat, and Nrf2 expression. Our findings clearly demonstrate anti-inflammatory and antioxidant effects of M2G in LPS-stimulated RAW 264.7 macrophages. Structure-activity relationships of biologically active MAAs are also discussed.

Inhibitory effects of mycosporine-2-glycine isolated from a halotolerant cyanobacterium on protein glycation and collagenase activity.

Mycosporine-like amino acids (MAAs) are known as multifunctional natural compounds. The MAA mycosporine-2-glycine (M2G), isolated from the halotolerant cyanobacterium Aphanothece halophytica, has potential therapeutic applications for the prevention of skin ageing. Purified M2G was endotoxin-free. M2G had greater inhibitory activity of protein cross-linking compared with well-known inhibitor, aminoguanidine and hindered bacterial collagenase activity. The mechanisms for these inhibitory activities of M2G are discussed in this study.

Temporal changes in environmental conditions of a mid-latitude estuary (southern Chile) and its influences in the cellular response of the euryhaline anemone Anthopleura hermaphroditica

The cellular response of the estuarine anemone Anthopleura hermaphroditica was assessed during a tidal cycle (low tide at noon) and compared between organisms acclimated to summer and winter environmental conditions (UV-B and PAR levels, salinity and temperature), with the aim of understanding the strategies used by this dominant invertebrate in an estuary of southern Chile. Anemones were gathered every two hours from 8:00 to 20:00 h from the low intertidal area of the Quempillén estuary and immediately snap frozen to carry out biochemical analyses (oxidative damage, antioxidant capacity, photo-protective compounds). Additionally, levels of environmental radiation (UV-B and PAR), salinity and water temperature were recorded during the field survey. Our results indicate that during summer, lipid peroxidation and protein carbonyl levels in A. hermaphroditica were 3.72 and 16.51 folds higher than during winter, respectively. Maximum lipid peroxidation levels in A. hermaphroditica during summer occurred after UV-B radiation peaked (14:00 h) when water temperatures reached 31 °C. Carbonyl protein levels increased progressively reaching maximum levels at the end of the day. On the contrary, during winter when radiation levels are low and water temperature remained almost constant in the estuary throughout the day, significant variation in salinity levels occurred due to oxidative damage levels that increased significantly at the end of the day. Surprisingly, the mean antioxidant capacity level in A. hermaphroditica during winter was 1.7 folds higher than in summer, a situation that was positively correlated to total phenolic compounds content. Mycosporine 2-glycine (λmax: 331 nm) was the only mycosporine like amino acid (MAA) found in A. hermaphroditica, a photo-protective compound with constant levels throughout the year. Anthopleura hermaphroditica, is an estuarine anemone that are adapted to tolerate rapid fluctuations in the environmental parameters during tidal changes. Those fluctuations are highly affected by seasonal components that expose this invertebrate to different intensity and duration of stress factors between summer and winter. Thus, an efficient antioxidant strategy added to the use of secondary metabolites (phenolic compounds and MAA) may efficiently intercept and neutralize ROS in this animal that lacks of physical protection, allowing it to succeed in a very unstable environment characterized by strong fluctuations of salinity, temperature and environmental radiation through the year.

Efficient Bioproduction of Mycosporine-2-glycine, Which Functions as Potential Osmoprotectant, using Escherichia coli Cells

Mycosporine-2-glycine (M2G) is known to be synthesized in halotolerant cyanobacterium Aphanothece halophytica. Escherichia coli cells in which the M2G synthetic genes of A. halophytica were introduced could synthesize M2G. Here, we report that M2G producing transformed E. coli cells showed salt tolerance compared to control cells. This result suggested that M2G could function as a potential osmoprotectant in E. coli. To our knowledge, this is the first report presenting the evidence that mycosporine-like amino acid confers salt tolerance on E. coli. Intracellular M2G content in the transformed E. coli cells were varied depending on NaCl concentration with maximum level at 0.75 M. Moreover, intracellular M2G level was affected by a supply of glycine with maximum level at 5 mM. In conclusion, we found that transformed E. coli cells could produce 205 μg of M2G/g fresh weight of cells under the best effective growth condition in this study. Thus, the results obtained here offer the potential for the bioproduction of mycosporine-like amino acids using the genetically engineered E. coli cells.

DNA damage protecting and free radical scavenging properties of mycosporine-2-glycine from the Dead Sea cyanobacterium in A375 human melanoma cell lines

Mycosporine-like amino acids (MAAs) are a group of natural sunscreen compounds that possess highly photoprotective properties. The most commonly found MAAs in marine organisms is shinorine, porphyra-334, and mycosporine-glycine. However, the halophilic species accumulate mycosporine-2-glycine (M2G) as the major MAA. In this study, we have investigated the protective effect of M2G against oxidative stress. In vitro radical scavenging activity revealed that M2G exhibited a significant inhibition with scavenging concentration (SC) 50 value of 22±1.4μM. In vivo analysis using the human melanoma A375 and a control cell line (NHSF) showed that M2G at low concentration (i.e. micromolar range) protected the cells against the oxidative stress (H2O2)–induced cell death. Comet assay to assess total DNA strand breaks demonstrated that M2G was not genotoxic and protected against the DNA damage by H2O2 treatment at the same level as ascorbic acid. To our knowledge, this is the first evidence demonstrating potential protective role of the natural sunscreen compound M2G against oxidative stress-induced DNA damage in human cell lines. The potent antioxidant activity combined with DNA protection ability of M2G may support its endorsement as a potential natural sunscreen with antioxidant property. These findings provide important clues for possible use of M2G in pharmaceutical and biotechnological applications.

Effects of starvation, ammonium concentration, and photosynthesis on the UV-dependent accumulation of mycosporine-like amino acids (MAAs) in the coral Stylophora pistillata

MEPS Marine Ecology Progress Series Contact the journal Facebook Twitter RSS Mailing List Subscribe to our mailing list via Mailchimp HomeLatest VolumeAbout the JournalEditorsTheme Sections MEPS 295:135-156 (2005) - doi:10.3354/meps295135 Effects of starvation, ammonium concentration, and photosynthesis on the UV-dependent accumulation of mycosporine-like amino acids (MAAs) in the coral Stylophora pistillata J. Malcolm Shick1,*, Christine Ferrier-Pagès2, Renaud Grover2, Denis Allemand2,3 1School of Marine Sciences, University of Maine, 5751 Murray Hall, Orono, Maine 04469-5751, USA2Centre Scientifique de Monaco, Avenue Saint-Martin, 98000 Monaco, Principality of Monaco3UMR 1112 INRA-UNSA, University of Nice-Sophia Antipolis, Parc Valrose, BP 71, 06108 Nice Cedex 2, France *Email: shick@maine.edu ABSTRACT: This study addresses several unresolved questions regarding the biosynthesis, metabolism, regulation, and diversity of MAAs in zooxanthellate scleractinian corals. Starved colonies of Stylophora pistillata accumulated the same concentrations of mycosporine-like amino acids (MAAs) as fed corals after 28 d of exposure to photosynthetically available radiation (PAR) and ultraviolet radiation (UVR), suggesting that dietary MAAs are of little quantitative importance in this phototrophic symbiosis. Starved corals continued to accumulate MAAs and conserved them disproportionally compared with declining protein and chlorophyll a, indicating the priority placed on maintaining this UV-sunscreen defense. In 2 different colonies (SP1 and SP2) exposed to enriched (10 µM) ammonium and PAR + UVR during starvation, the final concentrations of MAAs and chlorophyll a were identical. However, under ambient ammonium (<0.4 µM), SP2 produced MAAs at the expense of chlorophyll a, whereas SP1 maintained chlorophyll a levels but synthesized less MAA. Ammonium consistently affected only the accumulation of primary, Symbiodinium-MAAs (mycosporine glycine, shinorine, porphyra-334, and mycosporine-2 glycine) and not secondary MAAs derived from the former, probably in the host’s tissues. Mycosporine-2 glycine and palythine (a secondary MAA) were synthesized by SP1 but not SP2, suggesting (1) genotypic differences between the zooxanthellae in SP1 and SP2, and (2) a biosynthetic relationship between these 2 MAAs that we proposed previously. Exposure to UVR alone did not support large-scale biosynthesis of MAAs in S. pistillata, and accumulation of the full suite of MAAs required PAR + UVR; together with an inhibitory effect of DCMU, this indicates that photosynthesis is required for the UV-stimulated, de novo biosynthesis of MAAs. Cultures of zooxanthellae isolated from S. pistillata and exposed to PAR + UVR showed increased levels of shinorine, and some production of mycosporine-glycine. Host extract had no qualitative effect on the MAAs produced by these zooxanthellae. KEY WORDS: Mycosporine-like amino acids (MAAs) · Coral · Zooxanthellae · Ultraviolet radiation (UVR) · Dissolved ammonium · Photosynthesis Full text in pdf format PreviousNextExport citation RSS - Facebook - Tweet - linkedIn Cited by Published in MEPS Vol. 295. Online publication date: June 23, 2005 Print ISSN: 0171-8630; Online ISSN: 1616-1599 Copyright © 2005 Inter-Research.

Mycosporine-like amino acid (MAAs) production by Heterocapasa sp. (Dinophyceae) in indoor cultures

The possibility of using mycosporine-like amino acids (MAAs), with an apparent sunscreen function in nature, as ultraviolet radiation (UVR) blockers to prevent skin injury has been raised by diverse authors. Production of MAAs by the dinoflagellate Heterocapsa sp. (Dinophyceae) is shown here. Three major peaks with absorption maxima at 330.8, 332.0 and 333.2 nm were detected by high performance liquid chromatography (HPLC) analysis of methanolic extracts in all tested conditions. Analysis of crude extract by mass spectroscopy with electrospray ionization (MS-EI) showed a set of molecular ions ([M+H] +) with main peaks being at m/ z 242.4, 288.4, 303.3 and 333.3 u.m.a. According to these data, along with retention times, the MAA profile of Heterocapsa sp. is assumed to be composed of shinorine ( λ max=334 nm), mycosporine–2-glycine ( λ max=331 nm) and palythinol ( λ max=332 nm). A constitutive MAA content of about 4 μg (10 6 cells) −1 was measured under exposure to PAR only. A maximal accumulation of MAA per culture volume of 1.1 mg l −1 was obtained after 72 h of exposure to PAR+UVA, while the highest production rate (0.025 mg l −1 h −1) was computed after 24 h of exposure to PAR+UVA+UVB.

Mycosporine-like amino acid content in four species of sea anemones in the genus Anthopleura reflects phylogenetic but not environmental or symbiotic relationships.

We examine the occurrence of UV-absorbing, mycosporine-like amino acids (MAAs) in four sympatric species of sea anemones in the genus Anthopleura, all collected from intertidal habitats on the Pacific Coast of temperate North America. We compare patterns of MAAs in A. elegantissima of several types: specimens having predominately zooxanthellae (dinoflagellates comprising at least two species) or zoochlorellae as symbionts; those containing algal endosymbionts of both kinds, and naturally occurring aposymbiotic specimens that lack the endosymbionts typically found in most specimens. We also compare MAAs in zooxanthellate specimens of A. sola and A. xanthogrammica, and specimens from the asymbiotic species A. artemisia. Our findings indicate that the complements of the four major MAAs in these species of Anthopleura (mycosporine-taurine, shinorine, porphyra-334, and mycosporine-2 glycine) broadly reflect phylogenetic differences among the anemones rather than the taxon of endosymbionts, presence or absence of symbionts, or environmental factors. An exception, however, occurs in A. elegantissima, where mycosporine-2 glycine increases in concentration with the density of zooxanthellae. Our evidence also shows that A. elegantissima can accumulate MAAs from its food, which may explain the occasional occurrence of minor MAAs in some individuals.

Occurrence of ultraviolet radiation-absorbing mycosporine-like amino acids in coral mucus and whole corals of French Polynesia

Specimens of six scleractinian species were gathered during the austral spring (October–November) 1994 on the external slope of the barrier reef of Arue, Tahiti, and in the lagoon of Arutua, a Tuamotu island. Mucus of each specimen was collected and the optical density and volume excreted were measured. After treatment, mucus was analysed for mycosporine-like amino acids (MAAs) by high-performance liquid chromatography (HPLC). Nine UV-absorbing compounds were present in coral mucus at concentrations between 1 and 500 ng g-1 mucus. Palythine and mycosporine–gly were found in all mucus studied. Mycosporine–2glycine was recovered in 71% of specimens and shinorine in 28%. Porphyra-334 and palythinol were identified as minor MAAs. Three recently identified MAAs, palythine–serine, mycosporine–methylamine:serine and mycosporine–methylamine:threonine, were also found in mucus from Pocillopora. Within a genus, there was a qualitative similarity in MAAs determined by HPLC, irrespective of locality. Values for optical density of the mucus showed the ability of MAAs to protect the animal host and endosymbiotic algae from UV-solar flux and, as inferred from the recent literature, from oxidative forms of oxygen (HO2 . , O 2 - , HO.) derived from photosynthesis.

Two new UV-absorbing mycosporine-like amino acids from the sea anemoneAnthopleura elegantissima and the effects of zooxanthellae and spectral irradiance on chemical composition and content

Many tropical cnidarians living in shallow water contain a class of ultraviolet-A (UV-A, 320 to 400 nm) and ultraviolet-B (UV-B, 280 to 320 nm) absorbing compounds known as mycosporine-like amino acids (MAAs). These compounds may provide protection from the deleterious effects of solar UV radiation. Using a novel application of reverse-phase high performance liquid chromatography, we find that the temperate sea anemoneAnthopleura elegantissima (collected in 1988 from Bodega Bay, California, and in 1991 from Santa Barbara, California) contains four major MAAs: shinorine, porphyra-334, and two new compounds, mycosporine-taurine and mycosporine-2 glycine. Analysis of zooxanthellate (containing zooxanthellae) and naturally apozooxanthellate (lacking zooxanthellae) specimens acclimated in the presence and absence of UV for 28 d in the spring of 1988 suggests that this anemone, unlike some other anthozoans, does not regulate the concentration of its MAAs in response to UV radiation. The presence of similar concentration of MAAs in apozooxanthellate and zooxanthellate specimens indicates that symbiosis with algae is not required for these compounds to be present in the anemone. The total concentration of MAAs in the zooxanthellae is only about 12% of that in their host's tissues.

Survey of ultraviolet radiation-absorbing mycosporine-like amino acids in organs of coral reef holothuroids

Twelve deposit-feeding species of tropical holothuroid echinoderms (families Holothuriidae and Stichopodidae) were surveyed for the presence of UV-absorbing mycosporine-like amino acids (MAAs) during Austral summer at Hicks Reef, Great Barrier Reef (GBR). An additional species belonging to the Synaptidae was collected in Austral winter from Shrimp Reef, GBR. Tissues of all species contained MAAs, including mycosporine-glycine, shinorine, porphyra-334, mycosporine-2 glycine, palythine, asterina-330 and palythinol. The MAAs in holothuroids occur predominantly in their epidermis, which suggests a photoprotective function, since the highest concentrations of these UVabsorbing compounds would be expected in tissues directly exposed to sunlight. Concentrations of total MAAs in dorsal epidermal tissues ranged from 21.9 nmol mg-' protein (Stichopus variegatus) to 2053 nmol mg-' protein (Pearsonothuria graeffei). Taxonomic, tissue-specific and ecological relationships in the occurrence of MAAs in tropical deposit-feeding holothuroids are discussed.