Eckol

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 404200034 | Name = Eckol | ImageFile = Eckol.svg | ImageName = Chemical structure of eckol | ImageAlt = Chemical structure of eckol | PIN = 4-(3,5-Dihydroxyphenoxy)oxanthrene-1,3,6,8-tetrol | OtherNames = 1-(3,5-Dihydroxyphenoxy)-2,4,7,9-tetrahydroxydibenzo-1,4-dioxin |Section1={{Chembox Identifiers | CASNo = 88798-74-7 | CASNo_Ref = {{cascite|correct|??}} | CASNoOther = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4A5E8354UB | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 65819 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 471187 | PubChem = 145937 | SMILES = C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=C(C=C(C=C4O3)O)O)O)O)O | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 128740 | 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 | InChIKey = PCZZRBGISTUIOA-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = PCZZRBGISTUIOA-UHFFFAOYSA-N | MeSHName = }} |Section2={{Chembox Properties | C=18 | H=12 | O=9 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }}

'''Eckol''' is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus ''Ecklonia''<ref name=Moon>{{Cite journal|doi=10.1002/ptr.2298|pmid=17886227|title=Protective effect of phlorotannin components phloroglucinol and eckol on radiation-induced intestinal injury in mice |year=2008 |last1=Moon |first1=Changjong |last2=Kim |first2=Sung-Ho |last3=Kim |first3=Jong-Choon |last4=Hyun |first4=Jin Won |last5=Lee |first5=Nam Ho |last6=Park |first6=Jae Woo |last7=Shin |first7=Taekyun|journal=Phytotherapy Research|volume=22|issue=2|pages=238–42}}</ref> such as ''E. cava''<ref name=Kang>{{Cite journal|doi=10.1016/j.febslet.2005.10.008|pmid=16253238|title=Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells|year=2005|last1=Kang|first1=Kyoung Ah|last2=Lee|first2=Kyoung Hwa|last3=Chae|first3=Sungwook|last4=Zhang|first4=Rui|last5=Jung|first5=Myung Sun|last6=Lee|first6=Youngki|last7=Kim|first7=So Young|last8=Kim|first8=Hee Sun|last9=Joo|first9=Hong Gu|last10=Park|first10=Jae Woo|last11=Ham|first11=Young Min|last12=Lee|first12=Nam Ho|last13=Hyun|first13=Jin Won|journal=FEBS Letters|volume=579|issue=28|pages=6295–304|doi-access=free}}</ref> or ''E. kurome''<ref name=Fukuyama>{{cite journal |pmid=2525966 |year=1989 |last1=Fukuyama |first1=Y |last2=Kodama |first2=M |last3=Miura |first3=I |last4=Kinzyo |first4=Z |last5=Kido |first5=M|last6=Mori |first6=H |last7=Nakayama |first7=Y |last8=Takahashi |first8=M |title=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|volume=37|issue=2|pages=349–53|journal=Chemical & Pharmaceutical Bulletin|doi=10.1248/cpb.37.349|doi-access=free }}</ref> or in the genus ''Eisenia'' such as ''Eisenia bicyclis''.<ref name=Tae>{{Cite journal |doi=10.1002/jcb.24163 |title=Antithrombotic and profibrinolytic activities of eckol and dieckol |year=2012 |last1=Kim |first1=Tae Hoon |last2=Ku |first2=Sae-Kwang |last3=Bae |first3=Jong-Sup |journal=Journal of Cellular Biochemistry |volume=113 |issue=9 |pages=2877–83 |pmid=22511271}}</ref>

The molecule possesses a dibenzo-''p''-dioxin skeleton and a phloroglucinol component. The molecule can also be viewed as a phloroglucinol trimer.<ref>{{cite journal|doi=10.1046/j.1365-2621.2002.00603.x|title=Inhibitory activity of brown algal phlorotannins against hyaluronidase |year=2002| last1=Shibata |first1=Toshiyuki |last2=Fujimoto |first2=Ken |last3=Nagayama |first3=Kohki |last4=Yamaguchi |first4=Kuniko |last5=Nakamura |first5=Takashi |journal=International Journal of Food Science and Technology |volume=37 |issue=6 |pages=703|citeseerx=10.1.1.577.2261 }}</ref>

It exhibits an antiplasmin inhibitory effect<ref name=Fukuyama/> and a radioprotective effect in a mouse model.<ref name=Moon/><ref>{{cite journal|doi=10.1271/bbb1961.53.3025|title=Anti-plasmin inhibitor. Part IV. An anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome OKAMURA |year=1989 |last1=Nakayama |first1=Yasuo |last2=Takahashi |first2=Masayuki |last3=Fukuyama |first3=Yoshiyasu |last4=Kinzyo |first4=Zyunei |journal=Agricultural and Biological Chemistry |volume=53 |issue=11 |pages=3025|doi-access=free }}</ref> It also exhibits an ''in vitro'' cytoprotective effect against oxidative stress in Chinese hamster lung fibroblasts.<ref name=Kang/> It also shows antithrombotic and profibrinolytic activities.<ref name=Tae/>

== References == {{reflist}}

Category:Phlorotannins Category:Dibenzodioxins