Eckol

Eckol

Names
IUPAC name 4-(3,5-dihydroxyphenoxy)dibenzo-p-dioxin-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=
ChEBI	CHEBI:65819
ChEMBL	ChEMBL471187
ChemSpider	128740
Jmol interactive 3D	Image
PubChem	145937
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/h1-6,19-24H Key: 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/h1-6,19-24H Key: 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	372.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Eckol is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus Ecklonia^[1] such as E. cava^[2] or E. kurome^[3] or in the genus Eisenia such as Eisenia bicyclis.^[4]

The molecule possesses a dibenzo-p-dioxin skeleton and a phloroglucinol component. The molecule can also be viewed as a phloroglucinol trimer.^[5]

It exhibits an anti-plasmin inhibitory effect^[3] and a radioprotective effect in mice.^[1][6] It also exhibits a cytoprotective effect against oxidative stress in Chinese hamster lung fibroblasts.^[2] It also shows antithrombotic and profibrinolytic activities.^[4]

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. 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.