Phlorofucofuroeckol A

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Phlorofucofuroeckol A
Chemical structure of phlorofucofuroeckol A Phlorofucofuroeckol A.svg
Chemical structure of phlorofucofuroeckol A
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).

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]

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.


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