Triterpenoids from the stem bark of Vitellaria paradoxa (Sapotaceae) and derived esters exhibit cytotoxicity against a breast cancer cell line
| Autor: | Gabriel N. Folefoc, Kenneth G. Hull, Kenneth O. Eyong, Daniel Romo, Joseph H. Taube, Harquin Simplice Foyet, Anna A. Eno, Guerisson Bairy |
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| Rok vydání: | 2017 |
| Předmět: |
Stem bark
biology 010405 organic chemistry Stereochemistry Organic Chemistry biology.organism_classification 01 natural sciences Sapotaceae 0104 chemical sciences 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Triterpenoid chemistry Breast cancer cell line 030220 oncology & carcinogenesis Betulinic acid General Pharmacology Toxicology and Pharmaceutics Quercetin Cytotoxicity Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Medicinal Chemistry Research. 27:268-277 |
| ISSN: | 1554-8120 1054-2523 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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