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 journalArticle

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.
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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 journalArticle

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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

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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

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DO - 10.3390/molecules24061041

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VL - 24

JO - Molecules

T2 - Molecules

JF - Molecules

SN - 1420-3049

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