POLYPHENOLS OF BROWN ALGAE

  • Константин (Konstantin) Григорьевич (Grigor'evich) Боголицын (Bogolitsyn) Northern (Arctic) Federal University named after M.V. Lomonosov Email: k.bogolitsin@narfu.ru
  • Анна (Аnna) Сергеевна (Sergeevna) Дружинина (Druzhinina) Northern (Arctic) Federal University named after M.V. Lomonosov Email: annadruzhinina27@yandex.ru
  • Денис (Denis) Владимирович (Vladimirovich) Овчинников (Ovchinnikov) Northern (Arctic) Federal University named after M.V. Lomonosov Email: ovchinniko-deni@yandex.ru
  • Платон (Platon) Александрович (Aleksandrovich) Каплицин (Kaplitsin) Northern (Arctic) Federal University named after M.V. Lomonosov Email: platonkaplicin@yandex.ru
  • Елена (Elena) Валерьевна (Valer'evna) Шульгина (Shulgina) Northern (Arctic) Federal University named after M.V. Lomonosov Email: e.shulgina@narfu.ru
  • Анастасия (Аnastasiya) Эдуардовна (Eduardovna) Паршина (Parshina) Northern (Arctic) Federal University named after M.V. Lomonosov Email: parshanastasiya@yandex.ru
Keywords: brown algae, polyphenols, phlorotannins, extraction, liquid chromatography, mass-spectrometry, antioxidants, biological activity

Abstract

The modern state of research of marine brown algae polyphenolic compounds – phlorotannins, is analyzed. The data on the content of phlorotannins in biomass are presented depending on the species of algae and the place of growth. The biosynthesis, morphology, accumulation in the thallus, the physicochemical properties and biological role of these compounds are considered. The classical methods of isolating phlorotannins from algae are described, as well as modern methods, such as ultrasonic, microwave, enzymatic extraction, liquid extraction under pressure and supercritical fluid extraction. The ways of selective extraction of these compounds from extracts by methods of liquid-phase and solid-phase extraction are considered. Methods for studying the polymer composition of phlorotannins like gel permeation chromatography and ultrafiltration are presented. In the review of methods for quantitative determination and structural analysis of phlorotannins, special attention is paid to methods of nuclear magnetic resonance spectroscopy and chromatography-mass spectrometry using various ionization methods. The significant biological activity of phlorotannins is shown, which is represented by antioxidant, antitumor, anti-inflammatory, antibacterial, antiviral and other activities, which determines the prospects for the practical application of these polyphenolic compounds as therapeutic and prophylactic agents in the food, cosmetic and pharmacological industries.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Author Biographies

Константин (Konstantin) Григорьевич (Grigor'evich) Боголицын (Bogolitsyn), Northern (Arctic) Federal University named after M.V. Lomonosov
заведующий кафедрой теоретической и прикладной химии
Анна (Аnna) Сергеевна (Sergeevna) Дружинина (Druzhinina), Northern (Arctic) Federal University named after M.V. Lomonosov
инженер
Денис (Denis) Владимирович (Vladimirovich) Овчинников (Ovchinnikov), Northern (Arctic) Federal University named after M.V. Lomonosov
млаший научный сотрудник
Платон (Platon) Александрович (Aleksandrovich) Каплицин (Kaplitsin), Northern (Arctic) Federal University named after M.V. Lomonosov
инженер
Елена (Elena) Валерьевна (Valer'evna) Шульгина (Shulgina), Northern (Arctic) Federal University named after M.V. Lomonosov
млаший научный сотрудник
Анастасия (Аnastasiya) Эдуардовна (Eduardovna) Паршина (Parshina), Northern (Arctic) Federal University named after M.V. Lomonosov
лаборант

References

Bogolitsyn K.G., Kaplitsin P.A., Ul'ianovskii N.V., Pronina O.A. Khimiia rastitel'nogo syr'ia, 2012, no. 4, pp. 153–160. (in Russ.).

Spurr H.I. Extraction, separation and purification of polyphenols, polysaccharides and pigments from British seaweed for high-value applications: thesis (PhD), Leeds, 2014, 224 p.

Bogolitsyn K.G., Kaplitsin P.A., Dobrodeeva L.K., Druzhinina A.S., Ovchinnikov D.V., Parshina A.E., Shul'gina E.V. Sverkhkriticheskie fliuidy: teoriia i praktika, 2016, vol. 11, no. 3, pp. 58–70. (in Russ.).

Plaza M., Cifuentes A., Ibáñez E. Trends in Food Science and Technology, 2008, vol. 19, pp. 31–39.

Sánchez-Machado D.I., López-Cervantes J., López-Hernández J., Paseiro-Losada P. Food Chemistry, 2004, vol. 85, pp. 439–444.

Holdt S.L., Kraan S. Journal of Applied Phycology, 2011, vol. 23, pp. 543–597.

Kumar C.S., Ganesan P., Suresh P.V., Bhaskar N. Journal of Food Science and Technology, 2008, vol. 45, pp. 1–13.

Van Alstyne K.L. Journal of Chemical Ecology, 1995, vol. 21, pp. 45–58.

Koivikko R., Loponen J., Pihlaja K., Jormalainen V. Phytochemical Analysis, 2007, vol. 18, pp. 326–332.

Klindukh M.P., Obluchinskaia E.D. Vestnik MGTU, 2013, vol. 16, no. 3, pp. 466–471. (in Russ.).

Ragan M.A., Jensen A. Journal of Experimental Marine Biology and Ecology, 1978, vol. 34, pp. 245–258.

Glombitza K.W., Rösener H.U., Vilter H., Rauwald W. Planta Med., 1973, vol. 24(4), pp. 301–303.

Glombitza K.W., Rauwald H.W., Eckhardt G. Phytochemistry, 1975, vol. 14, pp. 1403–1405.

Glombitza K.W., Wiedenfeld G., Eckhardt G. Arch Pharm (Weinheim), 1978, vol. 311(5), pp. 393–399.

Achkar J., Xian M., Zhao H., Frost J.W. Journal of the American chemical society, 2005, vol. 127, pp. 5332–5333.

Koivikko R. Brown algal phlorotannins: Improving and applying chemical methods: doctoral dissertation (article-based). Turku, 2008, 61 p.

Vo T.S., Ngo D.H., Kim S.K. Process Biochemistry, 2012, vol. 47, pp. 386–394.

Schoenwaelder M.E.A., Clayton M.N. Journal of Phycology, 1998, vol. 34, pp. 969–980.

Schoenwaelder M.E.A. Phycologia, 2002, vol. 41, pp. 125–139.

Ragan M.A., Glombitza K.W. In Progress in Phycological Research, 1986, vol. 4, pp. 129−241.

Lüder U.H., Clayton M.N. Planta, 2004, vol. 218, no. 6, pp. 928–937.

Shibata T., Kawaguchi S., Hama Y., Inagaki M., Yamaguchi K., Nakamura T. Journal of Applied Phycology, 2004, vol. 16, pp. 291–296.

Fairhead V.A., Amsler C.D., McClintock J.B., Baker B.J. Polar Biology., 2005, vol. 28, pp. 680–686.

Nagayama K., Shibata T., Fujimoto K., Honjo T., Nakamura T. Aquaculture, 2003, vol. 218, pp. 601–611.

Machu L., Misurcova L., Ambrozova J.V., Orsavova J., Mlcek J., Sochor J., Jurikova T. Molecules, 2015, vol. 20, pp. 1118–1133.

Sabeena Farvin K.H., Jacobsen C. Food Chemistry, 2013, vol. 138, pp. 1670–1681.

Kim S.M., Kang S.W., Jeon J.-S., Jung Y.-J., Kim W.-R., Kim C.Y., Um B.-H. Food Chemistry, 2013, vol. 138, pp. 2399–2406.

Pádua D., Rocha E., Gargiulo D., Ramos A.A. Phytochemistry Letters., 2015, vol. 14, pp. 91–98.

Heffernan N., Brunton N.P., FitzGerald R.J., Smyth T.J. Mar. Drugs., 2015, vol. 13, pp. 509–528.

Martı´nez I., Castaneda T. Journal of Chromatographic Science, 2013, vol. 51, pp. 825–838.

Kadom S.U., Tiwari B.K., O’Donneli C.P. Journal of Agricultural and Food Chemistry, 2013, vol. 61, pp. 4667–4675.

Boettcher A.A., Targett N.M. Ecology, 1993, vol. 74, pp. 891–903.

Koivikko R., Loponen J., Honkanen T., Jormalainen V. Journal of Chemical Ecology, 2005, vol. 31, pp. 195–212.

Wang T., Jónsdóttir R., Liu H., Gu L., Kristinsson H.G., Raghavan S., Olafsdóttir G. Agricultural and food chemistry, 2012, vol. 60, pp. 5874–5883.

Ferreres F., Lopes G., Gil-Izquierdo A., Andrade P.B. et.al. Marine Drugs, 2012, vol. 10, pp. 2766–2781.

Audibert L., Fauchon M., Blanc N., Hauchard D., Ar Galla E. Phytochemical Analysis, 2010, vol. 21, pp. 399–405.

Shibata T., Ishimaru K., Kawaguchi S., Yoshikawa H., Hama Y. Journal of Applied Phycology, 2008, vol. 20, pp. 705−711.

Liu H., Gu L. Journal of Agricultural and Food Chemistry, 2012, vol. 60, pp. 1326−1334.

Nakamura T., Nagayama K., Uchida K., Tanaka R. Fisheries Science, 1996, vol. 62, pp. 923–926.

Mojzer E.B., Hrnči M.K., Škerget M., Knez Ž., Bren U. Molecules, 2016, vol. 21, pp. 901–939.

Hagerman A.E. Journal of Chemical Ecology, 1988, vol. 14, pp. 453–461.

Wissam Z., Ghada B., Wassim A., Warid K. International Journal of Pharmacy and Pharmaceutical Sciences, 2012, vol. 4, no. 3, pp. 675–682.

Díaz-Rubio M.E., Pérez-Jiménez J., Saura-Calixto F. International Journal of Food Sciences and Nutrition, 2009, vol. 60, pp. 23–34.

Rajbhar K., Dawda H., Mukundan U. Scientific Reviews and Chemical Communications, 2015, vol. 5, no. 1, pp. 1–6.

Ibañez E., Herrero M., Mendiola J.A., Castro-Puyana M. Marine bioactive compounds: sources, characterization and applications, Madrid, 2012, pp. 55–98.

Crisan C.C., Calinescu I., Zalaru C., Moldovan Z. UPB Scientific Bulletin, Series B: Chemistry and Materials Science, 2013, vol. 75(4), pp. 169–178.

Kadam S.U., Tiwari B.K., Smyth T.J., O’Donnell C.P. Ultrasonics Sonochemistry, 2014, vol. 23, pp. 308–316.

Pan X., Niu G., Liu H. Chemical Engineering and Processing, 2003, vol. 42, pp. 129–133.

Michalak I.Ł., Chojnacka T.K. Open Chemistry, 2015, vol. 13, pp. 1183–1195.

Li Z., Wang B., Zhang Q., Qu Y., Xu H., Li G. Journal of Applied Phycology, 2012, vol. 24, pp. 1527–1536.

Landbo A., Meyer A. Journal of Agricultural and Food Chemistry, 2001, vol. 49, pp. 3169–3177.

Wang T., Jónsdóttir R., Kristinsson H.G., Hreggvidsson G.O., Jónsson J.Ó. Food Science and Technology, 2010, vol. 43, pp. 1387–1393.

Siriwardhana N., Kim K.N., Lee K.W., Kim S.H., Ha J.H., Song C.B. International Journal of Food Science and Tech-nology, 2008, vol. 43, no. 4, pp. 587–596.

Xi J., Shen D., Zhao S., Lu B., Li Y., Zhang R. International Journal of Pharmaceutics, 2009, vol. 382, pp. 139–143.

Onofrejová L., Vašíčková J., Klejdus B., Stratil P., Mišurcová L., Kráčmar S., Kopecký J., Vacek J. Journal of Phar-maceutical and Biomedical Analysis, 2010, vol. 51, pp. 464–470.

Meireles M.A.A. Functional Ingredients from Algae for Foods and Nutraceuticals, Oxford, 2013, pp. 561–584.

Tanniou A., Esteban Serrano L., Vandanjon L., Ibanez E. Talanta, 2013, vol. 104, pp. 44–52.

Sivagnanam S.P., Yin S., Choi J.H., Park Y.B., Woo H.C., Chun B.S. Marine Drugs, 2015, vol. 13, pp. 3422–3442.

Saravana P.S., Tilahun A., Cho Y.-J., Choi J.H., Park Y.B. et. al. The Journal of Supercritical Fluids, 2017, vol. 120(2), pp. 295–303.

Kim S.M., Kang K., Jeon J.S., Jho E.H., Kim C.Y., Nho C.W., Um B.H. Applied Biochemistry and Biotechnology, 2011, vol. 165, pp. 1296–1307.

Goo H.R., Choi J.S., Na D.H. Archives of pharmacal research, 2010, vol. 3, pp. 539–544.

Lee J.H., Ko J.Y., Oh J.Y., Kim C.Y., Lee H.J., Kim J., Jeon Y.J. Food Chemistry, 2014, vol. 158, pp. 433–437.

Zou Y., Qian Z.J., Li Y., Kim M.M., Lee S.H., Kim S.K. Journal of Agricultural and Food Chemistry, 2008, vol. 56, pp. 7001–7009.

Hermund D.B., Yesiltas B., Honold P., Jónsdóttir R., Kristinsson H.G. Journal of Functional Foods, 2015, vol. 19, pp. 828–841.

Audibert L., Fauchon M., Blanc N., Hauchard D., Gall E.A. Phytochemical Analysis, 2010, vol. 21, pp. 399–405.

Leyton A., Vergara-Salinas J.R., Pérez-Correa J.R., Lienqueo M.E. Food Chemistry, 2017, vol. 237, pp. 312–319.

Li Y., Qian Z.J., Ryu B., Lee S.H., Kim M.M., Kim S.K. Bioorganic & Medicinal Chemistry, 2009, vol. 17, pp. 1963–1973.

Amarowicz R., Troszynska A., Shahidi F. J. Food. Lipids., 2005, no. 12, pp. 344–358.

Ahn G.-N., Kim K.-N., Cha S.-H., Song C.-B., Lee J., Heo M.-S., Yeo I.-K., Lee N.-H., Jee Y.-H., Kim J.-S., Heu M.-S., Jeon Y.-J. European Food Research and Technology, 2007, vol. 226, pp. 71–79.

GOST ISO 14502-1-2010. Chai. Metod opredeleniia obshchego soderzhaniia polifenolov. [GOST ISO 14502-1-2010. Tea. Method for determining the total content of polyphenols]. Moscow, 2010, 14 p. (in Russ.).

Kim A.R., Shin T.S., Lee M.S., Park J.Y., Park K.E., Yoon N.Y., Kim J.S., Choi J.S., Jang B.C., Byun D.S., Park N.K., Kim H.R. Journal of Agricultural and Food Chemistry, 2009, vol. 57, pp. 3483–3489.

Leyton A., Pezoa-Conte R., Barriga A., Buschmann A.H., Mäki-Arvela P., Mikkola J.-P., Lienqueo M.E. Algal Re-search, 2016, vol. 16, pp. 201–208.

Devi G.K., Manivannan K., Thirumaran G., Rajathi F.A.A., Anantharaman P. Asian Pacific Journal of Tropical Medi-cine, 2011, vol. 4, no. 3, pp. 205–211.

Yotsu-Yamashita M., Kondo S., Segawa S., Lin Y., Toyohara H., Ito H., Konoki K., Cho Y., Uchida T. Marine Drugs, 2013, no. 11, pp. 165–183.

Sugiura Y., Matsuda K., Yamada Y., Nishikawa M., Shioya K., Katsuzaki H., Imai K., Amano H. Bioscience, Biotech-nology, and Biochemistry, 2006, no. 70, pp. 2807–2811.

Parys S., Rosenbaum A., Kehraus S., Reher G., Glombitza K.W., König G.M. Journal of Natural Products, 2007, vol. 70, pp. 1865–1870.

Jégou C., Kervarec N., Cérantola S., Bihannic I., Stiger-Pouvreau V. Talanta, 2015, vol. 135, no. 1, pp. 1–6.

Vissers A.M., Caligiani A., Sforza S., Vinckena J., Gruppen H. Phytochemical analysis, 2017, vol. 28(6), pp. 487–495.

Truus K., Vaher M., Koel M., Mahar A., Taure I. Analytical and Bioanalytical Chemistry, 2004, vol. 379, pp. 849–852.

Koivikko R., Eränen J.K., Loponen J., Jormalainen V. Journal of Chemical Ecology, 2008, vol. 34, pp. 57–64.

Tierney M.S., Smyth T.J., Rai D.K., Soler-Vila A., Croft A.K., Brunton N. Food Chemistry, 2013, vol. 139, pp. 753–761.

Steevensz A.J., Mackinnon S.L., Hankinson R., Craft C., Connan S., Stengel D.B., Melanson J.E. Phytochemical anal-ysis, 2012, vol. 23, no. 5, pp. 547–553.

Aparna C., Madhavi Latha N., Supriya P., Gowrisankar D. Asian journal of pharmaceutical and clinical research, 2015, no. 8, pp. 28–33.

Karthik R., Manigandan V., Sheeba R., Saravanan R., Rajaian Rajesh P. Journal of Applied Phycology, 2016, no. 28, pp. 3561–3573.

Sugiura Y., Matsuda K., Yamada Y., Nishikawa M., Shioya K., Katsuzaki H., Imai K., Amano H. Bioscience, Biotech-nology, and Biochemistry, 2006, vol. 70, no. 11, pp. 2807–2811.

Kim D.-H., Eom S.-H., Kim T. H., Kim B.-Y., Kim Y.-M., Kim S.-B. Journal of Agricultural Science, 2013, vol. 5, no. 1, pp. 95–103.

Parys S., Kehraus S., Krick A., Glombitza K.-W., Carmeli S., Klimo K., Gerhäuser C., König G.M. Phytochemistry, 2010, vol. 71, pp. 221–229.

Ryu Y.B., Jeong H.J., Yoon S.Y., Park J.-Y., Kim Y.M., Park S.-J., Rho M.-C. Journal of Agricultural and Food Chemistry, 2011, vol. 59, pp. 6467–6473.

Gupta S., Abu-Ghannam N. Trends in Food Science & Technology, 2011, vol. 22, no. 6, pp. 315–326.

Kong C.S., Kim J.A., Yoon N.Y., Kim S.K. Food Chem. Toxicol., 2009, vol. 47, pp. 1653–1658.

Li Y., Qian Z.J., Kim M.M., Kim S.K. J. Food Biochem., 2011, vol. 35, pp. 357–369.

Hyun K.H., Yoon C.H., Kim R.K., Lim E.J., An S., Park M.J. et. al. Toxicol Appl Pharmacol., 2011, vol. 254, pp. 32–40.

Yoon N.Y., Lee S.H., Wijesekara I., Kim S.K. Fisheries and Aquatic Sciences, 2011, vol. 14, pp. 179–185.

Artan M., Li Y., Karadeniz F., Lee S.H., Kim M.M., Kim S.K. Bioorganic and Medicinal Chemistry, 2008, vol. 16, pp. 7921–7926.

Jung H.A., Oh S.H., Choi J.S. Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, pp. 3211–3215.

Yoon N.Y., Lee S.H., Kim S.K. J. Funct. Foods., 2009, vol. 1, pp. 331–335.

Bae J.-S. Food and Chemical Toxicology, 2011, vol. 49, pp. 1572–1577.

Lee M.H., Lee K.B., Oh S.M., Lee B.H., Chee H.Y. Journal of the Korean Society for Applied Biological Chemistry, 2010, vol. 53(4), pp. 504–507.

Urquiaga I., Leighton F. Biological Research, 2000, vol. 33, pp. 55–64.

Kim S.-K., Himaya S.W.A. Advances in Food and Nutrition Research, 2011, vol. 64, pp. 97–108.

Lee S.-H., Jeon Y.-J. Fitoterapia, 2013, vol. 86, pp. 129–136.

Li Y.-X., Wijesekara I., Li Y. Process Biochemistry, 2011, vol. 46, pp. 2219–2224.

Sivagnanam S.P., Yin S., Choi J.H., Park Y.B., Woo H.C., Chun B.S. Marine Drugs, 2015, vol. 13, pp. 3422–3442.

Nagayama K., Iwamura Y., Shibata T., Hirayama I., Nakamura T. Antimicrob Chemother, 2002, vol. 50, pp. 889–893.

Yeo M., Jung W., Kim G. Journal of Materials Chemistry, 2012, vol. 22, pp. 3568–3577.

Kim M., Kim G. Carbohydrate Polymers, 2012, vol. 90, pp. 592–601.

Sprygin V.G., Kushnerova N.F., Fomenko S.E., Sizova L.A., Momot T.V. Biologiia moria, 2013, vol. 39, no. 1, pp. 50–54. (in Russ.).

Published
2018-05-16
How to Cite
1. Боголицын (Bogolitsyn)К. (Konstantin) Г. (Grigor’evich), Дружинина (Druzhinina)А. (Аnna) С. (Sergeevna), Овчинников (Ovchinnikov)Д. (Denis) В. (Vladimirovich), Каплицин (Kaplitsin)П. (Platon) А. (Aleksandrovich), Шульгина (Shulgina)Е. (Elena) В. (Valer’evna), Паршина (Parshina)А. (Аnastasiya) Э. (Eduardovna) POLYPHENOLS OF BROWN ALGAE // chemistry of plant raw material, 2018. № 3. P. 5-21. URL: http://journal.asu.ru/cw/article/view/1898.
Section
Reviews