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Chemical Compound Review

Precocene 2     6,7-dimethoxy-2,2-dimethyl- chromene

Synonyms: Precocen 2, PRICOCENE II, Precocene II, Preconene II, Prococene II, ...
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Disease relevance of C09018


High impact information on C09018

  • Precocene II inhibits juvenile hormone biosynthesis by cockroach corpora allata in vitro [4].
  • In contrast, induction of a precocious adult molt by application of precocene II to third-stage nymphs caused a loss of br mRNA at the precocious adult molt [5].
  • Hybridization analysis of fat body JHBP mRNA in locusts that had been treated with precocene and a JH analog did not give clear evidence for regulation by JH [6].
  • In locusts deprived of JH with precocene, production of 21K protein and of lambda 21-hybridizing transcripts is induced by the JH analog, methoprene, in parallel with Vg and its mRNA [7].
  • Hepatotoxicity of precocene I in rats. Role of metabolic activation in vivo [8].

Chemical compound and disease context of C09018

  • The toxicities of coumarin, precocene I and precocene II to 24 hr hepatocyte cultures, determined as decreased survival, were also shown to be increased in serum-free medium [1].
  • In contrast, pretreatment of rats with DL-buthionine-SR-sulfoximine (BSO), an inhibitor of glutathione synthesis, potentiated the toxicity of an otherwise non-toxic dose of precocene II (100 mg/kg) [9].
  • In 24-h cultures from isoniazid-treated rats diethyldithiocarbamate inhibited high affinity MCOD activity by 55% and there was also a small but significant inhibition of precocene II toxicity [10].

Biological context of C09018


Anatomical context of C09018

  • Although phenobarbital treatment of rats increased the rate of liver microsomal metabolism of precocene I by approximately 50% (nmol products/nmol cytochrome P-450/min) compared to liver microsomes from control rats, hepatic damage caused by precocene I was not significantly affected [14].
  • To explore this, nutritive tube turnover has been investigated following the experimental inhibition of oocyte maturation both by the prevention of mating, and also the topical application of precocene II [15].
  • Effect of precocene on development of ovarian follicles in flesh fly, Sarcophaga ruficornis F [16].
  • Therefore, in addition to depletion of glutathione, precocene II appears to damage mitochondria and plasma membrane functions and can do so by more than one pathway [17].
  • Precocene treatment resulted into suppression of development of egg chamber, differentiation of follicular epithelium, degeneration of nurse cells, growth of oocyte and uptake of yolk granules by oocytes [16].

Associations of C09018 with other chemical compounds


Gene context of C09018

  • Antigonadotropic activities of Precocene 1 (P1), Precocene 2 (P2) and Ethoxyprecocene 2 (EP2) on the seed bug Oxycarenus lavaterae (F.) (Heteroptera, Lygaeidae), are reported [23].
  • Treatment of rats with a single i.p. dose of precocene I (300 mg/kg) resulted in extensive hepatic damage as evidenced by a marked increase of plasma glutamic pyruvic transaminase levels and histologic observation in liver sections of severe centrolobular necrosis [14].

Analytical, diagnostic and therapeutic context of C09018


  1. Effect of serum-free medium on cytochrome P450-dependent metabolism and toxicity in rat cultured hepatocytes. Hammond, A.H., Fry, J.R. Biochem. Pharmacol. (1992) [Pubmed]
  2. Microbial transformation of precocene II: oxidative reactions by Streptomyces griseus. Sariaslani, F.S., McGee, L.R., Ovenall, D.W. Appl. Environ. Microbiol. (1987) [Pubmed]
  3. Genotoxicity of the anti-juvenile hormone agent precocene II as revealed by the Drosophila wing spot test. Socha, R., Marec, F. Mutagenesis (1989) [Pubmed]
  4. Precocene II inhibits juvenile hormone biosynthesis by cockroach corpora allata in vitro. Pratt, G.E., Bowers, W.S. Nature (1977) [Pubmed]
  5. The pupal specifier broad directs progressive morphogenesis in a direct-developing insect. Erezyilmaz, D.F., Riddiford, L.M., Truman, J.W. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  6. Sequence of the hexameric juvenile hormone-binding protein from the hemolymph of Locusta migratoria. Braun, R.P., Wyatt, G.R. J. Biol. Chem. (1996) [Pubmed]
  7. Properties and sequence of a female-specific, juvenile hormone-induced protein from locust hemolymph. Zhang, J., McCracken, A., Wyatt, G.R. J. Biol. Chem. (1993) [Pubmed]
  8. Hepatotoxicity of precocene I in rats. Role of metabolic activation in vivo. Ravindranath, V., Boyd, M.R., Jerina, D.M. Biochem. Pharmacol. (1987) [Pubmed]
  9. Alteration of precocene II-induced hepatotoxicity by modulation of hepatic glutathione levels. Duddy, S.K., Hsia, M.T. Chem. Biol. Interact. (1989) [Pubmed]
  10. Involvement of cytochrome P4502E1 in the toxicity of dichloropropanol to rat hepatocyte cultures. Hammond, A.H., Fry, J.R. Toxicology (1997) [Pubmed]
  11. The effects of precocene II on reproduction and development of triatomine bugs (Reduviidae: Triatominae). Tarrant, C., Cupp, E.W., Bowers, W.S. Am. J. Trop. Med. Hyg. (1982) [Pubmed]
  12. Precocene-induced effects and possible role of juvenile hormone during embryogenesis of the milkweed bug Oncopeltus fasciatus. Dorn, A. Gen. Comp. Endocrinol. (1982) [Pubmed]
  13. Induction of DNA damage and repair synthesis in freshly isolated rat hepatocytes by the proallatocidin precocene II. Hsia, M.T., Kreamer, B.L., Duddy, S.K. Cancer Lett. (1985) [Pubmed]
  14. Metabolism and hepatotoxicity of the naturally occurring benzo[b]pyran precocene I. Halpin, R.A., Vyas, K.P., El-Naggar, S.F., Jerina, D.M. Chem. Biol. Interact. (1984) [Pubmed]
  15. Perturbed turnover of microtubule-based nutritive tubes in ovarioles of virgin and precocene-treated Dysdercus fasciatus. Stebbings, H. Arch. Insect Biochem. Physiol. (2002) [Pubmed]
  16. Effect of precocene on development of ovarian follicles in flesh fly, Sarcophaga ruficornis F. Kumar, K., Khan, I.A. Indian J. Exp. Biol. (2004) [Pubmed]
  17. Mechanism of toxicity of precocene II in rat hepatocyte cultures. Hammond, A.H., Garle, M.J., Fry, J.R. J. Biochem. Toxicol. (1995) [Pubmed]
  18. Maturation of muscle properties and its hormonal control in an adult insect. Rose, U., Ferber, M., Hustert, R. J. Exp. Biol. (2001) [Pubmed]
  19. Structural requirements for the direct and cytochrome P450-dependent reaction of cyclic alpha,beta-unsaturated carbonyl compounds with glutathione: a study with coumarin and related compounds. Fry, J.R., Fentem, J.H., Salim, A., Tang, S.P., Garle, M.J., Whiting, D.A. J. Pharm. Pharmacol. (1993) [Pubmed]
  20. An ion exchange liquid chromatography/mass spectrometry method for the determination of reduced and oxidized glutathione and glutathione conjugates in hepatocytes. Loughlin, A.F., Skiles, G.L., Alberts, D.W., Schaefer, W.H. Journal of pharmaceutical and biomedical analysis. (2001) [Pubmed]
  21. Effects of insect growth regulators on the nontarget soil arthropod Folsomia candida (Collembola). Campiche, S., Becker-van Slooten, K., Ridreau, C., Tarradellas, J. Ecotoxicol. Environ. Saf. (2006) [Pubmed]
  22. Analysis of precocenes in the essential oil of Ageratum spp. by reverse-phase high-performance liquid chromatography. Sharma, K., Sharma, O.P. Phytochemical analysis : PCA. (2001) [Pubmed]
  23. Effects of precocenes on ovarian development of the seed bug, Oxycarenus lavaterae (F.). Baldellou, M.I., Bellés, X. Rev. Esp. Fisiol. (1986) [Pubmed]
  24. The effects of precocene treatment on egg wax production in Gené's organ and egg viability in the cattle tick Boophilus microplus (Acarina Ixodidae): an ultrastructural study. Booth, T.F., Beadle, D.J., Hart, R.J. Exp. Appl. Acarol. (1986) [Pubmed]
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