8,8′-Bieckol

Last updated
8,8′-Bieckol
8,8'-Bieckol.PNG
Names
Preferred IUPAC name
9,9′-Bis(3,5-dihydroxyphenoxy)[2,2′-bioxanthrene]-1,1′,3,3′,6,6′,8,8′-octol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C36H22O18/c37-11-1-12(38)4-15(3-11)49-29-19(43)7-21(45)31-35(29)53-33-23(51-31)9-17(41)25(27(33)47)26-18(42)10-24-34(28(26)48)54-36-30(20(44)8-22(46)32(36)52-24)50-16-5-13(39)2-14(40)6-16/h1-10,37-48H
    Key: FHYNTHBAMAEFJB-UHFFFAOYSA-N
  • InChI=1/C36H22O18/c37-11-1-12(38)4-15(3-11)49-29-19(43)7-21(45)31-35(29)53-33-23(51-31)9-17(41)25(27(33)47)26-18(42)10-24-34(28(26)48)54-36-30(20(44)8-22(46)32(36)52-24)50-16-5-13(39)2-14(40)6-16/h1-10,37-48H
    Key: FHYNTHBAMAEFJB-UHFFFAOYAK
  • C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=C(C(=C(C=C4O3)O)C5=C(C=C6C(=C5O)OC7=C(O6)C(=CC(=C7OC8=CC(=CC(=C8)O)O)O)O)O)O)O)O)O
Properties
C36H22O18
Molar mass 742.55 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

8,8'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava [1] and Ecklonia kurome . [2]

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<i>Ecklonia cava</i> Species of seaweed

Ecklonia cava is an edible marine brown alga species found in the ocean off Japan and Korea. It is used as an herbal remedy in the form of an extract called Seanol, a polyphenolic extract, and Ventol, a phlorotannin-rich natural agent. Phlorotannins, such as fucodiphlorethol G, 7-phloro eckol, 6,6'-bieckol, eckol, 8,8'-bieckol, 8,4"'-dieckol and phlorofucofuroeckol A can be isolated from Ecklonia cava. Other components are common sterol derivatives.

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Phlorotannin

Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds or sargassacean species, and in a lower amount also in some red algae. Contrary to hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol (polyphloroglucinols). As they are called tannins, they have the ability to precipitate proteins. It has been noticed that some phlorotannins have the ability to oxidize and form covalent bonds with some proteins. In contrast, under similar experimental conditions three types of terrestrial tannins apparently did not form covalent complexes with proteins.

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Ecklonia stolonifera is a brown alga species in the genus Ecklonia found in the Sea of Japan. It is an edible species traditionally eaten in Japan.

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6,6-Bieckol Chemical compound

6,6'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava and Ecklonia stolonifera.

Eckstolonol Chemical compound

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Winogradskyella eckloniae is a Gram-negative, aerobic, rod-shaped and motile bacterium from the genus of Winogradskyella which has been isolated from the alga Ecklonia cava from the Jeju Island.

References

  1. Ahn, M. J.; Yoon, K. D.; Min, S. Y.; Lee, J. S.; Kim, J. H.; Kim, T. G.; Kim, S. H.; Kim, N. G.; Huh, H.; Kim, J. (2004). "Inhibition of HIV-1 reverse transcriptase and protease by phlorotannins from the brown alga Ecklonia cava". Biological & Pharmaceutical Bulletin. 27 (4): 544–547. doi: 10.1248/bpb.27.544 . PMID   15056863.
  2. Fukuyama, Y.; Kodama, M.; Miura, I.; Kinzyo, Z.; Mori, H.; Nakayama, Y.; Takahashi, M. (1989). "Anti-plasmin inhibitor. V. Structures of novel dimeric eckols isolated from the brown alga Ecklonia kurome OKAMURA". Chemical & Pharmaceutical Bulletin. 37 (9): 2438–2440. doi: 10.1248/cpb.37.2438 . PMID   2605688.