Two New Sesquiterpene Derivatives from the Tunisian Endemic <i>Ferula tunetana</i><scp>Pom</scp>.

Jabrane, Aymen; Jannet, Hichem Ben; Mighri, Zine; Mirjolet, Jean-François; Duchamp, Olivier; Harzallah‐Skhiri, Fethia; Lacaille‐Dubois, Marie‐Aleth

doi:10.1002/cbdv.200900025

Cited by 29 publications

(11 citation statements)

References 17 publications

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“…Colladonin (21) Cytotoxic against COLO205 (colon), KM12 (colon), A498 (kidney carcinoma), UO31 (renal), TC32 (Ewing's sarcoma) [48], HCT116 (human colorectal), HT-29 (human colorectal) [103] cancer cell lines, endocannabinoid system modulator [104].…”

Section: Secondary Metabolite Biological Activitiesmentioning

confidence: 99%

“…Korovin in the Korovin's monograph [25]. Typical chemical compounds of these species are highly oxygenated daucane esters and sesquiterpene coumarins [103,[149][150][151][152][153][154][155]. Although oleo-gum-resins of these species contain biologically active sesquiterpenoids, the noxious smell of their resins does not suggest any relation of these species to silphion.…”

Section: Secondary Metabolite Biological Activitiesmentioning

confidence: 99%

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Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

Miski

2021

Plants

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Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with the long-lost silphion. A preliminary conservation study has been initiated at the growth site of this rare endemic Ferula species. The results of this study and their implications on the regional extinction event, and future development of this species will be discussed.

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Section: Secondary Metabolite Biological Activitiesmentioning

confidence: 99%

Section: Secondary Metabolite Biological Activitiesmentioning

confidence: 99%

Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

Miski

2021

Plants

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“…Moreover, 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. Therefore, theroots are a better source for isolating sesquiterpene coumarins than the aerial parts [12,13].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant, 5-Lipoxygenase Inhibitory and Cytotoxic Activities of Compounds Isolated from the Ferula lutea Flowers

et al. 2014

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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), (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 OPEN ACCESSMolecules 2014, 19 16960 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.

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“…Only one previous work on F . tunetana roots which describes the isolation of a new sesquiterpene ester, tunetanin A, a new sesquiterpene coumarin, tunetacoumarin A, together with eight known compounds, coladin, coladonin, isosmarcandin, 13‐hydroxyfeselol, umbelliprenin, propiophenone, β ‐sitosterol and stigmasterol . Recent investigation of essential oil from flowers of Tunisian F. lutea , showed that it is rich in monoterpene hydrocarbons (80.4%) among which δ ‐3‐carene (31.2%) and α ‐pinene (25.8%) were the predominant compounds .…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition and In Vitro Evaluation of Antimicrobial, Antioxidant and Antigerminative Properties of the Seed Oil from the Tunisian Endemic Ferula tunetana Pomel ex Batt.

Znati

Filali

Jabrane

et al. 2016

Chemistry & Biodiversity

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Essential oil of the seeds from the endemic Tunisian plant Ferula tunetana Pomel ex Batt. was analyzed for its chemical composition and screened for its antimicrobial, antioxidant and antigerminative properties. The chemical composition of the isolated oil is reported for the first time. According to the GC/FID, GC/MS and C-NMR analysis results; 18 compounds were identified accounting for 84.6% of the total oil. The chemical composition of this essential oil was characterized by the presence of a high proportion of monoterpene hydrocarbons (77.3%) followed by oxygenated sesquiterpenes (4.1%) and sesquiterpene hydrocarbons (3.2%). α-Pinene (39.8%), β-pinene (11.5%) and (Z)-β-ocimene (7.5%) were the predominant compounds. Moreover, the isolated oil was tested for its antimicrobial activity using the disc-diffusion and the microdilution assays against six Gram-positive and five Gram-negative bacteria as well as towards two Candida species. The isolated oil was tested also for its antioxidant activity against DPPH, ABTS, O2∙ and hydrogen peroxide (H O ), and for its antigerminative potential. It was found that it exhibited interesting antimicrobial activity against Salmonella typhimurium LT2 DT104 (inhibition zone (IZ) 16.2 ± 1.0 mm) and Bacillus cereus ATCC 14579 (IZ 15.8 ± 1.0 mm). However, it exerted a moderate antioxidant activity against H O (IC 78.2 ± 2.98 μg/ml) and towards O2∙ (IC 89.2 ± 3.82 μg/ml). The antigerminative effect of this oil was also evaluated in this work. Results showed a toxic effect.

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Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetanaPom.

Cited by 29 publications

References 17 publications

Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

Antioxidant, 5-Lipoxygenase Inhibitory and Cytotoxic Activities of Compounds Isolated from the Ferula lutea Flowers

Chemical Composition and In Vitro Evaluation of Antimicrobial, Antioxidant and Antigerminative Properties of the Seed Oil from the Tunisian Endemic Ferula tunetana Pomel ex Batt.

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