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Chemical Compound Review

AC1NURXG     (4Z)-4-[(2-carboxy-6-hydroxy- phenyl)...

Synonyms: 63590-19-2
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Disease relevance of Ophiocordin

  • Our data demonstrate that balanol is a potent inhibitor of PKA and PKC in several whole-cell systems and causes no obvious toxicity [1].

High impact information on Ophiocordin

  • We tested the capacity of balanol to inhibit representative serine- and threonine-specific protein kinases from the protein kinase subfamily that shares a common conserved catalytic core with cyclic AMP-dependent protein kinase [2].
  • In addition, balanol congeners inhibit PKA and PKC with the specificity and potency predicted by in vitro experiments [1].
  • In neonatal rat myocytes and cultured A431 cells transiently transfected with a cyclic AMP response element-luciferase reporter construct, balanol inhibits the induction of luciferase activity by isoproterenol, indicating inhibition of PKA [1].
  • We have characterized the effects of balanol and 10"-deoxybalanol in intact cells to determine whether these compounds cross the cell membrane and whether the potency and specificity noted in vitro are preserved in vivo [1].
  • The progress of PKC inhibitors currently in clinical development, including LY333531, ISIS 3521 (CGP 64128A), bryostatin 1, GF109203x, Ro 32-0432 and Ro 31-8220, Go 6976 and Go 7611, CPR 1006, and balanol (SPC 100840) are discussed [3].

Biological context of Ophiocordin

  • Although balanol discriminates rather poorly between PKC and PKA, only minor modifications to its molecular structure are required to furnish compounds that are highly specific inhibitors of PKA [4].
  • The balanol analogues serve to test the model and to highlight differences in the active site local environment of PKA and PKC [5].

Associations of Ophiocordin with other chemical compounds

  • An unknown antibiotic, ophiocordin, C21H22N2O8, MW: 430, was isolated from submerged cultures of Cordyceps ophioglossoides, strain TU 276, grown in a glycerol soybean meal medium at 27 degrees C. The antibiotic was extracted from acidified culture fluids with n-butanol and purified by subsequent column chromatography on DEAE-Sephadex and cellulose [6].

Gene context of Ophiocordin

  • To elucidate balanol's specific inhibitory effects and provide a basis for understanding inhibition-regulated biological processes, a 2.1 A resolution crystal structure of balanol in complex with cAMP-dependent protein kinase (cAPK) was determined [7].
  • The Lance assay was further validated with a diverse panel of literature inhibitors, in which the PKC inhibitors staurosporine, Ro-318220, and the PKA inhibitor Balanol potently inhibited S6K [8].
  • Recently, we reported the isolation of the potent protein kinase C inhibitor balanol (1) from the fungus Verticillium balanoides [9].
  • A series of racemic balanol analogues with modification of the benzamido moiety of balanol have been synthesized and evaluated for their inhibitory activities against human protein kinase C isozymes (PKC-alpha, -beta I, -beta II, -gamma, -delta, -epsilon, and -eta) [10].


  1. Differential and selective inhibition of protein kinase A and protein kinase C in intact cells by balanol congeners. Gustafsson, A.B., Brunton, L.L. Mol. Pharmacol. (1999) [Pubmed]
  2. Inhibition of protein kinases by balanol: specificity within the serine/threonine protein kinase subfamily. Setyawan, J., Koide, K., Diller, T.C., Bunnage, M.E., Taylor, S.S., Nicolaou, K.C., Brunton, L.L. Mol. Pharmacol. (1999) [Pubmed]
  3. Protein kinase C in the treatment of disease: signal transduction pathways, inhibitors, and agents in development. Goekjian, P.G., Jirousek, M.R. Current medicinal chemistry. (1999) [Pubmed]
  4. Molecular design and biological activity of potent and selective protein kinase inhibitors related to balanol. Koide, K., Bunnage, M.E., Gomez Paloma, L., Kanter, J.R., Taylor, S.S., Brunton, L.L., Nicolaou, K.C. Chem. Biol. (1995) [Pubmed]
  5. Balanol analogues probe specificity determinants and the conformational malleability of the cyclic 3',5'-adenosine monophosphate-dependent protein kinase catalytic subunit. Akamine, P., Madhusudan, n.u.l.l., Brunton, L.L., Ou, H.D., Canaves, J.M., Xuong, N.H., Taylor, S.S. Biochemistry (2004) [Pubmed]
  6. Ophiocordin, an antifungal antibiotic of Cordyceps ophioglossoides. Kneifel, H., König, W.A., Loeffler, W., Müller, R. Arch. Microbiol. (1977) [Pubmed]
  7. Crystal structure of the potent natural product inhibitor balanol in complex with the catalytic subunit of cAMP-dependent protein kinase. Narayana, N., Diller, T.C., Koide, K., Bunnage, M.E., Nicolaou, K.C., Brunton, L.L., Xuong, N.H., Ten Eyck, L.F., Taylor, S.S. Biochemistry (1999) [Pubmed]
  8. Identification and characterization of a constitutively T-loop phosphorylated and active recombinant S6K1: expression, purification, and enzymatic studies in a high capacity non-radioactive TR-FRET Lance assay. Zhang, W.G., Shor, B., Yu, K. Protein Expr. Purif. (2006) [Pubmed]
  9. Comparison of balanol from Verticillium balanoides and ophiocordin from Cordyceps ophioglossoides. Boros, C., Hamilton, S.M., Katz, B., Kulanthaivel, P. J. Antibiot. (1994) [Pubmed]
  10. Synthesis and protein kinase C inhibitory activities of balanol analogues with modification of 4-hydroxybenzamido moiety. Hu, H., Mendoza, J.S., Lowden, C.T., Ballas, L.M., Janzen, W.P. Bioorg. Med. Chem. (1997) [Pubmed]
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