Luteoskyrin

Luteoskyrin is a carcinogenic mycotoxin with the molecular formula C30H22O12 which is produced by the mold Penicillium islandicum.[1][2][3][4] Luteoskyrin has strong cytotoxic effects.[5][6] Luteoskyrin can cause the yellow rice disease.[1]

Luteoskyrin
Names
IUPAC name
5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone
Other names
Flacomycelin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 244-631-1
KEGG
UNII
  • InChI=1S/C30H22O12/c1-5-3-7(31)9-11(19(5)33)27(41)29-13-14-24(38)17(29)26(40)16-22(36)10-8(32)4-6(2)20(34)12(10)28(42)30(14,16)18(23(13)37)25(39)15(29)21(9)35/h3-4,13-14,17-18,23-24,31-38H,1-2H3
  • Key: FAZDYVMEXQHRLI-UHFFFAOYSA-N
  • natural: InChI=1S/C30H22O12/c1-5-3-7(31)9-11(19(5)33)27(41)29-13-14-24(38)17(29)26(40)16-22(36)10-8(32)4-6(2)20(34)12(10)28(42)30(14,16)18(23(13)37)25(39)15(29)21(9)35/h3-4,13-14,17-18,23-24,31-34,37-40H,1-2H3/t13-,14-,17+,18+,23-,24-,29+,30+/m1/s1
    Key: KXNUPFFSGSRABD-TZRHFUAUSA-N
  • Cc1cc(c2c(c1O)C(=O)C34C5C6C(C3C(=O)C7=C(c8c(cc(c(c8C(=O)C67C(C5O)C(=O)C4=C2O)O)C)O)O)O)O
  • natural: Cc1cc(c2c(c1O)C(=O)[C@]34[C@@H]5[C@@H]6[C@H]([C@H]3C(=C7[C@@]6([C@@H]([C@@H]5O)C(=C4C2=O)O)C(=O)c8c(c(cc(c8O)C)O)C7=O)O)O)O
Properties
C30H22O12
Molar mass 574.494 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Weidenbörner, Martin (7 March 2013). Lexikon der Lebensmittelmykologie (in German). Springer-Verlag. p. 82. ISBN 978-3-642-57058-2.
  2. Hänsel, Rudolf; Keller, Konstantin; Rimpler, Horst; Schneider, Georg (8 March 2013). Hagers Handbuch der Pharmazeutischen Praxis: Drogen P-Z Folgeband 2 (in German). Springer-Verlag. ISBN 978-3-642-57881-6.
  3. Eisenbrand, Gerhard; Schreier, Peter (28 May 2014). RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006 (in German). Georg Thieme Verlag. p. 41. ISBN 978-3-13-179532-8.
  4. Ueno, Yoshio; Ishikawa, Ichijiro (September 1969). "Production of Luteoskyrin, a Hepatotoxic Pigment, by Penicillium islandicum Sopp". Applied Microbiology. 18 (3): 406–409. doi:10.1128/AM.18.3.406-409.1969. ISSN 0003-6919. PMC 377994. PMID 5373676.
  5. Keutel, J.; Möckel, H. (1 December 1969). "Induction of chromosomal breakage in cultured human leucocytes by luteoskyrin". Humangenetik. 7 (4): 344–348. doi:10.1007/BF00283556. ISSN 1432-1203. PMID 5365575. S2CID 7401409.
  6. Möckel, Horst. Chromosomenaberrationen an kultivierten menschlichen leukozyten (in German). Marburg. p. 39.

Further reading
  • Ueno, I.; Hoshino, M.; Maitani, T.; Kanegasaki, S.; Ueno, Y. (1 October 1993). "Luteoskyrin, an Anthraquinoid Hepatotoxin, and Ascorbic Acid Generate Hydroxyl Radical in vitro in the Presence of a Trace Amount of Ferrous Iron". Free Radical Research Communications. 19 (sup1): s95–s100. doi:10.3109/10715769309056s95. ISSN 8755-0199. PMID 8282236.
  • Okuto, Hiroshi; Sasada, Yoshio; Sakurai, Kiichi (February 1958). "X-ray Determination of the Molecular Weight of Luteoskyrin". Bulletin of the Chemical Society of Japan. 31 (2): 247–248. doi:10.1246/bcsj.31.247.
  • UENO, YOSHIO; UENO, IKUKO; MIZUMOTO, KIYOHISA; TATSUNO, TAKASHI (1 March 1968). "The Binding of Luteoskyrin, a Hepatotoxic Pigment of Penicillium islandicum Sopp, to Deoxyribonucleohistone". The Journal of Biochemistry. 63 (3): 395–397. doi:10.1093/oxfordjournals.jbchem.a128787. ISSN 0021-924X. PMID 5671672.
  • Busby, W. F. Jr.; Wogan, G. N. (1981). "Luteoskyrin [Pharmacokinetics, effects on mitochondrial function, DNA complex formation, inhibition of macromolecular synthesis, mycotoxins, Penicillium islandicum]". {{cite journal}}: Cite journal requires |journal= (help)


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