Chemistry of Natural Compounds

, Volume 44, Issue 6, pp 719–723 | Cite as

Synthesis of lomazarin and norlomazarin, pigments from Lomandra hastilis

  • D. N. PelageevEmail author
  • M. N. Panchenko
  • N. D. Pokhilo
  • V. A. Denisenko
  • V. F. Anufriev

5,8-Dihydroxy-2,3,6-trimethoxy-7-ethyl-1,4-naphthoquinone (1) was used to synthesize in high yield 5,8-dihydroxy-7(1′-hydroxyethyl)-2,3,6-trimethoxy-1,4-naphthoquinone (lomazarin, 3), a pigment from Lomandra hastilis. Alkaline hydrolysis of lomazarin produced mainly 5,6,8-trihydroxy-2,3-dimethoxy-1,4-naphthoquinone (9) through a retro-aldol decomposition of the 6-keto-form of 5,6,8-trihydroxy-7(1′-hydroxyethyl)-2,3-dimethoxy-1,4-naphthoquinone (13b) formed during the reaction. 2,5,8-Trihydroxy-7(1′-hydroxyethyl)-3,6-dimethoxy-1,4-naphthoquinone (norlomazarin, 4a), a pigment of L. hastilis, and its 3,5,8-trihydroxy-7(1′-hydroxyethyl)-2,6-dimethoxy isomer 4b were formed as a difficultly separable mixture in addition to quinone 9.

Key words

echinochrome trimethyl ether lomazarin norlomazarin Lomandra hastilis retro-aldol reaction spinochrome D dimethyl ether Echinotrix calamaris tricrozarin B Tritonia crocosmaeflora 



The work was financially supported partially by a grant of the RAS Presidium (Molecular and Cellular Biology Program), the interdisciplinary integrated project of the Far-East and Siberian Branches of the RAS (No. 07-II-CO-05-020), a grant of the RFBR No. 06-04-96974, and State Contract No. 02.522.11.2013.


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Copyright information

© Springer Science+Business Media, Inc. 2008

Authors and Affiliations

  • D. N. Pelageev
    • 1
    Email author
  • M. N. Panchenko
    • 2
  • N. D. Pokhilo
    • 1
  • V. A. Denisenko
    • 1
  • V. F. Anufriev
    • 1
  1. 1.Pacific Institute of Bioorganic Chemistry, Far-East BranchRussian Academy of Sciences, Russian Federation100-Letiya VladivostokaRussia
  2. 2.Institute of Chemistry and Applied EcologyFar-East State University, Russian Federationul. Oktyabr’skayaRussia

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