Extraction and Identification of Phlorotannins from the Brown Alga, Sargassum Fusiforme (Harvey) Setchell

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2017 Feb 24

PMID 28230766

Citations 77

Authors

Yajing Li

Xiaoting Fu

Delin Duan

Xiaoyong Liu

Jiachao Xu

Xin Gao

Affiliations

Soon will be listed here.

Abstract

Phlorotannins are a group of complex polymers of phloroglucinol (1,3,5-trihydroxybenzene), which are unique compounds from marine brown algae. In our present study, a procedure for extraction and enrichment of phlorotannins from with highly antioxidant potentials was established. After comparison of different extraction methods, the optimal extraction conditions were established as follows. The freeze-dried seaweed powder was extracted with 30% ethanol-water solvent with a solid/liquid ratio of 1:5 at temperature of 25 °C for 30 min. After extraction, the phlorotannins were fractioned by different solvents, among which the ethyl acetate fraction exhibited both the highest total phlorotannin content (88.48 ± 0.30 mg PGE/100 mg extract) and the highest antioxidant activities. The extracts obtained from these locations were further purified and characterized using a modified UHPLC-QQQ-MS method. Compounds with 42 different molecular weights were detected and tentatively identified, among which the fuhalol-type phlorotannins were the dominant compounds, followed by phlorethols and fucophlorethols with diverse degree of polymerization. Eckol-type phlorotannins including some newly discovered carmalol derivatives were detected in species for the first time. Our study not only described the complex phlorotannins composition in , but also highlighted the challenges involved in structural elucidation of these compounds.

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References

Cujic N, Savikin K, Jankovic T, Pljevljakusic D, Zdunic G, Ibric S . Optimization of polyphenols extraction from dried chokeberry using maceration as traditional technique. Food Chem. 2015; 194:135-42. DOI: 10.1016/j.foodchem.2015.08.008. View

Kim S, Kang K, Jeon J, Jho E, Kim C, Nho C . Isolation of phlorotannins from Eisenia bicyclis and their hepatoprotective effect against oxidative stress induced by tert-butyl hyperoxide. Appl Biochem Biotechnol. 2011; 165(5-6):1296-307. DOI: 10.1007/s12010-011-9347-3. View

Nakai M, Kageyama N, Nakahara K, Miki W . Phlorotannins as radical scavengers from the extract of Sargassum ringgoldianum. Mar Biotechnol (NY). 2006; 8(4):409-14. DOI: 10.1007/s10126-005-6168-9. View

Ghitescu R, Volf I, Carausu C, Buhlmann A, Gilca I, Popa V . Optimization of ultrasound-assisted extraction of polyphenols from spruce wood bark. Ultrason Sonochem. 2014; 22:535-41. DOI: 10.1016/j.ultsonch.2014.07.013. View

Steevensz A, MacKinnon S, Hankinson R, Craft C, Connan S, Stengel D . Profiling phlorotannins in brown macroalgae by liquid chromatography-high resolution mass spectrometry. Phytochem Anal. 2012; 23(5):547-53. DOI: 10.1002/pca.2354. View

Tierney M, Smyth T, Rai D, Soler-Vila A, Croft A, Brunton N . Enrichment of polyphenol contents and antioxidant activities of Irish brown macroalgae using food-friendly techniques based on polarity and molecular size. Food Chem. 2013; 139(1-4):753-61. DOI: 10.1016/j.foodchem.2013.01.019. View

Montero L, Sanchez-Camargo A, Garcia-Canas V, Tanniou A, Stiger-Pouvreau V, Russo M . Anti-proliferative activity and chemical characterization by comprehensive two-dimensional liquid chromatography coupled to mass spectrometry of phlorotannins from the brown macroalga Sargassum muticum collected on North-Atlantic coasts. J Chromatogr A. 2015; 1428:115-25. DOI: 10.1016/j.chroma.2015.07.053. View

Eom S, Lee S, Yoon N, Jung W, Jeon Y, Kim S . α-Glucosidase- and α-amylase-inhibitory activities of phlorotannins from Eisenia bicyclis. J Sci Food Agric. 2012; 92(10):2084-90. DOI: 10.1002/jsfa.5585. View

Yotsu-Yamashita M, Kondo S, Segawa S, Lin Y, Toyohara H, Ito H . Isolation and structural determination of two novel phlorotannins from the brown alga Ecklonia kurome Okamura, and their radical scavenging activities. Mar Drugs. 2013; 11(1):165-83. PMC: 3564165. DOI: 10.3390/md11010165. View

10.

Wang T, Jonsdottir R, Liu H, Gu L, Kristinsson H, Raghavan S . Antioxidant capacities of phlorotannins extracted from the brown algae Fucus vesiculosus. J Agric Food Chem. 2012; 60(23):5874-83. DOI: 10.1021/jf3003653. View

11.

Sailler B, Glombitza K . Halogenated phlorethols and fucophlorethols from the brown alga Cystophora retroflexa. Nat Toxins. 1999; 7(2):57-62. DOI: 10.1002/(sici)1522-7189(199903/04)7:2<57::aid-nt42>3.0.co;2-f. View

12.

Paskaleva E, Lin X, Duus K, McSharry J, Veille J, Thornber C . Sargassum fusiforme fraction is a potent and specific inhibitor of HIV-1 fusion and reverse transcriptase. Virol J. 2008; 5:8. PMC: 2267448. DOI: 10.1186/1743-422X-5-8. View

13.

Isaza Martinez J, Torres Castaneda H . Preparation and chromatographic analysis of phlorotannins. J Chromatogr Sci. 2013; 51(8):825-38. DOI: 10.1093/chromsci/bmt045. View

14.

Dahmoune F, Nayak B, Moussi K, Remini H, Madani K . Optimization of microwave-assisted extraction of polyphenols from Myrtus communis L. leaves. Food Chem. 2014; 166:585-595. DOI: 10.1016/j.foodchem.2014.06.066. View

15.

Kwon T, Kim T, Kim C, Park N . Antioxidant activity of various solvent fractions from edible brown alga, Eisenia bicyclis and its active compounds. J Food Sci. 2013; 78(5):C679-84. DOI: 10.1111/1750-3841.12109. View

16.

Heffernan N, Brunton N, FitzGerald R, Smyth T . Profiling of the molecular weight and structural isomer abundance of macroalgae-derived phlorotannins. Mar Drugs. 2015; 13(1):509-28. PMC: 4306949. DOI: 10.3390/md13010509. View

17.

Glombitza K, Hauperich S, Keusgen M . Phlorotannins from the brown algae Cystophora torulosa and Sargassum spinuligerum. Nat Toxins. 1997; 5(2):58-63. DOI: 10.1002/(SICI)(1997)5:2<58::AID-NT2>3.0.CO;2-Q. View

18.

Ryu Y, Jae Jeong H, Yoon S, Park J, Kim Y, Park S . Influenza virus neuraminidase inhibitory activity of phlorotannins from the edible brown alga Ecklonia cava. J Agric Food Chem. 2011; 59(12):6467-73. DOI: 10.1021/jf2007248. View

19.

Glombitza , Schmidt . Nonhalogenated and halogenated phlorotannins from the brown alga carpophyllum angustifolium. J Nat Prod. 1999; 62(9):1238-40. DOI: 10.1021/np990076c. View

20.

Meslet-Cladiere L, Delage L, Leroux C, Goulitquer S, Leblanc C, Creis E . Structure/function analysis of a type iii polyketide synthase in the brown alga Ectocarpus siliculosus reveals a biochemical pathway in phlorotannin monomer biosynthesis. Plant Cell. 2013; 25(8):3089-103. PMC: 3784601. DOI: 10.1105/tpc.113.111336. View