Skip to main content
SpringerLink
Log in

Seven new resin glycosides from the seeds of Quamoclit × multifida

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

Abstract

Seven new resin glycosides, multifidins III (1)–IX (7), were isolated from the seeds of Quamoclit × multifida (syn. Q. sloteri House) (Convolvulaceae), along with five known glycosides, quamoclinic acid B methyl ester (8), operculin XIII (9), quamoclin I (10), QM-10 (11), and QM-12 (12). Their structures were determined on the basis of spectroscopic data and chemical evidence. These compounds were of two different types, i.e., those with macrolactone structures and those with non-macrolactone structures. Additionally, cytotoxic activity towards HL-60 human leukemia cells of 1, 2, 5, 8, 9, 11, and 12 was evaluated. Among them, macrolactone-type resin glycosides (jalapins), 1, 2, and 9, specifically demonstrated clear cytotoxic activity with IC50 values of 3.46, 14.7, and 10.9 μM, respectively.

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. Shellard EJ (1961) The chemistry of some convolvulaceous resins part 1. Vera cruz jalap. Plant Med 9:102–116

    Article  CAS  Google Scholar 

  2. Mayer W (1855) Ueber die sogenannten jalappaharze. Justus Liebigs Annalen der Chemie 95:129–176

    Article  Google Scholar 

  3. Ono M (2017) Resin glycosides from Convolvulaceae plants. J Nat Med 71:591–604

    Article  CAS  Google Scholar 

  4. Hotta M, Ogata K, Nitta A, Hosikawa K, Yanagi M, Yamazaki K (eds) (1989) Useful plants of the world. Heibonsha Ltd., Tokyo, p 881

    Google Scholar 

  5. Ono M, Honda F, Karahashi A, Kawasaki T, Miyahara K (1997) Resin glycosides. XXV. multifidins I and II, new jalapins, from the seed of Quamoclit × multifida. Chem Pharm Bull 45:1955–1960

    Article  CAS  Google Scholar 

  6. Ono M, Kishida M, Ikegami Y, Takaki Y, Okawa M, Kinjo J, Yoshimitsu H, Nohara T, Miyahara K (2011) Components of convolvulin from Quamoclit × multifida. J Nat Med 65:95–102

    Article  CAS  Google Scholar 

  7. Ono M, Akiyama K, Kishida M, Okawa M, Kinjo J, Yoshimitsu H, Miyahara K (2013) Two new glycosidic acids, maltifidinic acids F and G, of the ether-insoluble resin glycosides (convolvulin) from the seeds of Quamoclit × multifida. J Nat Med 67:822–826

    Article  CAS  Google Scholar 

  8. Ono M, Yasuda S, Nishi K, Yamamoto K, Fuchizaki S, Higuchi S, Komatsu H, Okawa M, Kinjo J, Yoshimitsu H, Nohara T (2016) Two new triterpenoids from the seeds of blackberry (Rubus fructicosus). Nat Prod Res 30:904–911

    Article  CAS  Google Scholar 

  9. Yasuda S, Kuwata H, Kawamoto K, Shirakawa J, Atobe S, Hoshi Y, Yamasaki M, Nishiyama K, Tachibana H, Yamada K, Kobayashi H, Igoshi K (2012) Effect of highly lipolyzed goat cheese on HL-60 human leukemia cells: antiproliferative activity and induction of apoptotic DNA damage. J Dairy Sci 95:2248–2260

    Article  CAS  Google Scholar 

  10. Ono M, Takagi-Taki Y, Honda-Yamada F, Noda N, Miyahara K (2010) Components of ether-insoluble resin glycoside (convolvulin) from seeds of Quamoclit pennata. Chem Pharm Bull 58:666–672

    Article  CAS  Google Scholar 

  11. Ono M, Fujimoto K, Kawata M, Fukunaga T, Kawasaki T, Miyahara K (1992) Resin glycosides. XIII. Operculins VI, XI, XII, XIII, XIV and XV, the ether-soluble resin glycosides (jalapin) from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata). Chem Pharm Bull 40:1400–1403

    Article  CAS  Google Scholar 

  12. Ono M, Kuwabata K, Kawasaki T, Miyahara K (1992) Resin glycosides. XIV. Quamoclins I–IV, new ether-soluble resin glycosides (“jalapin”) from the seeds of Quamoclit pennata. Chem Pharm Bull 40:2674–2680

    Article  CAS  Google Scholar 

  13. Akiyama K, Yamamoto K, Mineno T, Okawa M, Kinjo J, Yoshimitsu H, Nohara T, Ono M (2014) Five new resin glycoside derivatives isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol. Chem Pharm Bull 62:125–133

    Article  CAS  Google Scholar 

  14. Ono M, Akiyama K, Yamamoto K, Mineno T, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T (2014) Four new acylated glycosidic acid methyl esters isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol. Chem Pharm Bull 62:830–835

    Article  CAS  Google Scholar 

  15. Ono M, Teramoto S, Naito S, Takahashi A, Yoneda A, Shinkai M, Taga N, Yauda S, Tsuchihasi R, Okawa M, Kinjo J, Yoshimitsu H, Nohara T (2018) Four new resin glycosides, murasakimasarins I–IV, from the tuber of Ipomoea batatas. J Nat Med 72:784–792

    Article  CAS  Google Scholar 

  16. Yu B, Luo J, Wang J, Zhang D, Yu S, Kong L (2013) Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities. Phytochemistery 95:421–427

    Article  CAS  Google Scholar 

  17. Fan BY, Gu YC, He Y, Li ZR, Luo JG, Kong LY (2014) Cytotoxic resin glycosides from Ipomoea aquatica and their effects on intracellular Ca2+ concentrations. J Nat Prod 77:2264–2272

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We express our appreciation to Mr. H. Harazono of Fukuoka University for the measurement of the FAB-MS. This research was supported in part by a Grant-in-Aid for Scientific Research (C) (JPS KAKENHI Grant number JP16K08306) and by the Research and Study Program/Project of Tokai University Educational System General Research Organization (Kanagawa, Japan).

Author information

Authors and Affiliations

  1. School of Agriculture, Tokai University, 9-1-1 Toroku, Higashi-ku, Kumamoto, 862-8652, Japan

    Masateru Ono, Maako Azuchi, Misato Ichio, Yuki Jiyoubi, Shuhei Tsutsumi & Shin Yasuda

  2. Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka, 814-0180, Japan

    Ryota Tsuchihasi, Masafumi Okawa & Junei Kinjo

  3. Faculty of Pharmaceutical Sciences, Sojo University, 4-22-2 Ikeda, Nishi-ku, Kumamoto, 860-0082, Japan

    Hitoshi Yoshimitsu & Toshihiro Nohara

Authors
  1. Masateru Ono
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maako Azuchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Misato Ichio
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yuki Jiyoubi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shuhei Tsutsumi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Shin Yasuda
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ryota Tsuchihasi
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Masafumi Okawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Junei Kinjo
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Hitoshi Yoshimitsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Toshihiro Nohara
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masateru Ono.

Ethics declarations

Conflict of interest

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ono, M., Azuchi, M., Ichio, M. et al. Seven new resin glycosides from the seeds of Quamoclit × multifida. J Nat Med 73, 11–22 (2019). https://doi.org/10.1007/s11418-018-1236-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-018-1236-4

Keywords

Search

Navigation