Chemical Structures of Saponins from Seeds of Edible Horse Chestnuts (Aesculus turbinata) after Treatment with Wooden Ashes and Their Hypoglycemic Activity

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  • Kimura Hideto
    The United Graduate School of Agricultural Sciences, Tottori University Kotobuki Seika Co., Ltd.
  • Watanabe Ai
    Kotobuki Seika Co., Ltd.
  • Jisaka Mitsuo
    The United Graduate School of Agricultural Sciences, Tottori University Department of Life Science and Biotechnology, Faculty of Life and Environmental Science, Shimane University
  • Yamamoto Tatsuyuki
    The United Graduate School of Agricultural Sciences, Tottori University Department of Life Science and Biotechnology, Faculty of Life and Environmental Science, Shimane University
  • Kimura Yasuo
    The United Graduate School of Agricultural Sciences, Tottori University Department of Biological and Environmental Chemistry, Faculty of Agriculture
  • Katsube Takuya
    Shimane Institute for Industrial Technology
  • Yokota Kazushige
    The United Graduate School of Agricultural Sciences, Tottori University Department of Life Science and Biotechnology, Faculty of Life and Environmental Science, Shimane University

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Other Title
  • あく抜き処理トチノキ種子のサポニン成分の化学構造と血糖値上昇抑制作用
  • アクヌキ ショリ トチノキ シュシ ノ サポニン セイブン ノ カガク コウゾウ ト ケットウチ ジョウショウ ヨクセイ サヨウ

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The seeds of Japanese horse chestnuts (Aesculus turbinata) contain large amounts of mixed triterpenoidal saponins called "escins". Recent studies have shown that escins have several biological activities including anti-inflammatory action and inhibitory effect on the absorption of ethanol or glucose. For the edible utilization of the seeds, the seeds are usually treated with wooden ashes to remove harshness. Here, we found the novel compounds derived from escin in the seeds of horse chestnuts after the food processing with wooden ashes. The instrumental analyses revealed the chemical structures of four types of the escin derivatives. Those were identified as deacetylated forms of escins I a, II a, I b and II b. However, tigloyl and angeloyl moieties of escins were more resistant to the hydrolysis with wood ashes. To determine the biological activity of deacetylated forms of escins, the fraction including four types of deacetylated escins was used for an oral glucose tolerance test in mice. The analysis revealed that a single oral administration of 300mg/kg of those saponins was effective to show significant hypoglycemic activity. Taken together, the results suggested the potential usefulness of the saponins generated during the food processing of horse chestnuts with wooden ashes for functional food.

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