2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity

Solene Deiva, Lindsay Ferguson, Mostafa E. Rateb, Roderick Williams, Federico Brucoli*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

We report for the first time the isolation of 2-furyl(phenyl)methanol (5) from the chloroform extracts of the Atractylis gummifera roots. A. gummifera is a thistle belonging to the Asteraceae family that produces the ent-kaurane diterpenoid glycoside atractyloside (ATR). ATR (1) was isolated and chemically modified to obtain its aglycone atractyligenin (2) and the methylated derivatives ATR-OMe (3) and genine-OMe (4). The compounds 1–5 were structurally characterised and evaluated against the intracellular amastigote, cultured within macrophages, and the extracellular promastigote of Leishmania donovani, the protozoan parasite responsible for the highly infective disease visceral leishmaniasis, which is fatal if untreated. The 2-furyl(phenyl)methanol 5 exhibited notable activity against the promastigote.
Original languageEnglish
Article number104420
Number of pages6
JournalFitoterapia
Volume140
Early online date14 Nov 2019
DOIs
Publication statusE-pub ahead of print - 14 Nov 2019

Fingerprint

Atractyloside
Methanol
Kaurane Diterpenes
Diterpenes
Macrophages
Glycosides
Chloroform
Derivatives

Keywords

  • Antileishmanial agents
  • Ent-kaurane diterpenoids
  • Structural characterisation
  • Leishmania donovani
  • Luciferase assay
  • Phenyl-furan chemical scaffold

Cite this

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title = "2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity",
abstract = "We report for the first time the isolation of 2-furyl(phenyl)methanol (5) from the chloroform extracts of the Atractylis gummifera roots. A. gummifera is a thistle belonging to the Asteraceae family that produces the ent-kaurane diterpenoid glycoside atractyloside (ATR). ATR (1) was isolated and chemically modified to obtain its aglycone atractyligenin (2) and the methylated derivatives ATR-OMe (3) and genine-OMe (4). The compounds 1–5 were structurally characterised and evaluated against the intracellular amastigote, cultured within macrophages, and the extracellular promastigote of Leishmania donovani, the protozoan parasite responsible for the highly infective disease visceral leishmaniasis, which is fatal if untreated. The 2-furyl(phenyl)methanol 5 exhibited notable activity against the promastigote.",
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author = "Solene Deiva and Lindsay Ferguson and Rateb, {Mostafa E.} and Roderick Williams and Federico Brucoli",
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2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity. / Deiva, Solene; Ferguson, Lindsay; Rateb, Mostafa E.; Williams, Roderick; Brucoli, Federico.

In: Fitoterapia, Vol. 140, 104420, 31.01.2020.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 2-furyl(phenyl)methanol isolated from Atractilis gummifera rhizome exhibits anti-leishmanial activity

AU - Deiva, Solene

AU - Ferguson, Lindsay

AU - Rateb, Mostafa E.

AU - Williams, Roderick

AU - Brucoli, Federico

PY - 2019/11/14

Y1 - 2019/11/14

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AB - We report for the first time the isolation of 2-furyl(phenyl)methanol (5) from the chloroform extracts of the Atractylis gummifera roots. A. gummifera is a thistle belonging to the Asteraceae family that produces the ent-kaurane diterpenoid glycoside atractyloside (ATR). ATR (1) was isolated and chemically modified to obtain its aglycone atractyligenin (2) and the methylated derivatives ATR-OMe (3) and genine-OMe (4). The compounds 1–5 were structurally characterised and evaluated against the intracellular amastigote, cultured within macrophages, and the extracellular promastigote of Leishmania donovani, the protozoan parasite responsible for the highly infective disease visceral leishmaniasis, which is fatal if untreated. The 2-furyl(phenyl)methanol 5 exhibited notable activity against the promastigote.

KW - Antileishmanial agents

KW - Ent-kaurane diterpenoids

KW - Structural characterisation

KW - Leishmania donovani

KW - Luciferase assay

KW - Phenyl-furan chemical scaffold

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