Preparation and chromatographic analysis of phlorotannins

Journal of Chromatographic Science

Volumn 51, Issue 8, 2013, Pages 825-838

  Isaza Martínez, José Hipólito ^a   Torres Castañeda, Harlen Gerardo ^a,b  

^a Faculty of Natural and Exact Sciences   (Colombia)

^b UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

[No Author keywords available]

Indexed keywords

PLANT EXTRACT; POLYPHENOL; TANNIN DERIVATIVE;

CHEMISTRY; FRACTIONATION; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; REVIEW;

CHEMICAL FRACTIONATION; CHROMATOGRAPHY, LIQUID; MASS SPECTROMETRY; PLANT EXTRACTS; POLYPHENOLS; TANNINS;

EID: 84882407964     PISSN: 00219665     EISSN: None     Source Type: Journal    
DOI: 10.1093/chromsci/bmt045     Document Type: Review

References (84)

1. Glombitza, K.W., Rösener, H.U.; Bifuhalol: Ein Diphenyläther aus Bifurcaria bifurcata; Phytochemistry, (1974); 13(7): 1245-1247.
2. Clifford, M.N.; Miscellaneous phenols in foods and beverages - Nature, occurrence and dietary burden; Journal of the Science of Food and Agriculture, (2000); 80(7): 1126-1137.
3. Yoshida, T., Ito, H., Isaza Martínez, J.H.; Pentameric ellagitannin oligomers in melastomataceous plants - Chemotaxonomic significance; Phytochemistry, (2005); 66(17): 1972-1983.
4. Isaza Martínez, J.H., Ito, H., Yoshida, T.; Oligomeric hydrolyzable tannins from Monochaetum multiflorum; Phytochemistry, (2004); 65(3): 359-367.
5. Haslam, E.; Natural polyphenols (vegetable tannins) as drugs: Possible modes of action; Journal of Natural Products, (1996); 59(2): 205-215.
6. Vo, T.S., Ngo, D.H., Kim, S.K.; Marine algae as a potential pharmaceutical source for anti-allergic therapeutics; Process Biochemistry, (2012); 47(3): 386-394.
7. Wang, T., Jónsdóttir, R., Liu, H., Gu, L., Kristinsson, H.G., Raghavan, S., et al.; Antioxidant capacities of phlorotannins extracted from the brown algae Fucus vesiculosus; Journal of Agricultural and Food Chemistry, (2012); 60(23): 5874-5883.
8. Llorente Mirandes, T., Ruiz Chancho, M.J., Barbero, M., Rubio, R., López Sánchez, J.F.; Determination of water-soluble arsenic compounds in commercial edible seaweed by LC-ICPMS; Journal of Agricultural and Food Chemistry, (1992); 59(24): 12963-12968.
9. Kim, S.K., Wijesekara, I.; Anticoagulant effect of marine algae. In Advances in food and nutrition research, Chapter 18, Kim, S.-K., (ed). Academic Press, SD, (2011), p. 235-244.
10. Ko, S.C., Cha, S.H., Heo, S.J., Lee, S.H., Kang, S.M., Jeon, Y.J.; Protective effect of Ecklonia cava on UVB-induced oxidative stress: In vitro and in vivo zebrafish model; Journal of Applied Phycology, (2011); 23(4): 697-708.
11. Okuda, T., Ito, H.; Tannins of constant structure in medicinal and food plants - Hydrolyzable tannins and polyphenols related to tannins; Molecules, (2011); 16(3): 2191-2217.
12. Rohr, G.E., Meier, B., Sticher, O., Analysis of procyanidins. In Studies in natural products chemistry, Attaur, R., (ed). Elsevier, New York, NY, (2000), p. 497-570.
13. Shibata, T., Fujimoto, K., Nagayama, K., Yamaguchi, K., Nakamura, T.; Inhibitory activity of brown algal phlorotannins against hyaluronidase; International Journal of Food Science and Technology, (2002); 37(6): 703-709.
14. Shibata, T., Ishimaru, K., Kawaguchi, S., Yoshikawa, H., Hama, Y.; Antioxidant activities of phlorotannins isolated from Japanese Laminariaceae; Journal of Applied Phycology, (2008); 20(5): 705-711.
15. Vo, T.S., Kim, S.K.; Potential anti-HIV agents from marine resources: An overview; Marine Drugs, (2010); 8(12): 2871-2892.
16. Cho, S., Yang, H., Jeon, Y.J., Lee, C.J., Jin, Y.H., Baek, N.I., et al.; Phlorotannins of the edible brown seaweed Ecklonia cava Kjellman induce sleep via positive allosteric modulation of gammaaminobutyric acid type A-benzodiazepine receptor: A novel neurological activity of seaweed polyphenols; Food Chemistry, (2012); 132(3): 1133-1142.
17. Kim, K.A., Kim, S.M., Kang, S.W., Jeon, S.I., Um, B.H., Jung, S.H.; Edible seaweed, Eisenia Bicyclis, protects retinal ganglion cells death caused by oxidative stress; Marine Biotechnology, (2012); 14(4): 383-395.
18. Glombitza, K.W., Rauwald, H.W., Eckhardt, G.; Fucole, Polyhydrox yoligophenyle aus Fucus vesiculosus; Phytochemistry, (1975); 14(5-6): 1403-1405.
19. Truus, K., Vaher, M., Koel, M., Mahar, A., Taure, I.; Analysis of bioactive ingredients in the brown alga Fucus vesiculosus by capillary electrophoresis and neutron activation analysis; Analytical and Bioanalytical Chemistry, (2004); 379(5-6): 849-52.
20. Glombitza, K.W., Pauli, K.; Fucols and phlorethols from the brown alga Scytothamnus Australis Hook. Et Harv. (Chnoosporaceae); Botanica Marina, (2003); 46(3): 315-320.
21. Glombitza, K.W., Zieprath, G.; Phlorotannins from the brown alga Analipus japonicus; Planta Medica, (1989); 55(2): 171-175.
22. Koch, M., Glombitza, K.W., Eckhard, G.; Phlorotannins of Phaeophycea Laminaria ochroleuca; Phytochemistry, (1980); 19(8): 1821-1823.
23. Glombitza, K.W., Koch, M., Eckhardt, G.; Chlorierte Phlorethole aus Laminaria ochroleuca; Phytochemistry, (1977); 16(6): 796-798.
24. Glombitza, K.W., Vogels, H.P.; Antibiotics from algae. XXXV. Phlorotannins from Ecklonia maxima; Planta Medica, (1985); 51(4): 308-312.
25. Sailler, B., Glombitza, K.W.; Phlorethols and fucophlorethols from the brown alga Cystophora retroflexa; Phytochemistry, (1999); 50(5): 869-881.
26. Glombitza, K.W., Rosener, H.U., Müller, D.; Bifuhalol und Diphlorethol aus Cystoseira tamariscifolia; Phytochemistry, (1975); 14(4): 1115-1116.
27. Glombitza, K.W., Forster, M., Eckhardt, G.; Polyhydroxyphenyläther aus der Phaeophycee Sargassum muticum; Phytochemistry, (1978); 17(3): 579-580.
28. Glombitza, K.W., Rösener, H.U., Koch, M.; Polyhydroxyoligophenyle und Phenyläther aus Bifurcaria bifurcata; Phytochemistry, (1976); 15(8): 1279-1281.
29. Sattler, E., Glombitza, K.W., Wehrli, F.W., Eckhardt, G.; Antibiotica aus Algen - XVI: Polyhydroxyphenyläther aus der Phaeophycee Halidrys siliquosa; Tetrahedron, (1977); 33(10): 1239-1244.
30. Keusgen, M., Glombitza, K.W.; Phlorethols, fuhalols and their derivatives from the brown alga Sargassum spinuligerum; Phytochemistry, (1995); 38(4): 975-985.
31. Grosse Damhues, J., Glombitza, K.W.; Isofuhalols, a type of phlorotannin from the brown alga Chorda filum; Phytochemistry, (1984); 23(11): 2639-2642.
32. Glombitza, K.W., Schmidt, A.; Trihydroxyphlorethols from the brown alga Carpophyllum angustifolium; Phytochemistry, (1999); 51(8): 1095-1100.
33. Glombitza, K.W., Li, S.M.; Hydroxyphlorethols from the brown alga Carpophyllum maschalocarpum; Phytochemistry, (1991); 30(8): 2741-2745.
34. Glombitza, K.W., Keusgen, M.; Fuhalols and deshydroxyfuhalols from the brown alga Ssargassum spinuligerum; Phytochemistry, (1995); 38(4): 987-995.
35. Keusgen, M., Falk, M., Walter, J.A., Glombitza, K.W.; A phloroglucinol derivative from the brown alga Sargassum spinuligerum; Phytochemistry, (1997); 46(2): 341-345.
36. Nakai, M., Kageyama, N., Nakahara, K., Miki, W.; Phlorotannins as radical scavengers from the extract of Sargassum ringgoldianum; Marine Biotechnology, (2006); 8(4): 409-414.
37. Glombitza, K.W., Gerstberger, G.; Phlorotannins with dibenzodioxin structural elements from the brown alga Eisenia arborea; Phytochemistry, (1985); 24(3): 543-551.
38. Yoon, N.Y., Chung, H.Y., Kim, H.R., Choi, J.S.; Acetyl- and butyrylcholinesterase inhibitory activities of sterols and phlorotannins from Ecklonia Stolonifera; Fisheries Science, (2008); 74(1): 200-207.
39. Yoon, N.Y., Eom, T.K., Kim, M.M., Kim, S.K.; Inhibitory effect of phlorotannins isolated from Ecklonia cava on mushroom tyrosinase activity and melanin formation in mouse B16F10 melanoma cells; Journal of Agricultural and Food Chemistry, (2009); 57(10): 4124-4129.
40. Lee, S.H., Yong, L., Karadeniz, F., Kim, M.M., Kim, S.K.; a-Glucosidase and a-amylase inhibitory activities of phloroglucinal derivatives from edible marine brown alga, Ecklonia cava; Journal of the Science of Food and Agriculture, (2009); 89(9): 1552-1558.
41. Shibata, T., Yamaguchi, K., Nagayama, K., Kawaguchi, S., Nakamura, T.; Inhibitory activity of brown algal phlorotannins against glycosidases from the viscera of the turban shell Turbo cornutus; European Journal of Phycology, (2002); 37(4): 493-500.
42. Moon, H.E., Islam, M.N., Ahn, B.R., Chowdhury, S.S., Sohn, H.S., Jung, H.A., et al.; Protein tyrosine phosphatase 1B and a-glucosidase inhibitory phlorotannins from edible brown algae, Ecklonia stolonifera and Eisenia bicyclis; Bioscience, Biotechnology and Biochemistry, (2011); 75(8): 1472-1480.
43. Yang, Y.I., Shin, H.C., Kim, S.H., Park, W.Y., Lee, K.T., Choi, J.H.; 6,60-Bieckol, isolated from marine alga Ecklonia cava, suppressed LPS-induced nitric oxide and PGE 2 production and inflammatory cytokine expression in macrophages: The inhibition of NFkB; International Immunopharmacology, (2012); 12(3): 510-517.
44. Shibata, T., Nagayama, K., Tanaka, R., Yamaguchi, K., Nakamura, T.; Inhibitory effects of brown algal phlorotannins on secretory phospholipase A2s, lipoxygenases and cyclooxygenases; Journal of Applied Phycology, (2003); 15(1): 61-66.
45. Kim, S.M., Kang, K., Jeon, J.S., Jho, E.H., Kim, C.Y., Nho, C.W., et al.; Isolation of phlorotannins from Eisenia bicyclis and their hepatoprotective effect against oxidative stress induced by tert-butyl hyperoxide; Applied Biochemistry and Biotechnology, (2011); 165(5-6): 1296-1307.
46. Kita, N., Fujimoto, K., Nakajima, I., Hayashi, R., Shibuya, K.; Screening test for deodorizing substances from marine algae and identification of phlorotannins as the effective ingredients in Eisenia bicyclis; Journal of Applied Phycology, (1990); 2(2): 155-162.
47. Nagayama, K., Iwamura, Y., Shibata, T., Hirayama, I., Nakamura, T.; Bactericidal activity of phlorotannins from the brown alga Ecklonia kurome; Journal of Antimicrobial Chemotherapy, (2002); 50(6): 889-893.
48. Shibata, T., Hama, Y., Miyasaki, T., Ito, M., Nakamura, T.; Extracellular secretion of phenolic substances from living brown algae; Journal of Applied Phycology, (2006); 18(6): 787-794.
49. Kang, H.S., Chung, H.Y., Kim, J.Y., Son, B.W., Jung, H.A., Choi, J.S.; Inhibitory phlorotannins from the edible brown alga Ecklonia stolonifera on total reactive oxygen species (ROS) generation; Archives of Pharmacal Research, (2004); 27(2): 194-198.
50. Kim, Y.C., An, R.B., Yoon, N.Y., Nam, T.J., Choi, J.S.; Hepatoprotective constituents of the edible brown alga Ecklonia stolonifera on tacrine-induced cytotoxicity in hep G2 Cells; Archives of Pharmacal Research, (2005); 28(12): 1376-1380.
51. Goo, H.R., Choi, J.S., Na, D.H.; Quantitative determination of major phlorotannins in Ecklonia stolonifera; Archives of Pharmacal Research, (2010); 33(4): 539-544.
52. Li, S.M., Glombitza, K.W.; Carmalols and phlorethofuhalols from the brown alga Carpophyllum maschalocarpum; Phytochemistry, (1991); 30(10): 3417-3421.
53. Zou, Y., Qian, Z.J., Li, Y., Kim, M.M., Lee, S.H., Kim, S.K.; Antioxidant effects of phlorotannins isolated from Ishige okamurae in free radical mediated oxidative systems; Journal of Agricultural and Food Chemistry, (2008); 56(16): 7001-7009.
54. Yoon, N.Y., Lee, S.H., Yong, L., Kim, S.K.; Phlorotannins from Ishige okamurae and their acetyl- and butyrylcholinesterase inhibitory effects; Journal of Functional Foods, (2009); 1(4): 331-335.
55. Glombitza, K.W., Grosse Damhues, J.; Antibiotics from algae XXXIII: Phlorotannins of the brown alga Himanthalia elongata; Planta Medica, (1985); 51(1): 42-46.
56. Glombitza, K.W., Keusgen, M., Hauperich, S.; Fucophlorethols from the brown algae Sargassum spinuligerum and Cystophora torulosa; Phytochemistry, (1997); 46(8): 1417-1422.
57. Parys, S., Kehraus, S., Krick, A., Glombitza, K.W., Carmeli, S., Klimo, K., et al.; In vitro chemopreventive potential of fucophlorethols from the brown alga Fucus vesiculosus L. by anti-oxidant activity and inhibition of selected cytochrome P450 enzymes; Phytochemistry, (2010); 71(2-3): 221-229.
58. Glombitza, K.W., Li, S.M.; Fucophlorethols from the brown alga Carpophyllum maschalocarpum; Phytochemistry, (1991); 30(10): 3423-3427.
59. Glombitza, K.W., Hauperich, S.; Phlorotannins from the brown alga Cystophora torulosa; Phytochemistry, (1997); 46(4): 735-740.
60. Eom, S.H., Lee, S.H., Yoon, N.Y., Jung, W.K., Jeon, Y.J., Kim, S.K., et al.; a-Glucosidase- and a-amylase-inhibitory activities of phlorotannins from Eisenia bicyclis; Journal of the Science of Food and Agriculture, (2012); 92(10): 2084-2090.
61. Li, Y., Lee, S.H., Le, Q.T., Kim, M.M., Kim, S.K.; Anti-allergic effects of phlorotannins on histamine release via binding inhibition between IgE and Fc1RI; Journal of Agricultural and Food Chemistry, (2008); 56(24): 12073-12080.
62. Li, Y.X., Wijesekara, I., Li, Y., Kim, S.K.; Phlorotannins as bioactive agents from brown algae; Process Biochemistry, (2011); 46(12): 2219-2224.
63. Sugiura, Y., Matsuda, K., Yamada, Y., Nishikawa, M., Shioya, K., Katsuzaki, H., et al.; Anti-allergic phlorotannins from the edible brown alga, Eisenia arborea; Food Science and Technology Research, (2007); 13(1): 54-60.
64. Steinhoff, F.S., Graeve, M., Bartoszek, K., Bischof, K., Wiencke, C.; Phlorotannin production and lipid oxidation as a potential protective function against high photosynthetically active and UV radiation in gametophytes of Alaria esculenta (Alariales, Phaeophyceae); Photochemistry and Photobiology, (2012); 88(1): 46-57.
65. Koivikko, R., Eränen, J.K., Loponen, J., Jormalainen, V.; Variation of phlorotannins among three populations of Fucus vesiculosus as revealed by HPLC and colorimetric quantification; Journal of Chemical Ecology, (2008); 34(1): 57-64.
66. Lim, S.N., Cheung, P.C.K., Ooi, V.E.C., Ang, P.O.; Evaluation of antioxidative activity of extracts from a brown seaweed, Sargassum siliquastrum; Journal of Agricultural and Food Chemistry, (1997); 50(13): 3862-3866.
67. Audibert, L., Fauchon, M., Blanc, N., Hauchard, D., Ar Gall, E.; Phenolic compounds in the brown seaweed Ascophyllum nodosum: Distribution and radical-scavenging activities; Phytochemical Analysis, (2010); 21(5): 399-405.
68. Stern, J.L., Hagerman, A.E., Steinberg, P.D., Winter, F.C., Estes, J.A.; A new assay for quantifying brown algal phlorotannins and comparisons to previous methods; Journal of Chemical Ecology, (1996); 22(7): 1273-1293.
69. Glombitza, K.W., Koch, M., Eckhardt, G.; Polyhydroxyphenyläther aus Laminaria ochroleuca; Phytochemistry, (1976); 15(6): 1082-1083.
70. Glombitza, K.W., Rauwald, H.W., Eckhardt, G.; Phlorotannine aus Himanthalia elongata; Phytochemistry, (1977); 16(10): 1614.
71. Grosse Damhues, J., Glombitza, K.W., Schulten, H.R.; An eight-ring phlorotannin from the brown alga Himanthalia elongata; Phytochemistry, (1983); 22(9): 2043-2046.
72. Glombitza, K.W., Schnabel, C., Koch, M.; Antibiotika aus Algen, 27: Niedermolecukulare Phlorotannins der Braunalgae Cystoseira baccata (Gmelin) Silva, II; Archiv der Pharmazie, (1981); 314(7): 602-608.
73. Glombitza, K.W., Knöss, W.; Sulphated phlorotannins from the brown alga Pleurophycus gardneri; Phytochemistry, (1992); 31(1): 279-281.
74. Keusgen, M., Glombitza, K.W.; Phlorotannins from the brown alga Sargassum spinuligerum; Planta Medica, (1991); 57: A20-A21.
75. Shibata, T., Kawaguchi, S., Hama, Y., Inagaki, M., Yamaguchi, K., Nakamura, T.; Local and chemical distribution of phlorotannins in brown algae; Journal of Applied Phycology, (2004); 16(4): 291-296.
76. Lee, S.H., Han, J.S., Heo, S.J., Hwang, J.Y., Jeon, Y.J.; Protective effects of dieckol isolated from Ecklonia cava against high glucose-induced oxidative stress in human umbilical vein endothelial cells; Toxicology in Vitro, (2010); 24(2): 375-381.
77. Wei, Y., Wang, C., Li, J., Guo, Q., Qi, H.; Inhibitory effects and mechanisms of high molecular-weight phlorotannins from Sargassum thunbergii on ADP-induced platelet aggregation; Chinese Journal of Oceanology and Limnology, (2009); 27(3): 558-563.
78. Chowdhury, M.T.H., Bangoura, I., Kang, J.Y., Park, N.G., Ahn, D.H., Hong, Y.K.; Distribution of phlorotannins in the brown alga Ecklonia cava and comparison of pretreatments for extraction; Fisheries and Aquatic Science, (2011); 14(3): 198-204.
79. Heo, S.J., Hwang, J.Y., Choi, J.I., Lee, S.H., Park, P.J., Kang, D.H., et al.; Protective effect of diphlorethohydroxycarmalol isolated from Ishige okamurae against high glucose-induced-oxidative stress in human umbilical vein endothelial cells; Food and Chemical Toxicology, (2010); 48(6): 1448-1454.
80. Heo, S.J., Hwang, J.Y., Choi, J.I., Han, J.S., Kim, H.J., Jeon, Y.J.; Diphlorethohydroxycarmalol isolated from Ishige okamurae, a brown Algae, a potent a-glucosidase and a-amylase inhibitor, alleviates postprandial hyperglycemia in diabetic mice; European Journal of Pharmacology, (2009); 615(1-3): 252-256.
81. Koch, M., Glombitza, K.W., Rösener, H.U.; Polyhydroxyphenyl ethers from Bifurcaria bifurcata; Phytochemistry, (1981); 20(6): 1373-1379.
82. Glombitza, K.W., Geisler, C., Eckhardt, G.; Phlorotanninvorstufen aus Dictyota dichotoma; Phytochemistry, (1977); 16(12): 2035-2036.
83. Sailler, B., Glombitza, K.W.; Halogenated phlorethols and fucophlorethols from the brown alga Cystophora retroflexa; Natural Toxins, (1999); 7(2): 57-62.
84. Steevensz, A.J., Mackinnon, S.L., Hankinson, R., Craft, C., Connan, S., Stengel, D.B., et al.; Profiling phlorotannins in brown macroalgae by liquid chromatography-high resolution mass spectrometry; Phytochemical Analysis, (2012); 23(5): 547-53.