Rugulosin

Last updated

Rugulosin
Rugulosin.svg
Names
IUPAC name
8,10,14,23,25,28-hexahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4(9),5,7,10,19(24),20,22,25-octaene-3,12,18,27-tetrone
Other names
NSC 160880
NSC 249990
Rugulosin A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-36H,1-2H3
    Key: QFDPVUTXKUGISP-UHFFFAOYSA-N
  • CC1=CC2=C(C(=C1)O)C(=C3C(=O)C4C(C5C3(C2=O)C6C(C5C47C(=C(C8=C(C7=O)C=C(C=C8O)C)O)C6=O)O)O)O
  • natural:Cc1cc2c(c(c1)O)C(=O)C3=C([C@H]4[C@H]([C@H]5[C@]3(C2=O)[C@@H]6[C@H]([C@H]5[C@]47C(=O)c8cc(cc(c8C(=O)C7=C6O)O)C)O)O)O
Properties
C30H22O10
Molar mass 542.496 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rugulosin is an anthraquinoid mycotoxin with the molecular formula C30H22O10 which is produced by Penicillium species. [1] [2] [3] Rugulosin is hepatotoxic and is cancerogenic. [4]

References

  1. "Rugulosin". Pubchem.
  2. Ueno, Yoshio; Sato, Norio; Ito, Teruo; Ueno, Ikuko; Enomoto, Makoto; Tsunoda, Hiroshi (1980). "Chronic Toxicity and Hepatocarcinogenicity of (+) Rugulosin, an Anthraquinoid Mycotoxin from Penicillium Species: Preliminary Surveys in Mice". The Journal of Toxicological Sciences. 5 (4): 295–302. doi: 10.2131/jts.5.295 . PMID   7218376.
  3. Ueno, Y; Ueno, I; Sato, N; Iitoi, Y; Saito, M (June 1971). "Toxicological approach to (+) rugulosin, an anthraquinoid mycotoxin of Penicillium rugulosum Thom". The Japanese Journal of Experimental Medicine. 41 (3): 177–188. PMID   5314585.
  4. Eisenbrand, Gerhard; Schreier, Peter (28 May 2014). RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006 (in German). Georg Thieme Verlag. ISBN   978-3-13-179532-8.

Further reading