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 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:65819 N

ChEMBL |

* ChEMBL471187 N

ChemSpider |

* 128740 N

PubChem CID

* 145937

UNII |

* 4A5E8354UB Y

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/h1-6,19-24H N

Key: PCZZRBGISTUIOA-UHFFFAOYSA-N 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 | 372.285 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

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 antiplasmin inhibitory effect[3] and a radioprotective effect in a mouse model.[1][6] It also exhibits an in vitro cytoprotective effect against oxidative stress in Chinese hamster lung fibroblasts.[2] It also shows antithrombotic and profibrinolytic activities.[4]

## References[edit]

1. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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.

* v
* t
* e

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
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template