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Chemical Compound Review

Heliotron     (7-hydroxy-5,6,7,8- tetrahydro-3H...

Synonyms: HELIOTRINE, AGN-PC-00HNKB, SureCN893305, CCRIS 9196, AG-J-79454, ...
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Disease relevance of AI3-51769

  • A dose of 40 mg DHH/kg approximated 200 mg heliotrine/kg in its effects on embryos, the principal abnormalities being skeletal, including retarded ossification, distorted ribs and long bones, cleft palate and feet defects [1].
  • E. coli WP2 and its repair-deficient derivatives were treated with the pyrrolizidine alkaloids, heliotrine and monocrotaline in the presence of a liver microsomal fraction [2].
  • The importance of monitoring indicators of toxicity was highlighted by changes in erythrocyte population composition and the presence of basophilic stippling following exposure to LD50 heliotrine [3].

Psychiatry related information on AI3-51769

  • The induction of MN was significantly higher in foetal than adult cells for 0.75 LD50 monocrotaline and benzidine after 21 h (p < 0.0005), and for one LD50 heliotrine at 12, 24 and 30 h after injection in a time-response study (p < 0.02) [3].

High impact information on AI3-51769

  • Inward turbulent particle transport observed in the rf heated plasma of the H-1 toroidal heliac is reproduced in the CHS heliotron/torsatron by generating a region of positive radial electric field shear (E'(r)>0) using electron cyclotron resonance heating of the plasma edge [4].
  • Induction of MN following LD50 heliotrine showed peak MN expression in PCE at 18 h after injection for adult bone marrow (2.6%) and at 24 h for foetal liver (7.9%) [3].
  • It was also shown for heliotrine that co-cultivation with chick embryo hepatocytes resulted in a much higher response than addition of activated rat-liver homogenate to the test medium [5].
  • Since VL was suspected to be derived from pyrrolizidine alkaloids (PAs) acquired as an adult, tests for feeding response to and oral administration of four PAs (a 4:1 mixture of intermedine/lycopsamine, heliotrine, monocrotaline, and retronecine) were conducted [6].
  • Senkirkine, heliotrine, and retrorsine did not stimulate oviposition [7].

Biological context of AI3-51769


Anatomical context of AI3-51769

  • Heliotrine resulted in the largest increases in mean value of micronucleated PCE, of 5.4% in adult bone marrow and 6.9% in foetal liver compared to control values of 0.7% and 0.9% for adult and foetal tissue respectively (p < 0.005) [3].
  • Preparations of cotton phosphatidylcholine (PC), both purified and as ATP-containing complexes (PC+ATP), as well as ATP alone, reduced the metabolic disorders in liver mitochondria of rats with acute heliotrine-induced hepatitis [8].

Associations of AI3-51769 with other chemical compounds


Analytical, diagnostic and therapeutic context of AI3-51769

  • Specifically deuteriated samples of heliotrine and epiheliotrine were prepared and fed to C. transiens larvae, and the steps in the biosynthetic process were monitored by gas chromatography/mass spectrometry [9].


  1. Comparison of the toxic effects of dehydroheliotridine and heliotrine in pregnant rats and their embryos. Peterson, J.E., Jago, M.V. J. Pathol. (1980) [Pubmed]
  2. Use of repair-deficient strains of Escherichia coli and liver microsomes to detect and characterise DNA damage caused by pyrrolizidine alkaloids heliotrine and monocrotaline. Green, M.H., Muriel, W.J. Mutat. Res. (1975) [Pubmed]
  3. Micronuclei in adult and foetal mice exposed in vivo to heliotrine, urethane, monocrotaline and benzidine. Sanderson, B.J., Clark, A.M. Mutat. Res. (1993) [Pubmed]
  4. Inward turbulent transport produced by positively sheared radial electric field in stellarators. Shats, M.G., Toi, K., Ohkuni, K., Yoshimura, Y., Osakabe, M., Matsunaga, G., Isobe, M., Nishimura, S., Okamura, S., Matsuoka, K. Phys. Rev. Lett. (2000) [Pubmed]
  5. Induction of SCEs by some pyrrolizidine alkaloids in V79 Chinese hamster cells co-cultured with chick embryo hepatocytes. Bruggeman, I.M., van der Hoeven, J.C. Mutat. Res. (1985) [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. Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae. Macel, M., Vrieling, K. J. Chem. Ecol. (2003) [Pubmed]
  8. Disturbances in oxidative phosphorylation in the liver of rats with heliotrine-induced hepatitis and restoration by phosphatidylcholine and ATP. Gizatullina, Z.Z., Fesenko, L.M., Dombrovskaya, N.V., Mokhova, E.N., Aripov, A.N., Gagel'gans, A.I., Atabekov, A.G. Biomed. Sci. (1991) [Pubmed]
  9. Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae). Schulz, S., Francke, W., Boppré, M., Eisner, T., Meinwald, J. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
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