A new β-hydroxydihydrochalcone from Tephrosia uniflora, and the revision of three β-hydroxydihydrochalcones to flavanones

Carolyne Chepkirui; Catarina Bourgard; Pieter J Gilissen; Albert Ndakala; Solomon Derese; Yukino Gütlin; Máté Erdélyi; Abiy Yenesew

doi:10.1016/j.fitote.2022.105166

A new β-hydroxydihydrochalcone from Tephrosia uniflora, and the revision of three β-hydroxydihydrochalcones to flavanones

Fitoterapia. 2022 Apr:158:105166. doi: 10.1016/j.fitote.2022.105166. Epub 2022 Feb 25.

Authors

Carolyne Chepkirui¹, Catarina Bourgard², Pieter J Gilissen³, Albert Ndakala⁴, Solomon Derese⁴, Yukino Gütlin², Máté Erdélyi⁵, Abiy Yenesew⁶

Affiliations

¹ Department of Chemistry, University of Nairobi, P.O. Box 30197-00100, Nairobi, Kenya; Department of Physical and Biological Sciences, Kabarak University, Private Bag 20157 Nakuru, Kenya.
² Department of Chemistry and Molecular Biology, Center for Antibiotic Resistance Research (CARe), University of Gothenburg, SE-412 96 Gothenburg, Sweden.
³ Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
⁴ Department of Chemistry, University of Nairobi, P.O. Box 30197-00100, Nairobi, Kenya.
⁵ Department of Chemistry - BMC, Uppsala University, SE-752 37 Uppsala, Sweden. Electronic address: mate.erdelyi@kemi.uu.se.
⁶ Department of Chemistry, University of Nairobi, P.O. Box 30197-00100, Nairobi, Kenya. Electronic address: ayenesew@uonbi.ac.ke.

PMID: 35219716
DOI: 10.1016/j.fitote.2022.105166

Abstract

The CH₂Cl₂/MeOH (1:1) extract of the stems of Tephrosia uniflora yielded the new β-hydroxydihydrochalcone (S)-elatadihydrochalcone-2'-methyl ether (1) along with the three known compounds elongatin (2), (S)-elatadihydrochalcone (3), and tephrosin (4). The structures were elucidated by NMR spectroscopic and mass spectrometric data analyses. Elongatin (2) showed moderate antibacterial activity (EC₅₀ of 25.3 μM and EC₉₀ of 32.8 μM) against the Gram-positive bacterium Bacilus subtilis, and comparable toxicity against the MCF-7 human breast cancer cell line (EC₅₀ of 41.3 μM). Based on the comparison of literature and predicted NMR data with that obtained experimentally, we propose the revision of the structures of three β-hydroxydihydrochalcones to flavanones.

Keywords: Antibacterial activity; Elongatin; Flavanone; Structure revision; Tephrosia uniflora; β-Hydroxydihydrochalcone.

MeSH terms

Flavanones* / chemistry
Flavanones* / pharmacology
Gram-Positive Bacteria
Humans
Molecular Structure
Plant Extracts / chemistry
Tephrosia* / chemistry

Substances

Flavanones
Plant Extracts