(-)-Luteoskyrin
-
(-)-Luteoskyrin
structure -
-
CAS No:
21884-44-6
-
Formula:
C30H22O12
-
Chemical Name:
(-)-Luteoskyrin
-
Synonyms:
5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b′]dinaphthalene-5,8,13,16(14H)-tetrone,1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-,(5aR,6S,13aR,14S,17R,18S,19S,20R)-;5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b′]dinaphthalene-5,8,13,16(14H)-tetrone,1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-;Rugulosin,8,8′-dihydroxy-,(1S,1′S,2R,2′R,3S,3′S,9aR,9′aR)-;Luteoskyrin;5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b′]dinaphthalene,rugulosin deriv.;(5aR,6S,13aR,14S,17R,18S,19S,20R)-1,4,7,9,12,15,17,20-Octahydroxy-3,11-dimethyl-5H,6H-6,13a,5a,14-[1,2,3,4]butanetetraylcycloocta[1,2-b:5,6-b′]dinaphthalene-5,8,13,16(14H)-tetrone;Luteoskyrin,(-)-;(-)-Luteoskyrin;5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b′]dinaphthalene-5,8,13,16(14H)-tetrone,1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-,[5aR-(5aR*,6S*,13aR*,14S*,17R*,18S*,19S*,20R*)]-;1402-11-5;10088-79-6;27618-64-0
-
CAS No:
(-)-Luteoskyrin Basic Attributes
602.545
574.49
244-631-1
160879
DTXSID0020787
YELLOW, RECTANGULAR CRYSTALS
Characteristics
230 Ų
1.3474
287 °C (decomp)
555.89°C (rough estimate)
1.6480 (estimate)
PRACTICALLY INSOL IN WATER; SOL IN AQ SODIUM BICARBONATE; SOL IN MOST ORGANIC SOLVENTS
Safety Information
CONVERTS TO A BROWNISH-RED QUINOID SUBSTANCE, LUMILUTEOSKYRIN, WHEN EXPOSED TO SUNLIGHT
FOOD POISONING ATTRIBUTABLE TO P ISLANDICUM, AND THE PROPERTIES, FORMATION, ANALYSIS, NATURAL OCCURRENCE, AND BIOL ACTIVITIES OF THE TOXIC METABOLITES, ESPECIALLY LUTEOSKYRIN, REVIEWED WITH 92 REF.[ENOMOTO M, UENO I; PENICILLIUM ISLANDICUM (TOXIC YELLOWED RICE) - LEUTEOSKYRIN - ISLANDITOXIN - CYCLOCHLOROTINE; MYCOTOXINS 303 (1974)]
Toxicity
...PRODUCED IN CULTURE BY PENICILLUM ISLANDICUM AND BY MYCELIA STERILIA. ...HAS OCCASIONALLY BEEN REPORTED AS ONE OF THE MAJOR ISOLATES FROM VARIOUS GRAINS, INCLUDING DOMESTIC AND IMPORTED RICE IN JAPAN, THE STAPLE DIET 'TEFF' IN ETHIOPIA AND BARLEY, AND AS A PREVALENT INFECTION IN PREPARED FOODSTUFFS IN SOUTH AFRICA.
Drug Information
...IS ABSORBED SLOWLY FOLLOWING ITS SC (3 DAILY INJECTIONS OF 5 UG/G) OR ORAL ADMIN (9 UG/ANIMAL) /OF (3)H-LUTEOSKYRIN/. RADIOACTIVITY WAS EXTREMELY HIGH IN THE LIVER WHEN COMPARED WITH THAT IN OTHER ORGANS... LUTEOSKYRIN WAS EXCRETED VIA THE BILE AND KIDNEYS, AS SHOWN BY CHEMICAL IDENTIFICATION OF LUTEOSKYRIN IN THE FECES AND URINE.
LUTEOSKYRIN IS A COMPLEX, MODIFIED BIANTHRAQUINONE DERIVATIVE. .../IT/ IMPAIRS MITOCHONDRIAL FUNCTION AND BINDS TO DNA AT SITE OF PYRIMIDINE BASES IN THE PRESENCE OF MAGNESIUM ION TO INHIBIT THE SYNTHESIS OF NUCLEAR RNA VIA MODIFICATION OF DNA-DEPENDENT RNA-POLYMERASE.
LUTEOSKYRIN, A METABOLITE OF A NUMBER OF PENICILLIUM SPECIES, IS...POTENT CARCINOGEN FOUND ON CONTAMINATED FOOD...USUALLY RICE.
luteoskyrin
(-)-Luteoskyrin Use and Manufacturing
A SIMPLE SCREENING METHOD FOR MOLDS PRODUCING THE INTRACELLULAR MYCOTOXIN LUTEOSKYRIN WAS DEVELOPED.
AN ANALYTICAL METHOD IS DESCRIBED FOR THE SIMULTANEOUS DETERMINATION OF 13 MYCOTOXINS, INCLUDING LUTEOSKYRIN BY HIGH PERFORMANCE THIN-LAYER CHROMATOGRAPHY.|MYCOTOXINS, INCL LUTEOSKYRIN, DETERMINED BY TLC.
Computed Properties
Molecular Weight:574.5
XLogP3:1.3
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:12
Exact Mass:574.11112613
Monoisotopic Mass:574.11112613
Topological Polar Surface Area:230
Heavy Atom Count:42
Complexity:1360
Undefined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Request for Quotation