Atromentin
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Atromentin
| Atromentin | |
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 Structural formula of atromentin
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2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione |
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Other names
2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone |
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| Identifiers | |
| CAS number | 519-67-5  = |
| PubChem | 99148 |
| ChemSpider | 89570  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C18H12O6 |
| Molar mass | 324.28 g/mol |
| Exact mass | 324.063388 u |
 Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Atromentin is a benzoquinone, a natural phenolic compound. It is found in Agaricomycetes fungi in the orders Agaricales and Thelephorales. It can also be synthetized.[1]
Occurrences
It can be isolated from cultures of Clitocybe subilludens[2] and in extracts of Hydnellum peckii.
The first enzymes in its biosynthesis have been characterised in Tapinella panuoides.[3] One of those is called Atromentin synthetase.[4]
Uses
It is an effective anticoagulant, and similar in biological activity to the well-known anticoagulant heparin.[5]
Atromentin possesses antibacterial activity, inhibiting the enzyme enoyl-acyl carrier protein reductase (essential for the biosynthesis of fatty acids) in the bacteria Streptococcus pneumoniae.[6]
Atromentin has been shown to be a smooth muscle stimulant.[7]
It also induces apoptosis in human leukemia U937 cells.[8]
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Atromentin synthetase on www.uniprot.org
- ^ 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.
- ^ 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.
- ^ Sullivan, G.; Guess, W. L. (1969). "Atromentin: A smooth muscle stimulant in Clitocybe subilludens". Lloydia 32 (1): 72–75. PMID 5815216.
- ^ 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
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