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Medicinal Chemistry Research

, Volume 27, Issue 1, pp 268–277 | Cite as

Triterpenoids from the stem bark of Vitellaria paradoxa (Sapotaceae) and derived esters exhibit cytotoxicity against a breast cancer cell line

  • Kenneth O. Eyong
  • Guerisson Bairy
  • Anna A. Eno
  • Joseph Taube
  • Kenneth G. Hull
  • Gabriel N. Folefoc
  • Harquin S. Foyet
  • Daniel Romo
Original Research

Abstract

A study of the chemical constituents of the stem bark of Vitellaria paradoxa (Sapotaceae) has resulted in the isolation and characterization of a new ursane-type triterpenoid, 2β,3β,19α-trihydroxyurs-12-en-28-oic acid (1), together with seven known compounds: betulinic acid (2), 1α,2β,3β,19α-tretrahydroxyurs-12-en-28-oic acid (3), β-sitosterol (7), sigmasterol (8), (-)-epicatechin (9), (+)-catechin (10) and quercetin (11). The structure of the novel, ursane-type acid 1 was elucidated on the basis of detailed spectroscopic analysis including IR, HRMS (ESI), 1D and 2D NMR and a comparison to previously described, related natural products. Preliminary cytotoxicity assays against the MDA-MB-231 breast cancer cell line indicated that betulinic acid 2 and its corresponding methyl ester 5 were the most active compounds tested with IC50 values of 19.9 μM (17.2–23.1 μM, 95% CI) and 32.9 μM (24.9–43.4 μM, 95% CI), respectively. Esterification of acids 1–3 afforded the corresponding methyl esters 4–6 for additional structure-activity relationship (SAR) analysis. In general, the activity against the MDA-MB-231 breast cancer cell line increased upon esterification of the triterpenoids screened.

Keywords

plant-derived natural products ursane family isolation structure elucidation Apoptosis/necrosis assay 

Notes

Acknowledgements

The authors would like to acknowledge the council for International Exchange of Scholars (CIES) for the J. William Fulbright Visiting Scholar program to Dr Kenneth Eyong. The Baylor CPRIT Synthesis and Drug Lead Discovery Laboratory (supported by the Cancer Prevention and Research Institute of Texas R1309 and Baylor University, College of Arts and Sciences) and the Molecular Bioscience Center hosted Dr. Eyong. The Departments of Chemistry & Biochemistry and Department of Biology at Baylor University are acknowledged for infrastructure and financial support. The University of Yaounde I and the Government of Cameroon are acknowledged for financial support through the Fonds d’Appuis a la Recherche.

Supplementary material

44_2017_2059_MOESM1_ESM.pdf (7.7 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Kenneth O. Eyong
    • 1
    • 2
  • Guerisson Bairy
    • 2
  • Anna A. Eno
    • 3
  • Joseph Taube
    • 4
  • Kenneth G. Hull
    • 1
  • Gabriel N. Folefoc
    • 2
  • Harquin S. Foyet
    • 5
  • Daniel Romo
    • 1
  1. 1.Department of Chemistry and Biochemistry and the CPRIT Synthesis and Drug-Lead Discovery LaboratoryBaylor UniversityWacoUSA
  2. 2.Department of Organic Chemistry, Faculty of ScienceUniversity of Yaounde IYaoundeCameroon
  3. 3.Department of Microbiology, Faculty of ScienceUniversity of Yaounde IYaoundeCameroon
  4. 4.Department of Biology and Institute for Biomedical StudiesBaylor UniversityWacoUSA
  5. 5.Department of Biological Sciences, Faculty of ScienceUniversity of MarouaMarouaCameroon

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