The Presence of a Cyclohexyldiamine Moiety Confers Cytotoxicity to Pentacyclic Triterpenoids

Sophie Hoenke; Martin A. Christoph; Sander Friedrich; Niels Heise; Benjamin Brandes; Hans-Peter Deigner; Ahmed Al-Harrasi; René Csuk

doi:10.3390/molecules26072102

Molecules (Apr 2021)

The Presence of a Cyclohexyldiamine Moiety Confers Cytotoxicity to Pentacyclic Triterpenoids

Sophie Hoenke,
Martin A. Christoph,
Sander Friedrich,
Niels Heise,
Benjamin Brandes,
Hans-Peter Deigner,
Ahmed Al-Harrasi,
René Csuk

Affiliations

Sophie Hoenke: Organic Chemistry, Martin–Luther University Halle–Wittenberg, Kurt–Mothes, Str. 2, D-06120 Halle (Saale), Germany
Martin A. Christoph: Organic Chemistry, Martin–Luther University Halle–Wittenberg, Kurt–Mothes, Str. 2, D-06120 Halle (Saale), Germany
Sander Friedrich: Organic Chemistry, Martin–Luther University Halle–Wittenberg, Kurt–Mothes, Str. 2, D-06120 Halle (Saale), Germany
Niels Heise: Organic Chemistry, Martin–Luther University Halle–Wittenberg, Kurt–Mothes, Str. 2, D-06120 Halle (Saale), Germany
Benjamin Brandes: Organic Chemistry, Martin–Luther University Halle–Wittenberg, Kurt–Mothes, Str. 2, D-06120 Halle (Saale), Germany
Hans-Peter Deigner: Institute of Precision Medicine, Medical and Life Science Faculty, Furtwangen University, Jakob–Kienzle–Str. 17, D-78054 Villigen–Schwenningen, Germany
Ahmed Al-Harrasi: Chair of Oman’s Medicinal Plants and Marine Natural Products, University of Nizwa, P.O. Box 33, Birkat Al-Mauz, PC 616 Nizwa, Oman
René Csuk: Organic Chemistry, Martin–Luther University Halle–Wittenberg, Kurt–Mothes, Str. 2, D-06120 Halle (Saale), Germany

DOI: https://doi.org/10.3390/molecules26072102
Journal volume & issue: Vol. 26, no. 7
p. 2102

Abstract

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Pentacyclic triterpenoids oleanolic acid, ursolic acid, betulinic acid, and platanic acid were acetylated and converted into several amides 9–31; the cytotoxicity of which has been determined in sulforhodamine B assays employing seral human tumor cell lines and nonmalignant fibroblasts. Thereby, a betulinic acid/trans-1,4-cyclohexyldiamine amide showed excellent cytotoxicity (for example, EC50 = 0.6 μM for HT29 colon adenocarcinoma cells).

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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