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Identification and characterization of organic and glycosidic acids in the crude resin glycoside fraction from the leaves and stems of Calystegia japonica

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Abstract

The alkaline hydrolysis of the crude resin glycoside fraction from the leaves and stems of the plant Calystegia japonica Choisy (Convolvulaceae) yielded organic acid and glycosidic acid fractions. The organic acid fraction was esterified with p-bromophenacyl bromide to obtain p-bromophenacyl 2R-methyl-3R-hydroxybutyrate (1) and p-bromophenacyl (E)-2-methylbut-2-enoate (2). By treating the glycosidic acid fraction with trimethylsilyldiazomethane–hexane, seven new methyl esters of glycosidic acids, namely calyjaponic acid A methyl ester (3) calyjaponic acid B methyl ester (5), calyjaponic acid C methyl ester (6), calyjaponic acid D methyl ester (7), calyjaponic acid E methyl ester (8), calyjaponic acid F methyl ester (9), and calyjaponic acid G methyl ester (10), were isolated along with one known ester (4). Their structures were characterized based on spectroscopic and chemical analyses. Compounds 3–8 had the same sugar moiety, α-L-rhamnopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 2)-[O-α-L-rhamnopyranosyl-(1 → 6)]-O-β-D-glucopyranose, and the aglycones of 3–8 were methyl 3S,11S-dihydroxyhexadecanoate, methyl 3S,12S-dihydroxyhexadecanoate, methyl 11S-hydroxyhexadecanoate, methyl 11S-hydroxypentadecanoate, methyl 3S,11S-dihydroxypentadecanoate, and methyl 3S,12S-dihydroxypentadecanoate, respectively. Compounds 9 and 10 were derivatives of 3 and 4, respectively, in which the C-6 of the second glucosyl residue was methylated. Compounds 6–8 contained methyl esters of unusual odd-carbon fatty acids as aglycones. The cytotoxicity of the crude resin glycoside fraction and 3 against HL-60 human promyelocytic leukemia cells was evaluated further; both were either weakly active or inactive compared to the positive control, cisplatin.

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Data availability

The data that support the findings of this study are available from the corresponding authors upon reasonable request.

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Acknowledgements

We express our appreciation to Mr. H. Harazono of Fukuoka University for the measurement of the MS. This research was supported in part by a Grant-in-Aid for Scientific Research (C) (JSPS KAKENHI Grant Numbers JP16K08306 and JP20K07117) 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

    Kazutaka Uemura, Saaya Kimura, Yuuki Saito, Syun Koyama, Hirotaka Nishikawa, Shin Yasuda & Masateru Ono

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

    Hiroyuki Miyashita & 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

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  1. Kazutaka Uemura
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Uemura, K., Kimura, S., Saito, Y. et al. Identification and characterization of organic and glycosidic acids in the crude resin glycoside fraction from the leaves and stems of Calystegia japonica. J Nat Med 77, 284–297 (2023). https://doi.org/10.1007/s11418-022-01669-4

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