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Planta Med 2019; 85(11/12): 965-972
DOI: 10.1055/a-0958-2566
Biological and Pharmacological Activities
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Cardenolides from the Leaves of Acokanthera oblongifolia [ 1 ]

Łukasz Pecio
1   Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation State Research Institute, Puławy, Poland
,
Emad M. Hassan
2   Medicinal and Aromatic Plants Research Department, National Research Centre, Giza, Egypt
,
Elsayed A. Omer
2   Medicinal and Aromatic Plants Research Department, National Research Centre, Giza, Egypt
,
Gabriela Gajek
3   Laboratory of Cytogenetics, Department of Molecular Biotechnology and Genetics, University of Lodz, Poland
,
Renata Kontek
3   Laboratory of Cytogenetics, Department of Molecular Biotechnology and Genetics, University of Lodz, Poland
,
Andrzej Sobieraj
4   Department of Neurology and Neurosurgery, Faculty of Medical Sciences, University of Warmia and Mazury, Olsztyn, Poland
,
Anna Stochmal
1   Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation State Research Institute, Puławy, Poland
,
Wiesław Oleszek
1   Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation State Research Institute, Puławy, Poland
› Author Affiliations
Further Information

Publication History

received 15 January 2019
revised 11 June 2019

accepted 12 June 2019

Publication Date:
27 June 2019 (online)

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Abstract

Three previously undescribed cardenolides, acovenosigenin A 3-O-α-L-acofriopyranoside (1), 14-anhydroacovenosigenin A 3-O-[β-D-glucopyranosyl-(1″→4′)-O-α-L-acofriopyranoside] (2), and 14-anhydroacovenosigenin A 3-O-[β-D-glucopyranosyl-(1″→4′)-O-α-L-acovenopyranoside] (3), together with the two already known ones, 14-anhydrodigitoxigenin 3-O-β-D-glucopyranoside (4) and acospectoside A (5), were isolated from the leaves of Acokanthera oblongifolia. The influence of cardenolides 1 – 3 and acovenoside A (found in the Acokanthera genus) on three cancer cell lines (HT29, HCT116, and AGS) was also investigated. The most promising results, in comparison with oxaliplatin, were obtained for compound 1, which was found to be highly cytotoxic for all tested cell lines, HT29 (IC50 = 63.49 nM), HCT116 (IC50 = 67.35 nM), and AGS (IC50 = 80.92 nM). Unfortunately, 1 also showed similar toxicity towards normal lymphocytes (IC50 = 98.03 nM).

Key words

Acokanthera oblongifolia - cardenolide - cancer - cytotoxicity - Apocynaceae

1 Dedicated to Professor Dr. Cosimo Pizza 70th birthday in recognition of his outstanding contribution to natural product research.


Supporting Information

    1H and 13C NMR (1D and 2D) spectra for compounds 1 – 3 (Figs. 1S–27S) and NMR spectroscopic data for compounds 4 and 5 (Figs. 28S–29S) are available as Supporting Information.

  • Supporting Information
 

  • References

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