Atromentin

Atromentin

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
CAS Number	519-67-5
ChemSpider	89570
Jmol interactive 3D	Image
PubChem	99148
InChI InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H Key: FKQQKMGWCJGUCS-UHFFFAOYSA-N InChI=1S/C18H12O6/c19-11-5-1-9(2-6-11)13-15(21)17(23)14(18(24)16(13)22)10-3-7-12(20)8-4-10/h1-8,19-21,24H Key: FKQQKMGWCJGUCS-UHFFFAOYSA-N
SMILES C1=CC(=CC=C1C2=C(C(=O)C(=C(C2=O)O)C3=CC=C(C=C3)O)O)O
Properties
Chemical formula	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).
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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. 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.