The chemical composition of Frullania tamarisci essential oil from Corsica was investigated using GC‐FID, GC–MS and NMR analyses. The essential oil compositions were further studied analyzing samples prepared from three different Corsican locations and during a seasonal vegetative cycle. 40 components, which accounted for 78.3–89.8% of the total amount of F. tamarisci essential oils were identified. The main components were tamariscol coeluted with pacifigorgiol (30.4–41.5%), germacra‐1(10)E,5E–dien‐11‐ol (3.6–7.1%), γ‐cylocostunolide (1.8–20.1%), γ‐dihydrocyclocostunolide (1.2–8.0%) and frullanolide (1.7–4.9%). Among them, germacra‐1(10)E,5E–dien‐11‐ol was never reported in the Frullania genus and pacifigorgiol, a tamariscol GC‐overlapped compound, was for the first time reported in Bryophytes. Finally using 1D and 2D NMR experiments, we reported γ‐dihydrocyclocostunolide as a new natural compound. Two Corsican F. tamarisci essential oils with different GC profiles were assessed for their phytotoxic behavior against onion seeds and seedling in order to evaluate their capacity to inhibit germination and alter the development of plantlets. According to the essential oil‐compositions, a stimulation of the onion seedling was observed when sesquiterpene lactones amount was higher, whilst the inhibition of roots growth occurs when sesquiterpene alcohols were predominantly.
Volatiles metabolites from the liverwort Plagiochila porelloides harvested in Corsica were investigated by chromatographic and spectroscopic methods. In addition to already reported constituents, three new compounds were isolated by preparative chromatography and their structures were elucidated by mass spectrometry (MS) and NMR experiments. Hence, an atypic aliphatic compound, named 1,2-dihydro-4,5-dehydronerolidol and two isomers, (E) and (Z), possessing an unusual humbertiane skeleton (called p-menth-1-en-3-[2-methylbut-1-enyl]-8-ol) are newly reported and fully characterized in this work. The in vitro antiprotozoal activity of essential oil and extract of P. porelloides against Trypanosoma brucei brucei and Leishmania mexicana mexicana and cytotoxicity were determined. Essential oil and Et2O extract showed a moderate activity against T. brucei with IC50 values: 2.03 and 5.18 μg/mL, respectively. It is noteworthy that only the essential oil showed a high selectivity (SI = 11.7). Diethyl oxide extract exhibited moderate anticancer (cancerous macrophage-like murine cells) activity and also cytotoxicity (human normal fibroblast) with IC50 values: 1.25 and 2.96 μg/mL, respectively.
Natural products (NPs) constitute a significant source of active biomolecules widely used in medicine, pharmacology and cosmetics. However, NPs structural characterization has the drawback of their chemical instability during the extraction steps and their likely transformation during the analytical protocol. In particular, tamariscol and conocephalenol are two compounds largely used in the cosmetic industry for their odorant properties. Thus, in the present study, we focused on the evolution of these two metabolites (extracted from Frullania tamarisci and Conocephalum conicum, respectively), as followed by NMR. Interestingly, we found that, once dissolved in deuterated chloroform, these two tertiary alcohols are both subjected to transformation processes, leading to degradation compounds with altered structures. Accordingly, these detected degradation compounds have been fully characterized by NMR and the experimental findings were supported by computational chemistry data.
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