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Eckol information


Eckol
Chemical structure of eckol
Names
Preferred IUPAC name
4-(3,5-Dihydroxyphenoxy)oxanthrene-1,3,6,8-tetrol
Other names
1-(3,5-Dihydroxyphenoxy)-2,4,7,9-tetrahydroxydibenzo-1,4-dioxin
Identifiers
CAS Number
  • 88798-74-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:65819 ☒N
ChEMBL
  • ChEMBL471187 ☒N
ChemSpider
  • 128740 ☒N
PubChem CID
  • 145937
UNII
  • 4A5E8354UB checkY
CompTox Dashboard (EPA)
  • DTXSID40237333 Edit this at Wikidata
InChI
  • InChI=1S/C18H12O9/c19-7-1-8(20)3-10(2-7)25-16-12(23)6-13(24)17-18(16)27-15-11(22)4-9(21)5-14(15)26-17/h1-6,19-24H ☒N
    Key: PCZZRBGISTUIOA-UHFFFAOYSA-N ☒N
  • InChI=1/C18H12O9/c19-7-1-8(20)3-10(2-7)25-16-12(23)6-13(24)17-18(16)27-15-11(22)4-9(21)5-14(15)26-17/h1-6,19-24H
    Key: PCZZRBGISTUIOA-UHFFFAOYAJ
SMILES
  • C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=C(C=C(C=C4O3)O)O)O)O)O
Properties
Chemical formula
C18H12O9
Molar mass 372.285 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Eckol is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus Ecklonia[1] such as E. cava[2] or E. kurome[3] or in the genus Eisenia such as Eisenia bicyclis.[4]

The molecule possesses a dibenzo-p-dioxin skeleton and a phloroglucinol component. The molecule can also be viewed as a phloroglucinol trimer.[5]

It exhibits an antiplasmin inhibitory effect[3] and a radioprotective effect in a mouse model.[1][6] It also exhibits an in vitro cytoprotective effect against oxidative stress in Chinese hamster lung fibroblasts.[2] It also shows antithrombotic and profibrinolytic activities.[4]

  1. ^ a b Moon, Changjong; Kim, Sung-Ho; Kim, Jong-Choon; Hyun, Jin Won; Lee, Nam Ho; Park, Jae Woo; Shin, Taekyun (2008). "Protective effect of phlorotannin components phloroglucinol and eckol on radiation-induced intestinal injury in mice". Phytotherapy Research. 22 (2): 238–42. doi:10.1002/ptr.2298. PMID 17886227.
  2. ^ a b Kang, Kyoung Ah; Lee, Kyoung Hwa; Chae, Sungwook; Zhang, Rui; Jung, Myung Sun; Lee, Youngki; Kim, So Young; Kim, Hee Sun; Joo, Hong Gu; Park, Jae Woo; Ham, Young Min; Lee, Nam Ho; Hyun, Jin Won (2005). "Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells". FEBS Letters. 579 (28): 6295–304. doi:10.1016/j.febslet.2005.10.008. PMID 16253238.
  3. ^ a b Fukuyama, Y; Kodama, M; Miura, I; Kinzyo, Z; Kido, M; Mori, H; Nakayama, Y; Takahashi, M (1989). "Structure of an anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome Okamura and inhibitory activities of its derivatives on plasma plasmin inhibitors". Chemical & Pharmaceutical Bulletin. 37 (2): 349–53. doi:10.1248/cpb.37.349. PMID 2525966.
  4. ^ a b Kim, Tae Hoon; Ku, Sae-Kwang; Bae, Jong-Sup (2012). "Antithrombotic and profibrinolytic activities of eckol and dieckol". Journal of Cellular Biochemistry. 113 (9): 2877–83. doi:10.1002/jcb.24163. PMID 22511271.
  5. ^ Shibata, Toshiyuki; Fujimoto, Ken; Nagayama, Kohki; Yamaguchi, Kuniko; Nakamura, Takashi (2002). "Inhibitory activity of brown algal phlorotannins against hyaluronidase". International Journal of Food Science and Technology. 37 (6): 703. CiteSeerX 10.1.1.577.2261. doi:10.1046/j.1365-2621.2002.00603.x.
  6. ^ Nakayama, Yasuo; Takahashi, Masayuki; Fukuyama, Yoshiyasu; Kinzyo, Zyunei (1989). "Anti-plasmin inhibitor. Part IV. An anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome OKAMURA". Agricultural and Biological Chemistry. 53 (11): 3025. doi:10.1271/bbb1961.53.3025.

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Eckol

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Eckol is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus Ecklonia such as E. cava or E. kurome or in...

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Ecklonia cava

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natural agent. Phlorotannins, such as fucodiphlorethol G, 7-phloro eckol, 6,6'-bieckol, eckol, 8,8'-bieckol, 8,4"'-dieckol and phlorofucofuroeckol A can be...

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Phlorotannin

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in six main subgroups: fucols, phlorethols, fucophloretols, fuhalols and eckols, which are only found in the Alariaceae. According to linkage type, phlorotannins...

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C36H22O18

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0806128 u) may refer to: Dieckol, an eckol-type phlorotannin 6,6'-Bieckol, an eckol-type phlorotannin 8,8′-Bieckol, an eckol-type phlorotannin This set index...

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Dieckol

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Bae, Jong-Sup (2012). "Antithrombotic and profibrinolytic activities of eckol and dieckol". Journal of Cellular Biochemistry. 113 (9): 2877–83. doi:10...

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Amitriptyline

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1016/0006-2952(93)90211-e. PMID 8100134. Bymaster FP, Nelson DL, DeLapp NW, Falcone JF, Eckols K, Truex LL, et al. (May 1999). "Antagonism by olanzapine of dopamine D1...

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Olanzapine

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(2): 720–727. PMID 8632342. Bymaster FP, Nelson DL, DeLapp NW, Falcone JF, Eckols K, Truex LL, et al. (May 1999). "Antagonism by olanzapine of dopamine D1...

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Ecklonia kurome

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species in the genus Ecklonia found in the Sea of Japan. The phlorotannins eckol, phlorofucofuroeckol A and 8,8'-bieckol can be found in Ecklonia kurome...

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Pop Unknown

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– bass Adrian Carrillo – drums Former members Gabe Wiley – drums Casper Eckols – bass Chepo Pena – bass Frances Garcia – guitar, keyboard Shane Wells –...

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C18H12O9

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The molecular formula C18H12O9 may refer to: Eckol Norstictic acid Variegatic acid This set index page lists chemical structure articles associated with...

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Arame

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phlorotannins phlorofucofuroeckol A, dioxinodehydroeckol, fucofuroeckol A, eckol, dieckol, triphloroethol A and 7-phloroethol. Extracts of this algae have...

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Ecklonia

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radiata Ecklonia stolonifera Ecklonia radicosa Ecklonia species produce eckol-type phlorotannins. The name of this genus honours Christian Friedrich Ecklon...

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Jennie Everton Clarke

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Clarke was educated at Xenia College. After Clarke's first husband Lee Eckols died in 1894, she married Rev. Alan G. Clarke in 1896; they divorced in...

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Naturally occurring phenols

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freshwater green alga Spongiochloris spongiosa. Phlorotannins, for instance eckol, are found in brown algae. Vidalenolone can be found in the tropical red...

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2015 Lamar Cardinals baseball team

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Will Hibbs - Junior 49 Charlie Farrugia - Freshman   Catchers 3 Justin Eckols - Senior 17 Brandon Provost - Senior 44 Kyle Markum - Senior Infielders...

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Texas Rodeo Cowboy Hall of Fame

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Doyal 2007 Red Doyal 2017 Skipper Driver 2016 Betty Barron Dusek 2010 Buck Eckols 2001 Diltzie Bland Edmondson 2011 Johnny Kirk Edmondson 2014 Sunny Edwards...

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Ecklonia stolonifera

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Ecklonia stolonifera contains the phlorotannins phlorofucofuroeckol A, eckol, dieckol, dioxinodehydroeckol (eckstolonol), 2-phloroeckol, phlorofucofuroeckol...

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Dictionary of natural phenols and polyphenols molecular formulas

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C18H10O9 Eckstolonol 370.032482 C20H18O7 Sesamolin 370.105253 C18H12O9 Eckol 372.048132 C20H20O7 Sinensetin 372.120903 C21H24O6 Arctigenin 372.157289...

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