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Eckol

Names
Preferred IUPAC name 4-(3,5-Dihydroxyphenoxy)oxanthrene-1,3,6,8-tetrol
Other names 1-(3,5-Dihydroxyphenoxy)-2,4,7,9-tetrahydroxydibenzo-1,4-dioxin
Identifiers
CAS Number	88798-74-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:65819
ChEMBL	ChEMBL471187
ChemSpider	128740
PubChem CID	145937
UNII	4A5E8354UB
CompTox Dashboard (EPA)	DTXSID40237333
InChI InChI=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/h1-6,19-24HKey: PCZZRBGISTUIOA-UHFFFAOYSA-N 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/h1-6,19-24HKey: PCZZRBGISTUIOA-UHFFFAOYAJ
SMILES C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=C(C=C(C=C4O3)O)O)O)O)O
Properties
Chemical formula	C18H12O9
Molar mass	372.285 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

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.

The molecule possesses a dibenzo-p-dioxin skeleton and a phloroglucinol component. The molecule can also be viewed as a phloroglucinol trimer.

It exhibits an antiplasmin inhibitory effect and a radioprotective effect in a mouse model. It also exhibits an in vitro cytoprotective effect against oxidative stress in Chinese hamster lung fibroblasts. It also shows antithrombotic and profibrinolytic activities.

References

1. ^ Moon, Changjong; Kim, Sung-Ho; Kim, Jong-Choon; Hyun, Jin Won; Lee, Nam Ho; Park, Jae Woo; Shin, Taekyun (2008). "Protective effect of phlorotannin components phloroglucinol and eckol on radiation-induced intestinal injury in mice". Phytotherapy Research. 22 (2): 238–42. doi:10.1002/ptr.2298. PMID 17886227.
2. ^ Kang, Kyoung Ah; Lee, Kyoung Hwa; Chae, Sungwook; Zhang, Rui; Jung, Myung Sun; Lee, Youngki; Kim, So Young; Kim, Hee Sun; Joo, Hong Gu; Park, Jae Woo; Ham, Young Min; Lee, Nam Ho; Hyun, Jin Won (2005). "Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells". FEBS Letters. 579 (28): 6295–304. doi:10.1016/j.febslet.2005.10.008. PMID 16253238.
3. ^ Fukuyama, Y; Kodama, M; Miura, I; Kinzyo, Z; Kido, M; Mori, H; Nakayama, Y; Takahashi, M (1989). "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". Chemical & Pharmaceutical Bulletin. 37 (2): 349–53. doi:10.1248/cpb.37.349. PMID 2525966.
4. ^ 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.
5. Shibata, Toshiyuki; Fujimoto, Ken; Nagayama, Kohki; Yamaguchi, Kuniko; Nakamura, Takashi (2002). "Inhibitory activity of brown algal phlorotannins against hyaluronidase". International Journal of Food Science and Technology. 37 (6): 703. CiteSeerX 10.1.1.577.2261. doi:10.1046/j.1365-2621.2002.00603.x.
6. Nakayama, Yasuo; Takahashi, Masayuki; Fukuyama, Yoshiyasu; Kinzyo, Zyunei (1989). "Anti-plasmin inhibitor. Part IV. An anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome OKAMURA". Agricultural and Biological Chemistry. 53 (11): 3025. doi:10.1271/bbb1961.53.3025.

• Phlorotannins
• Dibenzodioxins