Bioactive glyceroglycolipids from marine macroalgae: Isolation, purification, and food preservation potential

Authors

  • Yingying Sun 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China 2. Co-Innovation Center of Jiangsu Marine Bio-industry Technology, Lianyungang 222005, Jiangsu, China 3. Jiangsu Institute of Marine Resources Development, Lianyungang 222005, Jiangsu, China 4. Jiangsu Key Laboratory of Marine Genetic Resources and Breeding, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Yu Zhang 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Chenwei Mao 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Yang Mu 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China 5. Jiangsu Zhongjin Matai Medicinal Packaging Co., Ltd, Lianyungang 222002, Jiangsu, China
  • Tianle Li 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Xiujing Jiang 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Yadong Hu 6. Jiangsu Coast Development Group Co., Ltd, Nanjing 210095, China
  • Mingxuan Pan 6. Jiangsu Coast Development Group Co., Ltd, Nanjing 210095, China
  • You Yu 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Haonan Wang 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China
  • Xin Wei 1. Jiangsu Key Laboratory of Marine Bioresources and Environment, Jiangsu Ocean University, Lianyungang 222005, Jiangsu, China

Abstract

Macroalgae represent valuable marine resources, being rich in bioactive glyceroglycolipids with antioxidant and anti-inflammatory properties. In this study, the extraction processes for glyceroglycolipids from Palmaria palmata, Chorda filum, and Enteromorpha clathrata were systematically optimized. Using single-factor and response surface methodologies, optimal extraction conditions were established, achieving yields of 69.96 mg/g, 65.14 mg/g, and 85.73 mg/g, respectively. The resultant extracts were subsequently evaluated for their antioxidant and hygroscopic-moisturizing activities. It was observed that the glyceroglycolipid extracts exhibited a significant, concentration-dependent increase in the scavenging of DPPH, hydroxyl, and ABTS radicals, although their overall efficacy remained lower than that of vitamin C. In terms of hygroscopic and moisturizing properties, the extracts performed better than hyaluronic acid but were inferior to glycerol across varying humidity conditions. Further purification employing liquid-liquid extraction, thin-layer chromatography, and silica gel column chromatography enabled the isolation of specific glyceroglycolipid fractions. Additionally, treatment of Channa argus fillets with these glyceroglycolipids resulted in improved physicochemical indices compared to the control group, effectively delaying spoilage. These findings underscore the potential of marine macroalgae-derived glyceroglycolipids in food preservation, providing a solid foundation for further research and application within the food industry.      

Keywords: macroalgae, glyceroglycolipids, response surface design, anti-oxidant activity, food preservation

DOI: 10.25165/j.ijabe.20261901.10113

Citation: Sun Y Y, Zhang Y, Mao C W, Mu Y, Li T L, Jiang X J, et al. Bioactive glyceroglycolipids from marine macroalgae: Isolation, purification, and food preservation potential. Int J Agric & Biol Eng, 2026; 19(1): 270–282.

References

[1] Van Alstyne K L, Puglisi M P. DMSP in marine macroalgae and macroinvertebrates: Distribution, function, and ecological impacts. Aquatic Sciences, 2007; 69(3): 394–402.

[2] Wan A H L, Davies S J, Soler-Vila A, Fitzgerald R, Johnson M P. Macroalgae as a sustainable aquafeed ingredient. Reviews in Aquaculture, 2019; 11(3): 458–492.

[3] Verland M, Mydland L T, Skrede A. Marine macroalgae as sources of protein and bioactive compounds in feed for monogastric animals. Journal of the Science of Food and Agriculture, 2019; 99(1): 13–24.

[4] Leandro A, Pereira L, Gonçalves A M M. Diverse applications of marine macroalgae. Marine Drugs, 2019; 18(1): 17.

[5] Vicente T, Lemos M F L, Félix R, Valentão P, Félix C. Marine macroalgae, a source of natural inhibitors of fungal phytopathogens. Journal of Fungi (Basel), 2021; 7(12): 1006.

[6] Guo J Y, Qi M H, Chen H W, Zhou C, Ruan R, Yan X J, et al. Macroalgae-derived multifunctional bioactive substances: The potential applications for food and pharmaceuticals. Foods, 2022; 11(21): 3455.

[7] Sun Y Y, Dong S S, Zhang N S, Zhou J, Long Z K. Screening and isolation of glyceroglycolipids with antialgal activity from several marine macroalgae. Journal of Applied Phycology, 2021; 33(4): 2609–2616.

[8] Iván C, Francisco S. Chemistry and biology of bioactive glycolipids of marine origin. Marine Drugs, 2018; 16(9): 294.

[9] Al-Fadhli A. Glycolipids from the red alga Chondria armata (Kutz.) Okamura. Glycobiology, 2006; 16(10): 902–911.

[10] Xu X, Miao X. Glyceroglycolipid metabolism regulations under phosphate starvation revealed by transcriptome analysis in Synechococcus elongatus PCC 7942. Marine Drugs, 2020; 18(7): 360.

[11] Sanina N M, Kostetsky E Y, Shnyrov V L, Tsybulsky A V, Novikova O D, Portniagina O Y, et al. The influence of monogalactosyldiacylglycerols from different marine macrophytes on immunogenicity and conformation of protein antigen of tubular immunostimulating complex. Biochimie, 2012; 94(4): 1048–1056.

[12] Khotimchenko S V. Lipids from the marine alga Gracilaria verrucosa. Chemistry of Natural Compounds, 2005; 41(3): 285–288.

[13] Song Y Y, Li M, Wu Z Z, Chen J J, Yan X J. Rapid identification of lipid compositions from Porphyra haitanensis by UPLC-Q-TOF MS. Journal of Chinese Mass Spectrometry Society, 2015; 36(6): 528–534.

[14] Guo W J, Li G L, Hou Y X, Wang R R, Liu Y, Liu X H, et al. Chemical constituents from the red alga Symphyocladia latiuscula. Journal of Chinese Pharmaceutical Sciences, 2017; 26(10): 754–762.

[15] Deal M S, Hay M E, Wilson D, Fenical W. Galactolipids rather than phlorotannins as herbivore deterrents in the brown seaweed Fucus vesiculosus. Oecologia, 2003; 136: 107–114.

[16] Shevchenko N M, Anastiuk S D, Gerasimenko N I, Dmitrenok P S, Zviagintseva T N. Polysaccharide and lipid composition of the brown seaweed Laminaria gurjanovae. Russian Journal of Bioorganic Chemistry, 2007; 33: 88–98.

[17] Arunkumar K, Selvapalam N, Rengasamy R. The antibacterial compound sulphoglycerolipid 1-0 palmitoyl-3-0(6′-sulpho-α-quinovopyranosyl)-glycerol from Sargassum wightii Greville (Phaeophyceae). Botanica Marina, 2005; 48(5): 445–451.

[18] Sanina N M, Kostetsky E Y, Goncharova S N. Thermotropic behaviour of membrane lipids from brown marine alga Laminaria japonica. Biochemical Society Transactions, 2000; 28(6): 894–897.

[19] Kim Y H, Kim E H, Lee C, Kim M H, Rho J R. Two new monogalactosyl diacylglycerols from brown alga Sargassum thunbergii. Lipids, 2007; 42(4): 395–399.

[20] Nunes N, Rosa G P, Ferraz S, Barreto M C, Carvalho M A A P D. Fatty acid composition, TLC screening, ATR-FTIR analysis, anti-cholinesterase activity, and in vitro cytotoxicity to A549 tumor cell line of extracts of 3 macroalgae collected in Madeira. Journal of Applied Phycology, 2020; 32(2): 759–771.

[21] Rey F, Cartaxana P, Melo T, Calado R, Pereira R, Abreu H, et al. Domesticated populations of Codium tomentosum display lipid extracts with lower seasonal shifts than conspecifics from the wild—Relevance for biotechnological applications of this green seaweed. Marine Drugs, 2020; 18(4): 188.

[22] Lopes D, Moreira A S P, Rey F, da Costa E, Melo T, Maciel E, et al. Lipidomic signature of the green macroalgae Ulva rigida farmed in a sustainable integrated multi-trophic aquaculture. Journal of Applied Phycology, 2019; 31(2): 1369–1381.

[23] Fang X Y, Zhou S, Liu Y, Gao H, Liu X H, Liu X X, et al. Chemical constituents from green alga Ulva pertusa. Chinese Traditional and Herbal Drugs, 2017; 48(22): 4626–4631.

[24] Jiang R W, Hay M E, Fairchild C R, Prudhomme J, Roch K L, Aalbersberg W, et al. Antineoplastic unsaturated fatty acids from Fijian macroalgae. Phytochemistry, 2008; 69(13): 2495–2500.

[25] Williams D E, Sturgeon C M, Roberge M, Andersen R J. Nigricanosides A and B, antimitotic glycolipids isolated from the green alga Avrainvillea nigricans collected in Dominica. Journal of the American Chemical Society, 2007; 129(18): 5822–5823.

[26] Kostetsky E, Chopenko N, Barkina M, Velansky P, Sanina N. Fatty acid composition and thermotropic behavior of glycolipids and other membrane lipids of Ulva lactuca (Chlorophyta) inhabiting different climatic zones. Marine Drugs, 2018; 16(12): 494.

[27] Sun Y Y, Dong S S, Guo G, Guo L, Pu Y F. Antialgal activity of glycoglycerolipids derived from a green macroalgae Ulva prolifera on six species of red tide microalgae. IOP Conference Series: Materials Science and Engineering, 2019; 484: 012057.

[28] Thanh L T, Anh N V T, Hue P T. Molecular species of glycolipid and anti-inflammation activity of lipid fractions in the green algae Halimeda incrassata Lamx. collected from Truong Sa, Viet Nam. Vietnam Journal of Chemistry, 2021; 59(5): 639–647.

[29] Hoyo J, Guaus E, Torrent-Burgués J. Monogalactosyldiacylglycerol and digalactosyldiacylglycerol role, physical states, applications and biomimetic monolayer films. European Physical Journal E: Soft Matter, 2016; 39(3): 39.

[30] Slattery M, Lesser M P, Dunton K. Allelopathy in the tropical alga Lobophora variegata (Phaeophyceae): mechanistic basis for a phase shift on mesophotic coral reefs. Journal of Phycology, 2014; 50(3): 493–505.

[31] Nova P, Pimenta-Martins A, Maricato É, Nunes C, Abreu H, Coimbra M A, et al. Chemical composition and antioxidant potential of five algae cultivated in fully controlled closed systems. Molecules, 2023; 28(12): 4588.

[32] Plouguerné E, de Souza L M, Sassaki G L, Cavalcanti J F, Villela Romanos M T, da Gama B A, et al. Antiviral sulfoquinovosyldiacylglycerols (SQDGs) from the Brazilian brown seaweed Sargassum vulgare. Marine Drugs, 2013; 11(11): 4628–4640.

[33] Guo S S, Wang Z G. Glyceroglycolipids in marine algae: A review of their pharmacological activity. Frontiers in Pharmacology, 2022; 13: 1008797.

[34] Treyvaud Amiguet V, Jewell L E, Mao H, Sharma M, Hudson J B, Durst T, et al. Antibacterial properties of a glycolipid-rich extract and active principle from Nunavik collections of the macroalgae Fucus evanescens C. Agardh (Fucaceae). Canadian Journal of Microbiology, 2011; 57(9): 745–749.

[35] Le Strat Y, Mandin M, Ruiz N, Robiou du Pont T, Ragueneau E, Barnett A, et al. Quantification of xylanolytic and cellulolytic activities of fungal strains isolated from Palmaria palmata to enhance R-phycoerythrin extraction of Palmaria palmata: From seaweed to seaweed. Marine Drugs, 2023; 21(7): 393.

[36] Pierrick S, Søndergaard S P, Lindegaard G L, Susse W, Justine D, Céline R. Concise review of the red macroalga dulse, Palmaria palmata (L.) Weber & Mohr. Journal of Applied Phycology, 2023; 35(2): 523–550. doi: 10.1007/s10811-022-02899-5.

[37] Banskota A H, Stefanova R, Sperker S, Lall S P, Craigie J S, Hafting J T, et al. Polar lipids from the marine macroalga Palmaria palmata inhibit lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells. Phytochemistry, 2014; 101: 101–108.

[38] Chizhov A O, Dell A, Morris H R, Haslam S M, McDowell R A, Shashkov A S, et al. A study of fucoidan from the brown seaweed Chorda filum. Carbohydrate Research, 1999; 320(1-2): 108–119.

[39] Gerasimenko N, Menchinskaya E, Esipov A, Aminin D, Pislyagin E. Application of glyceroglycolipids, photosynthetic pigments and extracts of brown algae for suppression ROS. Open Journal of Marine Science. 2016; 6(3): 371–385. doi: 10.4236/ojms.2016.63031.

[40] Ma M F, Fu T Y, Wang Y M, Zhang A J, Gao P Y, Shang Q S, et al. Polysaccharide from edible alga Enteromorpha clathrata improves ulcerative colitis in association with increased abundance of Parabacteroides spp. in the gut microbiota of dextran sulfate sodium-fed mice. Marine Drugs, 2022; 20(12): 764.

[41] Pohl P, Zurheide F. Fatty acids and lipids of marine algae and the control of their biosynthesis by environmental factors. Marine Algae in Pharmaceutical Science. 1979; 2: 473–523.

[42] Pagano D, Cutignano A, Manzo E, Tinto F, Fontana A. Glycolipids synthesis: improved hydrazinolysis conditions for preparation of 1, 2-polyunsaturated fatty acyl-β-monogalactosyl-glycerols. Carbohydrate Research, 2016; 424: 21–23.

[43] Erwan P, Da G B A P, Pereira R C, Eliana B B. Glycolipids from seaweeds and their potential biotechnological applications. Frontiers in Cellular and Infection Microbiology, 2014; 4: 174.

[44] Parveez Ahamed A A, Rasheed M U, Peer Muhamed Noorani K, Reehana N, Santhoshkumar S, Mohamed Imran Y M, et al. In vitro antibacterial activity of MGDG-palmitoyl from Oscillatoria acuminata NTAPC05 against extended-spectrum β-lactamase producers. The Journal of Antibiotics, 2017; 70(6): 754–762.

[45] Furukawa T, Nishida M, Hada T, Kuramochi K, Sugawara F, Kobayashi S, et al. Inhibitory effect of sulfoquinovosyl diacylglycerol on prokaryotic DNA polymerase I activity and cell growth of Escherichia coli. Journal of Oleo Science, 2007; 56(1): 43–47.

[46] Schieber M, Chandel N S. ROS function in redox signaling and oxidative stress. Current Biology, 2014; 24(10): R453–R462.

[47] Nakai K, Tsuruta D. What are reactive oxygen species, free radicals, and oxidative stress in skin diseases. International Journal of Molecular Sciences, 2021; 22(19): 10799.

[48] Chaudhary P, Janmeda P, Docea A O, Yeskaliyeva B, Abdull Razis A F, Modu B, et al. Oxidative stress, free radicals and antioxidants: potential crosstalk in the pathophysiology of human diseases. Frontiers in Chemistry, 2023; 11: 1158198.

[49] Terme N, Boulho R, Kucma J P, Bourgougnon N, Bedoux G. Radical scavenging activity of lipids from seaweeds isolated by solid-liquid extraction and supercritical fluids. OCL, 2018; 25(5): D505.

[50] da Costa E, Melo T, Reis M, Domingues P, Calado R, Abreu M H, et al. Polar lipids composition, antioxidant and anti-inflammatory activities of the Atlantic red seaweed Grateloupia turuturu. Marine Drugs, 2021; 19(8): 414.

[51] Bruno A, Rossi C, Marcolongo G, Di Lena A, Venzo A, Berrie C P, et al. Selective in vivo anti-inflammatory action of the galactolipid monogalactosyldiacylglycerol. European Journal of Pharmacology, 2005; 524(1-3): 159–168.

[52] Gustafson K R, Cardellina J H, Fuller R W, Weislow O S, Kiser R F, Snader K M, et al. AIDS-antiviral sulfolipids from cyanobacteria (blue-green algae). Journal of the National Cancer Institute, 1989; 81(16): 1254–1258.

[53] Wei X, Jiang X X, Wang X, Li H, Yu Y, Sun Y Y. Marine macroalgae–derived glyceroglycolipid composite films for enhanced strawberry preservation with multifunctional bioactivities. LWT-Food Science and Technology, 2025; 211: 118803.

[54] Sun Y Y, Mu Y, Li T H, Wang S Y, Li Y X, Liu J, et al. Extraction, isolation and biological activity of two glycolipids from Bangia fusco-purpurea. Marine Drugs, 2024; 22(4): 144.

[55] Wei X, Hu X Q, Li T H, Li Y X, Yu Y, Jiang X J, et al. Comprehensive extraction and biological activities of mycosporine-like amino acids and glyceroglycolipids extracts from two macroalgae Ecklonia kurome and Ulva lactuca. Foods, 2025; 14(3): 440.

[56] Hou N N, Wang J, Zhang Q B. Isolation and evaluation of physicochemical properties of polysaccharides from Sargassum moelleri. Marine Sciences, 2017; 41(9): 102–109. (in Chinese)

[57] Cui M X, Wang X C, Wang Y, Wu J W, Liu K H. Ultrasonic-assisted extraction and anti-oxidation of polysaccharides from Gelidium pacifium Okam. Journal of Shanghai Ocean University, 2018; 27(5): 797–804. (in Chinese)

[58] Gao L W, Zhao X J, Zhao X Z. Optimization of extraction process of euglena gracilis polysaccharides and their moisture absorption and retention capacities. Food Research and Development, 2022; 43(20): 110–116. (in Chinese)

[59] Chen M, Sun Y, Zhao Y. Study on moisturizing effect of Dendrobium candidum extracts. Academic Journal of Shanghai University of Traditional Chinese Medicine, 2015; 29(6): 70–73. (in Chinese) doi: 10.16306/j.1008-861x.2015.06.018.

[60] Menikh A, Fragata M. Fourier transform infrared spectroscopic study of ion binding and intramolecular interactions in the polar head of digalactosyldiacylglycerol. European Biophysics Journal, 1993; 22(4): 249–258.

[61] Katsuoka M, Ogura C, Etoh H, Sakata K, Ina K. Galactosyl-and sulfoquinovosyldiacylglycerols isolated from the brown algae, Undaria pinnatifida and Costaria costata as repellents of the blue mussel, Mytilus edulis. Agricultural and Biological Chemistry, 1990; 54(11): 3043–3044.

[62] Guan Y, Lan W Q, Sun Y Q, Liu L, Zhou D P, Xie J. Effect of ultrasound-caffeic acid combined treatment on quality changes of sea bass during refrigeration. Food Science, 2022; 43(9): 207–214. (in Chinese)

[63] Abbas K A, Mohamed A, Jamilah B, Ebrahimian M. A review on correlations between fish freshness and pH during cold storage. American Journal of Biochemistry and Biotechnology, 2008; 4(4): 416–421.

[64] Zou J H, Yang H G, Tang D B, Cheng J R, Wang X P. Research progress on fresh-keeping technology of livestock and poultry meat. Meat Research, 2020; 34(10): 96–102. (in Chinese)

[65] Raharjo S, Sofos J N. Methodology for measuring malonaldehyde as a product of lipid peroxidation in muscle tissues: A review. Meat Science, 1993; 35(2): 145–169.

[66] Zhang Y L, Xiang J F, Zhu Y J, Sang Y F, Jiang S T, Lu J F, et al. Comparison of quality characteristics of live and dead crayfish during cold storage. Food Science, 2022; 43(1): 206–212. (in Chinese)

[67] Ferdouse J, Yamamoto Y, Taguchi S, Yoshizaki Y, Takamine K, Kitagaki H. Glycosylceramide modifies the flavor and metabolic characteristics of sake yeast. PeerJ, 2018; 6: e4768.

[68] Sun L, Forauer E C, Brown S, D’Amico D J. Application of bioactive glycolipids to control Listeria monocytogenes biofilms and as post-lethality contaminants in milk and cheese. Food Microbiology, 2021; 95: 103683.

Downloads

Published

2026-03-16

How to Cite

(1)
Sun, Y.; Zhang , Y.; Mao , C.; Mu , Y.; Li , T.; Jiang , X.; Hu, Y.; Pan , M.; Yu , Y.; Wang, H. Bioactive Glyceroglycolipids from Marine Macroalgae: Isolation, Purification, and Food Preservation Potential. Int J Agric & Biol Eng 2026, 19.

Issue

Section

Agro-product and Food Processing Systems