Dieckol

{{Chembox | ImageFile = Dieckol.svg | ImageSize = 250px | ImageAlt = Chemical structure of dieckol | PIN = 2,4,6-Trioxa-1(1),5(7,1)-dioxanthrena-3(1,4),7(1)-dibenzenaheptaphane-1²,1⁴,1⁷,1⁹,3³,3⁵,5²,5⁴,5⁹,7³,7⁵-undecol | OtherNames = |Section1={{Chembox Identifiers | CASNo = 88095-77-6 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = ZU0ESU4399 | InChI=1S/C36H22O18/c37-12-1-13(38)3-15(2-12)49-31-22(44)10-25(47)34-35(31)54-30-21(43)8-17(9-27(30)52-34)48-28-19(41)6-16(7-20(28)42)50-32-23(45)11-24(46)33-36(32)53-29-18(40)4-14(39)5-26(29)51-33/h1-11,37-47H | InChIKey = DRZQFGYIIYNNEC-UHFFFAOYSA-N | PubChem = 3008868 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 65769 | ChemSpiderID = 2278311 | SMILES = Oc4cc(O)c6Oc(cc(O)cc3O)c3Oc6c4Oc(cc2O)cc(O)c2Oc(cc1Oc5c(O)cc7O)cc(O)c1Oc5c7Oc(c8)cc(O)cc8O }} |Section2={{Chembox Properties | Formula = C₃₆H₂₂O₁₈ | MolarMass = 742.52 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Dieckol''' is a phlorotannin that can be found in arame (''Eisenia bicyclis''),<ref>{{Cite journal|pmid=20462757|year=2010|last1=Jung|first1=HA|last2=Oh|first2=SH|last3=Choi|first3=JS|title=Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity|volume=20|issue=11|pages=3211–5|doi=10.1016/j.bmcl.2010.04.093|journal=Bioorganic & Medicinal Chemistry Letters}}</ref><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|s2cid=2151927}}</ref> in ''Ecklonia cava''<ref>{{Cite journal|doi=10.1016/j.fct.2010.06.032|title=Dieckol isolated from Ecklonia cava inhibits α-glucosidase and α-amylase in vitro and alleviates postprandial hyperglycemia in streptozotocin-induced diabetic mice|year=2010|last1=Lee|first1=Seung-Hong|last2=Park|first2=Mi-Hwa|last3=Heo|first3=Soo-Jin|last4=Kang|first4=Sung-Myung|last5=Ko|first5=Seok-Chun|last6=Han|first6=Ji-Sook|last7=Jeon|first7=You-Jin|journal=Food and Chemical Toxicology|volume=48|issue=10|pages=2633–7|pmid=20600532}}</ref> or in ''Ecklonia stolonifera''.<ref>{{Cite journal|pmid=20422362|year=2010|last1=Goo|first1=HR|last2=Choi|first2=JS|last3=Na|first3=DH|title=Quantitative determination of major phlorotannins in Ecklonia stolonifera|volume=33|issue=4|pages=539–44|doi=10.1007/s12272-010-0407-y|journal=Archives of Pharmacal Research|s2cid=26981463}}</ref><ref>{{Cite journal|pmid=16880634|year=2006|last1=Joe|first1=MJ|last2=Kim|first2=SN|last3=Choi|first3=HY|last4=Shin|first4=WS|last5=Park|first5=GM|last6=Kang|first6=DW|last7=Kim|first7=YK|title=The inhibitory effects of eckol and dieckol from Ecklonia stolonifera on the expression of matrix metalloproteinase-1 in human dermal fibroblasts|volume=29|issue=8|pages=1735–9|journal=Biological & Pharmaceutical Bulletin|doi=10.1248/bpb.29.1735|doi-access=free}}</ref>

This compound shows antithrombotic and profibrinolytic activities.<ref name="Tae"/> It has also an effect on hair growth.<ref>{{Cite journal|doi=10.3390/ijms13056407|pmid=22754373|title=Effect of Dieckol, a Component of Ecklonia cava, on the Promotion of Hair Growth|year=2012|last1=Kang|first1=Jung-Il|last2=Kim|first2=Sang-Cheol|last3=Kim|first3=Min-Kyoung|last4=Boo|first4=Hye-Jin|last5=Jeon|first5=You-Jin|last6=Koh|first6=Young-Sang|last7=Yoo|first7=Eun-Sook|last8=Kang|first8=Sung-Myung|last9=Kang|first9=Hee-Kyoung|journal=International Journal of Molecular Sciences|volume=13|issue=12|pages=6407–23|pmc=3382810 |doi-access=free }}</ref>

Dieckol is a GSK-3β inhibitor.<ref>{{cite journal |title=Dieckol Ameliorates Aβ Production via PI3K/Akt/GSK-3β Regulated APP Processing in SweAPP N2a Cell |journal=Mar Drugs |date=15 March 2021 |volume=19 |issue=3 |pages=152 |doi=10.3390/md19030152 |pmc=8001366|pmid=33804171|author=Yoon JH, Lee N, Youn K, Jo MR, Kim HR, Lee DS, Ho CT, Jun M |doi-access=free }}</ref><ref>{{cite journal |title=Natural compounds from herbs and nutraceuticals as glycogen synthase kinase-3β inhibitors in Alzheimer's disease treatment |journal=CNS Neuroscience & Therapeutics |date=11 August 2024 |volume=30 |issue=8 |doi=10.1111/cns.14885 |pmc=11317746|pmid=39129397|author=Zheng Zhao, Ye Yuan, Shuang Li, Xiaofeng Wang, Xue Yang |article-number=e14885 }}</ref>

== See also == * Procyanidin B3, a proanthocyanidin dimer with the same hair growth-promoting effect

== References == {{Reflist}}

{{phlorotannin}}

Category:Phlorotannin dimers Category:Dibenzodioxins

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