Thymyl esters derivatives and a new natural product modhephanone from <i>Pulicaria mauritanica</i> Coss<i>.</i> (Asteraceae) root oil

Xu, Tao; Gherib, Mohammed; Bekhechi, Chahrazed; Atik-Bekkara, Fawzia; Casabianca, Hervé; Tomi, Félix; Casanova, Joseph; Bighelli, Ange

doi:10.1002/ffj.3223

Cited by 17 publications

(14 citation statements)

References 21 publications

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“…Essential oils with this compound as a major component have antibacterial, antifungal, and insecticidal properties [63,64,65]. 2,5-dimetoxy-p-cymene is a dominant component of EO Eupatorium triplinerve [62], Bubonium imbricatum [63], Ayapana triplinervis [66], Pulicaria mauritanica [67], Limbarda crithmoides [68], and Laggera crispata [69]. Therefore, it probably plays an essential role in the anticancer activity of EO in relation to the MOGGCCM and T98G cell lines.…”

Section: Discussionmentioning

confidence: 99%

Essential Oil from Arnica Montana L. Achenes: Chemical Characteristics and Anticancer Activity

Sugier

Jakubowicz-Gil

et al. 2019

Molecules

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Mountain arnica Arnica montana L. is a source of several metabolite classes with diverse biological activities. The chemical composition of essential oil and its major volatile components in arnica may vary depending on the geographical region, environmental factors, and plant organ. The objective of this study was to characterize the chemical composition of essential oil derived from A. montana achenes and to investigate its effect on induction of apoptosis and autophagy in human anaplastic astrocytoma MOGGCCM and glioblastoma multiforme T98G cell lines. The chemical composition of essential oil extracted from the achenes was examined with the use of Gas Chromatography–Mass Spectrometry GC-MS. Only 16 components of the essential oil obtained from the achenes of 3-year-old plants and 18 components in the essential oil obtained from the achenes of 4-year-old plants constituted ca. 94.14% and 96.38% of the total EO content, respectively. The main components in the EO from the arnica achenes were 2,5-dimethoxy-p-cymene (39.54 and 44.65%), cumene (13.24 and 10.71%), thymol methyl ether (8.66 and 8.63%), 2,6-diisopropylanisole (8.55 and 8.41%), decanal (7.31 and 6.28%), and 1,2,2,3-tetramethylcyclopent-3-enol (4.33 and 2.94%) in the 3- and 4-year-old plants, respectively. The essential oils were found to exert an anticancer effect by induction of cell death in anaplastic astrocytoma and glioblastoma multiforme cells. The induction of apoptosis at a level of 25.7–32.7% facilitates the use of this secondary metabolite in further studies focused on the development of glioma therapy in the future. Probably, this component plays a key role in the anticancer activity against the MOGGCCM and T98G cell lines. The present study is the first report on the composition and anticancer activities of essential oil from A. montana achenes, and further studies are required to explore its potential for future medicinal purposes.

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Section: Discussionmentioning

confidence: 99%

Essential Oil from Arnica Montana L. Achenes: Chemical Characteristics and Anticancer Activity

Sugier

Jakubowicz-Gil

et al. 2019

Molecules

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“…In some Inula, Doronicum and Pulicaria species, thymyl derivatives rather than sesquiterpenoids are the major root constituents. [20][21][22][23] A review by Talavera-Aleman and collaborators 24 estimated that only 10% of known functionalized thymyl derivatives have been employed in biological testing, showing vast array of diverse activities, such as antimicrobial 4,5,22,[25][26][27] (several papers reporting inhibitory activity against plants' pathogenic fungi 22,26 ), antioxidant, 28 antinociceptive, 29 anti-parasitic (antileishmanial), 30,31 antiprotozoal, 32 insecticidal 33 and piscicidal 34 activity. The usefulness of thymyl derivatives as transdermal drug delivery enhancers has also been reported.…”

Section: Introductionmentioning

confidence: 99%

“…The usefulness of thymyl derivatives as transdermal drug delivery enhancers has also been reported. 35 There are several papers reporting isolation, synthesys 4,23,29,33,36 and biological activity 4,5,22,25,[28][29][30]33 of thymyl esters. Grodnitzky and Coats 33 have tested insecticidal activity of thymyl esters of acetic, dichloracetic, trichloroacetic, chlorodifluoroacetic, pivalic and chloropivalic acid on Musca domestica.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Lazarević

Kolarević

Stojanović

et al. 2017

ACSi

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Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

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“…31 13-Acetoxymodhephene (19) was isolated in 1979 from the roots of Liabum eggersii Hieron (Asteraceae), 32 while rel-(1S,2S,5S,8S)-modhephan-3-one (20) was isolated from the essential oil of Pulicaria mauritanica Coss (Asteraceae) roots. 33 The 14-and 15-acetoxy derivatives (not shown) were also isolated from the roots of Pluchea sericea (Asteraceae) 34 for the former, and from the alpine plant Leontopodium alpinum (Asteraceae) 35 for the latter. Noteworthy, all the natural sources of modhephene and derivatives thereof mentioned above are part of the Asteraceae family.…”

Section: Simple Modhephene Derivativesmentioning

confidence: 99%

“…Dichrocephones A (32) and B (33) (Fig. 4) were found in 2013 in the plant Dichrocephala benthamii (Asteraceae).…”

Section: Dichrocephones a And Bmentioning

confidence: 99%

Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

et al. 2020

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Thymyl esters derivatives and a new natural product modhephanone from Pulicaria mauritanica Coss. (Asteraceae) root oil

Cited by 17 publications

References 21 publications

Essential Oil from Arnica Montana L. Achenes: Chemical Characteristics and Anticancer Activity

Essential Oil from Arnica Montana L. Achenes: Chemical Characteristics and Anticancer Activity

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

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