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Phlorotannin

January 01, 1970

Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds[1] or sargassacean species,[2] and in a lower amount also in some red algae.[3] Contrary to hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol[4] (polyphloroglucinols).[5] As they are called tannins, they have the ability to precipitate proteins. It has been noticed that some phlorotannins have the ability to oxidize and form covalent bonds with some proteins. In contrast, under similar experimental conditions three types of terrestrial tannins (procyanidins, profisetinidins, and gallotannins) apparently did not form covalent complexes with proteins.[6]

Chemical structure of tetrafucol A, a fucol-type phlorotannin found in the brown alga Ascophyllum nodosum
Durvillaea antarctica, a brown algae containing phlorotannins.

These phenolic compounds are integral structural components of cell walls in brown algae, but they also seem to play many other secondary ecological roles such as protection from UV radiation and defense against grazing.

Biosynthesis and localization edit

Most of the phlorotannins' biosynthesis is still unknown, but it appears they are formed from phloroglucinols via the acetate-malonate pathway.[7]

They are found within the cell in small vesicles called physodes, where the soluble, polar fraction is sequestrated,[8] and as part of the cell wall, where they are insoluble and act as a structural component.[9][10] Their concentration is known to be highly variable among different taxa as well as among geographical area, since they respond plastically to a variety of environmental factors.[11] Brown algaes also exude phlorotannins in surrounding seawater.[5][12]

It has been proposed that phlorotannins are first sequestered in physodes under their polar, reactive form before being oxidized and complexed to the alginic acid of brown algal cell wall by a peroxidase.[13] To this date (2012), not much is known about phlorotannins synthesis.[7] The formation of physodes, vesicles containing phenolic compounds, have been investigated for many years. These cytoplasmic constituents were thought to be synthesized in the chloroplast or its membrane, but more recent studies suggest that the formation may be related to the endoplasmic reticulum and Golgi bodies.[14]

The allocation of phlorotannins among tissues varies along with the species.[15]

The localization of phlorotannins can be investigated by light microscopy after vanillin–HCl staining giving an orange color.[16] The ultrastructural localization of physodes can be examined through transmission electron microscopy in samples primarily fixed in 2.5% glutaraldehyde and with postfixation with 1% osmium tetroxide. For staining, uranyl acetate and lead citrate can be used.

Extraction and assays edit

In many studies where individual phlorotannins are isolated, extracted phlorotannins are acetylated with acetic anhydride-pyridine to protect them from oxidation. Both lowering the temperature and the addition of ascorbic acid seem to prevent oxidation.

Usual assays to quantify phlorotannins in samples are the Folin-Denis and Prussian blue assays. A more specific assay makes use of 2,4-dimethoxybenzaldehyde (DMBA), a product that reacts specifically with 1,3-and 1,3,5-substituted phenols (e.g., phlorotannins) to form a colored product.[17]

Structural diversity edit

 
Eckol, a phlorotannin found in species of the genus Ecklonia.

The nomenclature system for the marine phlorotannins was originally introduced by Glombitza.[18]

Phlorotannins are classified following the arrangement of the phloroglucinol monomeres. More than 150 compounds are known, ranging from 126 Da to 650 kDa in molecular weight.[8][19] Most of them are found between 10 and 100kDa.[20]

They are distributed in six main subgroups: fucols, phlorethols, fucophloretols, fuhalols and eckols, which are only found in the Alariaceae.[7][21]

According to linkage type, phlorotannins can be classified into four subclasses, i.e., phlorotannins with an ether linkage (fuhalols and phlorethols, fuhalols are constructed of phloroglucinol units that are connected with para- and ortho-arranged ether bridges containing one additional OH-group in every third ring), with a phenyl linkage (fucols), with an ether and a phenyl linkage (fucophlorethols) and with a dibenzodioxin linkage in eckols and carmalols (derivatives of phlorethols containing a dibenzodioxin moiety), most of which have halogenated representatives in brown algae.[22]

Examples of phlorotannins are fucodiphlorethol G from the seaweed Ecklonia cava,[23] eckol from Ecklonia species[24] or phlorofucofuroeckol-B from Eisenia arborea.[25]

The structural diversity of higher molecular weight molecules can be screened through the use of the 'EDIT' Carbon-13 NMR technique.[26]

Roles edit

The functions of phlorotannins are still an actual research subject (2012). They show primary and secondary roles,[13] at both cellular and organismic scale.[27]

Primary roles edit

Structural edit

The structural role of phlorotannins in brown algal cell wall is a primary role of these polyphenolic compounds.[7][13] This primary role may however not be the main role of the phlorotannins, since studies show they are more abundant in cytoplasm or in the exuded form than in cell wall.[28]

Reproductive edit

Cytoplasmic as well as exuded phlorotannins seem to play a role in algal reproduction, by contributing to the formation of the zygote's cell wall[10] and perhaps avoiding multiple fertilization by inhibiting spermatozoid movement.[7]

Secondary roles edit

According to the Carbon Nutrient Balance Model, phlorotannins, which are predominantly carbon molecules free of nitrogen, are produced in higher yields in light environment. Light has greater importance than nitrogen availability.[29]

Studies shown that phlorotannins seem to act as a protection for brown algaes in a number of ways. Here are some examples.

Antiherbivory defense edit

Phlorotannin production strategy may be constitutive or inducible.[30] As studies demonstrated that herbivory can induce phlorotannin production, it has been suggested that they may have a role in algae defense.[11] However, results form other studies suggest that the deterrent role of phlorotannins on herbivory is highly dependent on both algae and herbivore species.[31] In Fucus vesiculosus, it is galactolipids, rather than phlorotannins, that act as herbivore deterrents against the sea urchin Arbacia punctulata.[32]

UV and heavy metals screening edit

Phlorotannins are mostly located at the periphery of the cells, as components of the cell wall. They also contribute to absorption of UV-B light (between 280 and 320 nm)[33] and show absorbance maxima at 200 and 265 nm,[8] corresponding to UV-C wavelengths. Studies also demonstrated that sunlight intensity is related to phlorotannins production in Ascophyllum nodosum and Fucus vesiculosus natural populations.[34] For these reasons, it has been suggested that phlorotannins act as photoprotective substances.[35] Further studies with Lessonia nigrescens[35] and Macrocystis integrifolia[36] demonstrated that both UV-A and UV-B radiation can induce soluble phlorotannins and that there is a correlation between induction of phlorotannins and reduction in the inhibition of photosynthesis and DNA damage, two major effects of UV radiation on vegetal tissues. The fact that phlorotannins are exudated in surrounding water enables them to reduce incident UV exposure on kelp meiospores, phytoplankton and other kelp forests inhabitants, where brown algal biomass is high and water motion is low.[36]

They may also be involved in metal sequestration such as divalent metal ions Sr2+, Mg2+, Ca2+, Be2+, Mn2+, Cd2+, Co2+, Zn2+, Ni2+, Pb2+ and Cu2+.[37] If the chelating properties of phlorotannins have been demonstrated in vitro, in situ studies suggest that this characteristic may be species-specific.[38][39]

Algicidal effect edit

Studies demonstrated that phlorotannins can act as an algicide against some dinoflagellates species.[40]

Therapeutic properties edit

It has demonstrated that phlorotannins can have anti-diabetic, anti-cancer, anti-oxidation, antibacterial, radioprotective and anti-HIV properties.[41][42] However, in vivo studies on the effects of these compounds are lacking, most of the research having so far been done in vitro.[41] Regarding anti-allergic property, there is in vivo study on the effect of these compounds.[43]

References edit

  1. ^ Van Alstyne, Kathryn L.; McCarthy, James J.; Hustead, Cynthia L.; Kearns, Laura J. (1999). (PDF). Journal of Phycology. 35 (3): 483. doi:10.1046/j.1529-8817.1999.3530483.x. S2CID 84608425. Archived from the original (PDF) on 2010-06-19.
  2. ^ Kamiya, Mitsunobu; Nishio, Takeshi; Yokoyama, Asami; Yatsuya, Kousuke; Nishigaki, Tomokazu; Yoshikawa, Shinya; Ohki, Kaori (2010). "Seasonal variation of phlorotannin in sargassacean species from the coast of the Sea of Japan". Phycological Research. 58: 53. doi:10.1111/j.1440-1835.2009.00558.x. S2CID 83823009.
  3. ^ http://eurekamag.com/research/011/190/presence-lectins-tannins-protease-inhibitors-venezuelan-marine-algae.php
  4. ^ Shibata, Toshiyuki; Kawaguchi, Shigeo; Hama, Yoichiro; Inagaki, Masanori; Yamaguchi, Kuniko; Nakamura, Takashi (2004). "Local and chemical distribution of phlorotannins in brown algae". Journal of Applied Phycology. 16 (4): 291. doi:10.1023/B:JAPH.0000047781.24993.0a. S2CID 13479924.
  5. ^ a b Ragan, Mark A.; Jensen, Arne (1978). "Quantitative studies on brown algal phenols. II. Seasonal variation in polyphenol content of Ascophyllum nodosum (L.) Le Jol. And Fucus vesiculosus (L.)". Journal of Experimental Marine Biology and Ecology. 34 (3): 245. doi:10.1016/S0022-0981(78)80006-9.
  6. ^ Stern, J. Lewis; Hagerman, Ann E.; Steinberg, Peter D.; Mason, Pamela K. (1996). "Phlorotannin-protein interactions". Journal of Chemical Ecology. 22 (10): 1877–99. doi:10.1007/BF02028510. PMID 24227114. S2CID 11031529.
  7. ^ a b c d e Riitta Koivikko, 2008, Brown algal phlorotannins: Improving and applying chemical methods 2016-03-03 at the Wayback Machine, Ph. D. Thesis, University of Turku, Turku, Finland.
  8. ^ a b c Ragan, Mark A.; Glombitza, K.-W. (1986). "Phlorotannins, brown algal polyphenols". Prog. Phycol. Res. 4: 129–241.
  9. ^ Schoenwaelder, M. E. A. (2002). "The occurrence and cellular significance of physodes in brown algae". Phycologia. 41 (2): 125–139. doi:10.2216/i0031-8884-41-2-125.1. S2CID 86505836.
  10. ^ a b Schoenwaelder, M. E. A.; Clayton, M. N. (1998). "Secretion of phenolic substances into the zygote wall and cell plate in embryos of Hormosira and Acrocarpis (Fucales, Phaeophyceae)". Journal of Phycology. 34 (6): 969–980. doi:10.1046/j.1529-8817.1998.340969.x. S2CID 85269965.
  11. ^ a b Jormalainen, V.; Honkanen, T.; Koivikko, R.; Eränen, J. (2003). "Induction of phlorotannin production in a brown alga: defense or resource dynamics?" (PDF). Oikos. 103 (3): 640–650. doi:10.1034/j.1600-0706.2003.12635.x.
  12. ^ Jennings, J.S.; Steinberg, P.D. (1994). "In situ exudation of phlorotannins by the sublittoral kelp Ecklonia radiata". Mar. Biol. 121 (2): 349–354. doi:10.1007/bf00346744. S2CID 85193166.
  13. ^ a b c Arnold, T. M.; Targett, N. M. (2003). "To grow and defend: lack of tradeoffs for brown algal phlorotannins". Oikos. 100 (2): 406–408. doi:10.1034/j.1600-0706.2003.11680.x.
  14. ^ Schoenwaelder, M.E.A.; Clayton, M.N. (2000). "Physode formation in embryos of Phyllospora comosa and Hormosira banksii (Phaeophyceae)". Phycologia. 39: 1–9. doi:10.2216/i0031-8884-39-1-1.1. S2CID 86193685.
  15. ^ Van Alstyne, Kathryn L. (1999). "Phlorotannin Allocation Among Tissues of Northeastern Pacific Kelps and Rockweeds". Journal of Phycology. 35 (3): 483–492. doi:10.1046/j.1529-8817.1999.3530483.x. S2CID 84608425.
  16. ^ Pellegrini, L (1980). "Cytological studies on physodes in the vegetative cells of Cystoseira stricter Sauvagea (Phaeophyta, Fucales)". J. Cell Sci. 41: 209–231. doi:10.1242/jcs.41.1.209. PMID 7364883.
  17. ^ Stern, J. Lewis (1996). "A new assay for quantifying brown algal phlorotannins and comparisons to previous methods". Journal of Chemical Ecology. 22 (7): 1273–1293. doi:10.1007/BF02266965. PMID 24226084. S2CID 20164807.
  18. ^ Glombitza, K. W. In Marine Natural Product Chemistry; Faulkner, D. J.; Fenical, W. H., Eds.; Plenum Press: New York, 1977; p 191.
  19. ^ Hay, M E; Fenical, W (1988). "Marine Plant-Herbivore Interactions: The Ecology of Chemical Defense". Annual Review of Ecology and Systematics. 19: 111. doi:10.1146/annurev.es.19.110188.000551.
  20. ^ Boettcher, A.A.; Targett, N.M. (1993). "Role of polyphenolic molecular-size in reduction of assimilation efficiency in Xiphister mucosus". Ecology. 74 (3): 891–903. doi:10.2307/1940814. JSTOR 1940814.
  21. ^ Targett, N.M.; Arnold, T. M. (1998). "Predicting the effects of brown algal phlorotannins on marine herbivores in tropical and temperate oceans". Journal of Phycology. 34: 195–205. doi:10.1046/j.1529-8817.1998.340195.x. S2CID 84808536.
  22. ^ La Barre, Stéphane; Potin, Philippe; Leblanc, Catherine; Delage, Ludovic (2010). "The Halogenated Metabolism of Brown Algae (Phaeophyta), Its Biological Importance and Its Environmental Significance". Marine Drugs. 8 (4): 988–1010. doi:10.3390/md8040988. PMC 2866472. PMID 20479964.
  23. ^ Young Min Ham, Jong Seok Baik, Jin Won Hyun and Nam Ho Lee, Bull. 2007. Isolation of a new phlorotannin, fucodiphlorethol G, from a brown alga Ecklonia cava 2012-04-25 at the Wayback Machine. Korean Chem. Soc. 28(9): 1595.
  24. ^ Moon, Changjong; Kim, Sung-Ho; Kim, Jong-Choon; Won Hyun, Jin; Ho Lee, Nam; Woo Park, Jae; Shin, Taekyun (2008). "Protective effect of phlorotannin components phloroglucinol and eckol on radiation-induced intestinal injury in mice". Phytotherapy Research. 22 (2): 238–242. doi:10.1002/ptr.2298. PMID 17886227. S2CID 43864248.
  25. ^ Sugiura, Yoshimasa; Matsuda, Kohji; Yamada, Yasuhiro; Nishikawa, Masashi; Shoiya, Kazufumi; Katsuzaki, Hirotaka; Imai, Kunio; Amano, Hideomi (2006). "Isolation of a New Anti-Allergic Phlorotannin, Phlorofucofuroeckol-B, from an Edible Brown Alga, Eisenia arborea". Biosci. Biotechnol. Biochem. 70 (11): 2807–11. doi:10.1271/bbb.60417. PMID 17090915. S2CID 12528644.
  26. ^ McInnes, A. G. (1984). "High-molecular-weight phloroglucinol-based tannins from brown algae: Structural variants". Hydrobiologia. 116–117: 597–602. doi:10.1007/BF00027755. S2CID 35724927.
  27. ^ Schoenwaelder, Monica E. A. (2002). "The occurrence and cellular significance of physodes in brown algae". Phycologia. 41 (2): 125–139. doi:10.2216/i0031-8884-41-2-125.1. S2CID 86505836.
  28. ^ Koivikko, Riitta; Loponen, Jyrki; Honkanen, Tuija; Jormalainen, Veijo (2005). "Contents of soluble, cell-wall-bound and exuded phlorotannins in the brown alga Fucus vesiculosus, with implications on their ecological functions". Journal of Chemical Ecology. 31 (1): 195–212. CiteSeerX 10.1.1.320.5895. doi:10.1007/s10886-005-0984-2. PMID 15839490. S2CID 1540749.
  29. ^ Pavia, Henrik; Toth, Gunilla B. (2000). "Influence of light and nitrogen on the phlorotannin content of the brown seaweeds Ascophyllum nodosum and Fucus vesiculosus". Hydrobiologia. 440 (1–3): 299–305. doi:10.1023/A:1004152001370. S2CID 15432634.
  30. ^ Hammerstrom, Kamille; Dethier, Megan N.; Duggins, David O. (1998). "Rapid phlorotannin induction and relaxation in five Washington kelps" (PDF). Mar. Ecol. Prog. Ser. 165: 293–305. Bibcode:1998MEPS..165..293H. doi:10.3354/meps165293.
  31. ^ Amsler, C.D.; Fairhead, V.A. (2006). "Defensive and sensory chemical ecology of brown algae". Adv. Bot. Res. 43: 1–91.
  32. ^ Deal, Michael S. (2003). "Galactolipids rather than phlorotannins as herbivore deterrents in the brown seaweed Fucus vesiculosus". Oecologia. 136 (1): 107–114. Bibcode:2003Oecol.136..107D. doi:10.1007/s00442-003-1242-3. PMID 12684854. S2CID 5821145.
  33. ^ Pavia, H.; Cervin, G.; Lindgren, A.; Aberg, Per (1997). "Effects of UV-B radiation and simulated herbivory on phlorotannins in the brown alga Ascophyllum nodosum". Marine Ecology Progress Series. 157: 139–146. Bibcode:1997MEPS..157..139P. doi:10.3354/meps157139.
  34. ^ Pavia, Henrik; Toth, Gunilla B. (2000). "Influence of light and nitrogen on the phlorotannin content of the brown seaweeds Ascophyllum nodosum and Fucus vesiculosus". Hydrobiologia. 440: 299–305. doi:10.1023/A:1004152001370. S2CID 15432634.
  35. ^ a b Gómez, Ivan; Huovinen, Pirjo (2010). "Induction of Phlorotannins During UV Exposure Mitigates Inhibition of Photosynthesis and DNA Damage in the Kelp Lessonia nigrescens". Photochemistry and Photobiology. 86 (5): 1056–63. doi:10.1111/j.1751-1097.2010.00786.x. hdl:10533/144818. PMID 20670358. S2CID 22064207.
  36. ^ a b Swanson, Andrew K; Druehl, Louis D (2002). "Induction, exudation and the UV protective role of kelp phlorotannins". Aquatic Botany. 73 (3): 241. doi:10.1016/S0304-3770(02)00035-9.
  37. ^ Ragan, Mark A; Smidsrød, Olav; Larsen, Bjørn (1979). "Chelation of divalent metal ions by brown algal polyphenols". Marine Chemistry. 7 (3): 265. Bibcode:1979MarCh...7..265R. doi:10.1016/0304-4203(79)90043-4.
  38. ^ Huovinen, Pirjo; Leal, Pablo; Gómez, Iván (2010). "Interacting effects of copper, nitrogen and ultraviolet radiation on the physiology of three south Pacific kelps". Marine and Freshwater Research. 61 (3): 330. doi:10.1071/MF09054. hdl:10533/141734.
  39. ^ Toth, G; Pavia, H (2000). "Lack of phlorotannin induction in the brown seaweed Ascophyllum nodosum in response to increased copper concentrations". Marine Ecology Progress Series. 192: 119–126. Bibcode:2000MEPS..192..119T. doi:10.3354/meps192119. INIST 1367809.
  40. ^ Nagayama, Koki; Shibata, Toshiyuki; Fujimoto, Ken; Honjo, Tuneo; Nakamura, Takashi (2003). "Algicidal effect of phlorotannins from the brown alga Ecklonia kurome on red tide microalgae". Aquaculture. 218 (1–4): 601. doi:10.1016/S0044-8486(02)00255-7.
  41. ^ a b Gupta, Shilpi; Abu-Ghannam, Nissreen (2011). "Bioactive potential and possible health effects of edible brown seaweeds". Trends in Food Science & Technology. 22 (6): 315. CiteSeerX 10.1.1.465.6140. doi:10.1016/j.tifs.2011.03.011.
  42. ^ Li, Yong-Xin; Wijesekara, Isuru; Li, Yong; Kim, Se-Kwon (2011). "Phlorotannins as bioactive agents from brown algae". Process Biochemistry. 46 (12): 2219. doi:10.1016/j.procbio.2011.09.015.
  43. ^ Sugiura, Yoshimasa; Usui, Masakatsu; Katsuzaki, Hirotaka; Imai, Kunio; Kakinuma, Makoto; Amano, Hideomi; Miyata, Masaaki (2018). "Orally Administered Phlorotannins from Eisenia arborea Suppress Chemical Mediator Release and Cyclooxygenase-2 Signaling to Alleviate Mouse Ear Swelling". Marine Drugs. 16 (8): 267. doi:10.3390/md16080267. PMC 6117712. PMID 30072652.

External links edit

  • Riitta Koivikko. 2008. , Ph. D. Thesis, University of Turku, Turku, Finland.
  • Gupta, Shilpi; Abu-Ghannam, Nissreen (2011). "Bioactive potential and possible health effects of edible brown seaweeds". Trends in Food Science & Technology. 22 (6): 315. CiteSeerX 10.1.1.465.6140. doi:10.1016/j.tifs.2011.03.011.

January 01, 1970
phlorotannin, this, article, uses, bare, urls, which, uninformative, vulnerable, link, please, consider, converting, them, full, citations, ensure, article, remains, verifiable, maintains, consistent, citation, style, several, templates, tools, available, assi. This article uses bare URLs which are uninformative and vulnerable to link rot Please consider converting them to full citations to ensure the article remains verifiable and maintains a consistent citation style Several templates and tools are available to assist in formatting such as reFill documentation and Citation bot documentation August 2022 Learn how and when to remove this message Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds 1 or sargassacean species 2 and in a lower amount also in some red algae 3 Contrary to hydrolysable or condensed tannins these compounds are oligomers of phloroglucinol 4 polyphloroglucinols 5 As they are called tannins they have the ability to precipitate proteins It has been noticed that some phlorotannins have the ability to oxidize and form covalent bonds with some proteins In contrast under similar experimental conditions three types of terrestrial tannins procyanidins profisetinidins and gallotannins apparently did not form covalent complexes with proteins 6 Chemical structure of tetrafucol A a fucol type phlorotannin found in the brown alga Ascophyllum nodosum Durvillaea antarctica a brown algae containing phlorotannins These phenolic compounds are integral structural components of cell walls in brown algae but they also seem to play many other secondary ecological roles such as protection from UV radiation and defense against grazing Contents 1 Biosynthesis and localization 2 Extraction and assays 3 Structural diversity 4 Roles 4 1 Primary roles 4 1 1 Structural 4 1 2 Reproductive 4 2 Secondary roles 4 2 1 Antiherbivory defense 4 2 2 UV and heavy metals screening 4 2 3 Algicidal effect 5 Therapeutic properties 6 References 7 External linksBiosynthesis and localization editMost of the phlorotannins biosynthesis is still unknown but it appears they are formed from phloroglucinols via the acetate malonate pathway 7 They are found within the cell in small vesicles called physodes where the soluble polar fraction is sequestrated 8 and as part of the cell wall where they are insoluble and act as a structural component 9 10 Their concentration is known to be highly variable among different taxa as well as among geographical area since they respond plastically to a variety of environmental factors 11 Brown algaes also exude phlorotannins in surrounding seawater 5 12 It has been proposed that phlorotannins are first sequestered in physodes under their polar reactive form before being oxidized and complexed to the alginic acid of brown algal cell wall by a peroxidase 13 To this date 2012 not much is known about phlorotannins synthesis 7 The formation of physodes vesicles containing phenolic compounds have been investigated for many years These cytoplasmic constituents were thought to be synthesized in the chloroplast or its membrane but more recent studies suggest that the formation may be related to the endoplasmic reticulum and Golgi bodies 14 The allocation of phlorotannins among tissues varies along with the species 15 The localization of phlorotannins can be investigated by light microscopy after vanillin HCl staining giving an orange color 16 The ultrastructural localization of physodes can be examined through transmission electron microscopy in samples primarily fixed in 2 5 glutaraldehyde and with postfixation with 1 osmium tetroxide For staining uranyl acetate and lead citrate can be used Extraction and assays editIn many studies where individual phlorotannins are isolated extracted phlorotannins are acetylated with acetic anhydride pyridine to protect them from oxidation Both lowering the temperature and the addition of ascorbic acid seem to prevent oxidation Usual assays to quantify phlorotannins in samples are the Folin Denis and Prussian blue assays A more specific assay makes use of 2 4 dimethoxybenzaldehyde DMBA a product that reacts specifically with 1 3 and 1 3 5 substituted phenols e g phlorotannins to form a colored product 17 Structural diversity edit nbsp Eckol a phlorotannin found in species of the genus Ecklonia The nomenclature system for the marine phlorotannins was originally introduced by Glombitza 18 Phlorotannins are classified following the arrangement of the phloroglucinol monomeres More than 150 compounds are known ranging from 126 Da to 650 kDa in molecular weight 8 19 Most of them are found between 10 and 100kDa 20 They are distributed in six main subgroups fucols phlorethols fucophloretols fuhalols and eckols which are only found in the Alariaceae 7 21 According to linkage type phlorotannins can be classified into four subclasses i e phlorotannins with an ether linkage fuhalols and phlorethols fuhalols are constructed of phloroglucinol units that are connected with para and ortho arranged ether bridges containing one additional OH group in every third ring with a phenyl linkage fucols with an ether and a phenyl linkage fucophlorethols and with a dibenzodioxin linkage in eckols and carmalols derivatives of phlorethols containing a dibenzodioxin moiety most of which have halogenated representatives in brown algae 22 Examples of phlorotannins are fucodiphlorethol G from the seaweed Ecklonia cava 23 eckol from Ecklonia species 24 or phlorofucofuroeckol B from Eisenia arborea 25 The structural diversity of higher molecular weight molecules can be screened through the use of the EDIT Carbon 13 NMR technique 26 Roles editThe functions of phlorotannins are still an actual research subject 2012 They show primary and secondary roles 13 at both cellular and organismic scale 27 Primary roles edit Structural edit The structural role of phlorotannins in brown algal cell wall is a primary role of these polyphenolic compounds 7 13 This primary role may however not be the main role of the phlorotannins since studies show they are more abundant in cytoplasm or in the exuded form than in cell wall 28 Reproductive edit Cytoplasmic as well as exuded phlorotannins seem to play a role in algal reproduction by contributing to the formation of the zygote s cell wall 10 and perhaps avoiding multiple fertilization by inhibiting spermatozoid movement 7 Secondary roles edit According to the Carbon Nutrient Balance Model phlorotannins which are predominantly carbon molecules free of nitrogen are produced in higher yields in light environment Light has greater importance than nitrogen availability 29 Studies shown that phlorotannins seem to act as a protection for brown algaes in a number of ways Here are some examples Antiherbivory defense edit Phlorotannin production strategy may be constitutive or inducible 30 As studies demonstrated that herbivory can induce phlorotannin production it has been suggested that they may have a role in algae defense 11 However results form other studies suggest that the deterrent role of phlorotannins on herbivory is highly dependent on both algae and herbivore species 31 In Fucus vesiculosus it is galactolipids rather than phlorotannins that act as herbivore deterrents against the sea urchin Arbacia punctulata 32 UV and heavy metals screening edit Phlorotannins are mostly located at the periphery of the cells as components of the cell wall They also contribute to absorption of UV B light between 280 and 320 nm 33 and show absorbance maxima at 200 and 265 nm 8 corresponding to UV C wavelengths Studies also demonstrated that sunlight intensity is related to phlorotannins production in Ascophyllum nodosum and Fucus vesiculosus natural populations 34 For these reasons it has been suggested that phlorotannins act as photoprotective substances 35 Further studies with Lessonia nigrescens 35 and Macrocystis integrifolia 36 demonstrated that both UV A and UV B radiation can induce soluble phlorotannins and that there is a correlation between induction of phlorotannins and reduction in the inhibition of photosynthesis and DNA damage two major effects of UV radiation on vegetal tissues The fact that phlorotannins are exudated in surrounding water enables them to reduce incident UV exposure on kelp meiospores phytoplankton and other kelp forests inhabitants where brown algal biomass is high and water motion is low 36 They may also be involved in metal sequestration such as divalent metal ions Sr2 Mg2 Ca2 Be2 Mn2 Cd2 Co2 Zn2 Ni2 Pb2 and Cu2 37 If the chelating properties of phlorotannins have been demonstrated in vitro in situ studies suggest that this characteristic may be species specific 38 39 Algicidal effect edit Studies demonstrated that phlorotannins can act as an algicide against some dinoflagellates species 40 Therapeutic properties editIt has demonstrated that phlorotannins can have anti diabetic anti cancer anti oxidation antibacterial radioprotective and anti HIV properties 41 42 However in vivo studies on the effects of these compounds are lacking most of the research having so far been done in vitro 41 Regarding anti allergic property there is in vivo study on the effect of these compounds 43 References edit Van Alstyne Kathryn L McCarthy James J Hustead Cynthia L Kearns Laura J 1999 Phlorotannin Allocation Among Tissues of Northeastern Pacific Kelps and Rockweeds PDF Journal of Phycology 35 3 483 doi 10 1046 j 1529 8817 1999 3530483 x S2CID 84608425 Archived from the original PDF on 2010 06 19 Kamiya Mitsunobu Nishio Takeshi Yokoyama Asami Yatsuya Kousuke Nishigaki Tomokazu Yoshikawa Shinya Ohki Kaori 2010 Seasonal variation of phlorotannin in sargassacean species from the coast of the Sea of Japan Phycological Research 58 53 doi 10 1111 j 1440 1835 2009 00558 x S2CID 83823009 http eurekamag com research 011 190 presence lectins tannins protease inhibitors venezuelan marine algae php Shibata Toshiyuki Kawaguchi Shigeo Hama Yoichiro Inagaki Masanori Yamaguchi Kuniko Nakamura Takashi 2004 Local and chemical distribution of phlorotannins in brown algae Journal of Applied Phycology 16 4 291 doi 10 1023 B JAPH 0000047781 24993 0a S2CID 13479924 a b Ragan Mark A Jensen Arne 1978 Quantitative studies on brown algal phenols II Seasonal variation in polyphenol content of Ascophyllum nodosum L Le Jol And Fucus vesiculosus L Journal of Experimental Marine Biology and Ecology 34 3 245 doi 10 1016 S0022 0981 78 80006 9 Stern J Lewis Hagerman Ann E Steinberg Peter D Mason Pamela K 1996 Phlorotannin protein interactions Journal of Chemical Ecology 22 10 1877 99 doi 10 1007 BF02028510 PMID 24227114 S2CID 11031529 a b c d e Riitta Koivikko 2008 Brown algal phlorotannins Improving and applying chemical methods Archived 2016 03 03 at the Wayback Machine Ph D Thesis University of Turku Turku Finland a b c Ragan Mark A Glombitza K W 1986 Phlorotannins brown algal polyphenols Prog Phycol Res 4 129 241 Schoenwaelder M E A 2002 The occurrence and cellular significance of physodes in brown algae Phycologia 41 2 125 139 doi 10 2216 i0031 8884 41 2 125 1 S2CID 86505836 a b Schoenwaelder M E A Clayton M N 1998 Secretion of phenolic substances into the zygote wall and cell plate in embryos of Hormosira and Acrocarpis Fucales Phaeophyceae Journal of Phycology 34 6 969 980 doi 10 1046 j 1529 8817 1998 340969 x S2CID 85269965 a b Jormalainen V Honkanen T Koivikko R Eranen J 2003 Induction of phlorotannin production in a brown alga defense or resource dynamics PDF Oikos 103 3 640 650 doi 10 1034 j 1600 0706 2003 12635 x Jennings J S Steinberg P D 1994 In situexudation of phlorotannins by the sublittoral kelpEcklonia radiata Mar Biol 121 2 349 354 doi 10 1007 bf00346744 S2CID 85193166 a b c Arnold T M Targett N M 2003 To grow and defend lack of tradeoffs for brown algal phlorotannins Oikos 100 2 406 408 doi 10 1034 j 1600 0706 2003 11680 x Schoenwaelder M E A Clayton M N 2000 Physode formation in embryos of Phyllospora comosa and Hormosira banksii Phaeophyceae Phycologia 39 1 9 doi 10 2216 i0031 8884 39 1 1 1 S2CID 86193685 Van Alstyne Kathryn L 1999 Phlorotannin Allocation Among Tissues of Northeastern Pacific Kelps and Rockweeds Journal of Phycology 35 3 483 492 doi 10 1046 j 1529 8817 1999 3530483 x S2CID 84608425 Pellegrini L 1980 Cytological studies on physodes in the vegetative cells of Cystoseira stricter Sauvagea Phaeophyta Fucales J Cell Sci 41 209 231 doi 10 1242 jcs 41 1 209 PMID 7364883 Stern J Lewis 1996 A new assay for quantifying brown algal phlorotannins and comparisons to previous methods Journal of Chemical Ecology 22 7 1273 1293 doi 10 1007 BF02266965 PMID 24226084 S2CID 20164807 Glombitza K W In Marine Natural Product Chemistry Faulkner D J Fenical W H Eds Plenum Press New York 1977 p 191 Hay M E Fenical W 1988 Marine Plant Herbivore Interactions The Ecology of Chemical Defense Annual Review of Ecology and Systematics 19 111 doi 10 1146 annurev es 19 110188 000551 Boettcher A A Targett N M 1993 Role of polyphenolic molecular size in reduction of assimilation efficiency in Xiphister mucosus Ecology 74 3 891 903 doi 10 2307 1940814 JSTOR 1940814 Targett N M Arnold T M 1998 Predicting the effects of brown algal phlorotannins on marine herbivores in tropical and temperate oceans Journal of Phycology 34 195 205 doi 10 1046 j 1529 8817 1998 340195 x S2CID 84808536 La Barre Stephane Potin Philippe Leblanc Catherine Delage Ludovic 2010 The Halogenated Metabolism of Brown Algae Phaeophyta Its Biological Importance and Its Environmental Significance Marine Drugs 8 4 988 1010 doi 10 3390 md8040988 PMC 2866472 PMID 20479964 Young Min Ham Jong Seok Baik Jin Won Hyun and Nam Ho Lee Bull 2007 Isolation of a new phlorotannin fucodiphlorethol G from a brown alga Ecklonia cava Archived 2012 04 25 at the Wayback Machine Korean Chem Soc 28 9 1595 Moon Changjong Kim Sung Ho Kim Jong Choon Won Hyun Jin Ho Lee Nam Woo Park Jae Shin Taekyun 2008 Protective effect of phlorotannin components phloroglucinol and eckol on radiation induced intestinal injury in mice Phytotherapy Research 22 2 238 242 doi 10 1002 ptr 2298 PMID 17886227 S2CID 43864248 Sugiura Yoshimasa Matsuda Kohji Yamada Yasuhiro Nishikawa Masashi Shoiya Kazufumi Katsuzaki Hirotaka Imai Kunio Amano Hideomi 2006 Isolation of a New Anti Allergic Phlorotannin Phlorofucofuroeckol B from an Edible Brown Alga Eisenia arborea Biosci Biotechnol Biochem 70 11 2807 11 doi 10 1271 bbb 60417 PMID 17090915 S2CID 12528644 McInnes A G 1984 High molecular weight phloroglucinol based tannins from brown algae Structural variants Hydrobiologia 116 117 597 602 doi 10 1007 BF00027755 S2CID 35724927 Schoenwaelder Monica E A 2002 The occurrence and cellular significance of physodes in brown algae Phycologia 41 2 125 139 doi 10 2216 i0031 8884 41 2 125 1 S2CID 86505836 Koivikko Riitta Loponen Jyrki Honkanen Tuija Jormalainen Veijo 2005 Contents of soluble cell wall bound and exuded phlorotannins in the brown alga Fucus vesiculosus with implications on their ecological functions Journal of Chemical Ecology 31 1 195 212 CiteSeerX 10 1 1 320 5895 doi 10 1007 s10886 005 0984 2 PMID 15839490 S2CID 1540749 Pavia Henrik Toth Gunilla B 2000 Influence of light and nitrogen on the phlorotannin content of the brown seaweeds Ascophyllum nodosum and Fucus vesiculosus Hydrobiologia 440 1 3 299 305 doi 10 1023 A 1004152001370 S2CID 15432634 Hammerstrom Kamille Dethier Megan N Duggins David O 1998 Rapid phlorotannin induction and relaxation in five Washington kelps PDF Mar Ecol Prog Ser 165 293 305 Bibcode 1998MEPS 165 293H doi 10 3354 meps165293 Amsler C D Fairhead V A 2006 Defensive and sensory chemical ecology of brown algae Adv Bot Res 43 1 91 Deal Michael S 2003 Galactolipids rather than phlorotannins as herbivore deterrents in the brown seaweed Fucus vesiculosus Oecologia 136 1 107 114 Bibcode 2003Oecol 136 107D doi 10 1007 s00442 003 1242 3 PMID 12684854 S2CID 5821145 Pavia H Cervin G Lindgren A Aberg Per 1997 Effects of UV B radiation and simulated herbivory on phlorotannins in the brown alga Ascophyllum nodosum Marine Ecology Progress Series 157 139 146 Bibcode 1997MEPS 157 139P doi 10 3354 meps157139 Pavia Henrik Toth Gunilla B 2000 Influence of light and nitrogen on the phlorotannin content of the brown seaweeds Ascophyllum nodosum and Fucus vesiculosus Hydrobiologia 440 299 305 doi 10 1023 A 1004152001370 S2CID 15432634 a b Gomez Ivan Huovinen Pirjo 2010 Induction of Phlorotannins During UV Exposure Mitigates Inhibition of Photosynthesis and DNA Damage in the Kelp Lessonia nigrescens Photochemistry and Photobiology 86 5 1056 63 doi 10 1111 j 1751 1097 2010 00786 x hdl 10533 144818 PMID 20670358 S2CID 22064207 a b Swanson Andrew K Druehl Louis D 2002 Induction exudation and the UV protective role of kelp phlorotannins Aquatic Botany 73 3 241 doi 10 1016 S0304 3770 02 00035 9 Ragan Mark A Smidsrod Olav Larsen Bjorn 1979 Chelation of divalent metal ions by brown algal polyphenols Marine Chemistry 7 3 265 Bibcode 1979MarCh 7 265R doi 10 1016 0304 4203 79 90043 4 Huovinen Pirjo Leal Pablo Gomez Ivan 2010 Interacting effects of copper nitrogen and ultraviolet radiation on the physiology of three south Pacific kelps Marine and Freshwater Research 61 3 330 doi 10 1071 MF09054 hdl 10533 141734 Toth G Pavia H 2000 Lack of phlorotannin induction in the brown seaweed Ascophyllum nodosum in response to increased copper concentrations Marine Ecology Progress Series 192 119 126 Bibcode 2000MEPS 192 119T doi 10 3354 meps192119 INIST 1367809 Nagayama Koki Shibata Toshiyuki Fujimoto Ken Honjo Tuneo Nakamura Takashi 2003 Algicidal effect of phlorotannins from the brown alga Ecklonia kurome on red tide microalgae Aquaculture 218 1 4 601 doi 10 1016 S0044 8486 02 00255 7 a b Gupta Shilpi Abu Ghannam Nissreen 2011 Bioactive potential and possible health effects of edible brown seaweeds Trends in Food Science amp Technology 22 6 315 CiteSeerX 10 1 1 465 6140 doi 10 1016 j tifs 2011 03 011 Li Yong Xin Wijesekara Isuru Li Yong Kim Se Kwon 2011 Phlorotannins as bioactive agents from brown algae Process Biochemistry 46 12 2219 doi 10 1016 j procbio 2011 09 015 Sugiura Yoshimasa Usui Masakatsu Katsuzaki Hirotaka Imai Kunio Kakinuma Makoto Amano Hideomi Miyata Masaaki 2018 Orally Administered Phlorotannins from Eisenia arborea Suppress Chemical Mediator Release and Cyclooxygenase 2 Signaling to Alleviate Mouse Ear Swelling Marine Drugs 16 8 267 doi 10 3390 md16080267 PMC 6117712 PMID 30072652 External links editRiitta Koivikko 2008 Brown algal phlorotannins Improving and applying chemical methods Ph D Thesis University of Turku Turku Finland Gupta Shilpi Abu Ghannam Nissreen 2011 Bioactive potential and possible health effects of edible brown seaweeds Trends in Food Science amp Technology 22 6 315 CiteSeerX 10 1 1 465 6140 doi 10 1016 j tifs 2011 03 011 Retrieved from https en wikipedia org w index php title Phlorotannin amp oldid 1222466468, wikipedia, wiki, book, books, library,

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