Phlorofucofuroeckol A

Phlorofucofuroeckol A
Names

IUPAC name 4,9-bis(3,5-dihydroxyphenoxy)-[1]benzofuro[3,2-a]oxanthrene-1,3,6,10,12-pentol
Identifiers
CAS Number	128129-56-6
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL510508
ChemSpider	115819
PubChem	130976
InChI 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
SMILES 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
Chemical formula	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]

References

↑ 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.
↑ 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.
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.
↑ 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.

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

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