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A new dimeric neolignan from Magnolia grandiflora L. seeds

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Abstract

Bioassay-guided fractionation of the MeOH extract of Magnolia grandiflora seeds resulted in the isolation of a new dimeric neolignan, named bishonokiol A (1), as well as two known neolignans magnolol (2) and honokiol (3). The structures of the compounds were determined on the basis of data obtained using NMR and MS. Bishonokiol A (1) showed potent anti-proliferative activities in four human cancer cell lines, with IC50 values ranging from 5.1 to 7.5 µM. Additionally, bishonokiol A (1) induced apoptosis, as well as down-regulated the expression of the anti-apoptotic protein Bcl-2 and caspase-3 cleavage in HepG2 cell line.

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References

  • Arora, S., S. Singh, G.A. Piazza, C.M. Contreras, J. Panyam, and A.P. Singh. 2012. Honokiol: A novel natural agent for cancer prevention and therapy. Current Molecular Medicine 10: 1244–1252.

    Article  Google Scholar 

  • Baker, D.D., M. Chu, U. Oza, and V. Rajgarhia. 2007. The value of natural products to future pharmaceutical discovery. Natural Product Reports 24: 1225–1244.

    Article  CAS  PubMed  Google Scholar 

  • Clark, A.M., A.S. EI-Feraly, and W.S. Li. 1981. Antimicrobial activity of phenolic constituents of Magnolia grandiflora L. Journal of Pharmaceutical Sciences 70(8): 951–952.

    Article  CAS  PubMed  Google Scholar 

  • Del Valle Mondragón, L., F.A. Tenorio López, J.C. Torres Narváez, G.G. Zarco Olvera, and G. Pastelín Hernández. 2004. Estudio de los extractos de Magnolia grandiflora sobreel músculo cardíacode cobayo. Archivos de Cardiologia de Mexico 74: 108–117.

    PubMed  Google Scholar 

  • Feltenstein, M.W., W. Schühly, J.E. Warnick, N.H. Fischer, and K.J. Sufka. 2004. Anti-inflammatory and anti-hyperalgesic effects of sesquiterpene lactones from Magnolia and Bear’s Foot. Pharmacology Biochemistry and Behavior 79: 299–302.

    Article  CAS  Google Scholar 

  • Ito, K., T. Iida, K. Ichino, M. Tsunezuka, M. Hattori, and T. Namba. 1982. Obovatol and obovatal, novel biphenyl ether lignans from the leaves of Magnolia obovata Thunb. Chemical & Pharmaceutical Bulletin 30(9): 3347–3353.

    Article  CAS  Google Scholar 

  • Lee, S.K., H.N. Kim, Y.R. Kang, C.W. Lee, H.M. Kim, D.C. Han, J. Shin, K.H. Bae, and B.M. Kwon. 2008. Obovatol inhibits colorectal cancer growth by inhibiting tumor cell proliferation and Inducing apoptosis. Bioorganic & Medicinal Chemistry 16: 8397–8402.

    Article  CAS  Google Scholar 

  • Mohamed, S.M., E.M. Hassan, and N.A. Ibrahim. 2010. Cytotoxic and antiviral activities of aporphine alkaloids of Magnolia grandiflora L. Natural Product Reports 24(15): 1395–1402.

    Article  CAS  Google Scholar 

  • Ngo, L.T., J.I. Okogun, and W.R. Folk. 2013. 21st century natural product research and drug development and traditional medicines. Natural Product Reports 30(4): 584–592.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Oh, J.H., L.L. Kang, J.O. Ban, Y.H. Kim, K.H. Kim, S.B. Han, and J.T. Hong. 2009. Anti-inflammatory effect of 4-O-methylhonokiol, a novel compound isolated from Magnolia officinalis through inhibition of NF-κΒ. Chemico-Biological Interactions 190: 506–514.

    Article  Google Scholar 

  • Schuehly, W., W. Voith, H. Teppner, and O. Kunert. 2010. Substituted dineolignans from Magnolia garrettii. Journal of Natural Products 73: 1381–1384.

    Article  CAS  PubMed  Google Scholar 

  • Schühly, W., I. Khan, and N.H. Fischer. 2001. The ethnomedicinal uses of Magnoliaceae from the Southeastern United States as leads in drug discovery. Pharmaceutical Biology 39: 63–69.

    Article  PubMed  Google Scholar 

  • Schühly, W., S.I. Khan, and N.H. Fischer. 2009. Neolignans from north American Magnolia species with cyclooxygenase 2 inhibitory activity. Inflammopharmacology 17: 106–110.

    Article  PubMed  Google Scholar 

  • Shen, C.C., C.L. Ni, Y.C. Shen, Y.L. Huang, C.H. Kuo, T.S. Wu, and C.C. Chen. 2009. Phenolic constituents from the stem bark of Magnolia officinalis. Journal of Natural Products 72: 168–171.

    Article  CAS  PubMed  Google Scholar 

  • Surh, Y.J. 2003. Cancer chemoprevention with dietary phytochemicals. Nature Reviews Cancer 3(10): 768–780.

    Article  CAS  PubMed  Google Scholar 

  • Yu, J.Y., J.J. Lee, J.K. Jung, Y.K. Min, J.Y. Ma, T.J. Kim, M.Y. Lee, and Y.P. Yun. 2012. Anti- platelet activity of diacetylated obovatol through regulating cyclooxygenase and lipoxygenase activities. Archives of Pharmacal Research 5(12): 2191–2198.

    Article  Google Scholar 

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China under Grant (no. 81302671, 81372899); the Natural Science Foundation of Anhui Province under Grant (no. 1408085QH162); the Natural Science Foundation of Bengbu Medical College under Grant (Bykf1326).

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Correspondence to Cheng-Zhu Wu.

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Hong-Mei Li and Su-Rong Zhao have contributed equally to this work.

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Li, HM., Zhao, SR., Huo, Q. et al. A new dimeric neolignan from Magnolia grandiflora L. seeds. Arch. Pharm. Res. 38, 1066–1071 (2015). https://doi.org/10.1007/s12272-014-0476-4

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  • DOI: https://doi.org/10.1007/s12272-014-0476-4

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