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Protein tyrosine phosphatase 1B inhibitory activities of ursane- and lupane-type triterpenes from Sorbus pohuashanensis

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Abstract

Protein tyrosine phosphatase 1B (PTP1B) is a non-transmembrane protein tyrosine phosphatase, and has received much attention as a molecular target for the treatment of insulin resistance diseases because of its critical roles in negatively regulating insulin- and leptin-signaling cascades. Six ursane-type triterpenes, 3β-acetoxy-urs-12-ene-28-oic acid (1), pomolic acid-3β-acetate (2), pomolic acid (3), ursolaldehyde (4), euscaphic acid (5) and 3β-acetoxy-urs-11-en-28,13-olide (6), and a lupane-type triterpene, betulinic acid (7), from the fruits of Sorbus pohuashanensis, exhibited significant PTP1B inhibitory activity, with IC50 values ranging from 3.5 to 54.8 μM. Kinetics analyses revealed that compounds 2, 3, and 7 are non-competitive PTP1B inhibitors, and compounds 1 and 6 are mixed-type PTP1B inhibitors.

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References

  1. Johnson TO, Ermolieff J, Jirousek MR (2002) Protein tyrosine phosphatase 1B inhibitors for diabetes. Nat Rev Drug Discov 1:696–709

    Article  CAS  PubMed  Google Scholar 

  2. Tonks NK, Muthuswamy SK (2007) A brake becomes an accelerator: PTP1B–a new therapeutic target for breast cancer. Cancer Cell 11:214–216

    Article  CAS  PubMed  Google Scholar 

  3. Zhang S, Zhang ZY (2007) PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. Drug Discov Today 12:373–381

    Article  CAS  PubMed  Google Scholar 

  4. Combs AP (2010) Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer. J Med Chem 53:2333–2344

    Article  CAS  PubMed  Google Scholar 

  5. Li H, Matsuura M, Li W, Li Q, Zhang Q, Koike K (2012) Chemical constituents from the fruits of Sorbus pohuashanensis. Biochem Syst Ecol 43:166–168

    Article  Google Scholar 

  6. Li S, Li W, Wang Y, Asada Y, Koike K (2010) Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities. Bioorg Med Chem Lett 20:5398–5401

    Article  CAS  PubMed  Google Scholar 

  7. Sasaki T, Li W, Morimura H, Li S, Li Q, Asada Y, Koike K (2011) Chemical constituents from Sambucus adnata and their protein tyrosine phosphatase-1B inhibitory activities. Chem Pharm Bull 59:1396–1399

    Article  CAS  PubMed  Google Scholar 

  8. Zhang YN, Zhang W, Hong D, Shi L, Shen Q, Li JY, Li J, Hu LH (2008) Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities. Bioorg Med Chem 16:8697–8705

    Article  CAS  PubMed  Google Scholar 

  9. Kimura K, Takada M, Ishii T, Tsuji-Naito K, Akagawa M (2012) Pyrroloquinoline quinone stimulates epithelial cell proliferation by activating epidermal growth factor receptor through redox cycling. Free Radic Biol Med 53:1239–1251

    Article  CAS  PubMed  Google Scholar 

  10. Na M, Yang S, He L, Oh H, Kim BS, Oh WK, Kim BY, Ahn JS (2006) Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata. Planta Med 72:261–263

    Article  CAS  PubMed  Google Scholar 

  11. Lin Z, Zhang Y, Zhang Y, Shen H, Hu L, Jiang H, Shen X (2008) Oleanolic acid derivative NPLC441 potently stimulates glucose transport in 3T3-L1 adipocytes via a multi-target mechanism. Biochem Pharmacol 76:1251–1262

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

This study was partially supported by a Grant-in-Aid for Young Scientists (B) (No. 23790025) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba, 274-8510, Japan

    Dongxia Li, Wei Li, Koji Higai & Kazuo Koike

  2. Medical College, Dalian University, Dalian, 116622, People’s Republic of China

    Dongxia Li

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  1. Dongxia Li
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  2. Wei Li
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  3. Koji Higai
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  4. Kazuo Koike
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Correspondence to Wei Li.

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Li, D., Li, W., Higai, K. et al. Protein tyrosine phosphatase 1B inhibitory activities of ursane- and lupane-type triterpenes from Sorbus pohuashanensis . J Nat Med 68, 427–431 (2014). https://doi.org/10.1007/s11418-013-0804-x

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  • DOI: https://doi.org/10.1007/s11418-013-0804-x

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