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New 8,12;8,20-diepoxy-8,14-secopregnane hexa- and hepta-glycosides from the roots of Asclepias tuberosa

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Abstract

Previously, phytochemical investigation of the roots of Asclepias tuberosa (Asclepiadaceae) led to the isolation of some 8,12;8,20-diepoxy-8,14-secopregnane tri-, tetra-, and penta-glycosides. An additional eight new minor 8,12;8,20-diepoxy-8,14-secopregnane glycosides were afforded in the recent investigation of this plant. These glycosides consisted of six or seven 2,6-dideoxy-hexopyranoses together with the aglycone, tuberogenin. The structures of each of these compounds were established using NMR, mass spectroscopic analysis and chemical evidence. As 8,12;8,20-diepoxy-8,14-secopregnane-type glycosides were observed only in A. tuberosa, these compounds were considered to be characteristic phytochemicals of this plant.

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Authors and Affiliations

  1. School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan

    Tsutomu Warashina

  2. School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan

    Toshio Miyase

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  1. Tsutomu Warashina
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  2. Toshio Miyase
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Correspondence to Tsutomu Warashina.

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Warashina, T., Miyase, T. New 8,12;8,20-diepoxy-8,14-secopregnane hexa- and hepta-glycosides from the roots of Asclepias tuberosa . J Nat Med 72, 347–356 (2018). https://doi.org/10.1007/s11418-017-1155-9

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