Dieckol

Dieckol
Names

IUPAC name 4-[4-[6-(3,5-dihydroxyphenoxy)-4,7,9-trihydroxydibenzo-p-dioxin-2-yl]oxy-3,5-dihydroxyphenoxy]dibenzo-p-dioxin-1,3,6,8-tetrol
Identifiers
CAS Number	88095-77-6
ChEBI	CHEBI:65769^Y
Jmol interactive 3D	Image
PubChem	3008868
InChI 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
SMILES Oc4cc(O)c6Oc(cc(O)cc3O)c3Oc6c4Oc(cc2O)cc(O)c2Oc(cc1Oc5c(O)cc7O)cc(O)c1Oc5c7Oc(c8)cc(O)cc8O
Properties
Chemical formula	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).
Infobox references

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]

References

↑ 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.
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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

Types of phlorotannins (tannins in brown algae)

Monomer	Phloroglucinol

Fucols	Difucol Trifucol Tetrafucol A Tetrafucol B cis-Pentafucol A

Phlorethols	Diphlorethol and diphlorethol A Triphloroethol A Tetraphlorethol A, B, C and E Pentaphlorethol-B Hexaphlorethol-A

Fucophlorethols	Fucophlorethol A and B Fucodiphlorethol A, D and G Fucotriphlorethol-B, G and H Fucotetraphlorethol-B, J and K Fucopentaphlorethol-E Bisfucotriphlorethol-A Bisfucotetraphlorethol-A Bisfucopentaphlorethol-A and B Bisfucoheptaphlorethol-A Difucophlorethol-A Difucofucotriphlorethol-A and B Difucofucotetraphlorethol-A Terfucopentaphlorethol-A Terfucohexaphlorethol-A and B Terfucoheptaphlorethol-A

Fuhalols	Bifuhalol Trifuhalol A Tetrafuhalol A

Isofuhalols	Tetraisofuhalol

Eckols	Dieckol Eckol Eckstolonol Phlorofucofuroeckol A and B 2-Phloroeckol 3-Phloroeckol 6,6'-Bieckol 7-Phloroeckol 8,4"'-Dieckol 8,8′-Bieckol

Halogenated phlorotannins	Bromotriphlorethol A1

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Dieckol

See also

References