Dieckol

Last updated
Dieckol
Dieckol.svg
Names
Preferred IUPAC name
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • 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
    Key: DRZQFGYIIYNNEC-UHFFFAOYSA-N
  • Oc4cc(O)c6Oc(cc(O)cc3O)c3Oc6c4Oc(cc2O)cc(O)c2Oc(cc1Oc5c(O)cc7O)cc(O)c1Oc5c7Oc(c8)cc(O)cc8O
Properties
C36H22O18
Molar mass 742.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dieckol is a phlorotannin that can be found in arame (Eisenia bicyclis), [1] [2] in Ecklonia cava [3] or in Ecklonia stolonifera . [4] [5]

This compound shows antithrombotic and profibrinolytic activities. [2] It has also an effect on hair growth. [6]

Dieckol is a GSK-3β inhibitor. [7] [8]

See also

References

  1. ↑ Jung, HA; Oh, SH; Choi, JS (2010). "Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity". Bioorganic & Medicinal Chemistry Letters. 20 (11): 3211–5. doi:10.1016/j.bmcl.2010.04.093. PMID   20462757.
  2. 1 2 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. S2CID   2151927.
  3. ↑ Lee, Seung-Hong; Park, Mi-Hwa; Heo, Soo-Jin; Kang, Sung-Myung; Ko, Seok-Chun; Han, Ji-Sook; Jeon, You-Jin (2010). "Dieckol isolated from Ecklonia cava inhibits α-glucosidase and α-amylase in vitro and alleviates postprandial hyperglycemia in streptozotocin-induced diabetic mice". Food and Chemical Toxicology. 48 (10): 2633–7. doi:10.1016/j.fct.2010.06.032. PMID   20600532.
  4. ↑ Goo, HR; Choi, JS; Na, DH (2010). "Quantitative determination of major phlorotannins in Ecklonia stolonifera". Archives of Pharmacal Research. 33 (4): 539–44. doi:10.1007/s12272-010-0407-y. PMID   20422362. S2CID   26981463.
  5. ↑ Joe, MJ; Kim, SN; Choi, HY; Shin, WS; Park, GM; Kang, DW; Kim, YK (2006). "The inhibitory effects of eckol and dieckol from Ecklonia stolonifera on the expression of matrix metalloproteinase-1 in human dermal fibroblasts". Biological & Pharmaceutical Bulletin. 29 (8): 1735–9. doi: 10.1248/bpb.29.1735 . PMID   16880634.
  6. ↑ Kang, Jung-Il; Kim, Sang-Cheol; Kim, Min-Kyoung; Boo, Hye-Jin; Jeon, You-Jin; Koh, Young-Sang; Yoo, Eun-Sook; Kang, Sung-Myung; Kang, Hee-Kyoung (2012). "Effect of Dieckol, a Component of Ecklonia cava, on the Promotion of Hair Growth". International Journal of Molecular Sciences. 13 (12): 6407–23. doi: 10.3390/ijms13056407 . PMC   3382810 . PMID   22754373.
  7. ↑ Yoon JH, Lee N, Youn K, Jo MR, Kim HR, Lee DS, Ho CT, Jun M (15 March 2021). "Dieckol Ameliorates Aβ Production via PI3K/Akt/GSK-3β Regulated APP Processing in SweAPP N2a Cell". Mar Drugs. 19 (3): 152. doi: 10.3390/md19030152 . PMC   8001366 . PMID   33804171.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ↑ Zheng Zhao, Ye Yuan, Shuang Li, Xiaofeng Wang, Xue Yang (11 August 2024). "Natural compounds from herbs and nutraceuticals as glycogen synthase kinase-3β inhibitors in Alzheimer's disease treatment". CNS Neuroscience & Therapeutics. 30 (8) e14885. doi:10.1111/cns.14885. PMC   11317746 . PMID   39129397.{{cite journal}}: CS1 maint: multiple names: authors list (link)


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