Skip to main content
SpringerLink
Log in

Three new steroidal saponins from Aspidistra letreae plants and their cytotoxic activities

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

Abstract

Three new steroidal saponins, aspiletreins A–C (1–3), together with 2H-chromen-2-one (4), and α-tocopherol (5), were isolated from whole Aspidistra letreae plants collected in Vietnam. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR, IR, and HRESIMS, and by comparison with the reported data in the literature. Compounds 1–3 exhibited moderate cytotoxicities against the LU-1, HeLa, MDA-MB-231, HepG2, and MKN-7 human cancer cell lines, with IC50 values ranging from 7.69 ± 0.40 to 20.46 ± 3.11 µM.

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

References

  1. Ly NS, Tillich HJ (2016) Aspidistra averyanovii and A. parviflora (Asparagaceae), two new species Central Vietnam. Phytotaxa 282:53–60

    Article  Google Scholar 

  2. Mori Y, Kawasaki T (1973) A new diosgenin glycoside, aspidistrin, from Aspidistra elatior Blume. Chem Pharm Bull 21:224–227

    Article  CAS  Google Scholar 

  3. Cui JM, Kang LP, Zhao Y, Zhao JY, Zhang J, Pang X, Yu HS, Jia DX, Liu C, Yu LY, Ma BP (2016) Steroidal saponins from the rhizomes of Aspidistra typica. PLoS ONE 11:e0150595

    Article  Google Scholar 

  4. Peng J, Zhao Y, Xu L, Kang LP, Cui JM, Yu HS, Zhang J, Ma BP (2017) Metabolite profiling of steroidal glycosides in the rhizome of Aspidistra sichuanensis using UPLC/Q-TOF MSE. Int J Mass Spectrom 415:63–84

    Article  CAS  Google Scholar 

  5. Hirai Y, Konishi T, Sanada S, Ida Y, Shoji J (1982) Studies on the constituents of Aspidistra elatior Blume. I. On the steroids of the underground part. Chem Pharm Bull 30:3476–3484

    Article  CAS  Google Scholar 

  6. Konishi T, Kiyosawa S, Shoji J (1984) Studies on the constituents of Aspidistra elatior Blume. II. On the steroidal glycosides of the leaves. Chem Pharm Bull 32:1451–1460

    Article  CAS  Google Scholar 

  7. Cui JM, Kang LP, Yu HS, Zhao Y, Xiong CQ, Liu C, Ma BP (2013) Two new furostanol saponins from Aspidistra typica. J Asian Nat Prod Res 15:525–531

    Article  CAS  Google Scholar 

  8. Zuo SQ, Liu YN, Yang Y, Guo ZQ, Liu CX, Guo ZY, He HB, Tu X, Zou K (2018) Aspidsaponins A–D, four new steroidal saponins from the rhizomes of Aspidistra elatior Blume and their cytotoxicity. Phytochem Lett 25:126–131

    Article  CAS  Google Scholar 

  9. Koketsu M, Kim M, Yamamoto T (1996) Antifungal activity against food-borne fungi of Aspidistra elatior Blume. J Agric Food Chem 44:301–303

    Article  CAS  Google Scholar 

  10. Xu XC, Zhang ZW, Chen YE, Yuan M, Yuan S, Bao JK (2015) Antiviral and antitumor activities of the lectin extracted from Aspidistra elatior. Z Naturforsch C J Biosci 70:7–13

    Article  CAS  Google Scholar 

  11. Liang X, Kong L, He M (2016) A new homoisoflavone compound as a potent antibacterial agent from Aspidistra typica Baill. J Chin Pharm Sci 25:700–703

    Google Scholar 

  12. Averyanov LV, Tillich HJ, Le TA, Pham VT, Maisak TV, Vu TC (2017) Aspidistra letreae (Asparagaceae), a new species from central Vietnam. Phytotaxa 308:137–140

    Article  Google Scholar 

  13. Duddeck H, Kaiser M (1982) 13C NMR spectroscopy of coumarin derivatives. Org Magn Reson 20:55–72

    Article  CAS  Google Scholar 

  14. Matsuo M, Urano S (1976) 13C NMR spectra of tocopherols and 2,2-dimethylchromanols. Tetrahedron 32:229–231

    Article  CAS  Google Scholar 

  15. Pettolino FA, Walsh C, Fincher GB, Bacic A (2012) Determining the polysaccharide composition of plant cell walls. Nat Protoc 7:1590–1607

    Article  CAS  Google Scholar 

  16. Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro-Wolff A, Gray-Goodich M, Campbell H, Mayo J, Boyd M (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 83:757–766

    Article  CAS  Google Scholar 

  17. Huang X, Kong L (2006) Steroidal saponins from roots of Asparagus officinalis. Steroids 71:171–176

    Article  CAS  Google Scholar 

  18. Hayes PY, Jahidin AH, Lehmann R, Penman K, Kitching W, De Voss JJ (2008) Steroidal saponins from the roots of Asparagus racemosus. Phytochemistry 69:796–804

    Article  CAS  Google Scholar 

  19. Xiang L, Wang Y, Yi X, Zheng G, He X (2016) Bioactive spirostanol saponins from the rhizome of Tupistra chinensis. Steroids 108:39–46

    Article  CAS  Google Scholar 

  20. Qu L, Ruan J, Wu S, Huang P, Yan J, Yu H, Zhang Y, Wang T (2018) Separation and bioactive assay of 25R/S-spirostanol saponin diastereomers from Yucca schidigera Roezl (Mojave) stems. Molecules 23(pii):E2562

    Article  Google Scholar 

  21. Ho VD, Hoang THN, Vo QH, Phan VK, Le TA, Pham VT, Nguyen MH, Kodama T, Ito T, Morita H, Raal A, Nguyen TH (2017) Cycloartane-type triterpene glycosides anopanins A–C with monoacyldigal actosylglycerols from Anodendron paniculatum. Phytochemistry 144:113–118

    Article  CAS  Google Scholar 

  22. Agrawal PK (1992) NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry 31:3307–3330

    Article  CAS  Google Scholar 

  23. Ho DV, Kodama T, Le HT, Phan KV, Do TT, Bui TH, Le AT, Win NN, Imagawa H, Ito T, Morita H, Nguyen HT (2015) A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora. Bioorg Med Chem Lett 25:3246–3250

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by Hue University (ID No. DHH2019-04-101) and in part by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (JSPS KAKENHI Grants JP17H02203 and 19H04649). We are grateful to Mr. Luong Vu Dang (Institute of Chemistry, VAST, Hanoi, Vietnam) for recording the NMR spectra.

Author information

Authors and Affiliations

  1. Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen, Hue, Vietnam

    Duc Viet Ho, Hung Quoc Vo, Khan Viet Nguyen & Hoai Thi Nguyen

  2. Faculty of Basic Science, Hue University of Agriculture and Forestry, Hue University, 102 Phung Hung, Hue, Vietnam

    Hanh Nhu Thi Hoang

  3. Faculty of Chemistry, Hue University of Education, Hue University, 34 Le Loi, Hue, Vietnam

    Ty Viet Pham

  4. Quang Tri Center of Science and Technology, Mientrung Inst. for Scientific Research, VAST, Dien Bien Phu, Dong Ha, Quang Tri, Vietnam

    Anh Tuan Le

  5. Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam

    Kiem Van Phan

  6. Faculty of Pharmacy, Ton Duc Thang University, Ho Chi Minh City, Vietnam

    Hien Minh Nguyen

  7. Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama, 930-0194, Japan

    Hiroyuki Morita

Authors
  1. Duc Viet Ho
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hanh Nhu Thi Hoang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hung Quoc Vo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Khan Viet Nguyen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ty Viet Pham
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Anh Tuan Le
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Kiem Van Phan
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Hien Minh Nguyen
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Hiroyuki Morita
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Hoai Thi Nguyen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Hiroyuki Morita or Hoai Thi Nguyen.

Ethics declarations

Conflict of interest

The authors declare that they have no conflicts of interest.

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 (PDF 3360 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ho, D.V., Hoang, H.N.T., Vo, H.Q. et al. Three new steroidal saponins from Aspidistra letreae plants and their cytotoxic activities. J Nat Med 74, 591–598 (2020). https://doi.org/10.1007/s11418-020-01395-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-020-01395-9

Keywords

Search

Navigation