Skip to main content
Log in

New spirostanol glycosides from Solanum nigrum and S. jasminoides

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

Abstract

A new characteristic steroidal glycoside possessing a hydroxyl group at C-23, inunigroside A (1), was isolated from the withered berries of Solanum nigrum L. On the basis of spectroscopic analysis, the structure of 1 was characterized as (5α,22S,23S,25R)-3β,23-dihydroxyspirostane 3-O-β-lycotetraoside. Next, a major steroidal sapogenol, (22R, 25S)-3β,15α-dihydroxy-spirost-5-ene (3), was obtained from the acid hydrolysate of the methanolic extract of the aerial parts of Solanum jasminoides L. A new bisdesmoside, 3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyl (22R,25S)-3β,15α-dihydroxyspirost-5-ene 15-O-α-l-rhamnopyranoside (4), named jasminoside A, was isolated from the methanolic extract of S. jasminoides.

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
Fig. 4

References

  1. Saijo R, Murakami K, Nohara T, Tomimatsu T, Sato A, Matsuoka K (1982) Studies on the constituents of the immature berries of Solanum nigrum L. Yakugaku Zasshi 102:300–305

    PubMed  CAS  Google Scholar 

  2. Nohara T, Ikeda T, Fujiwara Y, Matsushita S, Noguchi E, Yoshimitsu H, Ono M (2007) Physiological functions of solanaceous and tomato steroidal glycosides. J Nat Med 61:1–13

    Article  CAS  Google Scholar 

  3. Noguchi E, Fujiwara Y, Matsushita S, Ikeda T, Ono M, Nohara T (2006) Metabolism of tomato steroidal glycosides in human. Chem Pharm Bull 54:1312–1314

    Article  PubMed  CAS  Google Scholar 

  4. Nohara T (2010) Efficacy of tomato-saponin, esculeoside A. J Tradit Med 27:217–224

    CAS  Google Scholar 

  5. Nohara T, Ono M, Ikeda T, Fujiwara Y, El-Aasr M (2010) The tomato saponin, esculeoside A. J Nat Prod 73:1734–1741

    Article  CAS  Google Scholar 

  6. Yoshida K, Yahara S, Saijo R, Murakami K, Tomimatsu T, Nohara T (1887) Changes caused by included enzymes in the constituents of Solanum nigrum berries. Chem Pharm Bull 35:1645–1648

    Article  Google Scholar 

  7. Ito S, Takahama H, Kawaguchi T, Tanaka S, Iwaki MJ (2002) Post-transcriptional silencing of the tomatinase gene in Fusarium oxysporum f. sp lycopersici. Phytopathology 150:474–480

    Article  CAS  Google Scholar 

  8. Matsushita S, Yanai Y, Fusyuku A, Ikeda T, Ono M, Nohara T (2007) Distinction of absolute configuration at C-23 of C-23-hydroxyspirostane and C-23-hydroxy-spirosolane glycosides. Chem Pharm Bull 55:1079–1081

    Article  PubMed  CAS  Google Scholar 

  9. Freire R, Gonzalez AG, Suarez E (1970) New sources of steroid sapogenins––VIII: Sceptrumgenin and isoplexigenin A, B, C and D from Isoplexis sceptrum. Tetrahedron 26:3233–3244

    Article  Google Scholar 

  10. Matsushita S, Yoshizaki M, Fujiwara Y, Ikeda T, Ono M, Okawara T, Nohara T (2005) Facile conversion of 23-hydroxyspirosolane into pregnane. Tetrahedron Lett 46:3549–3551

    Article  CAS  Google Scholar 

  11. Soule S, Guenter C, Vazquez A, Argandona V, Moyna P, Ferreira F (2000) An aphid repellent glycoside from Solanum laxum. Phytochemistry 55:217–222

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Toshihiro Nohara.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ohno, M., Murakami, K., El-Aasr, M. et al. New spirostanol glycosides from Solanum nigrum and S. jasminoides . J Nat Med 66, 658–663 (2012). https://doi.org/10.1007/s11418-012-0637-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-012-0637-z

Keywords

Navigation