Atromentin

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Atromentin
2,5-Dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone
Structural formula of atromentin
Names
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
Identifiers
519-67-5 N
3D model (Jmol) Interactive image
ChemSpider 89570 YesY
PubChem 99148
Properties
C18H12O6
Molar mass 324.29 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YesYN ?)
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[edit]

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[edit]

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[edit]

  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. doi:10.1271/bbb.100451. PMID 21071857. 
  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. doi:10.1002/jps.2600601134. PMID 4332377. 
  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. doi:10.1016/j.fgb.2008.08.009. PMID 18805498. 
  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. doi:10.1038/ja.2006.108. PMID 17323650. 
  6. ^ Sullivan, G.; Guess, W. L. (1969). "Atromentin: A smooth muscle stimulant in Clitocybe subilludens". Lloydia. 32 (1): 72–75. PMID 5815216. 
  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. doi:10.1002/jps.2600540714. PMID 5862512.