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Chemical Compound Review

AC1LAS87     N-[[6-(2,3-dimethoxypropyl)- 4-hydroxy-5,5...

Synonyms: NSC114781
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Disease relevance of Pederin

  • However, we have recently identified an uncultured Pseudomonas sp. symbiont as the most likely producer of the defensive antitumor polyketide pederin in Paederus fuscipes beetles by cloning the putative biosynthesis genes [1].
  • On the basis of preliminary results described herein, we speculate that, despite their structural resemblance, psymberin and pederin/mycalamide induce toxicity through different mechanisms [2].
  • Short-term exposure of squamous carcinoma cells to 18-O-methyl mycalamide B or pederin caused an irreversible inhibition of cellular proliferation and induced cellular necrosis [3].
  • Crushing PF on the skin causes acute dermatitis within 24 hours, corresponding in shape and dimensions to the area affected by the substance released (pederin) [4].
  • The presence of some acantholytic foci, relatively far from the foci of clinically involved skin, in four of the cases considered suggests a possible role of pederin in inducing acantholysis indirectly [4].

High impact information on Pederin

  • The ped cluster, which is present only in beetle specimens with high pederin content, is located on a 54-kb region bordered by transposase pseudogenes and encodes a mixed modular polyketide synthase/nonribosomal peptide synthetase [5].
  • Evidence for a symbiosis island involved in horizontal acquisition of pederin biosynthetic capabilities by the bacterial symbiont of Paederus fuscipes beetles [6].
  • We have sequenced an extended region of the symbiont genome to gain further insight into the biology of this as-yet-unculturable bacterium and the evolution of pederin symbiosis [6].
  • However, a recent analysis of the putative pederin biosynthesis (ped) gene cluster strongly suggests that pederin is produced by bacterial symbionts [6].
  • It contains at least three novel catalytic domains that are predicted to be involved in pederin chain initiation and the formation of an unusual exomethylene bond [7].

Chemical compound and disease context of Pederin


Biological context of Pederin

  • Interestingly, competition studies demonstrated that 13-deoxytedanolide shared the binding site on the 60S large subunit with pederin and its marine-derived analogues [8].

Anatomical context of Pederin

  • The activities of 18-O-methyl mycalamide B and pederin were virtually indistinguishable when evaluated in DNA or protein synthesis assays, and in cytotoxicity assays using human carcinoma cell lines (IC50s 0.2-0.6 nM) [3].
  • Biosynthesis of the structurally complex hemolymph toxin pederin is an eminent character of Paederus females [9].


  1. Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei. Piel, J., Hui, D., Wen, G., Butzke, D., Platzer, M., Fusetani, N., Matsunaga, S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  2. Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products. Jiang, X., Williams, N., Brabander, J.K. Org. Lett. (2007) [Pubmed]
  3. The in vitro biological activities of synthetic 18-O-methyl mycalamide B, 10-epi-18-O-methyl mycalamide B and pederin. Richter, A., Kocienski, P., Raubo, P., Davies, D.E. Anticancer Drug Des. (1997) [Pubmed]
  4. Paederus fuscipes dermatitis. A histopathological study. Borroni, G., Brazzelli, V., Rosso, R., Pavan, M. The American Journal of dermatopathology. (1991) [Pubmed]
  5. A polyketide synthase-peptide synthetase gene cluster from an uncultured bacterial symbiont of Paederus beetles. Piel, J. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  6. Evidence for a symbiosis island involved in horizontal acquisition of pederin biosynthetic capabilities by the bacterial symbiont of Paederus fuscipes beetles. Piel, J., Höfer, I., Hui, D. J. Bacteriol. (2004) [Pubmed]
  7. Unprecedented diversity of catalytic domains in the first four modules of the putative pederin polyketide synthase. Piel, J., Wen, G., Platzer, M., Hui, D. Chembiochem (2004) [Pubmed]
  8. 13-Deoxytedanolide, a marine sponge-derived antitumor macrolide, binds to the 60S large ribosomal subunit. Nishimura, S., Matsunaga, S., Yoshida, M., Hirota, H., Yokoyama, S., Fusetani, N. Bioorg. Med. Chem. (2005) [Pubmed]
  9. Molecular identification of an endosymbiotic bacterium associated with pederin biosynthesis in Paederus sabaeus (Coleoptera: Staphylinidae). Kellner, R.L. Insect Biochem. Mol. Biol. (2002) [Pubmed]
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