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Rhamnetin Glycosides from the Genus Spiraea

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Rhamnetin (7-O-methylquercetin, 1) and its glycosides were found for the first time in the genus Spiraea (Rosaceae) during chromatographic studies of representatives from the subgenus Protospiraea. Leaves of S. salicifolia yielded 1, rhamnetin-3-O-β-D-glucopyranoside (2), and two new flavonoids 3 and 4 that were identified by UV, IR, and NMR spectroscopy and mass spectrometry as rhamnetin-3-O-(6-O-p-coumaroyl)-β-D-glucopyranoside (spiraearhamnin A, 3) and rhamnetin-3-O-(6-O-caffeoyl)-β-D-glucopyranoside (spiraearhamnin B, 4). Leaves of S. betulifolia and S. betulifolia var. aemiliana afforded 1 and 2 and glycosides of kaempferol, quercetin, and isorhamnetin. Species of the subgenus Metaspiraea (S. alpina, S. chamaedryfolia, S. dahurica, S. hypericifolia, and S. media) did not contain 1 or its derivatives.

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References

  1. J. B. Harborne, Comparative Biochemistry of the Flavonoids, Academic Press, London, New York, 1967, 383 pp.

    Google Scholar 

  2. M. I. Choudhary, N. Naheed, A. Abbaskhan, S. Ali, and Atta-ur-Rahman, Phytochemistry, 70, 1467 (2009).

    Article  CAS  PubMed  Google Scholar 

  3. K. Yoshida, A. Hishida, O. Iida, K. Hosokawa, and J. Kawabata, J. Agric. Food Chem., 56, 4367 (2008).

    Article  CAS  PubMed  Google Scholar 

  4. E. A. Karpova and E. P. Khramova, Contemp. Probl. Ecol., 7, 228 (2014).

    Article  Google Scholar 

  5. T.-S. Wu, C.-C. Hwang, P.-C. Kuo, T.-H. Kuo, A. G. Damu, and C.-R. Su, Chem. Pharm. Bull., 52, 1227 (2004).

    Article  CAS  PubMed  Google Scholar 

  6. B. T. Ahn, J. G. Kim, J. S. Ro, K. S. Lee, K. J. Oh, S. K. Park, S. G. Chung, and E. H. Cho, Korean J. Pharmacogn., 27, 178 (1996).

    CAS  Google Scholar 

  7. U. R. Mughal, R. Mehmood, A. Malik, B. Ali, and R. B. Tareen, Helv. Chim. Acta, 95, 100 (2012).

    Article  CAS  Google Scholar 

  8. E. A. Karpova and N. P. Lapteva, Turczaninowia, 17, 42 (2014).

    Article  Google Scholar 

  9. D. N. Olennikov and N. I. Kashchenko, Khim. Prir. Soedin., 883 (2017).

  10. K. R. Markham, Techniques of Flavonoid Identification, Academic Press, London, New York, 1982, 113 pp.

    Google Scholar 

  11. D. N. Olennikov, L. M. Tankhaeva, and S. V. Agafonova, Appl. Biochem. Microbiol., 47, 419 (2011).

    Article  CAS  Google Scholar 

  12. M. Ozipek, I. Calis, M. Ertan, and P. Ruedi, Phytochemistry, 37, 249 (1994).

    Article  CAS  PubMed  Google Scholar 

  13. A. Panighel, M. De Rosso, A. D. Vedova, and R. Flamini, Rapid Commun. Mass Spectrom., 29, 357 (2015).

    Article  CAS  PubMed  Google Scholar 

  14. N. Berardini, R. Fezer, J. Conrad, U. Beifuss, R. Carle, and A. Schieber, J. Agric. Food Chem., 53, 1563 (2005).

    Article  CAS  PubMed  Google Scholar 

  15. D. Gupta and J. Singh, Phytochemistry, 30, 2761 (1991).

    Article  CAS  PubMed  Google Scholar 

  16. D. N. Olennikov, N. K. Chirikova, and N. I. Kashchenko, Chem. Nat. Compd., 51, 1085 (2015).

    Article  CAS  Google Scholar 

  17. S. S. E. Manga, A. E. Tih, B. Abderamane, R. T. Ghogomu, A. Blond, and B. Bodo, Z. Naturforsch., C: J. Biosci., 67, 233 (2012).

    Article  CAS  Google Scholar 

  18. E. Lee, B.-H. Moon, Y. Park, S. Hong, S. Lee, Y. Lee, and Y. Lim, Bull. Korean Chem. Soc., 29, 507 (2008).

    Article  CAS  Google Scholar 

  19. W. Bai, X. Fang, W. Zhao, S. Huang, H. Zhang, and M. Qian, J. Food Drug Anal., 23, 645 (2015).

    Article  CAS  PubMed  Google Scholar 

  20. D. N. Olennikov and N. I. Kashchenko, Chem. Nat. Compd., 50, 633 (2014).

    Article  CAS  Google Scholar 

  21. D. N. Olennikov, L. M. Tankhaeva, A. V. Stolbikova, and E. V. Petrov, Chem. Nat. Compd., 47, 165 (2011).

    Article  CAS  Google Scholar 

  22. S. S. Azimova and V. I. Vinogradova, Natural Compounds. Flavonoids: Plant Sources, Structure and Properties, Springer, New York, 2013, p. 199.

    Google Scholar 

  23. D. N. Olennikov, N. I. Kashchenko, and N. K. Chirikova, Molecules, 19, 18296 (2014).

    Article  CAS  PubMed  Google Scholar 

  24. M. Jung and M. Park, Molecules, 12, 2130 (2007).

    Article  CAS  PubMed  Google Scholar 

  25. D. N. Olennikov and V. V. Partilkhaev, J. Planar Chromatogr., 25, 30 (2012).

    Article  CAS  Google Scholar 

  26. M. A. Aderogba, L. J. McGaw, M. Bezabih, and B. M. Abegaz, Nat. Prod. Res., 25, 1224 (2011).

    Article  CAS  PubMed  Google Scholar 

  27. D. N. Olennikov and N. I. Kashchenko, Chem. Nat. Compd., 49, 833 (2013).

    Article  CAS  Google Scholar 

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Acknowledgment

The work was sponsored by the RFBR and the Government of the Republic of Buryatia in the framework of Scientific Project No. 16-43-030857.

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Correspondence to D. N. Olennikov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2018, pp. 38–42.

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Olennikov, D.N., Chirikova, N.K. Rhamnetin Glycosides from the Genus Spiraea. Chem Nat Compd 54, 41–45 (2018). https://doi.org/10.1007/s10600-018-2255-9

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  • DOI: https://doi.org/10.1007/s10600-018-2255-9

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