Two coumarins and a thienylbutylamide from Anacyclus cyrtolepioides from the Algerian Septentrional Sahara

Benkiki, Naïma; Kabouche, Zahia; Bruneau, Christian

doi:10.1007/s10600-007-0205-z

Cited by 7 publications

(8 citation statements)

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“…In addition to these compounds, b-sitosterol (3) and 7-methoxycoumarin (4) were purified using preparative thin layer chromatography (PTLC) on silica gel plates (Figure 1). The structures of all the compounds were elucidated using different spectral data including 1 H NMR, 13 C NMR and EI-MS and comparing their spectral data with those described in the literature (Elgamal et al 1979;Mahato & Kundu 1994;Kovganko et al 1999;Ding et al 2000;De-Eknamkul & Potduang 2003;Khalilov et al 2003;Benkiki et al 2007;Weber et al 2008;Askari et al 2009;Mouffok et al 2012). The isolated compounds (1-4) were tested against the most susceptible cells, MOLT-4, however, they did not show promising activities with IC 50 values higher than 100 mM.…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxic activity and chemical constituents ofAnthemis mirheydari

Jassbi

Firuzi

Miri

et al. 2016

Pharmaceutical Biology

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Context The genus Anthemis L. (Asteraceae) comprises about 195 species which are widely used in the pharmaceutical, cosmetic and food industries. Objective Anthemis mirheydari Iranshar, an endemic plant from Iran, was investigated for its cytotoxic properties and chemical constituents. Materials and methods The whole parts of the plant (320 g) were extracted by dichloromethane and methanol for four days, successively. The cytotoxic activity of both dichloromethane and methanol extracts were assayed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric methods against three human cancer cell lines including LS180, MCF-7 and MOLT-4. Different concentrations (10-100 mg/mL) of the plant extracts were tested to obtain IC 50 values. The dichloromethane extract of A. mirheydari was subjected to silica gel-column and thin layer chromatography for purification of its chemical constituents and the isolated compounds were further tested against MOLT-4 cells. The structures of the pure compounds were elucidated using different spectral data including nuclear magnetic resonance and electron impact mass spectra. Results The IC 50 values of the dichloromethane extract were 30.8 ± 6.7, 25.2 ± 6.5 and 8.6 ± 1.1 mg/mL (means ± standard error) for the above-mentioned cell lines, respectively. Two triterpenoids, taraxasterol (1) and pseudotaraxasterol (2), one sterol, b-sitosterol (3) and one coumarin, 7-methoxycoumarin (4) were isolated from the extract. The IC 50 of the mixture of compounds 1 and 2 as well as compounds 3 and 4 were higher (4100 mM) than that reported for the dichloromethane extract against MOLT-4 cells. Conclusion The dichloromethane extract was the most active one among the tested material.ARTICLE HISTORY

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Section: Resultsmentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl 3 ): C 37.2 (C-1), 31.6 (C-2), 71.8 (C-3), 42.3 (C-4), 140.7 (C-5), 121.7 (C-6), 31.9 (C-7), 31.9 (C-8), 50.1 (C-9), 36.5 (C-10), 21.1 (C-11), 39. .1 (C-6), 162.8 (C-7), 100.9 (C-8), 155.9 (C-9), 112.6 (C-10), 55.7 (C-1 0 ) (Elgamal et al 1979;Benkiki et al 2007;Weber et al 2008;Askari et al 2009). …”

Section: The Spectral Datamentioning

confidence: 99%

Cytotoxic activity and chemical constituents ofAnthemis mirheydari

Jassbi

Firuzi

Miri

et al. 2016

Pharmaceutical Biology

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“…It is reported that Anacyclus pyrethrum is often included in many pharmaceutical preparations, based upon Indian medicine for the treatment of sciatica, paralysis, hemiplegia and amenorrhoea (1), and to treat toothache, rheumatic and neuralgic affections (2). Anacyclus cyrtolepidioides is widely used by the Saharan population as a condiment in foods or in milk drinking (3). Anacyclus officinarum contributes to treatment for epilepsy (3,4).…”

Section: Introductionmentioning

confidence: 99%

“…Anacyclus cyrtolepidioides is widely used by the Saharan population as a condiment in foods or in milk drinking (3). Anacyclus officinarum contributes to treatment for epilepsy (3,4). Anacyclus radiatus, Anacyclus valentinus, Anacyclus linearilobus and Anacyclus clavatus provided a source of some active principal components like flavonoids, alkaloids and terpenoids (5).…”

Section: Introductionmentioning

confidence: 99%

Competition of microwave-assisted hydro-distillation in highlighting volatile phytochemicals ofAnacyclus clavatusspecies

Aliboudhar

Tigrine-Kordjani

Meklati

2015

Journal of Essential Oil Research

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The microwave-assisted hydro-distillation (MAHD) technique has recently gained considerable attention in the field of essential oil extraction. MAHD was applied as a green technology for the extraction of essence from leaves and stems of Anacyclus clavatus, generally used as a digestive herb. Results from qualitative and statistical analysis were compared with those obtained by the classic hydro-distillation (HD) method. An extraction time of 80 minutes with MAHD provided yields of 0.015 ± 0.004% (w/w) vs. 0.018 ± 0.001% (w/w) reached after 3 hours by HD. Extracts were analyzed by gas chromatography-flame ionization detector (GC-FID) and GC-mass spectrometry (GC-MS). Despite the common main family and the two major constituents, germacrene D followed by δ-elemene in both extracts, chemical compositions were different. The oxygenated fraction represented 42.7% in MAHD extract vs. 36.1% in HD oil. MAHD offers advantages over HD in terms of energy savings, extraction time and product quality, namely in the high contribution of oxygenated compounds in the fragrance of the essence.

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“…It is an endemic plant in the Septentrional Sahara from Libya to Morocco. Anacyclus cyrtolepidioïdes is widely used by Saharian population in Algeria as a condiment in couscous or in milk drink and it's greatly enjoyed by camels 3 . Previous study of A. radiatus loisel reported the isolation of isorhamnetin, quercetin, isoscopeletin, taraxasterol, β-sitosterol, campesterol, stigmasterol and the germacranolide mariolin 4 .…”

Section: Introductionmentioning

confidence: 99%

Isolation and Structure Elucidation of Flavonol Glycosides, Methyl linoleate and Fatty Acids fromAnacyclus cyrtolepidioïdes(Pomel) Growing in Tunisia

Hammami

Bergaoui

Bouzidi

et al. 2011

Analytical Chemistry Letters

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Chemical investigation of butanol and acetone extracts from fresh flowers and aerial parts of Anacyclus cyrtolepidioïdes yielded Rutin 1, Nicotoflorin 2, methyl linoleate 3, a mixture of linoleic, palmitic and linolenic acids 4 indicated for the first time in this specie. The structural elucidations were established by means of efficient methods as 1 and 2D NMR techniques, Gas Chromatography and Electro-Spray Mass Spectrometry. Antifungal activity of both crude extracts and Rutin was studied against four Candida species: C. albicans ATCC 90028; C. glabrata ATCC 90030; C. Krusei ATCC 6258 and C. parapsilosis ATCC 22019 using disc diffusion method. Thus, Rutin was most active against C. albicans specie (20 mm inhibition zone diameter; C=1mg.mL -1 ).

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Two coumarins and a thienylbutylamide from Anacyclus cyrtolepioides from the Algerian Septentrional Sahara

Cited by 7 publications

References 5 publications

Cytotoxic activity and chemical constituents ofAnthemis mirheydari

Cytotoxic activity and chemical constituents ofAnthemis mirheydari

Competition of microwave-assisted hydro-distillation in highlighting volatile phytochemicals ofAnacyclus clavatusspecies

Isolation and Structure Elucidation of Flavonol Glycosides, Methyl linoleate and Fatty Acids fromAnacyclus cyrtolepidioïdes(Pomel) Growing in Tunisia

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