Skip to main content
SpringerLink
Log in

C21 steroid derivatives from the Dai herbal medicine Dai-Bai-Jie, the dried roots of Marsdenia tenacissima, and their screening for anti-HIV activity

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

Abstract

Twenty-three new C21 steroidal glycosides, marstenacissides C1–C10 (1–10), D1–D7 (11–17) and E1–E6 (18–23), and four new C21 steroids, 11α,12β-O-ditigloyl-tenacigenin C (24), 11α-O-benzoyl-12β-O-tigloyl-tenacigenin C (25), 11α-O-tigloyl-12β-O-benzoyl-tenacigenin C (26) and 11α-O-tigloyl-12β-O-benzoyl-marsdenin (27), were isolated from the Dai herbal medicine Dai-Bai-Jie, derived from the roots of Marsdenia tenacissima. The chemical structures of all compounds were established by spectroscopic techniques, including high-resolution mass spectrometry and NMR spectroscopy, as well as by comparison with reported spectral data. The anti-HIV activities of these compounds were screened, and the compounds obtained displayed inhibitory effects against HIV-1 with inhibition rates of 36.4–81.3% at 30 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

Similar content being viewed by others

References

  1. Li HT, Kang LP, Guo BL, Zhang ZL, Guan YH, Pang X, Peng CZ, Ma BP, Zhang LX (2014) Original plant identification of Dai nationality herb “daibaijie”. Chin J Chin Mater Med 39:27–31

    Google Scholar 

  2. Qiu SX, Luo SQ, Lin LZ, Cordell GA (1996) Further polyoxypregnane glycosides from Marsdenia tenacissima. Phytochemistry 41:1385–1388

    Article  CAS  Google Scholar 

  3. Xia ZH, Xing WX, Mao SL, Lao AN, Uzawa J, Yoshida S, Fujimoto Y (2004) Pregnane glycosides from the stems of Marsdenia tenacissima. J Asia Nat Prod Res 6:79–85

    Article  CAS  Google Scholar 

  4. Deng J, Liao ZX, Chen DF (2005) Marsdenosides A-H, polyoxypregnane glycosides from Marsdenia tenacissima. Phytochemistry 66:1040–1051

    Article  CAS  Google Scholar 

  5. Deng J, Liao ZX, Chen DF (2005) Two new C21 steroids from Marsdenia tenacissima. Chin Chem Let 16:487–490

    CAS  Google Scholar 

  6. Wang S, Lai YH, Tian B, Yang L (2006) Two new C21 steroidal glycosides from Marsdenia tenacissima (ROXB.) WIGHT et ARN. Chem Pharm Bull 54:696–698

    Article  CAS  Google Scholar 

  7. Wang XL, Li QF, Yu KB, Peng SL, Zhou Y, Ding LS (2006) Four new pregnane glycosides from the stems of Marsdenia tenacissima. Helv Chim Acta 89:2738–2744

    Article  CAS  Google Scholar 

  8. Li QF, Wang XL, Ding LS, Zhang C (2007) Polyoxypregnanes from the stems of Marsdenia tenacissima. Chin Chem Let 18:831–834

    Article  CAS  Google Scholar 

  9. Liu J, Yu ZB, Ye YH, Zhou YW (2008) A new C21 steroid glycoside from Marsdenia tenacissima. Chin Chem Lett 19:444–446

    Article  CAS  Google Scholar 

  10. Huang XD, Liu T, Wang S (2009) Two new polyoxypregnane glycosides from Marsdenia tenacissima. Helv Chim Acta 92:2111–2117

    Article  CAS  Google Scholar 

  11. Wang XL, Peng SL, Ding LS (2010) Further polyoxypregnane glycosides from Marsdenia tenacissima. J Asia Nat Prod Res 12:654–661

    Article  CAS  Google Scholar 

  12. Zhang H, Tan AM, Zhang AY, Chen R, Yang SB, Huang X (2010) Five new C21 steroidal glycosides from the stems of Marsdenia tenacissima. Steroids 75:176–183

    Article  CAS  Google Scholar 

  13. Xia ZH, Mao SL, Lao AN, Jun Uzawa, Yoshida S, Fujimoto Y (2011) Five new pregnane glycosides from the stems of Marsdenia tenacissima. J Asia Nat Prod Res 13:477–485

    Article  CAS  Google Scholar 

  14. Pang X, Kang LP, Fang XM, Zhao Y, Yu HS, Han LF, Li HT, Zhang LX, Guo BL, Yu LY, Ma BP (2017) Polyoxypregnane glycosides from the roots of Marsdenia tenacissima and their anti-HIV activities. Planta Med 83:126–134

    CAS  Google Scholar 

  15. Pang X, Kang LP, Yu HS, Zhao Y, Han LF, Zhang J, Xiong CQ, Zhang LX, Yu LY, Ma BP (2015) New polyoxypregnane glycosides from the roots of Marsdenia tenacissima. Steroids 93:68–76

    Article  CAS  Google Scholar 

  16. Niranjan PS, Nilendu P, Nirup BM, Sukdeb B, Kazuo K, Tamotsu N (2002) Polyoxypregnane glycosides from the flowers of Dregea volubilis. Phytochemistry 61:383–388

    Article  Google Scholar 

  17. Li JZ, Liu HY, Lin YJ, Hao XJ, Ni W, Chen CX (2008) Six new C21 steroidal glycosides from Asclepias curassavica. Steroids 73:594–600

    Article  CAS  Google Scholar 

  18. Umehara K, Endoh M, Miyase T, Kuroyanagi M, Ueno A (1994) Studies on differentiation inducers. IV. Pregnane derivatives from condurango cortex. Chem Pharm Bull 42:611–616

    Article  CAS  Google Scholar 

  19. Warashina T, Noro T (2000) Cardenolide and oxypregnane glycosides from the root of Asclepias incarnata L. Chem Pharm Bull 48:516–524

    Article  CAS  Google Scholar 

  20. Li JZ, Liu HY, Lin YJ, Hao XJ, Ni W, Chen CX (2008) Six new C21 steroidal glycosides from Asclepias curassavica. Steroids 73:594–600

    Article  CAS  Google Scholar 

  21. Warashina T, Noro T (2000) Steroidal glycosides from the aerial part of Asclepias incarnata. Chem Pharm Bull 48:99–107

    Article  CAS  Google Scholar 

  22. Zhang Q, Liu ZL, Mi ZY, Li XY, Jia PP, Zhou JM, Yin X, You XF, Yu LY, Guo F, Ma J, Liang C, Cen S (2011) High-throughput assay to identify inhibitors of Vpu-mediated down-regulation of cell surface BST-2. Antiviral Res 91:321–329

    Article  CAS  Google Scholar 

Download references

Acknowledgement

Thanks to Miss Meifeng Xu in National Center of Biomedical Analysis (NCBA) for the measurements of the NMR spectra.

Author information

Authors and Affiliations

  1. Beijing Institute of Radiation Medicine, Beijing, 100850, China

    Xu Pang, Li-Ping Kang, Yang Zhao & Bai-Ping Ma

  2. Tianjin University of Traditional Chinese Medicine, Tianjin, 300193, China

    Xu Pang, Li-Ping Kang, He-Shui Yu & Li-Feng Han

  3. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, China

    Xiao-Mei Fang & Li-Yan Yu

  4. Yunnan Branch of Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Jinghong, 666100, China

    Li-Xia Zhang

Authors
  1. Xu Pang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Li-Ping Kang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiao-Mei Fang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. He-Shui Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Li-Feng Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yang Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Li-Xia Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Li-Yan Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Bai-Ping Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bai-Ping Ma.

Ethics declarations

Conflict of interests

There are no conflicts of interests of all authors.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 11614 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pang, X., Kang, LP., Fang, XM. et al. C21 steroid derivatives from the Dai herbal medicine Dai-Bai-Jie, the dried roots of Marsdenia tenacissima, and their screening for anti-HIV activity. J Nat Med 72, 166–180 (2018). https://doi.org/10.1007/s11418-017-1126-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-017-1126-1

Keywords

Search

Navigation