Chemistry: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]

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

name peak absorbance nm systematic name Chemspider
Asterina-330 330 {[(3E)-5-Hydroxy-3-[(2-hydroxyethyl)iminio]-5-(hydroxymethyl)-2-methoxy-1-cyclohexen-1-yl]amino}acetate 10475832
Euhalothece-362 362
Mycosporine-2-glycine 334 [(E)-{3-[(Carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene}amino]acetic acid 10474079
Mycosporine-glycine 310 N-[(5S)-5-Hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxo-1-cyclohexen-1-yl]glycine 10476943
Mycosporine-glycine-valine 335
Mycosporine-glutamic acid-glycine 330
Mycosporine-methylamine-serine 327
Mycosporine-methylamine-threonine 327
Mycosporine-taurine 309
Palythenic acid 337
Palythene 360 [(E)-{5-Hydroxy-5-(hydroxymethyl)-2-methoxy-3-[(1E)-1-propen-1-ylamino]-2-cyclohexen-1-ylidene}ammonio]acetate 10475813
Palythine 320 N-[5-Hydroxy-5-(hydroxymethyl)-3-imino-2-methoxycyclohex-1-en-1-yl]glycine 10272813
Palythine-serine 320 N-[5-Hydroxy-5-(hydroxymethyl)-3-imino-2-methoxy-1-cyclohexen-1-yl]serine 10476937
Palythine-serine-sulfate 320
Palythinol 332
Porphyra-334 334 29390215
Shinorine 334
Usujirene 357

[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]

References

  1. ↑ "Metabolites from algae with economical impact". Comparative Biochemistry and Physiology. Toxicology & Pharmacology 146 (1–2): 60–78. 2007. doi:10.1016/j.cbpc.2006.05.007. PMID 16901759. 
  2. ↑ "Mycosporine-Like Amino Acids and Their Derivatives as Natural Antioxidants". Antioxidants 4 (3): 603–46. September 2015. doi:10.3390/antiox4030603. PMID 26783847. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Mycosporines and mycosporine-like amino acids: UV protectants or multipurpose secondary metabolites?". FEMS Microbiology Letters 269 (1): 1–10. April 2007. doi:10.1111/j.1574-6968.2007.00650.x. PMID 17286572. 
  4. ↑ Sen, Sutrishna; Mallick, Nirupama (2021-10-01). "Mycosporine-like amino acids: Algal metabolites shaping the safety and sustainability profiles of commercial sunscreens" (in en). Algal Research 58: 102425. doi:10.1016/j.algal.2021.102425. ISSN 2211-9264. https://www.sciencedirect.com/science/article/pii/S2211926421002447. 
  5. ↑ Arai, Takayuki; Nishijima, Miyuki; Adachi, Kyoko; Sano, Hiroshi (1992). "Isolation and structure of a UV absorbing substance from the marine bacterium Micrococcus sp.". MBI Report. 
  6. ↑ 6.0 6.1 "Occurrence of UV-Absorbing, Mycosporine-Like Compounds among Cyanobacterial Isolates and an Estimate of Their Screening Capacity". Applied and Environmental Microbiology 59 (1): 163–9. 1993. doi:10.1128/AEM.59.1.163-169.1993. PMID 16348839. Bibcode: 1993ApEnM..59..163G. 
  7. ↑ Okaichi T, Tokumura T. Isolation of cyclohexene derivatives from Noctiluca miliaris. 1980 Chemical Society of Japan
  8. ↑ 8.0 8.1 Kogej, Tina; Gostinčar, Cene; Volkmann, Marc; Gorbushina, Anna A.; Gunde-Cimerman, Nina (2006). "Mycosporines in Extremophilic Fungi—Novel Complementary Osmolytes?". Environmental Chemistry 3 (2): 105–110. doi:10.1071/En06012. 
  9. ↑ "Phylogenetic distribution of fungal mycosporines within the Pucciniomycotina (Basidiomycota)". Yeast 28 (8): 619–27. August 2011. doi:10.1002/yea.1891. PMID 21744380. 
  10. ↑ 10.0 10.1 "Natural Microbial UV Radiation Filters – Mycosporine-like Amino Acids". Folia Microbiologica 49 (4): 339–352. 2004. doi:10.1007/bf03354663. PMID 15530001. 
  11. ↑ "Evidence Regarding the UV Sunscreen Role of a Mycosporine-Like Compound in the Cyanobacterium Gloeocapsa sp". Applied and Environmental Microbiology 59 (1): 170–6. 1993. doi:10.1128/AEM.59.1.170-176.1993. PMID 16348840. Bibcode: 1993ApEnM..59..170G. 
  12. ↑ Korbee, Nathalie; Figueroa, Félix L.; Aguilera, José (March 2006). "Acumulación de aminoácidos tipo micosporina (MAAs): biosíntesis, fotocontrol y funciones ecofisiológicas". Revista chilena de historia natural 79 (1): 119–132. doi:10.4067/S0716-078X2006000100010. ISSN 0716-078X. 
  13. ↑ Bandaranayake WM. 1998. Mycosporines: are they nature’s sunscreens? Natural Product Reports. 159–171.
  14. ↑ "Mycosporine-like amino acids: relevant secondary metabolites. Chemical and ecological aspects". Marine Drugs 9 (3): 387–446. March 2011. doi:10.3390/md9030387. PMID 21556168. 
  15. ↑ "Comparative Profiling and Discovery of Novel Glycosylated Mycosporine-Like Amino Acids in Two Strains of the Cyanobacterium Scytonema cf. crispum". Applied and Environmental Microbiology 82 (19): 5951–9. October 2016. doi:10.1128/AEM.01633-16. PMID 27474710. Bibcode: 2016ApEnM..82.5951D. 
  16. ↑ 16.0 16.1 "O-Methyltransferase is shared between the pentose phosphate and shikimate pathways and is essential for mycosporine-like amino acid biosynthesis in Anabaena variabilis ATCC 29413". ChemBioChem 16 (2): 320–7. January 2015. doi:10.1002/cbic.201402516. PMID 25487723. 
  17. ↑ "Mycosporine-like amino acids (MAAs): chemical structure, biosynthesis and significance as UV-absorbing/screening compounds". Indian Journal of Experimental Biology 46 (1): 7–17. 2008. PMID 18697565. http://nopr.niscair.res.in/bitstream/123456789/4408/1/IJEB%2046(1)%207-17.pdf. 
  18. ↑ "Constitutive and UV-inducible synthesis of photoprotective compounds (carotenoids and mycosporines) by freshwater yeasts". Photochemical & Photobiological Sciences 3 (3): 281–6. March 2004. doi:10.1039/b310608j. PMID 14993945. 
  19. ↑ "Ultraviolet and osmotic stresses induce and regulate the synthesis of mycosporines in the cyanobacterium chlorogloeopsis PCC 6912". Archives of Microbiology 172 (4): 187–92. 1999. doi:10.1007/s002030050759. PMID 10525734. 
  20. ↑ Neale, PJ; Banaszak, AT; Jarriel, CR (1998). "Ultraviolet sunscreens in Gymnodinium sanguineum (Dinophyceae): mycosporine-like amino acids protect against inhibition of photosynthesis". J Phycol 34 (6): 928–938. doi:10.1046/j.1529-8817.1998.340928.x. 
  21. ↑ Sun, Yingying; Zhang, Naisheng; Zhou, Jing; Dong, Shasha; Zhang, Xin; Guo, Lei; Guo, Ganlin (January 2020). "Distribution, Contents, and Types of Mycosporine-Like Amino Acids (MAAs) in Marine Macroalgae and a Database for MAAs Based on These Characteristics" (in en). Marine Drugs 18 (1): 43. doi:10.3390/md18010043. PMID 31936139. 
  22. ↑ "Computational exploration of natural sunscreens". Physical Chemistry Chemical Physics 13 (13): 5584–6. April 2011. doi:10.1039/C0CP02901G. PMID 21350786. Bibcode: 2011PCCP...13.5584S. 
  23. ↑ "How seaweeds release the excess energy from sunlight to surrounding sea water". Physical Chemistry Chemical Physics 19 (24): 15745–15753. June 2017. doi:10.1039/C7CP02699D. PMID 28604867. Bibcode: 2017PCCP...1915745K. https://hal.archives-ouvertes.fr/hal-02991570/file/porphyra_water_preprint.pdf. 
  24. ↑ "A novel prokaryotic UVB photoreceptor in the cyanobacterium Chlorogloeopsis PCC 6912". Photochemistry and Photobiology 71 (4): 493–8. 2000. doi:10.1562/0031-8655(2000)0710493anpupi2.0.co2. PMID 10824604. 
  25. ↑ "Molecular photoprotection of human keratinocytes in vitro by the naturally occurring mycosporine-like amino acid (MAA) palythine". The British Journal of Dermatology 178 (6): 1353–1363. November 2017. doi:10.1111/bjd.16125. PMID 29131317. 
  26. ↑ "Differential susceptibility to oxidative stress of two scleractinian corals: antioxidant functioning of mycosporine-glycine". Comparative Biochemistry and Physiology. Part B, Biochemistry & Molecular Biology 139 (4): 721–30. 2004. doi:10.1016/j.cbpc.2004.08.016. PMID 15581804. 
  27. ↑ "Mycosporine glycine protects biological systems against photodynamic damage by quenching singlet oxygen with a high efficiency". Photochemistry and Photobiology 78 (2): 109–13. 2003. doi:10.1562/0031-8655(2003)0780109mgpbsa2.0.co2. PMID 12945577. 
  28. ↑ Dunlap, Walter C.; Yamamoto, Yorihiro (September 1995). "Small-molecule antioxidants in marine organisms: Antioxidant activity of mycosporine-glycine". Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology 112 (1): 105–114. doi:10.1016/0305-0491(95)00086-N. 
  29. ↑ "Biogeochemistry of a gypsum-encrusted microbial ecosystem". Geobiology 2 (3): 133–150. July 2004. doi:10.1111/j.1472-4677.2004.00029.x. 
  30. ↑ "Physiological Roles of a Substance 334 in Algae". Botanica Marina 19 (1). 1976. doi:10.1515/botm.1976.19.1.9. 
  31. ↑ "Effect of UV-B and high visual radiation on photosynthesis in freshwater (nostoc spongiaeforme) and marine (Phormidium corium) cyanobacteria". Indian Journal of Biochemistry & Biophysics 44 (4): 231–9. 2007. PMID 17970281. 
  32. ↑ "With 'biological sunscreen,' mantis shrimp see the reef in a whole different light". 3 July 2014. http://phys.org/news/2014-07-biological-sunscreen-mantis-shrimp-reef.html. 
  33. ↑ "Biological sunscreens tune polychromatic ultraviolet vision in mantis shrimp". Current Biology 24 (14): 1636–1642. July 2014. doi:10.1016/j.cub.2014.05.071. PMID 24998530. 
  34. ↑ Oren, Aharon (July 1997). "Mycosporine-like amino acids as osmotic solutes in a community of halophilic cyanobacteria". Geomicrobiology Journal 14 (3): 231–240. doi:10.1080/01490459709378046. 
  35. ↑ "UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria)". The Journal of Biological Chemistry 280 (48): 40271–81. December 2005. doi:10.1074/jbc.m505961200. PMID 16192267. 
  36. ↑ Tirkey, J.; Adhikary, S.P. (2005). "Cyanobacteria in biological soil crusts of india". Current Science 89 (3): 515–521. 
  37. ↑ Michalek-Wagner, K.; Willis, B.L. (2001). "Impacts of bleaching on the soft coral lobophytum compactum. ii. biochemical changes in adults and their eggs". Coral Reefs 19 (3): 240–246. doi:10.1007/pl00006959. 
  38. ↑ "Ultraviolet radiation-absorbing mycosporine-like amino acids in coral reef organisms: a biochemical and environmental perspective". J Phycol 34: 418–430. 1998. doi:10.1046/j.1529-8817.1998.340418.x. 

Further reading

  • "Mycosporines: are they nature's sunscreens?". Natural Product Reports 15 (2): 159–72. April 1998. doi:10.1039/a815159y. PMID 9586224. 
  • "An enzymatic route to sunscreens". ChemBioChem 12 (3): 363–5. February 2011. doi:10.1002/cbic.201000709. PMID 21290533. 
  • "Photoprotective compounds from marine organisms". Journal of Industrial Microbiology & Biotechnology 37 (6): 537–58. June 2010. doi:10.1007/s10295-010-0718-5. PMID 20401734. 
  • "The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds". Journal of Photochemistry and Photobiology B: Biology 66 (1): 2–12. 2002. doi:10.1016/s1011-1344(01)00269-x. PMID 11849977. 
  • "Effects of abiotic stressors on synthesis of the mycosporine-like amino acid shinorine in the Cyanobacterium Anabaena variabilis PCC 7937". Photochemistry and Photobiology 84 (6): 1500–5. 2008. doi:10.1111/j.1751-1097.2008.00376.x. PMID 18557824. 
  • Sinha, RP; Klish, M; Groninger, A; Hader, D-P (1998). "Ultraviolet-absorbing/screening substances in cyanobacteria, phytoplankton and macroalgae". J Photochem Photobiol B 47 (2–3): 83–94. doi:10.1016/s1011-1344(98)00198-5. 
  • Xu, Zhiguang; Gao, Kunshan (2009). "Impacts of UV radiation on growth and photosynthetic carbon acquisition inGracilaria lemaneiformis(Rhodophyta) under phosphorus-limited and replete conditions". Functional Plant Biology 36 (12): 1057–1064. doi:10.1071/fp09092. PMID 32688717. 



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