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Four new chamigrane sesquiterpenoids from the opistobranch mollusk Aplysia dactylomela

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Abstract

Four new chamigrane sesquiterpenoids, (6S,10S)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5.5]undec-2-ene-4-one, (4S,6S,10S)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5.5]undec-2-ene-4-ol, (3R,4S,6S,10R)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5.5]undecane-3,4-diol, and (6S,7S,11R)-2-chloro-3,7,11-trimethyl-10-methylidenespiro[5.5]undec-2-ene-7-ol, were isolated from the sea hare Aplysia dactylomela. The chemical structures of new compounds were established by NMR spectroscopy and mass spectrometry. The cytotoxic activity of some of the obtained compounds against promyelocytic HL-60 and monocytic THP-1 leukemia cells was demonstrated.

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References

  1. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, and M. R. Prinsep, Nat. Prod. Rep., 2006, 23, 26.

    Article  CAS  Google Scholar 

  2. C. S. Vairappan, M. Suzuki, T. Abe, and M. Masuda, Phytochemistry, 2001, 3, 517.

    Article  Google Scholar 

  3. K. Kurata, K. Taniguchi, Y. Agatsuma, and M. Suzuki, Phytochemistry, 1998, 47, 363

    Article  CAS  Google Scholar 

  4. K. Watanabe, K. Umeda, and M. Miyakado, Agric. Biol. Chem., 1989, 53, 2513.

    CAS  Google Scholar 

  5. S. J. Rochfort and R. J. Capon, Aust. J. Chem., 1996, 49, 19.

    CAS  Google Scholar 

  6. S. N. Fedorov, M. V. Reshetnyak, A. P. Shchedrin, S. G. Il’in, Yu. T. Struchkov, V. A. Stonik, and G. B. Elyakov, Dokl. Akad. Nauk SSSR, 1989, 305, 877 [Dokl. Chem., Int. Ed., 1989].

    CAS  Google Scholar 

  7. S. N. Fedorov, L. K. Shubina, A. I. Kalinovsky, E. G. Lyakhova, and V. A. Stonik, Tetrahedron Lett., 2000, 41, 1979.

    Article  CAS  Google Scholar 

  8. S. N. Fedorov, O. S. Radchenko, L. K. Shubina, A. I. Kalinovsky, A. V. Gerasimenko, D. Y. Popov, and V. A. Stonik, J. Am. Chem. Soc., 2001, 123, 504.

    Article  CAS  Google Scholar 

  9. E. G. Lyakhova, S. N. Fedorov, L. K. Shubina, O. S. Radchenko, A. I. Kalinovskii, P. S. Dmitrenok, and V. A. Stonik, Izv. Akad. Nauk. Ser. Khim., 2003, 970 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1022].

    Google Scholar 

  10. G. B. Elyakov and V. A. Stonik, Terpenoidy morskikh organizmov [Terpenoids from Sea Organisms], Nauka, Moscow, 1986, 272 pp. (in Russian).

    Google Scholar 

  11. J. A. Baltrop, T. C. Owen, A. H. Cory, and J. G. Cory, Bioorg. Med. Chem. Lett., 1991, 1, 611.

    Article  Google Scholar 

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Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 prosp. 100-let Vladivostoku, 690022, Vladivostok, Russian Federation

    L. K. Shubina, S. N. Fedorov, A. I. Kalinovskiy, A. S. Dmitrenok & V. A. Stonika

  2. Medical Research Center for Cancer Molecular Therapy, Dong-A University, 3-1, Dongdaesin-Dong, Seo-Gu, Busan, 602-714, Republic of Korea

    J. O. Jin, M. G. Song & J. Y. Kwak

Authors
  1. L. K. Shubina
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  2. S. N. Fedorov
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  3. A. I. Kalinovskiy
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  4. A. S. Dmitrenok
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  5. J. O. Jin
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  6. M. G. Song
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  7. J. Y. Kwak
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  8. V. A. Stonika
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Corresponding author

Correspondence to L. K. Shubina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2037–2042, October, 2007.

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Shubina, L.K., Fedorov, S.N., Kalinovskiy, A.I. et al. Four new chamigrane sesquiterpenoids from the opistobranch mollusk Aplysia dactylomela . Russ Chem Bull 56, 2109–2114 (2007). https://doi.org/10.1007/s11172-007-0329-0

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  • DOI: https://doi.org/10.1007/s11172-007-0329-0

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