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Identification and characterization of organic and glycosidic acids in crude resin glycoside fraction from Calystegia hederacea

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Abstract

Resin glycosides are well known as the purgative ingredients, which are characteristic of convolvulaceous plants. Calystegia hederacea Wall. is a perennial herbaceous vine that is widespread throughout India and East Asia. All parts of this plant are used for the treatment of menoxenia, gonorrhea, etc. Alkaline hydrolysis of the crude resin glycoside fraction of the whole plants of C. hederacea yielded four new glycosidic acids, calyhedic acids A, B, C, and D, along with two known glycosidic acids, calysolic acids A and C, and three known organic acids, 2S-methylbutyric, tiglic, and 2R,3R-nilic acids. Their structures were characterized on the basis of spectroscopic data and chemical evidence. Calyhedic acids A, B, and D were penta-, hexa-, and hepta-glycosides of 12S-hydroxyhexadecanoic acid, respectively, and cayhedic acid C was an isomer of calyhedic acid D, in which the 12S-hydroxyhexadecanoyl residue of calyhedic acid D was replaced by a 11S-hydroxyhexadecanoyl residue. Additionally, cytotoxic activity toward HL-60 human promyelocytic leukemia cells of the crude resin glycoside fraction, the glycosidic acid fraction, calyhedic acid A, and calysolic acid A from C. hederacea was evaluated. Furthermore, to clarify the structure–activity relationship of resin glycosides, the activities of six genuine resin glycosides with calysolic acid A or calysolic acid C as the glycosidic acid, which were isolated from C. soldanella, were examined. Among them, the crude resin glycoside fraction and five genuine resin glycosides with macrolactone structures demonstrated clear cytotoxic activities, while the glycosidic acid fraction, calyhedric acid A, calysolic acid A, and a genuine non-macrolactone-type resin glycoside were either inactive or exhibited weaker activity than the tested macrolactone-type resin glycosides.

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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).

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Authors and Affiliations

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

    Masateru Ono, Yoshino Ichihara, Nao Saito, Minami Yamada, Kana Yuuki, Masami Nawata, Shuhei Tsutsumi & Shin Yasuda

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

    Ryota Tsuchihashi, Masafumi Okawa & Junei Kinjo

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

    Hiroyuki Miyashita, Hitoshi Yoshimitsu & Toshihiro Nohara

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  1. Masateru Ono
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  2. Yoshino Ichihara
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Correspondence to Masateru Ono.

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Ono, M., Ichihara, Y., Saito, N. et al. Identification and characterization of organic and glycosidic acids in crude resin glycoside fraction from Calystegia hederacea. J Nat Med 74, 200–211 (2020). https://doi.org/10.1007/s11418-019-01366-9

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  • DOI: https://doi.org/10.1007/s11418-019-01366-9

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