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Chemistry of Natural Compounds

, Volume 49, Issue 3, pp 503–504 | Cite as

Synthesis of tricrozarin b, a pigment of Tritonia crocosmaeflora

  • O. P. ShestakEmail author
  • V. F. Anufriev
Article

Tricrozarin B (1) was isolated from bulbs of Tritonia crocosmaeflora Lemoine (Iridaceae) [1]. It, lomazarin (2) [2, 3], and tricrozarin A [4] are rare examples of polymethoxynaphthazarins isolated from higher plants. Tricrozarin B exhibited cytotoxic activity in vitro against Hela-S3 cells and antitumor activity in vivo against murine sarcoma S-180 [1] and melanoma B-16 [5].

The preparative production of tricrozarin B is interesting for further research of its biological activity and for use as starting material in the synthesis of other natural products and their analogs because of its poor availability.

Long before it was observed in nature, trimethoxynaphthazarin 1 was known as a derivative of spinochrome D, a pigment of the sea urchins Pseudocentrotus depressus and Echinotrix calamaris [3, 6], that was prepared by its methylation using diazomethane [6, 7].

Tricrozarin B ( 1) was obtained earlier in three steps in overall yield ~10% using cycloacylation of dihydroxydimethoxybenzene 3...

Keywords

MeOH Dimethyl Ether Diazomethane Naphthoquinone Me2CO 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgment

The work was financed by the Russian Academy of Sciences (RAS Presidium Grant No. 12-I-P6-11 Molecular and Cellular Biology, a grant of the RAS FEB, SB, and UB No. 12-II-SU-05-006, and a grant of the FEB RAS No. 12-III-A-05-062).

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  1. 1.G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East BranchRussian Academy of SciencesVladivostokRussian Federation

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