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Seven new resin glycosides from the seeds of Quamoclit × multifida

  • Masateru Ono
  • Maako Azuchi
  • Misato Ichio
  • Yuki Jiyoubi
  • Shuhei Tsutsumi
  • Shin Yasuda
  • Ryota Tsuchihasi
  • Masafumi Okawa
  • Junei Kinjo
  • Hitoshi Yoshimitsu
  • Toshihiro Nohara
Original Paper

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.

Keywords

Resin glycoside Jalapin Multifidin Quamoclit × multifida Convolvulaceae Cytotoxic activity 

Notes

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).

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK, part of Springer Nature 2018

Authors and Affiliations

  • Masateru Ono
    • 1
  • Maako Azuchi
    • 1
  • Misato Ichio
    • 1
  • Yuki Jiyoubi
    • 1
  • Shuhei Tsutsumi
    • 1
  • Shin Yasuda
    • 1
  • Ryota Tsuchihasi
    • 2
  • Masafumi Okawa
    • 2
  • Junei Kinjo
    • 2
  • Hitoshi Yoshimitsu
    • 3
  • Toshihiro Nohara
    • 3
  1. 1.School of AgricultureTokai UniversityKumamotoJapan
  2. 2.Faculty of Pharmaceutical SciencesFukuoka UniversityFukuokaJapan
  3. 3.Faculty of Pharmaceutical SciencesSojo UniversityKumamotoJapan

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