Daucovirgolides I-L, four congeners of the antimalarial daucovirgolide G from Daucus virgatus

Repeated chromatographic purifications of aerial parts of the Tunisian plant Daucus virgatus led to the isolation of four new germacranolides, named daucovirgolides I-L (2–5), along with the Plasmodium transmission-blocking agent daucovirgolide G. The chemical structures of the new compounds were de...

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Published inFitoterapia Vol. 137; p. 104188
Main Authors Sirignano, Carmina, Snene, Alì, Tenoh, Alain Rodrigue, El Mokni, Ridha, Rigano, Daniela, Habluetzel, Annette, Hammami, Saoussen, Taglialatela-Scafati, Orazio
Format Journal Article
LanguageEnglish
Published Netherlands Elsevier B.V 01.09.2019
Elsevier Science Ltd
Subjects
Antimalarial
Antimalarial agents
Biological activity
Congeners
Daucus
Daucus virgatus
Germacranolides
NMR
Nuclear magnetic resonance
Organic chemistry
Plasmodium
Sesquiterpenoids
Spectrometry
Transmission-blocking
Transmission-blocking
Germacranolides
Antimalarial
Daucus virgatus
NMR
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Summary:Repeated chromatographic purifications of aerial parts of the Tunisian plant Daucus virgatus led to the isolation of four new germacranolides, named daucovirgolides I-L (2–5), along with the Plasmodium transmission-blocking agent daucovirgolide G. The chemical structures of the new compounds were defined as mono- or di-angeloylated germacrane-type sesquiterpenoids by spectroscopic (mainly 1D and 2D NMR) and spectrometric methods (ESIMS). The low potency exhibited by daucovirgolides I-L further supports the observation that strict structural requirements do exist for the Plasmodium transmission blocking activity in the daucovirgolide series. In particular, the endocyclic double bond system seems to be crucial for bioactivity. [Display omitted]
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2019.104188