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New isoflavone glucosides in yabumame (Amphicarpaea bracteata (L.) Fernald subsp. edgeworthii (Benth.) H.Ohashi var. japonica (Oliv.) H.Ohashi) and their effect on leukotriene B4 production in mast cells

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Abstract

Yabumame (Amphicarpaea bracteata (L.) Fernald subsp. edgeworthii (Benth.) H.Ohashi var. japonica (Oliv.) H.Ohashi) is a legume plant that the Ainu people eat as a traditional food, although the bioactive ingredients other than vitamins have not been studied. In this study, the structures of yabumame isoflavone glucosides were determined and their effect on leukotriene (LT) B4, a chemical mediator of type I allergy, produced in mast cells, was investigated in vitro. Seven compounds were isolated from yabumame. Their structures were determined by spectroscopic and spectrometric analyses, which were genistein-7-O-β-d-glucoside (1), formononetin-7-O-(2″-O-β-d-glucosyl)-β-d-glucoside (2), formononetin-7-O-β-d-glucoside (3), biochanin A-7-O-(2″-O-β-d-glucosyl)-β-d-glucoside (4), formononetin-7-O-(6″-O-malonyl)-β-d-glucoside (5), biochanin A-7-O-(2″-O-β-d-glucosyl-6″-O-β-d-glucosyl)-β-d-glucoside (6), and biochanin A-7-O-(6″-O-malonyl)-β-d-glucoside (7). Compounds 2, 4, and 6 were determined as new compounds. Compound 3 showed statistically significant suppressive effect on LTB4 production in mast cells, although the activity was not strong. On the other hand, biochanin A, an aglycone common to compounds 4, 6, and 7, strongly inhibited the LTB4 production. The results suggest that some of yabumame isoflavone glucosides might contribute to mitigate type I allergy.

Graphic abstract

Seven isoflavone glucosides including 3 new compounds were found in yabumame and their anti-allergic effect was evaluated.

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Acknowledgements

This work has been supported by the Tojuro lijima Foundation for Food Science and Technology.

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Authors and Affiliations

  1. Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, 165 Koencho, Kitami, Hokkaido, 090-8507, Japan

    Lifeng Yang, Jyunichi Kirikoshi, Daiki Sato, Takashi Yamagishi & Hirofumi Arai

  2. Jinan Fruit Research Institute, All China Federation of Supply and Marketing Cooperatives, 16001 East Road Jingshi, Jinan, 250220, Shandong, China

    Lifeng Yang & Maoyu Wu

  3. Department of Life Science, Kyushu Sangyo University, 2-3-1 Matsukadai, Higashi-ku, Fukuoka, 813-8503, Japan

    Mikako Takasugi

  4. National Institutes of Biomedical Innovation, Health and Nutrition, 108-4 Ohashi, Nayoro, Hokkaido, 096-0065, Japan

    Atsuyuki Hishida, Shigeki Hayashi & Nobuo Kawahara

  5. Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hokkaido University of Science, Maeda 7-15-4-1, Teine, Sapporo, Hokkaido, 006-8585, Japan

    Megumi Mizukami

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  1. Lifeng Yang
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Correspondence to Hirofumi Arai.

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Yang, L., Kirikoshi, J., Sato, D. et al. New isoflavone glucosides in yabumame (Amphicarpaea bracteata (L.) Fernald subsp. edgeworthii (Benth.) H.Ohashi var. japonica (Oliv.) H.Ohashi) and their effect on leukotriene B4 production in mast cells. J Nat Med 75, 28–36 (2021). https://doi.org/10.1007/s11418-020-01439-0

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