From Wikipedia, the free encyclopedia
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
ChEBI
ChEMBL
ChemSpider
UNII
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
C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=C(C=C(C=C4O3)O)O)O)O)O
Properties
C 18 H 12 O 9
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).
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
^
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 .
^
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 .
^
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 .
^
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 .
^ 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 .
^ 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 .
Monomer Fucols Phlorethols Fucophlorethols Fuhalols Isofuhalols Eckols Halogenated phlorotannins