Skip to main content
SpringerLink
Log in

Thannilignan glucoside and 2-(β-glucopyranosyl)-3-isoxazolin-5-one derivative, two new compounds isolated from Terminalia bellirica

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

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

Two new compounds, thannilignan 9-O-β-glucoside (1) and 2-(β-glucopyranosyl)-3-isoxazolin-5-one derivative (2), and seven known compounds were isolated from the methanol extract of Terminalia bellirica leaves, collected in Bangladesh. The structures of the compounds were elucidated using spectroscopic analysis. Among these isolated compounds, corilagin (3) was cytotoxic against human gastric adenocarcinoma cell line AGS at an IC50 of 20.8 μM, and β-d-glucopyranose 1,3,6-trigallate (4) exhibited the ability to overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) resistance.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

References

  1. von Karstedt SV, Montinaro A, Walczak H (2017) Exploring the TRAILs less travelled: TRAIL in cancer biology and therapy. Nat Rev Cancer 17:352–366

    Article  Google Scholar 

  2. Ahmed F, Karmakar UK, Arai MA, Ishikawa N, Sadhu SK, Ishibashi M (2017) Germacranolides from Enhydra fluctuans with TRAIL-resistance abrogating activity. Nat Prod Commun 12:1169–1170

    Google Scholar 

  3. Karmakar UK, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2017) Boesenberols I–K, new isopimarane diterpenes from Boesenbergia pandurate with TRAIL-resistance overcoming activity. Tetrahedron Lett 58:3838–3841

    Article  CAS  Google Scholar 

  4. Abdelfattah MS, Elmallah MIY, Mohamed AA, Ishibashi M (2017) Sharkquinone, a new ana-quinonoid tetracene derivative from marine-derived Streptomyces sp. EGY1 with TRAIL resistance-overcoming activity. J Nat Med 71:564–569

    Article  CAS  Google Scholar 

  5. Ishibashi M (2021) Screening study of cancer-related cellular signals from microbial natural products. J Antibiot (Tokyo) 74:629–638

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  7. Gunawan-Puteri MDPT, Kawabata J (2010) Novel α-glucosidase inhibitors from Macaranga Tanarius leaves. Food Chem 123:384–389

    Article  CAS  Google Scholar 

  8. Kim TI, Shin B, Kim GJ, Choi H, Lee CS, Woo MH, Oh DC, Son JK (2017) DNA topoisomerase inhibitory activity of constituents from the fruits of Illicium verum. Chem Pharm Bull (Tokyo) 65:1179–1184

    Article  CAS  Google Scholar 

  9. Valsaraj R, Pushpangadan P, Smitt UW, Adsersen A, Christensen SB, Sittie A, Nyman U, Nielsen C, Olsen CE (1997) New anti-HIV-1, antimalarial, and antifungal compounds from Terminalia bellerica. J Nat Prod 60:739–742

    Article  CAS  Google Scholar 

  10. Jayasinghe ULB, Balasooriya BAIS, Bandara AGD, Fujimoto Y (2004) Glycosides from Grewia damine and Filicium decipiens. Nat Prod Res 18:499–502

    Article  CAS  Google Scholar 

  11. Nono RN, Barboni L, Teponno RB, Quassinti L, Bramucci M, Vitali LA, Petrelli D, Lupidi G, Tapondjou AL (2014) Antimicrobial, antioxidant, anti-inflammatory activities and phytoconstituents of extracts from the roots of Dissotis thollonii Cogn. (Melastomataceae). S Afr J Bot 93:19–26

    Article  CAS  Google Scholar 

  12. Gade IS, Chadeneau C, Richard TS, Atchade AT, Talla E, Seite P, Vannier B, Guillard J, Laurent S, Henoumont C, Nwabo AHK (2021) Muller JM (2021) A new flavonoid glycoside from Tapinanthus sp (Loranthaceae) and evaluation of anticancer activity of extract and some isolated compounds. Nat Prod Res. https://doi.org/10.1080/14786419.2021.1963243

    Article  PubMed  Google Scholar 

  13. Lai YC, Lee SS (2013) Chemical constituents from Dendropanax dentiger. Nat Prod Commun 8:363–365

    CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to thank Sayaka Kado (Center for Analytical Instrumentation, Chiba University) for the HR-ESI-MS measurements. This work was supported by KAKENHI (Grant Nos. 20H03394 and 20K16024) from the Japan Society for the Promotion of Science.

Author information

Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan

    Teruhisa Manome, Yasumasa Hara & Masami Ishibashi

  2. Plant Molecular Science Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan

    Yasumasa Hara & Masami Ishibashi

  3. Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka, 1000, Bangladesh

    Firoj Ahmed

  4. Pharmacy Discipline, Khulna University, Khulna, 9208, Bangladesh

    Samir K. Sadhu

Authors
  1. Teruhisa Manome
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yasumasa Hara
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Firoj Ahmed
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Samir K. Sadhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Masami Ishibashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Yasumasa Hara or Masami Ishibashi.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 17203 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Manome, T., Hara, Y., Ahmed, F. et al. Thannilignan glucoside and 2-(β-glucopyranosyl)-3-isoxazolin-5-one derivative, two new compounds isolated from Terminalia bellirica. J Nat Med 76, 482–489 (2022). https://doi.org/10.1007/s11418-021-01593-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-021-01593-z

Keywords

Search

Navigation