Abstract
A phytochemical investigation of the Ferula lutea (Poir.) Maire flowers has led to the isolation of a new compound, (E)-5-ethylidenefuran-2(5H)-one-5-O-β-d-glucopyranoside (1), designated ferunide, 4-hydroxy-3-methylbut-2-enoic acid (2), reported for the first time as a natural product, together with nine known compounds, verbenone-5-O-β-d-glucopyranoside (3), 5-O-caffeoylquinic acid (4), methyl caffeate (5), methyl 3,5-O-dicaffeoylquinate (6), 3,5-O-dicaffeoylquinic acid (7), isorhamnetin-3-O-α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside, narcissin (8), (−)-marmesin (9), isoimperatorin (10) and 2,3,6-trimethylbenzaldehyde (11). Compounds 3–10 were identified for the first time in Ferula genus. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR experiments, mass spectroscopy and X-ray diffraction analysis (compound 2), as well as by comparison with literature data. The antioxidant, anti-inflammatory and cytotoxic activities of isolated compounds were evaluated. Results showed that compound 7 exhibited the highest antioxidant activity with IC50 values of 18 ± 0.5 µmol/L and 19.7 ± 0.7 µmol/L by DPPH radical and ABTS radical cation, respectively. The compound 6 exhibited the highest anti-inflammatory activity with an IC50 value of 5.3 ± 0.1 µmol/L against 5-lipoxygenase. In addition, compound 5 was found to be the most cytotoxic, with IC50 values of 22.5 ± 2.4 µmol/L, 17.8 ± 1.1 µmol/L and 25 ± 1.1 µmol/L against the HCT-116, IGROV-1 and OVCAR-3 cell lines, respectively.
Highlights
Plants are still used as a source of large-scale original and novel chemical structures
It is well known that the Ferula genus has a variety of coumarins [7], phenolics such as chlorogenic acid, gallic acid and pyrogallol [8]
The cytotoxic activity was evaluated using the MTT assay on the HCT-116 human colon cancer cell line and IGROV-1, OVCAR-3 human ovary cells lines
Summary
Plants are still used as a source of large-scale original and novel chemical structures. A successful chemical survey of the roots of the F. lutea has contributed to the isolation of new dihydrofuranocoumarins, together with eight known compounds [6]. It is well known that the Ferula genus has a variety of coumarins [7], phenolics such as chlorogenic acid, gallic acid and pyrogallol [8]. The Ferula genus is referred to be a good source of biologically active compounds like sesquiterpene derivatives [9,10], daucanes [11], germacranes [9] and sesquiterpene coumarins identified in the roots of the plants. We report on the isolation and structural elucidation of six compounds from the n-butanol extract of the flowers of F. lutea: two new compounds: ethylidenefuran(E)-5-ethylidenefuran-2(5H)one-5-O-β-D-glucopyranoside (1),named ferunide, and4-hydroxy-3-methylbut-2-enoic acid (2), and three known compounds:verbenone-5-O-β-D-glucopyranoside (3), chlorogenic acid (4), methyl caffeate (5). The cytotoxic activity was evaluated using the MTT assay on the HCT-116 human colon cancer cell line and IGROV-1, OVCAR-3 human ovary cells lines
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