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
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).
