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词条 Mycosporine-like amino acid
释义

  1. Background

  2. Chemistry

  3. Examples

  4. Functions

     Ultraviolet light responses  Protection from UV radiation  Protection from oxidative damage  Accessory pigments in photosynthesis  Photoreceptors  Environmental stress responses  Salt stress  Desiccation stress  Thermal stress 

  5. References

  6. Further reading

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]

Background

MAAs are widespread in the microbial world and have been reported in many microorganisms including heterotrophic bacteria,[3] cyanobacteria,[4] microalgae,[5] ascomycetous [7] and basidiomycetous[6] fungi, as well as some multicellular organisms such as macroalgae and marine animals.[7] 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.[8] 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.[9]

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.[10] The ring structure is thought to absorb UV light and accommodate free radicals. All MAAs absorb ultraviolet wavelengths, typically between 310 and 362 nm.[7][11] They are considered to be amongst the strongest natural absorbers of UV radiation.[12] 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.[13] 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.[13]

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
[14]

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,[15] cyanobacteria,[16] marine dinoflagellates[17] and some Antarctic diatoms.[18] When MAAs absorb UV light the energy is dissipated as heat.[19][20] UV-B photoreceptors have been identified in cyanobacteria as the molecules responsible for the UV light induced responses, including synthesis of MAAs.[21]

An MAA known as palythine, derived from seaweed, has been found to protect human skin cells from UV radiation even in low concentrations.[22]

"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).[18] 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.[23][24] MAA-glycine (mycosporine-glycine) is able to quench singlet oxygen and hydroxyl radicals very quickly and efficiently.[25] 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.[26]

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.[27] Further studies done in marine cyanobacteria showed that the MAAs synthesized in response to UV-B correlated with an increase in photosynthetic pigments.[28] 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.[29] Three of the filter MAAs are identified with porphyra-334, mycosporine-gly, and gadusol.[30]

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.[18] 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.[31] The same phenomenon was noted for some halotolerant fungi.[32] 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.[33] Particularly cyanobacteria species that are exposed to desiccation, UV radiation and oxidation stress have been shown to possess MAA’s in an extracellular matrix.[34] However it has been shown that MAAs do not provide sufficient protection against high doses of UV radiation.[4]

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.[35][36] 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.[18]

References

1. ^{{cite journal | vauthors = Cardozo KH, Guaratini T, Barros MP, Falcão VR, Tonon AP, Lopes NP, Campos S, Torres MA, Souza AO, Colepicolo P, Pinto E | title = Metabolites from algae with economical impact | journal = Comparative Biochemistry and Physiology. Toxicology & Pharmacology : CBP | volume = 146 | issue = 1–2 | pages = 60–78 | year = 2007 | pmid = 16901759 | doi = 10.1016/j.cbpc.2006.05.007 }}
2. ^{{cite journal | vauthors = Wada N, Sakamoto T, Matsugo S | title = Mycosporine-Like Amino Acids and Their Derivatives as Natural Antioxidants | journal = Antioxidants | volume = 4 | issue = 3 | pages = 603–46 | date = September 2015 | pmid = 26783847 | doi = 10.3390/antiox4030603 | url = http://www.mdpi.com/2076-3921/4/3/603 | pmc=4665425}}
3. ^{{cite journal | last1 = Arai | first1 = Takayuki | last2 = Nishijima | first2 = Miyuki | last3 = Adachi | first3 = Kyoko | last4 = Sano | first4 = Hiroshi | name-list-format = vanc | year = 1992 | title = Isolation and structure of a UV absorbing substance from the marine bacterium Micrococcus sp. | journal = MBI Report }}
4. ^1 {{cite journal | vauthors = Garcia-Pichel F, Castenholz RW | title = Occurrence of UV-Absorbing, Mycosporine-Like Compounds among Cyanobacterial Isolates and an Estimate of Their Screening Capacity | journal = Applied and Environmental Microbiology | volume = 59 | issue = 1 | pages = 163–9 | year = 1993 | pmid = 16348839 | pmc = 202072 | doi = | url = }}
5. ^Okaichi T, Tokumura T. Isolation of cyclohexene derivatives from Noctiluca miliaris. 1980 Chemical Society of Japan
6. ^{{cite journal | vauthors = Libkind D, Moliné M, Sommaruga R, Sampaio JP, van Broock M | title = Phylogenetic distribution of fungal mycosporines within the Pucciniomycotina (Basidiomycota) | journal = Yeast | volume = 28 | issue = 8 | pages = 619–27 | date = August 2011 | pmid = 21744380 | pmc = | doi = 10.1002/yea.1891 }}
7. ^1 {{cite journal | vauthors = Rezanka T, Temina M, Tolstikov AG, Dembitsky VM | year = 2004 | title = Natural Microbial UV Radiation Filters – Mycosporine-like Amino Acids | url = | journal = Folia Microbiologica | volume = 49 | issue = 4| pages = 339–352 | doi=10.1007/bf03354663}}
8. ^{{cite journal | vauthors = Garcia-Pichel F, Wingard CE, Castenholz RW | title = Evidence Regarding the UV Sunscreen Role of a Mycosporine-Like Compound in the Cyanobacterium Gloeocapsa sp | journal = Applied and Environmental Microbiology | volume = 59 | issue = 1 | pages = 170–6 | year = 1993 | pmid = 16348840 | pmc = 202073 | doi = }}
9. ^{{Cite journal|last=Korbee|first=Nathalie|last2=Figueroa|first2=Félix L.|last3=Aguilera|first3=José|name-list-format = vanc|date=March 2006|title=Acumulación de aminoácidos tipo micosporina (MAAs): biosíntesis, fotocontrol y funciones ecofisiológicas|url=http://www.scielo.cl/scielo.php?script=sci_abstract&pid=S0716-078X2006000100010&lng=es&nrm=iso&tlng=es|journal=Revista chilena de historia natural|volume=79|issue=1|pages=119–132|doi=10.4067/S0716-078X2006000100010|issn=0716-078X}}
10. ^Bandaranayake WM. 1998. Mycosporines: are they nature’s sunscreens? Natural Product Reports. 159–171.
11. ^{{cite journal | vauthors = Carreto JI, Carignan MO | title = Mycosporine-like amino acids: relevant secondary metabolites. Chemical and ecological aspects | journal = Marine Drugs | volume = 9 | issue = 3 | pages = 387–446 | date = March 2011 | pmid = 21556168 | doi = 10.3390/md9030387 | pmc = 3083659 }}
12. ^{{cite journal | vauthors = D'Agostino PM, Javalkote VS, Mazmouz R, Pickford R, Puranik PR, Neilan BA | title = Comparative Profiling and Discovery of Novel Glycosylated Mycosporine-Like Amino Acids in Two Strains of the Cyanobacterium Scytonema cf. crispum | journal = Applied and Environmental Microbiology | volume = 82 | issue = 19 | pages = 5951–9 | date = October 2016 | pmid = 27474710 | doi = 10.1128/AEM.01633-16 | pmc=5038028}}
13. ^1 {{cite journal | vauthors = Pope MA, Spence E, Seralvo V, Gacesa R, Heidelberger S, Weston AJ, Dunlap WC, Shick JM, Long PF | title = 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 | journal = ChemBioChem | volume = 16 | issue = 2 | pages = 320–7 | date = January 2015 | pmid = 25487723 | doi = 10.1002/cbic.201402516 }}
14. ^{{cite journal | vauthors = Singh SP, Kumari S, Rastogi RP, Singh KL, Sinha RP | title = Mycosporine-like amino acids (MAAs): chemical structure, biosynthesis and significance as UV-absorbing/screening compounds | journal = Indian Journal of Experimental Biology | volume = 46 | issue = 1 | pages = 7–17 | year = 2008 | pmid = 18697565 | doi = | url = http://nopr.niscair.res.in/bitstream/123456789/4408/1/IJEB%2046(1)%207-17.pdf }}
15. ^{{cite journal | vauthors = Libkind D, Pérez P, Sommaruga R, Diéguez Mdel C, Ferraro M, Brizzio S, Zagarese H, van Broock M | title = Constitutive and UV-inducible synthesis of photoprotective compounds (carotenoids and mycosporines) by freshwater yeasts | journal = Photochemical & Photobiological Sciences | volume = 3 | issue = 3 | pages = 281–6 | date = March 2004 | pmid = 14993945 | doi = 10.1039/b310608j }}
16. ^{{cite journal | vauthors = Portwich A, Garcia-Pichel F | title = Ultraviolet and osmotic stresses induce and regulate the synthesis of mycosporines in the cyanobacterium chlorogloeopsis PCC 6912 | journal = Archives of Microbiology | volume = 172 | issue = 4 | pages = 187–92 | year = 1999 | pmid = 10525734 | doi = 10.1007/s002030050759 }}
17. ^{{cite journal | last1 = Neale | first1 = PJ | last2 = Banaszak | first2 = AT | last3 = Jarriel | first3 = CR | name-list-format = vanc | year = 1998 | title = Ultraviolet sunscreens in Gymnodinium sanguineum (Dinophyceae): mycosporine-like amino acids protect against inhibition of photosynthesis | url = | journal = J Phycol | volume = 34 | issue = | pages = 928–938 | doi=10.1046/j.1529-8817.1998.340928.x}}
18. ^1 2 3 4 5 {{cite journal | vauthors = Oren A, Gunde-Cimerman N | title = Mycosporines and mycosporine-like amino acids: UV protectants or multipurpose secondary metabolites? | journal = FEMS Microbiology Letters | volume = 269 | issue = 1 | pages = 1–10 | date = April 2007 | pmid = 17286572 | doi = 10.1111/j.1574-6968.2007.00650.x }}
19. ^{{cite journal | vauthors = Sampedro D | title = Computational exploration of natural sunscreens | journal = Physical Chemistry Chemical Physics | volume = 13 | issue = 13 | pages = 5584–6 | date = April 2011 | pmid = 21350786 | doi = 10.1039/C0CP02901G }}
20. ^{{cite journal | vauthors = Koizumi K, Hatakeyama M, Boero M, Nobusada K, Hori H, Misonou T, Nakamura S | title = How seaweeds release the excess energy from sunlight to surrounding sea water | journal = Physical Chemistry Chemical Physics | volume = 19 | issue = 24 | pages = 15745–15753 | date = June 2017 | pmid = 28604867 | doi = 10.1039/C7CP02699D }}
21. ^{{cite journal | vauthors = Portwich A, Garcia-Pichel F | title = A novel prokaryotic UVB photoreceptor in the cyanobacterium Chlorogloeopsis PCC 6912 | journal = Photochemistry and Photobiology | volume = 71 | issue = 4 | pages = 493–8 | year = 2000 | pmid = 10824604 | doi = 10.1562/0031-8655(2000)0710493anpupi2.0.co2| url = }}
22. ^{{cite journal | vauthors = Lawrence KP, Gacesa R, Long PF, Young AR | title = Molecular photoprotection of human keratinocytes in vitro by the naturally occurring mycosporine-like amino acid (MAA) palythine | journal = The British Journal of Dermatology | pages = n/a–n/a | date = November 2017 | pmid = 29131317 | doi = 10.1111/bjd.16125 }}
23. ^{{cite journal | vauthors = Yakovleva I, Bhagooli R, Takemura A, Hidaka M | title = Differential susceptibility to oxidative stress of two scleractinian corals: antioxidant functioning of mycosporine-glycine | journal = Comparative Biochemistry and Physiology. Part B, Biochemistry & Molecular Biology | volume = 139 | issue = 4 | pages = 721–30 | year = 2004 | pmid = 15581804 | doi = 10.1016/j.cbpc.2004.08.016 }}
24. ^{{cite journal | vauthors = Suh HJ, Lee HW, Jung J | title = Mycosporine glycine protects biological systems against photodynamic damage by quenching singlet oxygen with a high efficiency | journal = Photochemistry and Photobiology | volume = 78 | issue = 2 | pages = 109–13 | year = 2003 | pmid = 12945577 | doi = 10.1562/0031-8655(2003)0780109mgpbsa2.0.co2}}
25. ^{{cite journal|last1=Dunlap|first1=Walter C.|last2=Yamamoto|first2=Yorihiro|name-list-format=vanc|title=Small-molecule antioxidants in marine organisms: Antioxidant activity of mycosporine-glycine|journal=Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology|date=September 1995|volume=112|issue=1|pages=105–114|doi=10.1016/0305-0491(95)00086-N}}
26. ^{{cite journal|vauthors = Canfield DE, Sorensen KB, Oren A |title=Biogeochemistry of a gypsum-encrusted microbial ecosystem|journal=Geobiology|date=July 2004|volume=2|issue=3|pages=133–150|doi=10.1111/j.1472-4677.2004.00029.x}}
27. ^{{cite journal|vauthors = Sivalingam PM, Ikawa T, Nisizawa K|title=Physiological Roles of a Substance 334 in Algae|journal=Botanica Marina|date=1976|volume=19|issue=1|doi=10.1515/botm.1976.19.1.9}}
28. ^{{cite journal | vauthors = Bhandari R, Sharma PK | title = Effect of UV-B and high visual radiation on photosynthesis in freshwater (nostoc spongiaeforme) and marine (Phormidium corium) cyanobacteria | journal = Indian Journal of Biochemistry & Biophysics | volume = 44 | issue = 4 | pages = 231–9 | year = 2007 | pmid = 17970281 | doi = | url = }}
29. ^{{cite web|url=http://phys.org/news/2014-07-biological-sunscreen-mantis-shrimp-reef.html|title=With 'biological sunscreen,' mantis shrimp see the reef in a whole different light|date=3 July 2014|accessdate=4 July 2014}}
30. ^{{cite journal | vauthors = Bok MJ, Porter ML, Place AR, Cronin TW | title = Biological sunscreens tune polychromatic ultraviolet vision in mantis shrimp | journal = Current Biology | volume = 24 | issue = 14 | pages = 1636–1642 | date = July 2014 | pmid = 24998530 | doi = 10.1016/j.cub.2014.05.071 }}
31. ^{{cite journal|last1=Oren|first1=Aharon|name-list-format=vanc|title=Mycosporine‐like amino acids as osmotic solutes in a community of halophilic cyanobacteria|journal=Geomicrobiology Journal|date=July 1997|volume=14|issue=3|pages=231–240|doi=10.1080/01490459709378046}}
32. ^1 {{cite journal|last1=Kogej|first1=Tina|last2=Gostinčar|first2=Cene|last3=Volkmann|first3=Marc|last4=Gorbushina|first4=Anna A.|last5=Gunde-Cimerman|first5=Nina |name-list-format = vanc |title=Mycosporines in Extremophilic Fungi—Novel Complementary Osmolytes?|journal=Environmental Chemistry|date=2006|volume=3|issue=2|pages=105–110|doi=10.1071/En06012}}
33. ^{{cite journal | vauthors = Wright DJ, Smith SC, Joardar V, Scherer S, Jervis J, Warren A, Helm RF, Potts M | title = UV irradiation and desiccation modulate the three-dimensional extracellular matrix of Nostoc commune (Cyanobacteria) | journal = The Journal of Biological Chemistry | volume = 280 | issue = 48 | pages = 40271–81 | date = December 2005 | pmid = 16192267 | doi = 10.1074/jbc.m505961200 }}
34. ^{{cite journal | last1 = Tirkey | first1 = J. | last2 = Adhikary | first2 = S.P. | name-list-format = vanc | year = 2005 | title = Cyanobacteria in biological soil crusts of india | url = | journal = Current Science | volume = 89 | issue = 3| pages = 515–521 }}
35. ^{{cite journal | last1 = Michalek-Wagner | first1 = K. | last2 = Willis | first2 = B.L. | name-list-format = vanc | year = 2001 | title = Impacts of bleaching on the soft coral lobophytum compactum. ii. biochemical changes in adults and their eggs | url = | journal = Coral Reefs | volume = 19 | issue = 3| pages = 240–246 | doi=10.1007/pl00006959}}
36. ^{{cite journal | vauthors = Dunlap WC, Shick JM | year = 1998 | title = Ultraviolet radiation-absorbing mycosporine-like amino acids in coral reef organisms: a biochemical and environmental perspective | url = | journal = J Phycol | volume = 34 | issue = | pages = 418–430 | doi=10.1046/j.1529-8817.1998.340418.x}}

Further reading

{{refbegin|33em}}
  • {{cite journal | vauthors = Bandaranayake WM | title = Mycosporines: are they nature's sunscreens? | journal = Natural Product Reports | volume = 15 | issue = 2 | pages = 159–72 | date = April 1998 | pmid = 9586224 | doi = 10.1039/a815159y }}
  • {{cite journal | vauthors = Schmidt EW | title = An enzymatic route to sunscreens | journal = ChemBioChem | volume = 12 | issue = 3 | pages = 363–5 | date = February 2011 | pmid = 21290533 | doi = 10.1002/cbic.201000709 }}
  • {{cite journal | vauthors = Rastogi RP, Sinha RP, Singh SP, Häder DP | title = Photoprotective compounds from marine organisms | journal = Journal of Industrial Microbiology & Biotechnology | volume = 37 | issue = 6 | pages = 537–58 | date = June 2010 | pmid = 20401734 | doi = 10.1007/s10295-010-0718-5 }}
  • {{cite journal | vauthors = Rozema J, Björn LO, Bornman JF, Gaberscik A, Häder DP, Trost T, Germ M, Klisch M, Gröniger A, Sinha RP, Lebert M, He YY, Buffoni-Hall R, de Bakker NV, van de Staaij J, Meijkamp BB | display-authors = 6 | title = The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds | journal = Journal of Photochemistry and Photobiology. B, Biology | volume = 66 | issue = 1 | pages = 2–12 | year = 2002 | pmid = 11849977 | doi = 10.1016/s1011-1344(01)00269-x }}
  • {{cite journal | vauthors = Singh SP, Klisch M, Sinha RP, Häder DP | title = Effects of abiotic stressors on synthesis of the mycosporine-like amino acid shinorine in the Cyanobacterium Anabaena variabilis PCC 7937 | journal = Photochemistry and Photobiology | volume = 84 | issue = 6 | pages = 1500–5 | year = 2008 | pmid = 18557824 | doi = 10.1111/j.1751-1097.2008.00376.x | url = }}
  • {{cite journal | last1 = Sinha | first1 = RP | last2 = Klish | first2 = M | last3 = Groninger | first3 = A | last4 = Hader | first4 = D-P | name-list-format = vanc | year = 1998 | title = Ultraviolet-absorbing/screening substances in cyanobacteria, phytoplankton and macroalgae | url = | journal = J Photochem Photobiol B | volume = 47 | issue = | pages = 83–94 | doi=10.1016/s1011-1344(98)00198-5}}
  • {{cite journal | last1 = Xu | first1 = Zhiguang | last2 = Gao | first2 = Kunshan | name-list-format = vanc | year = 2009 | title = Impacts of UV radiation on growth and photosynthetic carbon acquisition inGracilaria lemaneiformis(Rhodophyta) under phosphorus-limited and replete conditions | url = | journal = Functional Plant Biology | volume = 36 | issue = 12| page = 1057 | doi=10.1071/fp09092}}
{{refend}}

1 : Amino acids
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