Mycosporine-like amino acid

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Mycosporine-like amino acids (MAAs) are small secondary metabolites produced by organisms that live in environments with high volumes of sunlight, usually marine environments. The exact number of compounds within this class of natural products is yet to be determined, since they have only relatively recently been discovered and novel molecular species are constantly being discovered; however, to date their number is around 30. [1] [2] They are commonly described as “microbial sunscreens” although their function is believed not to be limited to sun protection. [3] MAAs represent high potential in cosmetics, and biotechnological applications. Indeed, their UV-absorbing properties would allow to create products derived from natural photoprotectors, potentially harmless to the environment and efficient against UV damage. [4]

Contents

Background

MAAs are widespread in the microbial world and have been reported in many microorganisms including heterotrophic bacteria, [5] cyanobacteria, [6] microalgae, [7] ascomycetous [8] and basidiomycetous [9] fungi, as well as some multicellular organisms such as macroalgae and marine animals. [10] Most research done on MAAs is on their light absorbing and radiation protecting properties. The first thorough description of MAAs was done in cyanobacteria living in a high UV radiation environment. [11] The major unifying characteristic among all MAAs is UV light absorption. All MAAs absorb UV light that can be destructive to biological molecules (DNA, proteins, etc.). Though most MAA research is done on their photo-protective capabilities, they are also considered to be multi-functional secondary metabolites that have many cellular functions. [3] MAAs are effective antioxidant molecules and are able to stabilize free radicals within their ring structure. In addition to protecting cells from mutation via UV radiation and free radicals, MAAs are able to boost cellular tolerance to desiccation, salt stress, and heat stress. [12]

Chemistry

Mycosporine–like amino acids are rather small molecules (<400 Da). The structures of over 30 MAAs have been resolved and all contain a central cyclohexenone or cyclohexenimine ring and a wide variety of substitutions. [13] The ring structure is thought to absorb UV light and accommodate free radicals. All MAAs absorb ultraviolet wavelengths, typically between 310 and 362 nm. [10] [14] They are considered to be amongst the strongest natural absorbers of UV radiation. [15] It is this light absorbing property that allows MAAs to protect cells from the harmful UV-B and UV-A components of sunlight. Biosynthetic pathways of MAAs depend on the specific MAA molecule and the organism that is producing it. These biosynthetic pathways often share common enzymes and metabolic intermediates with pathways of the primary metabolism. [16] An example is the shikimate pathway that is classically used to produce the aromatic amino acids (phenylalanine, tyrosine and tryptophan); with many intermediates and enzymes from this pathway utilized in MAA biosynthesis. [16]

Examples

namepeak absorbance nmsystematic nameChemspider
Asterina-330330{[(3E)-5-Hydroxy-3-[(2-hydroxyethyl)iminio]-5-(hydroxymethyl)-2-methoxy-1-cyclohexen-1-yl]amino}acetate10475832
Euhalothece-362362
Mycosporine-2-glycine334[(E)-{3-[(Carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene}amino]acetic acid10474079
Mycosporine-glycine310N-[(5S)-5-Hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxo-1-cyclohexen-1-yl]glycine10476943
Mycosporine-glycine-valine335
Mycosporine-glutamic acid-glycine330
Mycosporine-methylamine-serine327
Mycosporine-methylamine-threonine327
Mycosporine-taurine309
Palythenic acid337
Palythene360[(E)-{5-Hydroxy-5-(hydroxymethyl)-2-methoxy-3-[(1E)-1-propen-1-ylamino]-2-cyclohexen-1-ylidene}ammonio]acetate10475813
Palythine320N-[5-Hydroxy-5-(hydroxymethyl)-3-imino-2-methoxycyclohex-1-en-1-yl]glycine10272813
Palythine-serine320N-[5-Hydroxy-5-(hydroxymethyl)-3-imino-2-methoxy-1-cyclohexen-1-yl]serine10476937
Palythine-serine-sulfate320
Palythinol332
Porphyra-33433429390215
Shinorine334
Usujirene357

[17]

Functions

Ultraviolet light responses

Protection from UV radiation

Ultraviolet UV-A and UV-B radiation is harmful to living systems. An important tool used to deal with UV exposure is the biosynthesis of small-molecule sunscreens. MAAs have been implicated in UV radiation protection. The genetic basis for this implication comes from the observed induction of MAA synthesis when organisms are exposed to UV radiation. This has been observed in aquatic yeasts, [18] cyanobacteria, [19] marine dinoflagellates [20] and some Antarctic diatoms. [3] MAAs have also been identified in 572 species of other algae : 45 species in Chlorophyta, 41 species in Phaeophyta, 486 species in Rhodophyta [21] which also present anti-aging, anti-inflammatory, antioxidative and wound healing properties. When MAAs absorb UV light the energy is dissipated as heat. [22] [23] UV-B photoreceptors have been identified in cyanobacteria as the molecules responsible for the UV light induced responses, including synthesis of MAAs. [24] Helioguard™365 containing Porphyra-334 and shinorine derived from Porphyra umbilicalis is already a creme on the market were developed by Mibelle AG biochemistry and shows preventive effects against UVA. An MAA known as palythine, derived from seaweed, has been found to protect human skin cells from UV radiation even in low concentrations. [25]

"MAAs, in addition to their environmental benefits, appear to be multifunctional photoprotective compounds," says Dr. Karl Lawrence, lead author of a paper on the research. "They work through the direct absorption of UVR [ultraviolet radiation] photons, much like the synthetic filters. They also act as potent antioxidants, which is an important property as exposure to solar radiation induces high levels of oxidative stress, and this is something not seen in synthetic filters."

Protection from oxidative damage

Some MAAs protect cells from reactive oxygen species (i.e. singlet oxygen, superoxide anions, hydroperoxyl radicals, and hydroxyl radicals). [3] Reactive oxygen species can be created during photosynthesis; further supporting the idea that MAAs provide protection from UV light. Mycosporine-glycine is a MAA that provides antioxidant protection even before Oxidative stress response genes and antioxidant enzymes are induced. [26] [27] MAA-glycine (mycosporine-glycine) is able to quench singlet oxygen and hydroxyl radicals very quickly and efficiently. [28] Some oceanic microbial ecosystems are exposed to high concentrations of oxygen and intense light; these conditions are likely to generate high levels of reactive oxygen species. In these ecosystems, MAA-rich cyanobacteria may be providing antioxidant activity. [29]

Accessory pigments in photosynthesis

MAAs are able to absorb UV light. A study published in 1976 demonstrated that an increase in MAA content was associated with an increase in photosynthetic respiration. [30] Further studies done in marine cyanobacteria showed that the MAAs synthesized in response to UV-B correlated with an increase in photosynthetic pigments. [31] Though not absolute proof, these findings do implicate MAAs as accessory pigments to photosynthesis.

Photoreceptors

The eyes for the mantis shrimp contain four different kinds of mycosporine-like amino acids as filters, which combined with two different visual pigments assist the eye to detect six different bands of ultraviolet light. [32] Three of the filter MAAs are identified with porphyra-334, mycosporine-gly, and gadusol. [33]

Environmental stress responses

Salt stress

Osmotic stress is defined as difficulty maintaining proper fluids in the cell within a hypertonic or hypotonic environment. MAAs accumulate within a cell’s cytoplasm and contribute to the osmotic pressure within a cell, thus relieving pressure from salt stress in a hypertonic environment. [3] As evidence of this, MAAs are seldom found in large quantities in cyanobacteria living in freshwater environments. However, in saline and hypertonic environments, cyanobacteria often contain high concentrations of MAAs. [34] The same phenomenon was noted for some halotolerant fungi. [8] But, the concentration of MAAs within cyanobacteria living in hyper-saline environments is far from the amount required to balance the salinity. Therefore, additional osmotic solutes must be present as well.

Desiccation stress

Desiccation (drought) stress is defined as conditions where water becomes the growth limiting factor. MAAs have been reportedly found in high concentrations in many microorganisms exposed to drought stress. [35] Particularly cyanobacteria species that are exposed to desiccation, UV radiation and oxidation stress have been shown to possess MAA’s in an extracellular matrix. [36] However it has been shown that MAAs do not provide sufficient protection against high doses of UV radiation. [6]

Thermal stress

Thermal (heat) stress is defined as temperatures lethal or inhibitory towards growth. MAA concentrations have been shown to be up-regulated when an organism is under thermal stress. [37] [38] Multipurpose MAAs could also be compatible solutes under freezing conditions, because a high incidence of MAA producing organisms have been reported in cold aquatic environments. [3]

Related Research Articles

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants are frequently added to industrial products, such as polymers, fuels, and lubricants, to extend their usable lifetimes. Food are also treated with antioxidants to forestall spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.

<span class="mw-page-title-main">Ultraviolet</span> Form of electromagnetic radiation

Ultraviolet (UV) is a form of electromagnetic radiation with wavelength shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight, and constitutes about 10% of the total electromagnetic radiation output from the Sun. It is also produced by electric arcs; Cherenkov radiation; and specialized lights; such as mercury-vapor lamps, tanning lamps, and black lights. Although long-wavelength ultraviolet is not considered an ionizing radiation because its photons lack the energy to ionize atoms, it can cause chemical reactions and causes many substances to glow or fluoresce. Many practical applications, including chemical and biological effects, derive from the way that UV radiation can interact with organic molecules. These interactions can involve absorption or adjusting energy states in molecules, but do not necessarily involve heating.

<span class="mw-page-title-main">Cyanobacteria</span> Phylum of photosynthesising prokaryotes

Cyanobacteria, also called Cyanobacteriota or Cyanophyta, are a phylum of gram-negative bacteria that obtain energy via photosynthesis. The name cyanobacteria refers to their color, which similarly forms the basis of cyanobacteria's common name, blue-green algae, although they are not usually scientifically classified as algae. They appear to have originated in a freshwater or terrestrial environment. Sericytochromatia, the proposed name of the paraphyletic and most basal group, is the ancestor of both the non-photosynthetic group Melainabacteria and the photosynthetic cyanobacteria, also called Oxyphotobacteria.

<span class="mw-page-title-main">Sunscreen</span> Topical skin product that helps protect against sunburn

Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that helps protect against sunburn and most importantly prevent skin cancer. Sunscreens come as lotions, sprays, gels, foams, sticks, powders and other topical products. Sunscreens are common supplements to clothing, particularly sunglasses, sunhats and special sun protective clothing, and other forms of photoprotection.

<span class="mw-page-title-main">Sunless tanning</span> Indoor tanning lotion

Sunless tanning, also known as UV filled tanning, self tanning, spray tanning, or fake tanning, refers to the effect of a suntan without exposure to the Sun. Sunless tanning involves the use of oral agents (carotenids), or creams, lotions or sprays applied to the skin. Skin-applied products may be skin-reactive agents or temporary bronzers (colorants).

<span class="mw-page-title-main">Phycocyanin</span> Protein complexes in algae

Phycocyanin is a pigment-protein complex from the light-harvesting phycobiliprotein family, along with allophycocyanin and phycoerythrin. It is an accessory pigment to chlorophyll. All phycobiliproteins are water-soluble, so they cannot exist within the membrane like carotenoids can. Instead, phycobiliproteins aggregate to form clusters that adhere to the membrane called phycobilisomes. Phycocyanin is a characteristic light blue color, absorbing orange and red light, particularly near 620 nm, and emits fluorescence at about 650 nm. Allophycocyanin absorbs and emits at longer wavelengths than phycocyanin C or phycocyanin R. Phycocyanins are found in cyanobacteria. Phycobiliproteins have fluorescent properties that are used in immunoassay kits. Phycocyanin is from the Greek phyco meaning “algae” and cyanin is from the English word “cyan", which conventionally means a shade of blue-green and is derived from the Greek “kyanos" which means a somewhat different color: "dark blue". The product phycocyanin, produced by Aphanizomenon flos-aquae and Spirulina, is for example used in the food and beverage industry as the natural coloring agent 'Lina Blue' or 'EXBERRY Shade Blue' and is found in sweets and ice cream. In addition, fluorescence detection of phycocyanin pigments in water samples is a useful method to monitor cyanobacteria biomass.

<span class="mw-page-title-main">Aggregating anemone</span> Species of sea anemone

The aggregating anemone, or clonal anemone, is the most abundant species of sea anemone found on rocky, tide swept shores along the Pacific coast of North America. This cnidarian hosts endosymbiotic algae called zooxanthellae that contribute substantially to primary productivity in the intertidal zone. The aggregating anemone has become a model organism for the study of temperate cnidarian-algal symbioses.

<span class="mw-page-title-main">Avobenzone</span> Oil-soluble ingredient used in sunscreen products

Avobenzone is an organic molecule and an oil-soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays.

<span class="mw-page-title-main">UV filter</span> Camera parts, features and technologies

UV filters are compounds, mixtures, or materials that block or absorb ultraviolet (UV) light. One of the major applications of UV filters is their use as sunscreens to protect skin from sunburn and other sun/UV related damage. After the invention of digital cameras changed the field of photography, UV filters have been used to coat glass discs fitted to camera lenses to protect hardware that is sensitive to UV light.

<span class="mw-page-title-main">Padimate O</span> Water-insoluble oily ingredient used in some sunscreens

Padimate O is an organic compound related to the water-soluble compound PABA that is used as an ingredient in some sunscreens. This yellowish water-insoluble oily liquid is an ester formed by the condensation of 2-ethylhexanol with dimethylaminobenzoic acid. Other names for padimate O include 2-ethylhexyl 4-dimethylaminobenzoate, Escalol 507, octyldimethyl PABA, and OD-PABA.

Photoprotection is the biochemical process that helps organisms cope with molecular damage caused by sunlight. Plants and other oxygenic phototrophs have developed a suite of photoprotective mechanisms to prevent photoinhibition and oxidative stress caused by excess or fluctuating light conditions. Humans and other animals have also developed photoprotective mechanisms to avoid UV photodamage to the skin, prevent DNA damage, and minimize the downstream effects of oxidative stress.

<span class="mw-page-title-main">Biological pigment</span> Substances produced by living organisms

Biological pigments, also known simply as pigments or biochromes, are substances produced by living organisms that have a color resulting from selective color absorption. Biological pigments include plant pigments and flower pigments. Many biological structures, such as skin, eyes, feathers, fur and hair contain pigments such as melanin in specialized cells called chromatophores. In some species, pigments accrue over very long periods during an individual's lifespan.

<span class="mw-page-title-main">Pyrimidine dimer</span> Type of damage to DNA

Pyrimidine dimers are molecular lesions formed from thymine or cytosine bases in DNA via photochemical reactions, commonly associated with direct DNA damage. Ultraviolet light induces the formation of covalent linkages between consecutive bases along the nucleotide chain in the vicinity of their carbon–carbon double bonds. The photo-coupled dimers are fluorescent. The dimerization reaction can also occur among pyrimidine bases in dsRNA —uracil or cytosine. Two common UV products are cyclobutane pyrimidine dimers (CPDs) and 6–4 photoproducts. These premutagenic lesions alter the structure of the DNA helix and cause non-canonical base pairing. Specifically, adjacent thymines or cytosines in DNA will form a cyclobutane ring when joined together and cause a distortion in the DNA. This distortion prevents replication or transcription machinery beyond the site of the dimerization. Up to 50–100 such reactions per second might occur in a skin cell during exposure to sunlight, but are usually corrected within seconds by photolyase reactivation or nucleotide excision repair. In humans, the most common form of DNA repair is nucleotide excision repair (NER). In contrast, organisms such as bacteria can counterintuitively harvest energy from the sun to fix DNA damage from pyrimidine dimers via photolyase activity. If these lesions are not fixed, polymerase machinery may misread or add in the incorrect nucleotide to the strand. If the damage to the DNA is overwhelming, mutations can arise within the genome of an organism and may lead to the production of cancer cells. Uncorrected lesions can inhibit polymerases, cause misreading during transcription or replication, or lead to arrest of replication. It causes sunburn and it triggers the production of melanin. Pyrimidine dimers are the primary cause of melanomas in humans.

<span class="mw-page-title-main">Aromatic amino acid</span> Amino acid having an aromatic ring

An aromatic amino acid is an amino acid that includes an aromatic ring.

<span class="mw-page-title-main">EXPOSE</span> External facility on the ISS dedicated to astrobiology experiments

EXPOSE is a multi-user facility mounted outside the International Space Station (ISS) dedicated to astrobiology. EXPOSE was developed by the European Space Agency (ESA) for long-term spaceflights and was designed to allow exposure of chemical and biological samples to outer space while recording data during exposure.

Cyanobionts are cyanobacteria that live in symbiosis with a wide range of organisms such as terrestrial or aquatic plants; as well as, algal and fungal species. They can reside within extracellular or intracellular structures of the host. In order for a cyanobacterium to successfully form a symbiotic relationship, it must be able to exchange signals with the host, overcome defense mounted by the host, be capable of hormogonia formation, chemotaxis, heterocyst formation, as well as possess adequate resilience to reside in host tissue which may present extreme conditions, such as low oxygen levels, and/or acidic mucilage. The most well-known plant-associated cyanobionts belong to the genus Nostoc. With the ability to differentiate into several cell types that have various functions, members of the genus Nostoc have the morphological plasticity, flexibility and adaptability to adjust to a wide range of environmental conditions, contributing to its high capacity to form symbiotic relationships with other organisms. Several cyanobionts involved with fungi and marine organisms also belong to the genera Richelia, Calothrix, Synechocystis, Aphanocapsa and Anabaena, as well as the species Oscillatoria spongeliae. Although there are many documented symbioses between cyanobacteria and marine organisms, little is known about the nature of many of these symbioses. The possibility of discovering more novel symbiotic relationships is apparent from preliminary microscopic observations.

<i>Chroococcidiopsis</i> Genus of bacteria

Chroococcidiopsis is a photosynthetic, coccoidal bacterium. A diversity of species and cultures exist within the genus, with a diversity of phenotypes. Some extremophile members of the order Chroococidiopsidales are known for their ability to survive harsh environmental conditions, including both high and low temperatures, ionizing radiation, and high salinity.

<span class="mw-page-title-main">Scytonemin</span> Chemical compound

Scytonemin is a secondary metabolite and an extracellular matrix (sheath) pigment synthesized by many strains of cyanobacteria, including Nostoc, Scytonema, Calothrix, Lyngbya, Rivularia, Chlorogloeopsis, and Hyella. Scytonemin-synthesizing cyanobacteria often inhabit highly insolated terrestrial, freshwater and coastal environments such as deserts, semideserts, rocks, cliffs, marine intertidal flats, and hot springs.

<span class="mw-page-title-main">Exobiology Radiation Assembly</span>

Exobiology Radiation Assembly (ERA) was an experiment that investigated the biological effects of space radiation. An astrobiology mission developed by the European Space Agency (ESA), it took place aboard the European Retrievable Carrier (EURECA), an unmanned 4.5 tonne satellite with a payload of 15 experiments.

<span class="mw-page-title-main">Slime coat</span> Fish integument

The slime coat is the coating of mucus covering the body of all fish. An important part of fish anatomy, it serves many functions, depending on species, ranging from locomotion, care and feeding of offspring, to resistance to disease and parasites.

References

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