Skip to main content
Log in

Polyphenolic components of knotwood extracts from Abies sibirica

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

An extract from the knotwood of Abies sibirica (Siberian fir) was studied by HPLC, NMR spectroscopy, and mass spectrometry with the goal to identify new sources of phytoestrogens, which are promising medicinal agents, and to obtain new representatives of natural compounds of the indicated group. The following compounds were found in the extract and identified: 2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-4-[1-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran (1), 5′-(7-hydroxymatairesinyl)-5″-(7‴-hydroxymatairesinol) (2), 2,3-bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diol (3, (−)-secoisolariciresinol), and 3-(4-hydroxy-3-methoxybenzyl)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)dihydro-furan-2(3H)-one (4). Compound 2 was previously unknown.

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. J. D. Ford, L. B. Davin, N. G. Lewis, in Plant Polyphenols 2: Chemistry, Biology, Pharmacology, Ecology, Eds G. G. Gross, R. W. Hemingway, T. Yoshida, Kluwer Academic/Plenum Publishers, New York, 1999, 675 pp.

  2. R. Kumar, D. E. Tsvetkov, V. Varshney, N. E. Nifantiev, Ind. Crops Prod., 2020, 145, 112077; DOI: https://doi.org/10.1016/j.indcrop.2019.112077.

    Article  CAS  Google Scholar 

  3. D. V. Yashunsky, V. M. Menshov, D. E. Tsvetkov, Yu. E. Tsvetkov, A. A. Belko, G. G. Vasiyarov, E. V. Titova, A. V. Pimenov, A. A. Onuchin, V. A. Dokichev, Yu. V. Tomilov, N. E. Nifantiev, Russ. Chem. Bull., 2014, 63, 2571; DOI: https://doi.org/10.1007/s11172-014-0780-7.

    Article  CAS  Google Scholar 

  4. D. E. Tsvetkov, R. Kumar, R. Devrani, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, A. Ya. Yashin, Ya. I. Yashin, V. K. Varshney, N. E. Nifantiev, Russ. Chem. Bull., 2019, 68, 2298; DOI: https://doi.org/10.1007/s11172-019-2703-0.

    Article  CAS  Google Scholar 

  5. N. E. Nifantiev, D. V. Yashunsky, V. M. Menshov, Yu. E. Tsvetkov, D. E. Tsvetkov, Sposob vydeleniya sekoizolaritsirezinola i digidrokvertsetina iz drevesiny [Method of Isolation of Secoisolariciresinol and Dihydroquercetin From Wood], RF Patent 2 359 666, published: 27.06.2009, Byul. izobret. [Invention Bull.], 2009, 18 (in Russian).

  6. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, V. M. Menshov, D. V. Yashunsky, A. Ya. Yashin, Ya. I. Yashin, R. Kumar, V. K. Varshney, N. E. Nifantiev, J. Biol. Act. Prod. Nat., 2016, 6, 272; DOI: https://doi.org/10.1080/22311866.2016.1253502.

    CAS  Google Scholar 

  7. D. E. Tsvetkov, R. Kumar, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, A. Ya. Yashin, Ya. I. Yashin, V. K. Varshney, N. E. Nifantiev, Russ. Chem. Bull., 2019, 68, 1756; DOI: https://doi.org/10.1007/s11172-019-2621-1.

    Article  CAS  Google Scholar 

  8. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, R. Kumar, V. K. Varshney, N. E. Nifantiev, Russ. J. Bioorg. Chem., 2021, 47, 103; DOI: https://doi.org/10.1134/S1068162021010271.

    Article  Google Scholar 

  9. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, N. E. Nifantiev, Russ. Chem. Bull., 2019, 69, 2390; DOI: https://doi.org/10.1007/s11172-020-3050-x.

    Article  Google Scholar 

  10. M. V. Kiselevskii, O. S. Zhukova, L. V. Fetisova, A. V. Trishin, N. Yu. Anisimova, A. E. Shcherbakov, D. V. Yashunskii, D. E. Tsvetkov, V. M. Men’shov, N. E. Nifant’ev, Bull. Exp. Biol. Med. (Engl. Transl.), 2010, 149, 511; DOI: https://doi.org/10.1007/s10517-010-0981-5.

    Article  Google Scholar 

  11. G. Loers, D. V. Yashunsky, N. E. Nifantiev, M. Schachner, J. Nat. Prod., 2014, 77, 1554.

    Article  CAS  Google Scholar 

  12. S. Ya. Sokolov, O. A. Svyazeva, V. A. Kubli, Arealy derev’ev i kustarnikov SSSR [Areas of USSR Trees and Bushes], vol. 1, Nauka, Leningrad, 1977, p. 11 (in Russian).

    Google Scholar 

  13. G. V. Krylov, I. I. Maradudin, N. I. Mikheev, N. F. Kozakova, Pikhta [Silver Fir], Agropromizdat, Moscow, 1986, p. 26 (in Russian).

    Google Scholar 

  14. I. A. Gubanov, I. L. Krylova, V. L. Tikhonova, Dikorastushchie poleznye rasteniya SSSR [Useful Wild Plants of the USSR], Ed. T. A. Rabotnov, Mysl’, Moscow, 1976, p. 34 (in Russian).

  15. A. A. Efremov, I. D. Zykova, V. A. Senashova, I. D. Grodnitskaya, N. V. Pashenova, Khimiya rastitel’nogo syr’ya [Chemistry of Plant Raw Materials], 2020, 4, 203; DOI: https://doi.org/10.14258/jcprm.2020047505 (in Russian).

    Article  Google Scholar 

  16. G. L. Wang, Y. L. Li, W. D. Zhang, X. W. Yang, W. C. Liu, J. Ye, Z. J. Zhu, H. Chen, Chin. Chem. Let., 2012, 23, 1251; DOI: https://doi.org/10.1016/j.cclet.2012.09.013.

    Article  CAS  Google Scholar 

  17. X.-W. Yanga, S.-M. Li, Y.-H. Shena, W.-D. Zhang, Chem. Biodiver., 2008, 5, 56; DOI: https://doi.org/10.1002/cbdv.200890015.

    Article  Google Scholar 

  18. A. K. F. Albertson, J.-P. Lumb, Angew. Chem., Int. Ed., 2015, 54, 2204; DOI: https://doi.org/10.1002/anie.201408641.

    Article  CAS  Google Scholar 

  19. F. Allais, T. J. L. Pla, P.-H. Ducrot, Synthesis, 2011, 9, Art. No. T14311SS, 1456; DOI: https://doi.org/10.1055/s-0030-1259982.

    Article  Google Scholar 

  20. P. C. Eklund, S. M. Willfor, A. I. Smeds, F. J. Sundell, R. E. Sjoholm, B. R. Holmbom, J. Nat. Prod., 2004, 67, 927; DOI: https://doi.org/10.1021/np0340706.

    Article  CAS  Google Scholar 

  21. J. Huh, J. H. Song, S. R. Kim, H. M. Cho, H.-J. Ko, H. Yang, S. H. Sung, J. Nat. Prod., 2019, 82, 232; DOI: https://doi.org/10.1021/acs.jnatprod.8b00590.

    Article  CAS  Google Scholar 

  22. S. M. Willfor, M. O. Ahotupa, J. E. Hemming, M. H. T. Reunanen, P. C. Eklund, R. E. Sjoholm, C. S. E. Eckerman, S. P. Pohjamo, M. R. Holmbom, J. Agric. Food. Chem., 2003, 51, 7600; DOI: https://doi.org/10.1021/jf030445h.

    Article  Google Scholar 

  23. V. G. Leont’eva, L. D. Modonova, N. A. Tyukavkina, E. G. Puntusova, Chem. Nat. Compd., 1977, 13, 288; DOI: https://doi.org/10.1007/bf00573542.

    Article  Google Scholar 

  24. A. L. Webb, M. L. McCullough, Nutr. Cancer., 2005, 51, 117; DOI: https://doi.org/10.1207/s15327914nc5102_1.

    Article  CAS  Google Scholar 

  25. V. B. Krylov, N. A. Ushakova, N. E. Ustyuzhanina, M. E. Preobrazhenskaya, D. V. Yashunsky, D. E. Tsvetkov, V. M. Menshov, G. V. M. Sharma, P. R. Krishna, N. E. Nifantiev, Russ. Chem. Bull., 2010, 59, 232; DOI: https://doi.org/10.1007/s11172-010-0067-6.

    Article  CAS  Google Scholar 

  26. V. B. Krylov, N. E. Ustyuzhanina, A. A. Grachev, N. E. Nifantiev, Tetrahedron Lett., 2008, 49, 5877; DOI: https://doi.org/10.1016/j.tetlet.2008.07.135.

    Article  CAS  Google Scholar 

  27. M. Correia-da-Silva, E. Sousa, B. Duarte, F. Marques, L. M. Cunha-Ribeiro, M. M. Pinto, Eur. J. Med. Chem., 2011, 46, 2347; DOI: https://doi.org/10.1016/j.ejmech.2011.03.016.

    Article  CAS  Google Scholar 

  28. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, Yu. V. Tomilov, V. A. Dokichev, N. E. Nifantiev, Russ. Chem. Bull., 2015, 64, 1413; DOI: https://doi.org/10.1007/s11172-015-1025-0.

    Article  CAS  Google Scholar 

  29. F. Abe, T. Yamauchi, Chem. Pharm. Bull., 1990, 38, 2143; DOI: https://doi.org/10.1248/cpb.38.2143.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. E. Nifantiev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1356–1362, July, 2021.

The authors are grateful to the Program for the Development of Scientific Schools of the N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tsvetkov, D.E., Dmitrenok, A.S., Tsvetkov, Y.E. et al. Polyphenolic components of knotwood extracts from Abies sibirica. Russ Chem Bull 70, 1356–1362 (2021). https://doi.org/10.1007/s11172-021-3223-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3223-2

Key words

Navigation