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New diterpenoids with estrogen sulfotransferase inhibitory activity from Leonurus sibiricus L.

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Abstract

Four new diterpenoids (14), along with eight known diterpenoids (512) were isolated from the acetone extract of Leonurus herb (aerial parts of Leonurus sibiricus L.). The structures of the compounds were determined by spectroscopic methods. Among the isolated compounds, compounds 2, 3, 8, 9 and 10 showed inhibitory activity against human liver cytosol estrogen sulfotransferase (E-ST), which plays a key role in the maintenance of cellular estrogen levels. Compound 2 showed the strongest activity with an IC50 value of 7.9 μM, which is comparable to the activity of the positive control, meclofenamic acid (IC50 5.4 μM).

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References

  1. Falany CN (1997) Enzymology of human cytosolic sulfotransferases. FASEB J 11:206–216

    PubMed  CAS  Google Scholar 

  2. The Ministry of Health, Labour and Welfare of Japan (2011) The Japanese pharmacopoeia, 16th edn. Pharmaceuticals and Medical Devices Agency, Tokyo, p 1591

  3. Wu H, Fronczek FR, Ferreira D, Burandt CL, Zjawiony JK (2011) Labdane diterpene from Leonurus sibiricus. J Nat Prod 74:831–836

    Article  PubMed  CAS  Google Scholar 

  4. Piozzi F, Bruno M, Rosselli S, Maggio A (2007) Structure and biological activity of the furan-diterpenoids from the genera Leonotis and Leonurus. Hetrocycles 74:31–52

    Article  CAS  Google Scholar 

  5. Hon PM, Wang EN, Lam SKM, Choy YM, Lee CM, Wong HNC (1993) Preleoheterin and leoheterin, two labdane diterpenes from Leonurus heterophyllus. Phytochemistry 33:639–641

    Article  CAS  Google Scholar 

  6. Rodrigues B, Savona G (1980) Diterpenoids from Galeopsis angustifolia. Phytochemistry 19:1805–1807

    Article  Google Scholar 

  7. Hon PM, Lee CM, Shang HS, Cui YX, Wong HNC, Chang HM (1991) Prehispanolone, a labdane diterpene from Leonurus heterophyllus. Phytochemistry 30:354–356

    Article  CAS  Google Scholar 

  8. Gray CA, Rivett DEA, Davies-Coleman MT (2003) The absolute stereochemistry of a diterpene from Ballota aucheri. Phytochemistry 63:409–413

    Article  PubMed  CAS  Google Scholar 

  9. Rustaiyan A, Mosslemin-Kupaii MH, Papastergiou F, Jakupovic J (1995) Persianone, a dimeric diterpene from Ballota auche. Phytochemistry 40:875–879

    Article  CAS  Google Scholar 

  10. Hersel U, Steck M, Seifert K (2000) A new route to 2,7- and 7-functionalized Labdanes. Eur J Org Chem 2000:1609–1615

    Article  Google Scholar 

  11. Boalino DM, McLean S, Reynolds WF, Tinto WF (2004) Labdane diterpenes of Leonurus sibiricus. J Nat Prod 67:714–717

    Article  PubMed  CAS  Google Scholar 

  12. Romero-Gonzaléz RR, Ávila-Núñez JL, Aubert L, Alonso-Amelot ME (1995) Labdane diterpenes from Leonurus japonicus leaves. Phytochemistry 67:965–970

    Article  Google Scholar 

  13. Marcos IS, Castañeda L, Basabe P, Díez D, Urones JG (2008) Synthesis of sibiricinone A, sibiricinone B and leoheterin. Tetrahedron 64:10860–10866

    Article  CAS  Google Scholar 

  14. King RS, Ghosh AA, Wu J (2006) Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab 7:745–753

    Article  PubMed  CAS  Google Scholar 

  15. Saruwatari A, Issiki M, Tamura H (2008) Inhibitory effects of various beverages on the sulfoconjugation of 17b-estradiol in human colon carcinoma Caco-2 cells. Biol Pharm Bull 31:2131–2136

    Article  PubMed  CAS  Google Scholar 

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Acknowledgments

This work was supported in part by MEXT-supported program for the Strategic Research Foundation at Private Universities and Keio Gijuku Academic Development Funds.

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Correspondence to Fumiyuki Kiuchi.

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Narukawa, Y., Niimura, A., Noguchi, H. et al. New diterpenoids with estrogen sulfotransferase inhibitory activity from Leonurus sibiricus L.. J Nat Med 68, 125–131 (2014). https://doi.org/10.1007/s11418-013-0781-0

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  • DOI: https://doi.org/10.1007/s11418-013-0781-0

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