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Four new resin glycosides from Ipomoea muricata seeds: muricatins XIV–XVII

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Abstract

Ipomoea muricata (L.) Jacq. seeds (Convolvulaceae) are used as a traditional laxative and carminative medicine. Muricatins XIV (1), XV (2), XVI (3), and XVII (4), were isolated from I. muricata seeds as four new resin glycosides, along with seven known compounds, three of which were isolated for the first time as natural products; their structures were determined using MS and NMR spectroscopy. Compounds 1–4 are macrolactones (jalapins); the sugar moieties of 1, 2, and 4 are partially acylated with 2S-methylbutyric acid, while that of 3 is esterified with 2S-methylbutyric and 2S-methyl-3S-hydroxybutyric acids. In addition, the antiviral activities of the seven compounds obtained in this study, together with five known compounds obtained in our previous study into resin glycosides from I. muricata seeds, were evaluated against herpes simplex virus type 1 (HSV-1); their cytotoxicities against HL-60 human promyelocytic leukemia cells were also investigated. All examined jalapins exhibited similar or slightly weaker anti-HSV-1 activities than acyclovir, the positive control; however, the glycosidic acid of 4 was inactive, while its methyl ester was weakly active. On the other hand, cytotoxicity testing against HL-60 cells showed similar results to those observed during anti-HSV-1 activity testing, with the exception that one jalapin was less active.

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Acknowledgements

We express our appreciation to Mr. H. Harazono of Fukuoka University for the measurement of the FAB-MS and ESI-TOF-MS. This research was partially supported by the Research and Study Project of Tokai University General Research Organization (Kanagawa, Japan).

Funding

This research was partially supported by a Grant-in-Aid for Scientific Research (C) (JSPS KAKENHI Grant Numbers JP16K08306 and JP20K07117).

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Authors and Affiliations

  1. School of Agriculture, Tokai University, 871-12 Sugido, Mashiki-Cho, Kamimashiki-Gun, Kumamoto, 861-2205, Japan

    Masateru Ono, Daiki Tenmaya, Maki Tarumi, Syouri Satou, Kotone Tsuji, Hirotaka Nishikawa & Shin Yasuda

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

    Hiroyuki Miyashita, Jian-Rong Zhou, Kazumi Yokomizo & Hitoshi Yoshimitsu

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

    Ryota Tsuchihashi, Masafumi Okawa & Junei Kinjo

Authors
  1. Masateru Ono
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  2. Daiki Tenmaya
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  3. Maki Tarumi
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  4. Syouri Satou
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  6. Hirotaka Nishikawa
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  7. Shin Yasuda
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  8. Hiroyuki Miyashita
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  9. Jian-Rong Zhou
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  10. Kazumi Yokomizo
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  11. Hitoshi Yoshimitsu
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  12. Ryota Tsuchihashi
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  13. Masafumi Okawa
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  14. Junei Kinjo
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Contributions

Prof. Dr. Ono supervised the research, wrote the manuscript, and analyzed the data. Mr. D. Tenmaya, M. Tarumi, S. Satou, and K. Tsuji purified the compounds. Mr. Nishikawa and Prof. Dr. Yasuda were responsible for the antitumor activity. Prof. Dr. K. Yokomizo and Dr. J. Zhou were responsible for the anti-HSV-1 assay. Dr. Miyashita, Prof. Dr. Yoshimitsu, Dr. Tsuchihasi, Prof. Dr. Okawa, and Prof. Dr. Kinjo performed instrumental analysis and data analysis.

Corresponding author

Correspondence to Masateru Ono.

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Ono, M., Tenmaya, D., Tarumi, M. et al. Four new resin glycosides from Ipomoea muricata seeds: muricatins XIV–XVII. J Nat Med (2024). https://doi.org/10.1007/s11418-024-01787-1

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