Phlorofucofuroeckol A

Last updated
Phlorofucofuroeckol A
Phlorofucofuroeckol A.svg
Names
Preferred IUPAC name
4,9-Bis(3,5-dihydroxyphenoxy)[1]benzofuro[3,2-a]oxanthrene-1,3,6,10,12-pentol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C30H18O14/c31-10-1-11(32)4-14(3-10)40-24-17(36)7-16(35)22-23-21(42-28(22)24)9-20(39)25-29(23)43-27-19(38)8-18(37)26(30(27)44-25)41-15-5-12(33)2-13(34)6-15/h1-9,31-39H
    Key: SLWPBUMYPRVYIJ-UHFFFAOYSA-N
  • C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=CC(=C5C(=C43)OC6=C(O5)C(=C(C=C6O)O)OC7=CC(=CC(=C7)O)O)O)O)O)O
Properties
C30H18O14
Molar mass 602.45 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phlorofucofuroeckol A is a phlorotannin isolated from brown algae species such as Eisenia bicyclis (an edible seaweed called arame in Japan), [1] Ecklonia cava , [2] Ecklonia kurome [3] or Ecklonia stolonifera . [4]

The molecule possesses both the dibenzo-1,4-dioxin and dibenzofuran elements. [3]

Related Research Articles

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Arame Species of edible kelp

Arame, sea oak is a species of kelp, of the brown algae, best known for its use in Japanese cuisine.

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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.

<i>Ecklonia</i> Genus of seaweeds

Ecklonia is a genus of kelp belonging to the family Lessoniaceae.

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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.

Eckol Chemical compound

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.

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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.

Ecklonia kurome is a brown alga species in the genus Ecklonia found in the Sea of Japan.

Dieckol Chemical compound

Dieckol is a phlorotannin that can be found in arame, in Ecklonia cava or in Ecklonia stolonifera.

8,8′-Bieckol Chemical compound

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

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

Eckstolonol is a phlorotannin found in the edible brown algae arame and turuarame.

Fucosterol Chemical compound

Fucosterol is a sterol isolated from algae such as Ecklonia cava or Ecklonia stolonifera.

<i>Saururus chinensis</i> Species of flowering plant in the family Saururaceae

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References

  1. Eom, Sung-Hwan; Lee, Sang-Hoon; Yoon, Na-Young; Jung, Won-Kyo; Jeon, You-Jin; Kim, Se-Kwon; Lee, Myung-Suk; Kim, Young-Mog (2012). "Α-Glucosidase- and α-amylase-inhibitory activities of phlorotannins from Eisenia bicyclis". Journal of the Science of Food and Agriculture. 92 (10): 2084–90. doi:10.1002/jsfa.5585. PMID   22271637.
  2. Ahn, MJ; Yoon, KD; Min, SY; Lee, JS; Kim, JH; Kim, TG; Kim, SH; Kim, NG; 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): 544–7. doi: 10.1248/bpb.27.544 . PMID   15056863.
  3. 1 2 Fukuyama, Y; Kodama, M; Miura, I; Kinzyo, Z; Mori, H; Nakayama, Y; Takahashi, M (1990). "Anti-plasmin inhibitor. VI. Structure of phlorofucofuroeckol A, a novel phlorotannin with both dibenzo-1,4-dioxin and dibenzofuran elements, from Ecklonia kurome Okamura". Chemical & Pharmaceutical Bulletin. 38 (1): 133–5. doi: 10.1248/cpb.38.133 . PMID   2337936.
  4. Kim, AR; Lee, MS; Shin, TS; Hua, H; Jang, BC; Choi, JS; Byun, DS; Utsuki, T; Ingram, D; Kim, HR (2011). "Phlorofucofuroeckol a inhibits the LPS-stimulated iNOS and COX-2 expressions in macrophages via inhibition of NF-κB, Akt, and p38 MAPK". Toxicology in Vitro. 25 (8): 1789–95. doi:10.1016/j.tiv.2011.09.012. PMID   21963823.