Bi- and bisbibenzyls from the roots of Dichapetalum heudelotii and their antiproliferative activities

Dorcas Osei-Safo; Godwin Akpeko Dziwornu; Antonio Salgado; Suthananda Naidu Sunassee; Mary Anti Chama

doi:10.1016/j.fitote.2017.09.001

Bi- and bisbibenzyls from the roots of Dichapetalum heudelotii and their antiproliferative activities

Fitoterapia. 2017 Oct:122:95-100. doi: 10.1016/j.fitote.2017.09.001. Epub 2017 Sep 4.

Authors

Dorcas Osei-Safo¹, Godwin Akpeko Dziwornu², Antonio Salgado³, Suthananda Naidu Sunassee⁴, Mary Anti Chama⁵

Affiliations

¹ Chemistry Department, School of Physical and Mathematical Sciences, College of Basic and Applied Sciences, University of Ghana, P. O. Box LG 56, Legon, Accra, Ghana. Electronic address: dosei-safo@ug.edu.gh.
² Chemistry Department, School of Physical and Mathematical Sciences, College of Basic and Applied Sciences, University of Ghana, P. O. Box LG 56, Legon, Accra, Ghana; Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa. Electronic address: dzwgod001@myuct.ac.za.
³ Centro de Espectroscopía de RMN (CERMN), CAI Químicas, University of Alcalá, E-28805, Alcalá de Henares, Madrid, Spain. Electronic address: a.salgado@uah.es.
⁴ Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa; South African Medical Research Council Drug Discovery and Development Research Unit, University of Cape Town, Rondebosch 7701, South Africa. Electronic address: sunny.sunassee@uct.ac.za.
⁵ Chemistry Department, School of Physical and Mathematical Sciences, College of Basic and Applied Sciences, University of Ghana, P. O. Box LG 56, Legon, Accra, Ghana.

PMID: 28882670
DOI: 10.1016/j.fitote.2017.09.001

Abstract

Two new bisbibenzyls, heudelotol A (1) and B (2), along with the known bibenzyls, (E)-combretastatin A-1 (3) and combretastatin B-1 (4) have been isolated from the ethyl acetate extract of the roots of Dichapetalum heudelotii. Structure elucidation of all four isolated compounds was achieved using UV, IR, 1D and 2D NMR spectroscopy and HR-Mass Spectrometry. The compounds exhibited varying antiproliferative activity against six cancer cell lines using the CellTiter-Glo® Luminiscent Cell Viability Assay. Compound 3 was found to be the most active with sub-micromolar growth inhibition concentrations against all the cell lines (GI₅₀ 0.03-0.72μM). However, it was about ten-fold less active than the positive control, taxol. The new bisbibenzyls heudelotol A and B exhibited good activity against human pancreatic adenocarcinoma (GI₅₀ 9.04μM) and Burkitt's lymphoma (GI₅₀ 4.67μM) respectively, and average activity against the other cancer cell lines.

Keywords: Antiproliferative activity; Bisbibenzyls; Combretastatins; Dichapetalaceae; Dichapetalum heudelotii.

MeSH terms

Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Bibenzyls / isolation & purification
Bibenzyls / pharmacology*
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Magnoliopsida / chemistry*
Molecular Structure
Plant Roots / chemistry
Stilbenes / isolation & purification
Stilbenes / pharmacology*

Substances

Antineoplastic Agents, Phytogenic
Bibenzyls
Stilbenes
combretastatin B-1
heudelotol A
heudelotol B
combretastatin A-1