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MedKoo Cat#: 461559 | Name: Luteoskyrin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Luteoskyrin is a hepatotoxic and hepatocarcinogenic bisdihydroanthraquinone produced by Penicillium islandicum Sopp.

Chemical Structure

Luteoskyrin
Luteoskyrin
CAS#21884-44-6

Theoretical Analysis

MedKoo Cat#: 461559

Name: Luteoskyrin

CAS#: 21884-44-6

Chemical Formula: C30H22O12

Exact Mass: 574.1111

Molecular Weight: 574.49

Elemental Analysis: C, 62.72; H, 3.86; O, 33.42

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Luteoskyrin; Flavomycelin;
IUPAC/Chemical Name
(5aS,6S,13aR,14S,17R,18S,19R,20R)-1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-14-hydro-5H,6H-6,13a,5a,14-(epibutane[1,2,3,4]tetrayl)cycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16-tetraone
InChi Key
KXNUPFFSGSRABD-KCIWCSDFSA-N
InChi Code
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+/m0/s1
SMILES Code
Cc1cc(O)c(C(C2=C(O)[C@@H]3[C@@H]4O)=O)c(C([C@]52[C@H]4[C@H]6[C@@]3(C(c7c(C8=O)c(O)cc(C)c7O)=O)C8=C(O)[C@@H]5[C@@H]6O)=O)c1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 574.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Masuda T, Ito J, Akuzawa S, Ishii K, Takagi H, Ueno Y. Hepatic accumulation and hepatotoxicity of luteoskyrin in mice. Toxicol Lett. 1992 Jun;61(1):9-20. PubMed PMID: 1609444. 2: Tseng HH, Tseng TC. Effects of naled and dichlorvos on growth and production of Luteoskyrin byPenicillium islandicum. Mycotoxin Res. 1993 Mar;9(1):35-40. doi: 10.1007/BF03192230. PubMed PMID: 23606065. 3: Ueno Y, Ishikawa I. Production of luteoskyrin, a hepatotoxic pigment, by Penicillium islandicum Sopp. Appl Microbiol. 1969 Sep;18(3):406-9. PubMed PMID: 5373676; PubMed Central PMCID: PMC377994. 4: Ueno I, Sekijima M, Hoshino M, Ohya-Nishiguchi H, Ueno Y. Spin-trapping and direct EPR investigations on the hepatotoxic and hepatocarcinogenic actions of luteoskyrin, an anthraquinoid mycotoxin produced by Penicillium islandicum Sopp. Generations of superoxide anion and luteoskyrin semiquinone radical in the redox systems consisted of luteoskyrin and liver NADPH- or NADH-dependent reductases. Free Radic Res. 1995 Jul;23(1):41-50. PubMed PMID: 7647918. 5: Ueno I. Sex and age differences in luteoskyrin hepatotoxicity. Ann Nutr Aliment. 1977;31(4-6):789-802. PubMed PMID: 566069. 6: Ueno I, Hoshino M, Maitani T, Kanegasaki S, Ueno Y. Luteoskyrin, an anthraquinoid hepatotoxin, and ascorbic acid generate hydroxyl radical in vitro in the presence of a trace amount of ferrous iron. Free Radic Res Commun. 1993;19 Suppl 1:S95-100. PubMed PMID: 8282236. 7: Ghosh AC, Manmade A, Kobbe B, Townsend JM, Demain AL. Production of luteoskyrin and isolation of a new metabolite, pibasterol, from Penicillium islandicum Sopp. Appl Environ Microbiol. 1978 Mar;35(3):563-6. PubMed PMID: 565188; PubMed Central PMCID: PMC242880. 8: Mizutani K, Kumagai S, Mochizuki N, Kitagawa Y, Sugita-Konishi Y. Determination of a yellow rice toxin, luteoskyrin, in rice by using liquid chromatography-tandem mass spectrometry with electrospray ionization. J Food Prot. 2009 Jun;72(6):1321-6. PubMed PMID: 19610349. 9: Tseng HH, Tseng TC. Effects of butylated hydroxyanisole, butylated hydroxytoluene and tertiary butylhydroquinone on growth and luteoskyrin production byPenicillium islandicum. Mycopathologia. 1995;129(2):73-8. doi: 10.1007/BF01103463. PubMed PMID: 20878563. 10: KITAGAWA I, SHIBATA S. Metabolic products of fungi. X. The structure of rubroskyrin and its relation to the structure of luteoskyrin. Pharm Bull. 1956 Aug;4(4):309-13. PubMed PMID: 13378957. 11: Akuzawa S, Yamaguchi H, Masuda T, Ueno Y. Radical-mediated modification of deoxyguanine and deoxyribose by luteoskyrin and related anthraquinones. Mutat Res. 1992 Apr;266(2):63-9. PubMed PMID: 1373839. 12: Ueno I. Pharmacokinetic studies on the hepatotoxicity of luteoskyrin. (III) quantitative determination of luteoskyrin in the liver. Jpn J Pharmacol. 1976 Feb;(1):1-5. PubMed PMID: 944335. 13: Ueno Y, Habano W, Yamaguchi H, Masuda T, Morimura S, Nemoto K, Kojima S, Tashiro F. Transformation of mammalian cells by luteoskyrin. Food Chem Toxicol. 1991 Sep;29(9):607-13. PubMed PMID: 1937291. 14: BUU-HOI NP, ZAJDELA F. [Is luteoskyrin the hepatotoxic principle in "yellowed" rice?]. Med Exp Int J Exp Med. 1962;6:29-32. French. PubMed PMID: 13875256. 15: UENO I, UENO Y, TATSUNO T, URAGUCHI K. MITOCHONDRIAL RESPIRATORY IMPAIRMENT BY LUTEOSKYRIN, A HEPATOTOXIC PIGMENT OF PENICILLIUM ISLANDICUM SOPP. Jpn J Exp Med. 1964 Jun;34:135-52. PubMed PMID: 14192592. 16: SHIBATA S, KITAGAWA I, NISHIKAWA H. Metabolic products of fungi. XII. The identification of flavomycelin and luteoskyrin. Pharm Bull. 1957 Aug;5(4):383-4. PubMed PMID: 13494140. 17: UENO Y, UENO I, TATSUNO T, URAGUCHI K. [THE EFFECTS OF LUTEOSKYRIN, TOXIC SUBSTANCE FROM PENICILLIUM ISLANDICUM SOPP, ON THE SWELLING OF MITOCHONDRIA]. Jpn J Exp Med. 1964 Aug;34:197-209. French. PubMed PMID: 14233270. 18: Ueno Y, Ueno I, Mizumoto K, Tatsuno T. The binding of luteoskyrin, a hepatotoxic pigment of Penicillium islandicum sopp, to deoxyribonucleohistone. J Biochem. 1968 Mar;63(3):395-7. PubMed PMID: 5671672. 19: UMEDA M. CYTOTOXIC EFFECTS OF THE MYCOTOXINS OF PENICILLIUM ISLANDICUM SOPP, LUTEOSKYRIN AND CHLORINE-CONTAINING PEPTIDE ON CHANG'S LIVER CELLS AND HELA CELLS. Acta Pathol Jpn. 1964 Aug;14:373-94. PubMed PMID: 14277872. 20: Ueno I, Horiuchi T, Enomoto M. Effects of chemical agents on the hepatotoxicity and hepatic accumulation of luteoskyrin. Toxicol Appl Pharmacol. 1980 Feb;52(2):278-84. PubMed PMID: 7189068.

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