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Chemical Compound Review

norsolorinate     2-hexanoyl-1,3,6,8- tetrahydroxy-anthracene...

Synonyms: CHEBI:71356, NSC-138557, LS-20686, NSC138557, NSC 138557, ...
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High impact information on NSC 138557

  • In contrast, the mutants Dis-1 and Dis-2, which are derived from NOR-1 by insertional inactivation of fas-1, produced unexpectedly low amounts of norsolorinic acid in the presence of hexanoylNAC [1].
  • CONCLUSIONS: The impaired ability of Dis-1 and Dis-2, harboring modified FAS-1 enzymes, to carry out norsolorinic acid synthesis implies the need for FAS-1 (and possibly also FAS-2) to physically associate with the PKS before biosynthesis can begin [1].
  • We describe a novel screen for detecting mutants defective in stc gene cluster activity by use of a genetic block early in the ST biosynthetic pathway that results in the accumulation of the first stable intermediate, norsolorinic acid (NOR), an orange-colored compound visible with the unaided eye [2].
  • Furthermore, microscopic observations showed that the ST and AF precursor norsolorinic acid accumulated in peroxisomes of all three Aspergilli [3].
  • An 8-kb SacI subclone of cosmid NorA complemented fas-1A only, resulting in accumulation of norsolorinic acid [4].

Biological context of NSC 138557

  • Southern analysis of genomic DNA isolated from the NA-accumulating transformants indicated that the wild-type nor-1 gene in the chromosome had been replaced by the nonfunctional allele carried on pNA51-82 [5].
  • An Aspergillus parasiticus cDNA library was screened with monoclonal antibody raised against a purified A. parasiticus 43-kDa protein demonstrating norsolorinic acid reductase (NOR) activity [6].
  • The green-spored, prototrophic diploids resembled haploid wild-type strains in that they produced high levels of aflatoxin, low levels of versicolorin A, and no detectable norsolorinic acid [7].

Anatomical context of NSC 138557


Associations of NSC 138557 with other chemical compounds

  • Conventional quantitative chromatographic analyses of separated materials indicated that aflatoxin from Aspergillus parasiticus, norsolorinic acid from a mutant of A. parasiticus, and secalonic acid D from Penicillium oxalicum were concentrated in the mycelium-substrate matrices and not in the spores [9].
  • Isolation of the Anthraquinone Norsolorinic acid from Cinchona ledgeriana1 [10].
  • The reaction catalyzed by the dehydrogenase was optimum at pH 8.5 and between 25 degrees to 35 degrees C. The Km of the enzyme for NA and NADPH was determined to be 3.45 microM and 103 microM respectively [11].

Analytical, diagnostic and therapeutic context of NSC 138557


  1. Demonstration of the catalytic roles and evidence for the physical association of type I fatty acid synthases and a polyketide synthase in the biosynthesis of aflatoxin B1. Watanabe, C.M., Wilson, D., Linz, J.E., Townsend, C.A. Chem. Biol. (1996) [Pubmed]
  2. Aspergillus nidulans mutants defective in stc gene cluster regulation. Butchko, R.A., Adams, T.H., Keller, N.P. Genetics (1999) [Pubmed]
  3. Fundamental contribution of beta-oxidation to polyketide mycotoxin production in planta. Maggio-Hall, L.A., Wilson, R.A., Keller, N.P. Mol. Plant Microbe Interact. (2005) [Pubmed]
  4. Structure and function of fas-1A, a gene encoding a putative fatty acid synthetase directly involved in aflatoxin biosynthesis in Aspergillus parasiticus. Mahanti, N., Bhatnagar, D., Cary, J.W., Joubran, J., Linz, J.E. Appl. Environ. Microbiol. (1996) [Pubmed]
  5. Structural and functional analysis of the nor-1 gene involved in the biosynthesis of aflatoxins by Aspergillus parasiticus. Trail, F., Chang, P.K., Cary, J., Linz, J.E. Appl. Environ. Microbiol. (1994) [Pubmed]
  6. Molecular characterization of an Aspergillus parasiticus dehydrogenase gene, norA, located on the aflatoxin biosynthesis gene cluster. Cary, J.W., Wright, M., Bhatnagar, D., Lee, R., Chu, F.S. Appl. Environ. Microbiol. (1996) [Pubmed]
  7. Aflatoxins and anthraquinones from diploids of Aspergillus parasiticus. Bennett, J.W. J. Gen. Microbiol. (1979) [Pubmed]
  8. Enzymatic conversion of norsolorinic acid to averufin in aflatoxin biosynthesis. Yabe, K., Nakamura, Y., Nakajima, H., Ando, Y., Hamasaki, T. Appl. Environ. Microbiol. (1991) [Pubmed]
  9. Separation of mycotoxin-containing sources in grain dust and determination of their mycotoxin potential. Palmgren, M.S., Lee, L.S. Environ. Health Perspect. (1986) [Pubmed]
  10. Isolation of the Anthraquinone Norsolorinic acid from Cinchona ledgeriana1. Dorairaj, S., Banerjee, A.K., Achari, B., Pakrashi, S.C. Planta Med. (1988) [Pubmed]
  11. The affinity purification and characterization of a dehydrogenase from Aspergillus parasiticus involved in aflatoxin B1 biosynthesis. Chuturgoon, A.A., Dutton, M.F. Prep. Biochem. (1991) [Pubmed]
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