Abstract
This study presents results for the isolation, fractionation and characterization of Arctic brown algae polyphenols. New analytical data on the structure, functional nature and polymolecular properties of brown algal phlorotannins were obtained using modern analytical methods (size exclusion chromatography, liquid chromatography–mass spectrometry and fluorescence spectroscopy). The interrelation of radical scavenging activity and molecular weight of the algal polyphenolic components has also been established. Relatively high radical scavenging activity (776 ± 36 mg of ascorbic acid per g of extract) is observed for phlorotannin subfractions with average molecular weights from 8 to 18 kDa, enriched with phlorotannin oligomers with three to eight phloroglucinol units. Radical scavenging activity decreases with increasing molecular mass.
Graphical abstract
Similar content being viewed by others
References
Abdelhamid A, Jouini M, Bel Haj Amor H, Mzoughi Z, Dridi M, Ben Said R, Bouraoui A (2018) Phytochemical analysis and evaluation of the antioxidant, anti-inflammatory, and antinociceptive potential of phlorotannin-rich fractions from three Mediterranean brown seaweeds. Mar Biotech 20(1):60–74. https://doi.org/10.1007/s10126-017-9787-z
Audibert L, Fauchon L, Blanc N, Hauchard D (2010) Phenolic compounds in the brown seaweed Ascophyllum nodosum: distribution and radical-scavenging activities. Phytochem Anal 21:399–405. https://doi.org/10.1002/pca.1210
Barbosa M, Lopes G, Valentão P, Ferreres F, Gil-Izquierdo Á, Pereira DM, Andrade PB (2018) Edible seaweeds’ phlorotannins in allergy: a natural multi-target approach. Food Chem 265:233–241. https://doi.org/10.1016/j.foodchem.2018.05.074
Boettcher AA, Targett NM (1993) Role of polyphenolic molecular-size in reduction of assimilation efficiency in Xiphister mucosus. Ecol 74(3):891–903. https://doi.org/10.2307/1940814
Farvin SKH, Jacobsen C (2013) Phenolic compounds and antioxidant activities of selected species of seaweeds from Danish coast. Food Chem 138(2–3):1670–1681. https://doi.org/10.1016/j.foodchem.2012.10.078
Ferreres F, Lopes G, Gil-Izquierdo A, Andrade P, Sousa C, Mouga T, Valentão P (2012) Phlorotannin extracts from fucales characterized by HPLC-DAD-ESI-MSn: approaches to hyaluronidase inhibitory capacity and antioxidant properties. Mar Drugs 10(12):2766–2781
Glombitza KW, Rauwald HW, Eckhardt G (1977) Fucophloretholes, polyhydroxyoligophenyl ethers from Fucus vesiculosus. Planta Med 32(1):33–45
Gupta S, Abu-Ghannam N (2011) Bioactive potential and possible health effects of edible brown seaweeds. Trends Food Sci Tech 22(6):315–326. https://doi.org/10.1016/j.tifs.2011.03.011
Heffernan N, Brunton NP, Fitz Gerald RJ, Smyth TJ (2015) Profiling of the molecular weight and structural isomer abundance of macroalgae-derived phlorotannins. Mar Drugs 13(1):509–528. https://doi.org/10.3390/md13010509
Hermund DB, Yesiltas B, Honold P, Jónsdóttir R, Kristinsson HG, Jacobsen C (2015) Characterisation and antioxidant evaluation of Icelandic F. vesiculosus extracts in vitro and in fish-oil-enriched milk and mayonnaise. J Funct Food 19(2):828–841. https://doi.org/10.1016/j.jff.2015.02.020
Holdt SL, Kraan S (2011) Bioactive compounds in seaweed: functional food applications and legislation. J AppL Phycol 23:543–597. https://doi.org/10.1007/s10811-010-9632-5
Jung HA, Oh SH, Choi JS (2010) Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity. Bioorg Med Chem Lett 20(11):3211–3215. https://doi.org/10.1016/j.bmcl.2010.04.093
Kadom SU, Tiwari BK, O’Donneli CP (2013) Application of novel extraction technologies for bioactives from marine algae. J Agric Food Chem 61(20):4667–4675. https://doi.org/10.1021/jf400819p
Kantz K, Singleton VL (1990) Isolation and determination of polymeric polyphenols using Sephadex LH-20 and analysis of grape tissue extracts. Am J Enol Vitic 41:223–228
Kim SK, Himaya SWA (2011) Medicinal effects of phlorotannins from marine Brown Algae. Adv Food Nutr Res 64:97–108. https://doi.org/10.1016/B978-0-12-387669-0.00008-9
Kim SM, Kang SW, Jeon JS, Jung YJ, Kim WR, Kim CY, Um BH (2013) Determination of major phlorotannins in Eisenia bicyclis using hydrophilic interaction chromatography: seasonal variation and extraction characteristics. Food Chem 138(4):2399–2406. https://doi.org/10.1016/j.foodchem.2012.11.057
Kojima-Yuasa A (2018) Biological and pharmacological effects of polyphenolic compounds from Ecklonia cava. In: Watson RR, Preedy VR, Zibadi S (eds) Polyphenols: mechanisms of action in human health and disease, 2nd edn. Academic Press, USA, pp 41–52
Kong CS, Kim JA, Yoon NY, Kim SK (2009) Induction of apoptosis by phloroglucinol derivative from Ecklonia cava in MCF-7 human breast cancer cells. Food Chem Toxicol 47(7):1653–1658. https://doi.org/10.1016/j.fct.2009.04.013
Kumar CS, Ganesan P, Suresh PV, Bhaskar N (2008) Seaweeds as a source of nutritionally beneficial compounds—a review. J Food Sci Technol 45(1):1–13
Lee SH, Jeon YJ (2013) Anti-diabetic effects of brown algae derived phlorotannins, marine polyphenols through diverse mechanisms. Fitoter 86:129–136. https://doi.org/10.1016/j.fitote.2013.02.013
Lezcano V, Fernández C, Parodi ER, Morelli S (2017) Antitumor and antioxidant activity of the freshwater macroalga Cladophora surera. J Appl Phycol 30(5):2913–2921. https://doi.org/10.1007/s10811-018-1422-5
Li Y, Qian Z-J, Kim M-M, Kim S-K (2011a) Cytotoxic activities of phlorethol and fucophlorethol derivatives isolated from Laminariaceae Ecklonia cava. J Food Biochem 35(2):357–369. https://doi.org/10.1111/j.1745-4514.2010.00387.x
Li YX, Wijesekara I, Li Y (2011b) Phlorotannins as bioactive agents from brown algae. Process Biochem 46(12):2219–2224
Liu H, Gu L (2012) Phlorotannins from brown algae (Fucus vesiculosus) inhibited the formation of advanced glycation End products by scavenging reactive carbonyls. J Agric Food Chem 60:1326–1334. https://doi.org/10.1021/jf204112f
Nakamura T, Nagayama K, Uchida K, Tanaka R (1996) Antioxidant activity of phlorotannins Isolated from the brown alga Eisenia bicyclis. Fish Sci 62(6):923–926
Ragan MA, Glombitza KW (1986) Phlorotannins, brown algal polyphenols. Prog Phycol Res 4(1):129–241
Ragan MA, Jensen A (1978) Quantitative studies on brown algal phenols. II Seasonal variation in polyphenol content of Ascophyllum nodosum (L.) Le Jol. and Fucus vesiculosus. J Exp Mar Biol Ecol 34(3):245–258. https://doi.org/10.1016/S0022-0981(78)80006-9
Shibata T, Ishimaru K, Kawaguchi S, Yoshikawa H, Hama Y (2008) Antioxidant activities of phlorotannins isolated from Japanese Laminariaceae. J Appl Phycol 20:705–711. https://doi.org/10.1007/s10811-007-9254-8
Sivagnanam SP, Yin S, Choi JH, Park YB, Woo HC, Chun BS (2015) Biological properties of fucoxanthin in oil recovered from two brown seaweeds using supercritical CO2 extraction. Mar Drugs 13(6):3422–3442. https://doi.org/10.3390/md13063422
Wang T, Jónsdóttir R, Liu H (2012) Antioxidant capacities of phlorotannins extracted from the brown algae Fucus vesiculosus. J Agric Food Chem 60:5874–5883. https://doi.org/10.1021/jf3003653
Zenthoefer M, Geisen U, Hofmann-Peiker K, Fuhrmann M, Kerber J, Kirchhöfer R, Hennig S, Peipp M, Geyer R, Piker L, Kalthoff H (2017) Isolation of polyphenols with anticancer activity from the Baltic Sea brown seaweed Fucus vesiculosus using bioassay-guided fractionation. J Appl Phycol 29(4):2021–2037. https://doi.org/10.1007/s10811-017-1080-z
Acknowledgements
The research work was carried out within the financial support of the Ministry of Education and Science of the Russian Federation (Grant No. 4.3273.2017/PCh). The work was carried out using the equipment of the “Arctic” Core Facility Center of the Lomonosov Northern (Arctic) Federal University named after M.V. Lomonosov (Unique identification number RFMEFI59417X0013).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Bogolitsyn, K., Druzhinina, A., Kaplitsin, P. et al. Relationship between radical scavenging activity and polymolecular properties of brown algae polyphenols. Chem. Pap. 73, 2377–2385 (2019). https://doi.org/10.1007/s11696-019-00760-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-019-00760-7