New Cardenolide Glycosides from the Seeds of Digitalis purpurea and Their Cytotoxic Activity

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  • KURODA Minpei
    Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • KUBO Satoshi
    Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • MATSUO Yukiko
    Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • ATOU Tomomi
    Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • SATOH Junichi
    Department of Hygiene and Health Sciences, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • FUJINO Tomofumi
    Department of Hygiene and Health Sciences, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • HAYAKAWA Makio
    Department of Hygiene and Health Sciences, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
  • MIMAKI Yoshihiro
    Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy

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  • New Cardenolide Glycosides from the Seeds of <i>Digitalis purpurea</i> and Their Cytotoxic Activity

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A chemical investigation of Digitalis purpurea seeds led to the isolation of three new cardenolide glycosides (1, 8 and 11), together with 12 known cardenolide glycosides (2–7, 9, 10 and 12–15). The structures of 1, 8 and 11 were determined by 1D and 2D NMR spectroscopic analyses and the results of an acid or enzymatic hydrolysis. The cytotoxic activity of the isolated compounds (1–15) against HL-60 leukemia cells was examined. Compounds 2, 9, 11 and 12 showed potent cytotoxicity against HL-60 cells with respective 50% inhibition concentration (IC50) values of 0.060, 0.069, 0.038, and 0.034 µM. Compounds 2, 9 and 11 also exhibited potent cytotoxic activity against HepG2 human liver cancer cells with respective IC50 values of 0.38, 0.79, and 0.71 µM. An investigation of the structure-activity relationship showed that the cytotoxic activity was reduced by the introduction of a hydroxy group at C-16 of the digitoxigenin aglycone, methylation of the C-3' hydroxy group at the fucopyranosyl moiety, and acetylation of the C-3' hydroxy group at the digitoxopyranoyl moiety.

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