New Cardenolide Glycosides from the Seeds of <i>Digitalis purpurea</i> and Their Cytotoxic Activity
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- KURODA Minpei
- Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- KUBO Satoshi
- Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- MATSUO Yukiko
- Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- ATOU Tomomi
- Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- SATOH Junichi
- Department of Hygiene and Health Sciences, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- FUJINO Tomofumi
- Department of Hygiene and Health Sciences, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- HAYAKAWA Makio
- Department of Hygiene and Health Sciences, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
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- MIMAKI Yoshihiro
- Department of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy
Bibliographic Information
- Other Title
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- New Cardenolide Glycosides from the Seeds of Digitalis purpurea and Their Cytotoxic Activity
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Abstract
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.
Journal
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 77 (6), 1186-1192, 2013
Japan Society for Bioscience, Biotechnology, and Agrochemistry
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Keywords
Details 詳細情報について
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- CRID
- 1390001206479834368
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- NII Article ID
- 10031184679
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- NII Book ID
- AA10824164
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- COI
- 1:STN:280:DC%2BC3sjhtFWjuw%3D%3D
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- ISSN
- 13476947
- 09168451
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- NDL BIB ID
- 024646890
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- PubMed
- 23748755
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed