Skip to main content
Log in

Cadinane sesquiterpenoids isolated from Santalum album using a screening program for Wnt signal inhibitory activity

  • Note
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

Upon screening compounds having Wnt signal inhibitory activity through evaluating TCF/β-catenin transcriptional (TOP) activity, eight cadinane sesquiterpenoids, including three new compounds (13), were isolated from wood extracts of Santalum album (Santalaceae). Structures of compounds 13 were elucidated by spectral data to have a cadinane skeleton with an aromatic ring. Of the eight compounds isolated, compound 4, identified as mansonone I, was found to be active against TOP, having an IC50 of 1.2 μM.

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.

Fig. 1
Fig. 2
Fig. 3

References

  1. Nusse R, Clevers H (2017) Wnt/β-catenin signaling, disease, and emerging therapeutic modalities. Cell 169:985–999

    Article  CAS  Google Scholar 

  2. Anastas JN, Moon RT (2013) Wnt signaling pathways as therapeutic targets in cancer. Nat Rev Cancer 13:11–26

    Article  CAS  Google Scholar 

  3. Ishibashi M (2019) Screening for natural products that affect Wnt signaling activity. J Nat Med 73:697–705

    Article  Google Scholar 

  4. Fuentes RG, Arai MA, Ishibashi M (2015) Natural compounds with Wnt signal modulating activity. Nat Prod Rep 32:1622–1628

    Article  CAS  Google Scholar 

  5. Li X, Ohtsuki T, Koyano T, Kowithayakorn T, Ishibashi M (2009) New Wnt/β-catenin signaling inhibitors isolated from Eleutherine palmifolia. Chem Asian J 4:540–547

    Article  CAS  Google Scholar 

  6. Kim JP, Kim WG, Koshino H, Jung J, Yoo ID (1996) Sesquiterpene O-naphthoquinones from the root bark of Ulmus davidiana. Phytochemistry 43:425–430

    Article  CAS  Google Scholar 

  7. Chen CM, Chen ZT, Hong YL (1990) A mansonone from Helicteres angustifolia. Phytochemistry 29:980–982

    Article  CAS  Google Scholar 

  8. Guo X, Liao C, Ma L, Gu L (2003) 4-Hydroxy-3,6,9-trimethyl-2,3-dihydro-benzo[de]chromene-7,8-dione. Acta Cryst E59:o558–o560

    Google Scholar 

  9. Tiew P, Ioset JR, Kokpol U, Schenk K, Jaiboon N, Chaichit N, Chavasiri W, Hostettmann K (2002) Four new sesquiterpenoid derivatives from the heartwood of Mansonia gagei. J Nat Prod 65:1332–1335

    Article  CAS  Google Scholar 

  10. Zhang Y, Liu YB, Li L, Ma SG, Qu J, Jliang JD, Chen XG, Zhang D, Yu SS (2015) Terpenoids from the roots of Alangium chinense. J Asian Nat Prod Res 17:1025–1038

    Article  CAS  Google Scholar 

  11. Mori N, Toume K, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2011) 2-Methoxy-1,4-naphthoquinone isolated from Impatiens balsamina in a screening program for activity to inhibit Wnt signaling. J Nat Med 65:234–236

    Article  CAS  Google Scholar 

  12. Lindhagen E, Nygren P, Larsson R (2008) The fluorometric microculture cytotoxicity assay. Nat Protoc 3:1364–1369

    Article  CAS  Google Scholar 

  13. Toume K, Kamiya K, Arai MA, Mori N, Sadhu SK, Ahmed F, Ishibashi M (2013) Xylogranin B, a potent Wnt signal inhibitory limonoid from Xylocarpus granatum. Org Lett 15:6106–6109

    Article  CAS  Google Scholar 

  14. Ohishi K, Toume K, Arai MA, Sadhu SK, Ahmed F, Mizoguchi T, Ito M, Ishibashi M (2014) Ricinine: a pyridone alkaloid from Ricinus communis that activates the Wnt signaling pathway through casein kinase 1α. Bioorg Med Chem 22:4597–4601

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to thank Professor Jeremy Nathans (John Hopkins University School of Medicine) for the STF/293 cells and Professor Ronald T. Moon (University of Washington) for the Super FOPFlash plasmid.

Funding

This study was supported by KAKENHI Grant Numbers 18H02582 and 17H03992 from the Japan Society for the Promotion of Science (JSPS).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Masami Ishibashi.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 830 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sato, T., Arai, M.A., Yixizhuoma et al. Cadinane sesquiterpenoids isolated from Santalum album using a screening program for Wnt signal inhibitory activity. J Nat Med 74, 476–481 (2020). https://doi.org/10.1007/s11418-019-01380-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-019-01380-x

Keywords

Navigation