2. Academic Validation
  3. Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities

Jozibrevine D from Ancistrocladus ileboensis, the fifth alkaloid in a series of six possible atropo-diastereomeric naphthylisoquinoline dimers, showing antiparasitic and antileukemic activities

  • Bioorg Med Chem Lett. 2023 Apr 15:86:129258. doi: 10.1016/j.bmcl.2023.129258.
Jun Li 1,  Nasir Tajuddeen 2,  Doris Feineis 3,  Virima Mudogo 4,  Marcel Kaiser 5,  Ean-Jeong Seo 6,  Thomas Efferth 6,  Gerhard Bringmann 7
Affiliations

Affiliations

  • 1 Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany; Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011 Urumqui, People's Republic of China.
  • 2 Department of Chemistry, Ahmadu Bello University, 810107 Zaria, Nigeria.
  • 3 Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
  • 4 Faculté des Sciences, Université de Kinshasa, B.P. 202, Kinshasa XI, Democratic Republic of the Congo.
  • 5 Swiss Tropical and Public Health Institute, Kreuzstrasse 2, CH-4123 Allschwil, Switzerland; University of Basel, Petersplatz 1, CH-4003 Basel, Switzerland.
  • 6 Institute of Pharmaceutical and Biomedical Sciences, Department of Pharmaceutical Biology, University of Mainz, Staudinger Weg 5, D-55128 Mainz, Germany.
  • 7 Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany. Electronic address: bringman@chemie.uni-wuerzburg.de.
PMID: 36972793 DOI: 10.1016/j.bmcl.2023.129258
Abstract

A new dimeric naphthylisoquinoline alkaloid, jozibrevine D (4e), was isolated from the Central-African liana Ancistrocladus ileboensis. It is a Dioncophyllaceae-type metabolite, being R-configured at C-3 and lacking an oxygen function at C-6 in both isoquinoline moieties. The two identical monomers of jozibrevine D are symmetrically linked via the sterically constrained 3',3''-positions of the naphthalene units so that the central biaryl linkage is rotationally hindered and the alkaloid is, thus, C2-symmetric. With the two outer biaryl bonds being chiral, too, 4e possesses three consecutive stereogenic axes. The absolute stereostructure of the new compound was assigned by 1D and 2D NMR, ruthenium-mediated oxidative degradation, and electronic circular dichroism (ECD) spectroscopy. Jozibrevine D (4e) is the fifth discovered isomer in a series of six possible natural atropo-diastereomeric dimers. It shows potent, and selective, antiprotozoal activity against P. falciparum (IC50 = 0.14 μM), and it also exhibits good cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells (IC50 = 11.47 μM) and their multidrug-resistant CEM/ADR5000 subline (IC50 = 16.61 μM).

Keywords

Alkaloids; Antileukemic; Antiplasmodial; Axial chirality; Dimers; Jozibrevine D; Naphthylisoquinolines.

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