Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis

Weam Siheri, Godwin U. Ebiloma, John O. Igoli, Alexander I. Gray, Marco Biddau, Pilaslak Akrachalanont, Samya Samya Sh M D Alenezi, Mohammad A. Alwashih, RuAngelie Edrada Ebel, Sylke Müller, Catherine E. Lawrence, James Fearnley, David G. Watson, Harry P. De Koning

Research output: Contribution to journal › Article

Abstract

Twelve propolis samples from different parts of Libya were investigated for their phytochemical constituents. Ethanol extracts of the samples and some purified compounds were tested against Trypanosoma brucei, Plasmodium falciparum and against two helminth species, Trichinella spiralis and Caenorhabditis elegans, showing various degrees of activity. Fourteen compounds were isolated from the propolis samples, including a novel compound Taxifolin-3-acetyl-4’-methyl ether (4), a flavanonol derivative. The crude extracts showed moderate activity against T. spiralis and C. elegans, while the purified compounds had low activity against P. falciparum. Anti-trypanosomal activity (EC50 = 0.7 µg/mL) was exhibited by a fraction containing a cardol identified as bilobol (10) and this fraction had no effect on Human Foreskin Fibroblasts (HFF), even at 2.0 mg/mL, thus demonstrating excellent selectivity. A metabolomics study was used to explore the mechanism of action of the fraction and it revealed significant disturbances in trypanosomal phospholipid metabolism, especially the formation of choline phospholipids. We conclude that a potent and highly selective new trypanocide may be present in the fraction.
LanguageEnglish
Article number1041
Number of pages12
JournalMolecules
Volume24
Issue number6
DOIs
Publication statusPublished - 15 Mar 2019

Fingerprint

Propolis
Trichinella spiralis
Caenorhabditis elegans
Plasmodium falciparum
isolation
Phospholipids
Trypanocidal Agents
Libya
Foreskin
Methyl Ethers
Trypanosoma brucei brucei
Metabolomics
Helminths
Phytochemicals
Fibroblasts
Choline
Complex Mixtures
Metabolism
Ethanol
Derivatives

Keywords

  • trypanosoma brucei
  • bilobol
  • alkylresorcinol
  • metabolomics
  • anthelminthic activity

Cite this

Siheri, Weam ; Ebiloma, Godwin U. ; Igoli, John O. ; Gray, Alexander I. ; Biddau, Marco ; Akrachalanont, Pilaslak ; Samya Sh M D Alenezi, Samya ; Alwashih, Mohammad A. ; Edrada Ebel, RuAngelie ; Müller, Sylke ; Lawrence, Catherine E. ; Fearnley, James ; Watson, David G. ; De Koning, Harry P. / Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis. In: Molecules. 2019 ; Vol. 24, No. 6.
@article{d89ddd2bd3844f85bd545ce00e73b2b5,
title = "Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis",
abstract = "Twelve propolis samples from different parts of Libya were investigated for their phytochemical constituents. Ethanol extracts of the samples and some purified compounds were tested against Trypanosoma brucei, Plasmodium falciparum and against two helminth species, Trichinella spiralis and Caenorhabditis elegans, showing various degrees of activity. Fourteen compounds were isolated from the propolis samples, including a novel compound Taxifolin-3-acetyl-4’-methyl ether (4), a flavanonol derivative. The crude extracts showed moderate activity against T. spiralis and C. elegans, while the purified compounds had low activity against P. falciparum. Anti-trypanosomal activity (EC50 = 0.7 µg/mL) was exhibited by a fraction containing a cardol identified as bilobol (10) and this fraction had no effect on Human Foreskin Fibroblasts (HFF), even at 2.0 mg/mL, thus demonstrating excellent selectivity. A metabolomics study was used to explore the mechanism of action of the fraction and it revealed significant disturbances in trypanosomal phospholipid metabolism, especially the formation of choline phospholipids. We conclude that a potent and highly selective new trypanocide may be present in the fraction.",
keywords = "trypanosoma brucei, bilobol, alkylresorcinol, metabolomics, anthelminthic activity",
author = "Weam Siheri and Ebiloma, {Godwin U.} and Igoli, {John O.} and Gray, {Alexander I.} and Marco Biddau and Pilaslak Akrachalanont and {Samya Sh M D Alenezi}, Samya and Alwashih, {Mohammad A.} and {Edrada Ebel}, RuAngelie and Sylke M{\"u}ller and Lawrence, {Catherine E.} and James Fearnley and Watson, {David G.} and {De Koning}, {Harry P.}",
year = "2019",
month = "3",
day = "15",
doi = "10.3390/molecules24061041",
language = "English",
volume = "24",
journal = "Molecules",
issn = "1420-3049",
number = "6",

}

Siheri, W, Ebiloma, GU, Igoli, JO, Gray, AI, Biddau, M, Akrachalanont, P, Samya Sh M D Alenezi, S, Alwashih, MA, Edrada Ebel, R, Müller, S, Lawrence, CE, Fearnley, J, Watson, DG & De Koning, HP 2019, 'Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis' Molecules, vol. 24, no. 6, 1041. https://doi.org/10.3390/molecules24061041

Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis. / Siheri, Weam; Ebiloma, Godwin U.; Igoli, John O.; Gray, Alexander I.; Biddau, Marco; Akrachalanont, Pilaslak; Samya Sh M D Alenezi, Samya; Alwashih, Mohammad A.; Edrada Ebel, RuAngelie; Müller, Sylke; Lawrence, Catherine E.; Fearnley, James; Watson, David G.; De Koning, Harry P.

In: Molecules, Vol. 24, No. 6, 1041, 15.03.2019.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis

AU - Siheri, Weam

AU - Ebiloma, Godwin U.

AU - Igoli, John O.

AU - Gray, Alexander I.

AU - Biddau, Marco

AU - Akrachalanont, Pilaslak

AU - Samya Sh M D Alenezi, Samya

AU - Alwashih, Mohammad A.

AU - Edrada Ebel, RuAngelie

AU - Müller, Sylke

AU - Lawrence, Catherine E.

AU - Fearnley, James

AU - Watson, David G.

AU - De Koning, Harry P.

PY - 2019/3/15

Y1 - 2019/3/15

N2 - Twelve propolis samples from different parts of Libya were investigated for their phytochemical constituents. Ethanol extracts of the samples and some purified compounds were tested against Trypanosoma brucei, Plasmodium falciparum and against two helminth species, Trichinella spiralis and Caenorhabditis elegans, showing various degrees of activity. Fourteen compounds were isolated from the propolis samples, including a novel compound Taxifolin-3-acetyl-4’-methyl ether (4), a flavanonol derivative. The crude extracts showed moderate activity against T. spiralis and C. elegans, while the purified compounds had low activity against P. falciparum. Anti-trypanosomal activity (EC50 = 0.7 µg/mL) was exhibited by a fraction containing a cardol identified as bilobol (10) and this fraction had no effect on Human Foreskin Fibroblasts (HFF), even at 2.0 mg/mL, thus demonstrating excellent selectivity. A metabolomics study was used to explore the mechanism of action of the fraction and it revealed significant disturbances in trypanosomal phospholipid metabolism, especially the formation of choline phospholipids. We conclude that a potent and highly selective new trypanocide may be present in the fraction.

AB - Twelve propolis samples from different parts of Libya were investigated for their phytochemical constituents. Ethanol extracts of the samples and some purified compounds were tested against Trypanosoma brucei, Plasmodium falciparum and against two helminth species, Trichinella spiralis and Caenorhabditis elegans, showing various degrees of activity. Fourteen compounds were isolated from the propolis samples, including a novel compound Taxifolin-3-acetyl-4’-methyl ether (4), a flavanonol derivative. The crude extracts showed moderate activity against T. spiralis and C. elegans, while the purified compounds had low activity against P. falciparum. Anti-trypanosomal activity (EC50 = 0.7 µg/mL) was exhibited by a fraction containing a cardol identified as bilobol (10) and this fraction had no effect on Human Foreskin Fibroblasts (HFF), even at 2.0 mg/mL, thus demonstrating excellent selectivity. A metabolomics study was used to explore the mechanism of action of the fraction and it revealed significant disturbances in trypanosomal phospholipid metabolism, especially the formation of choline phospholipids. We conclude that a potent and highly selective new trypanocide may be present in the fraction.

KW - trypanosoma brucei

KW - bilobol

KW - alkylresorcinol

KW - metabolomics

KW - anthelminthic activity

UR - https://www.mdpi.com/journal/molecules

U2 - 10.3390/molecules24061041

DO - 10.3390/molecules24061041

M3 - Article

VL - 24

JO - Molecules

T2 - Molecules

JF - Molecules

SN - 1420-3049

IS - 6

M1 - 1041

ER -

Siheri W, Ebiloma GU, Igoli JO, Gray AI, Biddau M, Akrachalanont P et al. Isolation of a novel flavanonol and an alkylresorcinol with highly potent anti-trypanosomal activity from Libyan propolis. Molecules. 2019 Mar 15;24(6). 1041. https://doi.org/10.3390/molecules24061041

Access to Document