Sesquiterpenes from aerial parts of Ferula vesceritensis

Oughlissi-Dehak, Karima; Lawton, Philippe; Michalet, Serge; Bayet, Christine; Darbour, Nicole; Hadj-Mahammed, Mahfoud; Badjah-Hadj-Ahmed, Yacine A.; Dijoux‐Franca, Marie‐Geneviève; Guilet, David

doi:10.1016/j.phytochem.2008.03.010

Cited by 22 publications

(25 citation statements)

References 22 publications

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“…Along with several known compounds, eight new sesquiterpenoids were eventually isolated and characterized. The known compound obtained belonged to three major classes, namely, sesquiterpene lactones [isoalantolactone ( 1a ),11 dihydroisoalantolactone ( 1b ),12 peruvin ( 3 ),13 damsin ( 4a ),14 dihydrodamsin ( 5a ),15 acetoxydihydrodamsin ( 5b ),16 dihydrocoronopilin ( 6 ),17 and secoambrosanolide ( 11 )18], their acidic precursors [pre‐isoalantolactone ( 2 )19 and damsinic acid ( 8 )20], and daucane alcohols [lasidiol anisate 12 21,22]. Sesquiterpene lactones and acids are widespread in plants from the genus Ambrosia , but, with the exception of peruvin ( 3 ), none of these known compounds had been isolated from American populations of A. artemisiifolia , where the occurrence of sesquiterpene acids and daucanes is unreported.…”

Section: Resultsmentioning

confidence: 99%

Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter

et al. 2012

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Allergy to common ragweed (Ambrosia artemisiifolia L.) is increasingly important from a clinical standpoint, but surprisingly, little is known on the secondary metabolites of this plant and their potential involvement in the severity of the allergic reactions induced by its pollen. Along with known compounds, eight novel sesquiterpenoids were isolated from the aerial parts of A. artemisiifolia, evidencing the presence of large amounts of electrophilic α,β‐unsaturated carbonyl derivatives. Because compounds of this type were also present in pollen, their reactivity with thiols was investigated and correlated to the activation of TRPA1, a polymodal sensor highly expressed in the aerial pathways and involved in airways sensory irritation, a common complication of allergy to Ambrosia.

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Section: Resultsmentioning

confidence: 99%

Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter

et al. 2012

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“…In a previous study, the effect of sesquiterpene coumarins, farnesiferol A and feselol, was investigated on the inhibition of the MDR-like transporter from the protozoan Cryptosporidium parvum. The study revealed that the compounds could bind to the nucleotide-binding domain of the MDR-like efflux pump from Cryptosporidium parvum [18]. Driportlandin, a sesquiterpene coumarin from Euphorbia portlandica, has been shown to inhibit P-gp at 9 µM after 30 min exposure.…”

Section: Discussionmentioning

confidence: 99%

Farnesiferol A fromFerula persicaand Galbanic Acid fromFerula szowitsianaInhibit P-Glycoprotein-Mediated Rhodamine Efflux in Breast Cancer Cell Lines

et al. 2011

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In multidrug resistance (MDR), cancer cells exposed to anticancer agents develop resistance to a wide variety of chemicals and chemotherapeutic agents. Sesquiterpene coumarins are reported to inhibit P-glycoprotein and/or increase cytotoxicity of anticancer drugs in P-gp-overexpressing cell lines. In the current study, we investigated the effects of galbanic acid (from the roots of Ferula szowitsiana) and farnesiferol A (from the roots of Ferula persica) on functionality of the drug transporter P-glycoprotein (P-gp) using a rhodamine 123 efflux assay in a doxorubicin resistant breast cancer cell line (MCF7/Adr). Compared to verapamil, the well-known inhibitor of P-gp, galbanic acid (5, 10, and 25 µg/mL), significantly inhibited the P-gp activity. In inhibition of the P-gp transporter, farnesiferol A (0.5 µg/mL) was more potent than verapamil at 15 min exposure. Our results indicate that the plant derived sesquiterpene coumarins, farnesiferol A and galbanic acid, may be promising candidates to be considered for further studies on the reversal of multidrug resistance phenotype in chemotherapy of cancer patients.

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“…[5] Many bioactive compounds have been reported from Ferula species,[6789] but the biological activities of drimane-type sesquiterpene coumarins have poorly been documented. [3410]…”

Section: Introductionmentioning

confidence: 99%

Drimane-type Sesquiterpene Coumarins from Ferula gummosa Fruits Enhance Doxorubicin Uptake in Doxorubicin-resistant Human Breast Cancer Cell Line

Iranshahi

Barthomeuf

Bayet-Robert

et al. 2014

Journal of Traditional and Complementary Medicine

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Multidrug resistance (MDR) is the main cause of failure in the chemotherapy of cancer patients. The present study aimed to evaluate the effects of sesquiterpene coumarins of Ferula gummosa fruits on P-glycoprotein (P-gp)–mediated MDR. Drimane-type sesquiterpene coumarins from the fruits of F. gummosa were extracted with dichloromethane and subjected to column chromatography. The effects of the isolated compounds on P-gp–mediated MDR were evaluated in the breast cancer cell line MCF-7 which shows high resistance to doxoribicin (MCF-7/Dox). Phytochemical investigation of dichloromethane extract of F. gummosa fruits resulted in three sesquiterpene coumarins including conferone (1), mogoltacin (2), and feselol (3). The structures of these compounds were confirmed by 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy. Exposure of cells to conferone, mogoltacin, feselol, and verapamil (positive control) enhanced doxorubicin uptake by MCF-7/Dox cells. This effect was dose dependent, but varied with the structure of the chemical. At 25 μM, all the tested sesquiterpene coumarins restored at least 50% of the reference uptake (uptake by sensitive cells); but at 10 μM, their potency varied where conferone showed the highest potency and feselol showed the lowest potency. Conferone, mogoltacin, and feselol from F. gummosa suppress P-gp–mediated drug efflux in highly resistant human breast cancer cells.

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Sesquiterpenes from aerial parts of Ferula vesceritensis

Cited by 22 publications

References 22 publications

Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter

Sesquiterpenoids from Common Ragweed (Ambrosia artemisiifolia L.), an Invasive Biological Polluter

Farnesiferol A fromFerula persicaand Galbanic Acid fromFerula szowitsianaInhibit P-Glycoprotein-Mediated Rhodamine Efflux in Breast Cancer Cell Lines

Drimane-type Sesquiterpene Coumarins from Ferula gummosa Fruits Enhance Doxorubicin Uptake in Doxorubicin-resistant Human Breast Cancer Cell Line

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