Abstract
The photoadaptive responses of macroalgal communities to abiotic stresses have been studied, and a number of UV-absorbing molecules have been identified. Among these compounds, photoprotective compounds such as mycosporine-like amino acids and carotenoids have been isolated from various red macroalgal species. However, several substances still need to be characterized. We describe the preparation of photoprotective extracts obtained from Solieria chordalis. Two solvents, 2-octyl dodecanol and octyldodecyl ester of l-pyrrolidone carboxylic acid, were selected based on their cosmetic functions for performing an ultrasound-assisted extraction. The efficiency of extraction was monitored by spectrophotometry and in vitro photoprotective activity measurements. 2-Octyl dodecanol and octyldodecyl ester of l-pyrrolidone carboxylic acid extracts showed maximum absorption wavelengths ranging from 280 to 340 nm and 270 to 350 nm, respectively. The anti UV-B capacity for protecting a synthetic chlorophyll solution was assessed by measuring its pseudo first-order degradation kinetics at room temperature. Under irradiation at 312 nm, chlorophyll introduced in the 2-octyl dodecanol S. chordalis extract showed the slowest degradation kinetics with a half-life t1/2 of 121.0 min. Several compounds were detected in the seaweed extract by high-performance liquid chromatography. Among them, the mycosporine-like amino acid, palythenic acid, was detected in the algal extract.
Acknowledgments
The co-authors thank the Solabia group and Sasol Ltd for providing emollient solvents. The authors thank A. Boucaud, A. Le Mentec, O. Clohessy, and S. Kehoe for technical assistance provided for some parts of this work.
References
Afonso, C.A.M. and J.G. Crespo. 2005. Green separation processes. Ed. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, ISBN 978-3-527-30985-6.Search in Google Scholar
Anastas, P.T. and J.C. Warner. 1998. Green chemistry: theory and practice. Oxford University Press, New York.Search in Google Scholar
Ar Gall, E., L. Cornec and E. Deslandes. 2008. Oligocarrageenans and tissue-dependant oxidative burst in Solieria chordalis (Rhodophyceae, Gigartinales). Phycol. Res. 56: 7–12.Search in Google Scholar
Bedoux, G. and N. Bourgougnon. 2014. Bioactivity of secondary metabolites from macroalgae. In: (D. Sahoo and J. Seckbach, eds.) Cellular origins, life in extreme habitats and astrobiology. Springer, Dordrecht, Netherlands. pp. 19.Search in Google Scholar
Bourgougnon, N. and V. Stiger-Pouvreau. 2012. Chemodiversity and bioactivity within red and brown macroalgae along the French coasts, metropole and overseas departements and territories. In: Handbook of marine macroalgae, biotechnology and applied phycology. Wiley-Blackwell, Chichester, UK. pp. 58–105.Search in Google Scholar
Bourgougnon, N., G. Bedoux, A. Sangiardi and V. Stiger-Pouvreau. 2011. Las algas: potencial nutritivo y aplicaciones cosméticas. En: Las Algas como Recurso, Valorización, Aplicaciones Industriales y Tendencias, Centro Tecnológico del Mar-Fundación CETMAR (ed.) 81-94 ISBN: 978-84-615-3593-4.Search in Google Scholar
Carreto, J.I. and M.O. Carignan. 2011. Mycosporine-like amino acids: relevant secondary metabolites. Chemical ecological aspects. Mar. Drugs 9: 387–446.10.3390/md9030387Search in Google Scholar
Carreto, J.I., M.O. Carignan, G. Daleo and S.G. De Marco. 1990. Occurrence of mycosporine-like amino acids in the red tide dinoflagellate Alexandrium excavatum: UV-photoprotective compounds? J. Plankton Res. 12: 909–921.10.1093/plankt/12.5.909Search in Google Scholar
Carreto, J.I., M.O. Carignan and N.G. Montoya. 2001. Comparative studies on mycosporine-like amino acids, paralytic shellfish toxins and pigment profiles of the toxic dinoflagellates Alexandrium tamarense, A. catenella and A. minutum. Mar. Ecol. Prog. Ser. 223: 49–60.10.3354/meps223049Search in Google Scholar
Conde, F.R., M.S. Churio and C.M. Previtali. 2000. The photoprotector mechanism of mycosporine-like amino acids, excited-state properties and photostability of porphyra-334 in aqueous solution. J. Photochem. Photobiol. B Biol. 56: 139–144.Search in Google Scholar
Cuny, P., J.C. Romano, B. Beker and J. F. Rontani. 1999. Comparison of the photodegradation rates of chlorophyll chlorin ring and phytol side chain in phytodetritus: is the phytyldiol versus phytol ratio (CPPI) a new biogeochemical index? J. Exp. Mar. Biol. Ecol. 237: 271–290.10.1016/S0022-0981(99)00010-6Search in Google Scholar
Demasi, F. and G.M. Gargiulo. 1982. Solieria chordalis (C. Ag.) J. Ag. (Rhodophyta, Gigartinales) en Méditerranée. Allonia 25: 109–111.Search in Google Scholar
Deming-Adams, B. 1990. Carotenoids and photoprotection in plants: a role for the xanthophyll zeaxanthin. Biochim. Biophys. Acta1020: 1–24.10.1016/0005-2728(90)90088-LSearch in Google Scholar
EU cosmetic regulation, Regulation (ec) No 1223/2009 of the European parliament and of the council of 30 November 2009 on cosmetic products, Web site 2013, www.eur-lex.europa.eu/.Search in Google Scholar
Figueroa, F.L., L. Escassi, E. Pérez-Rodriguez, N. Korbee, A. Delia Giles and G. Johnsen. 2003. Effects of short-term irradiation on photoinhibition and accumulation of mycosporine-like amino acids in sun and shade species of the red algal genus Porphyra. J. Photochem. Photobiol. B: Biol. 69: 21–30.10.1016/S1011-1344(02)00388-3Search in Google Scholar
Floc’h, J.Y., E. Deslandes and Y. Le Gall. 1987. Evidence for vegetative propagation of the carrageenophyte Solieriachordalis (Solieriaceae, Rhodophyceae) on the coast of Brittany (France) and in culture. Bot. Mar. 30: 315–321.Search in Google Scholar
Franklin, L.A., G. Kräbs and R. Kuhlenkamp. 2001. Blue light and UV-A radiation control the synthesis of mycosporine-like amino acids in Chondrus crispus (Florideophyceae). J. Phycol. 37: 257–270.10.1046/j.1529-8817.2001.037002257.xSearch in Google Scholar
Gabrielson, P.W. and M.H. Hommersand. 1982. The Atlantic species of Solieria (Gigartinales, Rhodophyta): their morphology, distribution and affinities. J. Phycol. 18: 31–45.Search in Google Scholar
Gröniger, A. and D.P. Häder. 2000. Stability of mycosporine-like amino acids. Recent Res. Devel. Photochem. Photobiol. 4: 247–252.Search in Google Scholar
Gruber, A., M.Y. Roleda, I. Bartsch, D. Hanelt and C. Wiencke. 2011. Sporogenesis under ultraviolet radiation in Laminaria digitata (Phaeophyceae) reveals protection of photosensitive meiospores within soral tissue: physiological and anatomical evidence. J. Phycol. 47: 603–614.10.1111/j.1529-8817.2011.00998.xSearch in Google Scholar PubMed
Heo, S.J., S.C. Ko, S.H. Cha, D.H. Kang, H.S. Park, Y.U. Choi, D. Kim, W.K. Jung and Y.J. Jeon. 2009. Effect of phlorotannins isolated from Ecklonia cava on melanogenesis and their protective effect against photo-oxidative stress induced by UV-B radiation. Toxicol. In Vitro 23: 1123–1130.10.1016/j.tiv.2009.05.013Search in Google Scholar PubMed
Holzinger, A., L. Di Piazza, C. Lütz and M.Y. Roleda. 2011. Sporogenic and vegetative tissues of Saccharina latissima (Laminariales, Phaeophyceae) exhibit distinctive sensitivity to experimentally enhanced ultraviolet radiation: photosynthetically active radiation ratio. Phycol. Res. 59: 221–235.Search in Google Scholar
Hoyer, K., U. Karsten, T. Sawall and C. Wiencke. 2001. Photoprotective substances in Antarctic macroalgae and their variation with respect to depth distribution, different tissues and developmental stages. Mar. Ecol. Prog. Ser. 211: 117–129.Search in Google Scholar
Huovinen, P., J. Matos, I. Sousa Pinto and F.L. Figueroa. 2006. The role of ammonium in photoprotection against high irradiance in red alga Grateloupia lanceola. Aquatic Bot. 84: 308–316.10.1016/j.aquabot.2005.12.002Search in Google Scholar
Hupel, M., N. Poupart and E. Ar Gall. 2011. Development of a new in vitro method to evaluate the photoprotective sunscreen activity of plant extracts against high UV-B radiation. Talanta 86: 362–371.10.1016/j.talanta.2011.09.029Search in Google Scholar
IUPAC Recommendations 2006. 2007. Glossary of terms used in photochemistry, 3rd Edition, Braslavsky, S. E. Pure Appl. Chem.79: 293–465.Search in Google Scholar
Karentz, D., F.S. McEuen, M.C. Land and W.C. Dunlap. 1991. Survey of mycosporine-like amino acid compounds in Antarctic organisms: potential protection from ultraviolet exposure. Mar. Biol. 108: 157–166.10.1007/BF01313484Search in Google Scholar
Karsten, U. and C. Wiencke. 1999. Factors controlling the formation of UV-absorbing mycosporine-like amino acids in the marine red alga Palmaria palmata from Spitsbergen (Norway). J. Plant Physiol. 155: 407–415.10.1016/S0176-1617(99)80124-2Search in Google Scholar
Karsten, U., T. Sawall and C. Wiencke. 1998. A survey of the distribution of UV-absorbing substances in tropical macroalgae. Phycol. Res. 46: 271–279.10.1111/j.1440-1835.1998.tb00122.xSearch in Google Scholar
Kräbs, G., K. Bischof, D. Hanelt, U. Karsten and C. Wiencke. 2002. Wavelength-dependent induction of UV-absorbing mycosporine-like amino acids in the red alga Chondrus crispus under natural solar radiation. J. Exp. Mar. Biol. Ecol. 268: 69–82.10.1016/S0022-0981(01)00380-XSearch in Google Scholar
Kundu, S., A. Pal and A.K. Dikshit. 2005. UV induced degradation of herbicide 2,4-D: kinetic, mechanism and effect of various conditions on the degradation. Separ. Purif. Technol. 44: 121–129.Search in Google Scholar
Llewellyn, C.A. and R.L. Airs. 2010. Distribution and abundance of MAAs in 33 species of microalgae across 13 classes. Mar. Drugs 8: 1273–1291.10.3390/md8041273Search in Google Scholar PubMed PubMed Central
Matsumura, Y. and H.N. Ananthaswamy. 2004. Toxic effects of ultraviolet radiation on the skin. Toxicol. Appl. Pharmacol. 195: 298–308.10.1016/j.taap.2003.08.019Search in Google Scholar PubMed
Mineur, F., A. Le Roux, H. Stegenga, M. Verlaque and C.A. Maggs. 2012. Four new exotic red seaweeds on European shores. Biol. Invasions 14: 1635–1641.10.1007/s10530-012-0186-0Search in Google Scholar
Muthusamy, V. and T.J. Piva. 2013. UVB-stimulated TNFα release from human melanocyte and melanoma cells is mediated by p38 MAPK. Int. J. Mol. Sci. 14: 17029–17054.10.3390/ijms140817029Search in Google Scholar PubMed PubMed Central
Oren, A. and N. Gunde-Cimerman. 2007. Mycosporines and mycosporines-like amino acids: UV protectants or multipropose secondary metabolites? FEM Microbiol. Lett. 269: 1–10.10.1111/j.1574-6968.2007.00650.xSearch in Google Scholar PubMed
Peinado, N.K., R.T.A. Diaz, F.L. Figueroa and E.W. Helbling. 2004. Ammonium and UV radiation stimulate the accumulation of mycosporine-like amino acids in Porphyra columbina (Rhodophyta) from Patagonia, Argentina. J. Phycol. 40: 248–259.10.1046/j.1529-8817.2004.03013.xSearch in Google Scholar
Pessoa, M.F. 2012. Algae and aquatic macrophytes responses to cope to ultraviolet radiation – a Review. Emir. J. Food Agric. 24: 527–545.10.9755/ejfa.v24i6.527545Search in Google Scholar
Rastogi, R.P., R.P. Sinha, S.P. Sing and D.P. Häder. 2010. Photoprotective compounds from marine organisms. J. Ind. Microbiol. Biotechnol. 37: 537–558.10.1007/s10295-010-0718-5Search in Google Scholar
Reef, R., P. Kaniewska and O. Hoegh-Guldberg. 2009. Coral skeletons defend against ultraviolet radiation. PLoS One 4: e7995.10.1371/journal.pone.0007995Search in Google Scholar
Richa, R.P. Rastogi, S. Kumari, K.L. Singh, V.K. Kannaujiya, G. Singh, M. Kesheri and R.P. Sinha. 2011. Biotechnological potential of mycosporine-like amino acids and phycobiliproteins of cyanobacterial origin. Biotechnol. Bioinf. Bioeng. 1: 159–171.Search in Google Scholar
Rodríguez-Bernaldo de Quirós, A., M.A. Lage-Yusty and J. López-Hernandez. 2010. Determination of phenolic compounds in macroalgae for Human consumption. Food Chem. 21: 634–638.10.1016/j.foodchem.2009.12.078Search in Google Scholar
Roleda, M.Y., U. Lütz-Meindl, C. Wiencke and C. Lütz. 2010. Physiological, biochemical, and ultrastructural responses of the green macroalga Urospora penicilliformis from Arctic Spitsbergen to UV radiation. Protoplasma 243: 105–116.Search in Google Scholar
Roleda, M.Y., C.D. Nyberg and A. Wulff. 2012. UVR defense mechanisms in eurytopic and invasive Gracilaria vermiculophylla (Gracilariales, Rhodophyta). Physiol. Plant. 146: 205–216.10.1111/j.1399-3054.2012.01615.xSearch in Google Scholar
Rosic, N. 2012. Phylogenic analysis of genes involved in mycosporine-like amino acid biosynthesis in symbiotic dinoflagellates. Appl. Microbiol. Biotechnol. 94: 29–37.10.1007/s00253-012-3925-3Search in Google Scholar
Rozema, J., L.O. Bjorn, J.F. Bornman, A. Gabersci, D.P. Häder, T. Trost, M. Germ, M. Klish, A. Gröniger, R.P. Sinha, M. Lebert, Y.Y. He, R. Buffoni-Hall, N.V.J. de Bakker, J. van de Staaij and B.B. Meijkamp. 2002. The role of UV-B radiation in aquatic and terrestrial ecosystems-an experimental and functional analysis of the evolution of UV-absorbing compounds. J. Photochem. Photobiol. B Biol. 66: 2–12.10.1016/S1011-1344(01)00269-XSearch in Google Scholar
Santabarbara, S. 2006. Limited sensitivity of pigment photo- oxidation in isolated thylakoids to singlet excited state quenching in photosystem II antenna. Arch. Biochem. Biophys. 455: 77–88.10.1016/j.abb.2006.08.017Search in Google Scholar PubMed
Schubert, N., E. Garcia-Mendoza and I. Pacheco-Ruize. 2006. Carotenoid composition of marine red algae. J. Phycol. 42: 1208–1216.10.1111/j.1529-8817.2006.00274.xSearch in Google Scholar
Sinha, R.P., M. Klisch, A. Gröniger and D.P. Häder. 1998. Ultraviolet-absorbing/screening substances in cyanobacteria, phytoplankton and macroalgae. J. Photochem. Photobio. B 47: 83–94.Search in Google Scholar
Sinha, R.P., M. Klish, A. Gröniger and D.P. Häder. 2000. Mycosporine-like amino acids in the marine red alga Gracilaria cornea – effects of UV and heat. Environ. Exp. Bot. 43: 33–43.10.1016/S0098-8472(99)00043-XSearch in Google Scholar
Sommaruga, R., K. Whitehead, J.M. Shick and C.S. Lobban. 2006. Mycosporine-like amino acids in the zooxanthella-ciliate symbiosis Maristentor dinoferus. Protist 157: 185–191.10.1016/j.protis.2006.01.002Search in Google Scholar
Stengel, D.B., S. Connan and Z.A. Popper. 2011. Algal chemodiversity and biodiversity: source of natural variability and implications for commercial application. Biotechnol. Adv. 29: 483–501.10.1016/j.biotechadv.2011.05.016Search in Google Scholar
Talarico, L. and G. Maranzana. 2000. Light and adaptive responses in red macroalgae: an overview. J. Photochem. Photobiol. B: Biol. 56: 1–11.10.1016/S1011-1344(00)00046-4Search in Google Scholar
Tavennec, M. 2009. La gestion d’une problématique algale dans un secteur hautement touristique la presqu’île de Rhuys. Personal communication 110p.Search in Google Scholar
Torres, A., M. Hochberg, I. Pergament, R. Smoum, V. Niddam, V.M. Dembitsky, M. Temina, I. Dor, O. Lev, M. Srebnik and C.D. Enk. 2004. A new UV absorbing mycosporine with photo protective activity from the lichenized ascomycete Collema cristatum. Eur. J. Biochem. 271: 780–784.10.1111/j.1432-1033.2004.03981.xSearch in Google Scholar
Tsujino, I., K. Yade and I. Sekikawa. 1980. Isolation and structure of a new amino acid, Shinorine, from the red alga Chondrus yendoi, Yamada et Mikami. Bot. Mar. 23: 65–68.Search in Google Scholar
Whitehead, K. and J.I. Hedges. 2002. Analysis of mycosporine-like amino acids in plankton by liquid chromatography electrospray ionization mass spectrometry. Mar. Chem. 80: 27–39.10.1016/S0304-4203(02)00096-8Search in Google Scholar
Whitehead, K. and J.I. Hedges. 2005. Photodegradation and photosensitization of mycosporine-like amino acids. J. Photochem. Photobiol. 80: 115–121.10.1016/j.jphotobiol.2005.03.008Search in Google Scholar PubMed
Whitehead, K., D. Karentz and J.I. Hedges. 2001. Mycosporine-like amino acids (MAAs) in phytoplankton, a herbivorous pteropod (Limacina helicina), and its pteropod predator (Clione antarctica) in McMurdo Bay, Antarctica. Mar. Biol. 139: 1013–1019.Search in Google Scholar
Yuan, Y.V., N.D. Westcott, C. Hu and D.D. Kitts. 2009. Mycosporine-like amino acid composition of edible red alga Palmaria palmata (dulse) harvested from the west and east coasts of Grand Manan Island, New Brunswick. Food Chem. 112: 321–328.10.1016/j.foodchem.2008.05.066Search in Google Scholar
Zvezdanović, J.B., T. Cvetić, S. Veljović-Jovanović and D. Marković. 2009. Chlorophyll bleaching by UV-irradiation in vitro and in situ: Absorption and fluorescence studies. Radiat. Phys. Chem. 78: 25–32.10.1016/j.radphyschem.2008.07.006Search in Google Scholar
©2014 by De Gruyter
