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Open Access Articles- Top Results for Atromentin

Atromentin

Atromentin
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone
Structural formula of atromentin
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IUPAC name
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
Other names
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone
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519-67-5 7pxN
ChemSpider 89570 7pxY
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
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C18H12O6
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN
Infobox references

Atromentin is a natural chemical compound found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be prepared by laboratory synthesis.[1] Chemically, it is a polyphenol and a benzoquinone.

Occurrences

Atromentin has been found in cultures of Clitocybe subilludens[2] and in extracts of Hydnellum peckii. The first enzymes in its biosynthesis have been characterized in Tapinella panuoides.[3] One of those is called atromentin synthetase.[4]

Biological activities

A number of in vitro biological actives of atromentin have been studied. Atromentin possesses in vitro antibacterial activity, inhibiting the enzyme enoyl-acyl carrier protein reductase (essential for the biosynthesis of fatty acids) in the bacteria Streptococcus pneumoniae.[5] Atromentin has been shown to be a smooth muscle stimulant.[6] It also induces apoptosis in isolated human leukemia U937 cells.[7] It is also an anticoagulant.[8]

References

  1. Ye, Y. Q.; Koshino, H.; Abe, N.; Nakamura, T.; Hashizume, D.; Takahashi, S. (2010). "Synthesis of atromentin and its O-alkylated natural products". Bioscience, biotechnology, and biochemistry 74 (11): 2342–2344. PMID 21071857. doi:10.1271/bbb.100451.  edit
  2. Sullivan, G.; Garrett, R. D.; Lenehan, R. F. (1971). "Occurrence of atromentin and thelephoric acid in cultures ofclitocybe subilludens". Journal of Pharmaceutical Sciences 60 (11): 1727–1729. PMID 4332377. doi:10.1002/jps.2600601134.  edit
  3. Schneider, P.; Bouhired, S.; Hoffmeister, D. (2008). "Characterization of the atromentin biosynthesis genes and enzymes in the homobasidiomycete Tapinella panuoides". Fungal Genetics and Biology 45 (11): 1487–1496. PMID 18805498. doi:10.1016/j.fgb.2008.08.009.  edit
  4. Atromentin synthetase on www.uniprot.org
  5. Zheng CJ, Sohn MJ, Kim WG. (2006). "Atromentin and leucomelone, the first inhibitors specific to enoyl-ACP reductase (FabK) of Streptococcus pneumoniae". Journal of Antibiotics 59 (12): 808–12. PMID 17323650. doi:10.1038/ja.2006.108. 
  6. Sullivan, G.; Guess, W. L. (1969). "Atromentin: A smooth muscle stimulant in Clitocybe subilludens". Lloydia 32 (1): 72–75. PMID 5815216.  edit
  7. Atromentin-Induced Apoptosis in Human Leukemia U937 Cells. Kim Jin Hee and Choong Hwan Lee, Journal of microbiology and biotechnology, 2009, vol. 19, no9, pages 946-950, INIST:21945937
  8. Khanna JM, Malone MH, Euler KL, Brady LR. (1965). "Atromentin – anticoagulant from Hydnellum diabolus". Journal of Pharmaceutical Science 54 (7): 1016–20. PMID 5862512. doi:10.1002/jps.2600540714.