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Chemical Compound Review

Retronecin     (1R,8S)-7-(hydroxymethyl)- 2,3,5,8...

Synonyms: RETRONECINE, Senecifolinene, SureCN673883, CCRIS 5776, AG-K-83825, ...
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Disease relevance of Senecifolinene


High impact information on Senecifolinene


Chemical compound and disease context of Senecifolinene


Biological context of Senecifolinene

  • Enzymic hydrolysis of retronecine di-isovalerate occurred primarily at the allylic 9-ester group [7].
  • Pupae contain ca. 45% of the labeled retronecine originally ingested, metabolized, and stored by larvae; ca. 12% of larval radioactivity could be recovered from the defensive secretions of adults sampled successively over two and a half months [8].
  • Esterification at C-9 v. C-7 can be distinguished for non-cyclic esters of retronecine in the positive ion spectra [9].

Anatomical context of Senecifolinene

  • A long-term feeding experiment lasting for almost four months revealed that retronecine esters synthesized from [14C]retronecine in the larvae are transferred from larvae via pupae into the exocrine glands of adult beetles [8].

Associations of Senecifolinene with other chemical compounds

  • Lactating rats dosed with these differently labelled pyrrolizidine alkaloids (PAs) excreted within 3 h approx. 0.08% of the applied radioactivity in the milk mainly as yet not identified water-soluble retronecine-derived metabolites and with approx. 0.02% as unchanged PAs [10].

Gene context of Senecifolinene

  • In contrast, a smaller amount of danaidone (5.7 to 7.0 microg/ male) was formed when males ingested retronecine or heliotrine, and those fed with an HCI salt of monocrotaline or retrorsine produced only traces of danaidone (<0.5 microg/male) [11].
  • Results from this study indicate that (i) DHP is a common reactive metabolite for retronecine-type of pyrrolizidine alkaloids, (ii) the formation of DHP-derived DNA adducts in the liver DNA of rats treated with monocrotaline suggests that monocrotaline-induced tumorigenicity is through a genotoxic mechanism [12].

Analytical, diagnostic and therapeutic context of Senecifolinene

  • A third retronecine-based ELISA detects 3 with an I50 of 3000 +/- 600 ppb (3 +/- 0.6 ppm) and detection limits of 600-10,000 ppb [13].
  • The simple necine base retronecine was not present at detectable levels in the perfusion medium [14].


  1. Semisynthetic pyrrolizidine alkaloid N-oxide antitumor agents. Esters of heliotridine. Zalkow, L.H., Glinski, J.A., Gelbaum, L.T., Moore, D., Melder, D., Powis, G. J. Med. Chem. (1988) [Pubmed]
  2. Induction of endogenous avian tumor virus gene expression by pyrrolizidine alkaloids. Pearson, M.N., Karchesy, J.J., Deeney, A.O., Deinzer, M.L., Beaudreau, G.S. Chem. Biol. Interact. (1984) [Pubmed]
  3. Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse, and hamster hepatocytes. Mori, H., Sugie, S., Yoshimi, N., Asada, Y., Furuya, T., Williams, G.M. Cancer Res. (1985) [Pubmed]
  4. Toxicokinetics of riddelliine, a carcinogenic pyrrolizidine alkaloid, and metabolites in rats and mice. Williams, L., Chou, M.W., Yan, J., Young, J.F., Chan, P.C., Doerge, D.R. Toxicol. Appl. Pharmacol. (2002) [Pubmed]
  5. Microsomal formation of a pyrrolic alcohol glutathione conjugate of clivorine. Firm evidence for the formation of a pyrrolic metabolite of an otonecine-type pyrrolizidine alkaloid. Lin, G., Cui, Y.Y., Hawes, E.M. Drug Metab. Dispos. (1998) [Pubmed]
  6. Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): Their origins and male behavioral responses to pyrrolizidine alkaloids. Honda, Y., Honda, K., Omura, H. J. Insect Physiol. (2006) [Pubmed]
  7. Hydrolysis and hepatotoxicity of retronecine diesters. Mattocks, A.R. Toxicol. Lett. (1982) [Pubmed]
  8. Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults. Pasteels, J.M., Theuring, C., Witte, L., Hartmann, T. J. Chem. Ecol. (2003) [Pubmed]
  9. Positive and electron capture negative ion methane chemical ionization mass spectrometry of pyrrolizidine alkaloids. Karchesy, J., Deinzer, M., Griffin, D., Rohrer, D.C. Biomed. Mass Spectrom. (1984) [Pubmed]
  10. Transfer of [3H]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues. Lüthy, J., Heim, T., Schlatter, C. Toxicol. Lett. (1983) [Pubmed]
  11. Differential utilization of pyrrolizidine alkaloids by males of a danaid butterfly, Parantica sita, for the production of danaidone in the alar scent organ. Honda, K., Honda, Y., Yamamoto, S., Omura, H. J. Chem. Ecol. (2005) [Pubmed]
  12. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, monocrotaline, leading to DNA adduct formation in vivo. Wang, Y.P., Yan, J., Beger, R.D., Fu, P.P., Chou, M.W. Cancer Lett. (2005) [Pubmed]
  13. Enzyme-linked immunosorbent assay detection of pyrrolizidine alkaloids: immunogens based on quaternary pyrrolizidinium salts. Roseman, D.M., Wu, X., Kurth, M.J. Bioconjug. Chem. (1996) [Pubmed]
  14. Metabolism of [14C]monocrotaline by isolated perfused rat liver. Lamé, M.W., Jones, A.D., Morin, D., Segall, H.J. Drug Metab. Dispos. (1991) [Pubmed]
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