Skip to main content
Log in

Spinazarin and ethylspinazarin, pigments of the sea urchin Scaphechinus mirabilis

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

2,3,5,8-Tetrahydroxy-1,4-naphthoquinone (spinazarin) and 6-ethyl-2,3,5,8-tetrahydroxy-1,4-naphthoquinone (ethylspinazarin) were first isolated from the sea urchin Scaphechinus mirabilis. The structures of spinazarins were established based on analysis of spectroscopic data. A preparative synthetic route to ethylspinazarin was proposed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R. H. Thomson, Naturally Occurring Quinones; 2nd ed., Academic Press, London-New York, 1971; 3rd ed., Chapman and Hall, London-New York, 1987; 4th ed., Blackie Academic and Professional, London-New York, 1997.

    Google Scholar 

  2. (a) M. Service and A. C. Wardlaw, Comp. Biochem. Physiol., 1984, 79, 161; (b) Pat. GBR 2159056; Chem. Abstrs, 1986, 104, 83795; (c) V. Ph. Anufriev, V. L. Novikov, O. B. Maximov, G. B. Elyakov, D. O. Levitsky, A. V. Lebedev, S. M. Sadretdinov, A. V. Shvilkin, N. I. Afonskaya, M. Ya. Ruda, and N. M. Cherpachenko, Bioorg. Med. Chem. Lett., 1998, 8, 587.

  3. (a) RF Pat. No. 2137472; Byul. Izobret., 1999, 26, 132, 284239b; (b) RF Pat. No. 2134107; Byul. Izobret., 1999}, 22 (in Russian)

  4. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, and M. R. Prinsep, Nat. Prod. Rep., 2004, 21, 1.

    Article  CAS  Google Scholar 

  5. N. P. Mischenko, S. A. Fedoreyev, N. D. Pokhilo, V. Ph. Anufriev, V. A. Denisenko, and V. P Glazunov, J. Nat. Prod., 2005, 68, 1390.

    Article  CAS  Google Scholar 

  6. (a) R. Huot and P. Brassard, Can. J. Chem., 1974, 54, 838; (b) V. Ph. Anufriev and V. L. Novikov, Tetrahedron Lett., 1995, 36, 2515.

  7. R. E. Moore, H. Singh, and P. J. Scheuer, J. Org. Chem., 1966, 31, 3645.

    Article  CAS  Google Scholar 

  8. V. P. Glazunov, A. Ya. Chizhova, M. I. Shuvalova, and V. F. Anufriev, Izv. Akad. Nauk. Ser. Khim., 2001, 91 [Russ. Chem. Bull., Int. Ed., 2001, 50, 88].

    Google Scholar 

  9. B. F. Anufriev, S. G. Polonik, N. D. Pokhilo, and N. N. Balaneva, Izv. Akad. Nauk. Ser. Khim., 2003, 2128 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2247]; (b) RF Pat. 2193550; Byul. Izobret., 2002, 33 (in Russian).

  10. L. F. Fieser, M. Fieser, Reagents for Organic Synthesis, J. Wiley and Sons, New York-London-Sydney, 1968.

    Google Scholar 

  11. G. V. Malinovskaya, A. Ya. Chizhova, and V. F. Anufriev, Izv. Akad. Nauk. Ser. Khim., 1999, 1019 [Russ. Chem. Bull., 1999, 48, 1010 (Engl. Transl.)].

    Google Scholar 

  12. N. P. Mishchenko, S. A. Fedoreev, V. P. Glazunov, V. A. Denisenko, N. P. Krasovskaya, L. I. Glebko, L. G. Maslov, P. S. Dmitrenok, and V. P. Bagirova, Khim. Farm. Zhurn., 2004, 38, 50 [Pharm. Chem. J., 2004, 38 (Engl. Transl.)].

    CAS  Google Scholar 

  13. Yu. V Karyakin and I. I. Angelov, Chistye khimicheskie veshchestva [Pure Chemicals], Khimiya, Moscow, 1974, p. 398 (in Russian).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. F. Anufriev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 788–791, April, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yakubovskaya, A.Y., Pokhilo, N.D., Mishchenko, N.P. et al. Spinazarin and ethylspinazarin, pigments of the sea urchin Scaphechinus mirabilis . Russ Chem Bull 56, 819–822 (2007). https://doi.org/10.1007/s11172-007-0122-0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0122-0

Key words

Navigation