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]

See also

Related Research Articles

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Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds or sargassacean species, and in a lower amount also in some red algae. Contrary to hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol (polyphloroglucinols). 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 apparently did not form covalent complexes with proteins.

<span class="mw-page-title-main">Eckol</span> Chemical compound

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 the genus Eisenia such as Eisenia bicyclis.

<span class="mw-page-title-main">Phlorofucofuroeckol A</span> Chemical compound

Phlorofucofuroeckol A is a phlorotannin isolated from brown algae species such as Eisenia bicyclis, Ecklonia cava, Ecklonia kurome or Ecklonia stolonifera.

Ecklonia stolonifera is a brown alga species in the genus Ecklonia found in the Sea of Japan. It is an edible species traditionally eaten in Japan.

Ecklonia kurome is a brown alga species in the genus Ecklonia found in the Sea of Japan.

<span class="mw-page-title-main">8,8′-Bieckol</span> Chemical compound

8,8'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava and Ecklonia kurome.

<span class="mw-page-title-main">6,6'-Bieckol</span> Chemical compound

6,6'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava and Ecklonia stolonifera.

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<span class="mw-page-title-main">7-Phloroeckol</span> Chemical compound

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<span class="mw-page-title-main">Fucosterol</span> Chemical compound

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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.