Biological activity of natural sesquiterpenoids containing a gem-dimethylcyclopropane unit

Durán‐Peña, María Jesús; Botubol-Ares, José Manuel; Hanson, James R.; Collado, Isidro G.; Hernández-Galán, Rosario

doi:10.1039/c5np00024f

Cited by 63 publications

(48 citation statements)

References 113 publications

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“…[40] Some other studies connected structural and pharmacological properties of spathulenol and α-bisabolol with a good antimicrobial activity. [41,42] Some other potential candidate responsible for good antimicrobial potential, found as a component in these EO's, was diterpene alcohol phytol. [43] Non terpene compounds such as heptacosane and nonacosane, as well as fatty acid like hexadecanoic acid found in these EO's as major components, were previously recognized as responsible for a good antimicrobial activity as well.…”

Section: Resultsmentioning

confidence: 99%

Centaurea rupestris L.: Cytogenetics, Essential Oil Chemistry and Biological Activity

Carev¹,

Maravić²,

Bektašević³

et al. 2018

Croat. Chem. Acta

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Centaurea species are used in eastern Mediterranean ethnopharmacology due to variety of bioactive compounds they comprise. Aim of this work was to characterize the Centaurea rupestris L. hydrodistilled essential oil chemical composition and test its biological activity: antimicrobial effect, antioxidant potential and inhibition of cholinesterases. Plant material authentication was by chromosome number counting and genome size assessment with the flow cytometry. Hydrodistilled essential oils were characterized using gas chromatography/mass spectrometry technique GC-MS and GC-FID. The antimicrobial effect was tested using disk diffusion and microdilution methods, antioxidant potential was tested with DPPH and FRAP methods and cholinesterases inhibition was tested with Ellman method. Genome size for C. rupestris species: sample A presented 2C=3.60 (0.10) pg and sample B 2C=3.62 (0.08) pg. The chromosome number was 2n=20 for both samples. The main essential oil constituents in isolated sample A oil, detected with GC-MS and GC-FID were: germacrene D (24.3 %), heptacosane (14.4 %), phytol (6.7 %), β-caryophyllene (5.0 %) and pentacosane (4.5 %). Sample B essential oil had the main constituents: hexadecanoic acid (18.7 %), heptacosane (13.8 %), α-linolenic acid (11.8 %), nonacosane (7.8 %) and germacrene D (5.4 %). Both samples of oil showed broad spectrum antimicrobial effect with good activity against emerging Gram-positive and Gram-negative opportunistic pathogens and pathogenic fungi which indicates the pharmaceutical potential of the C. rupestris essential oil.

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Section: Resultsmentioning

confidence: 99%

Centaurea rupestris L.: Cytogenetics, Essential Oil Chemistry and Biological Activity

Carev¹,

Maravić²,

Bektašević³

et al. 2018

Croat. Chem. Acta

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“…[19] Applying the MIRC reaction to 2a on functionalized targets smoothly inserted the gem-dimethyl cyclopropane in complex structures (5b-d). The gem-dimethyl cyclopropane motif,f or instance,i so fparticular interest in the pharmaceutical industry,a nd versatile methods for preparation of this building block are lacking.…”

Section: Angewandte Chemiementioning

confidence: 99%

“…The gem-dimethyl cyclopropane motif,f or instance,i so fparticular interest in the pharmaceutical industry,a nd versatile methods for preparation of this building block are lacking. [19] Applying the MIRC reaction to 2a on functionalized targets smoothly inserted the gem-dimethyl cyclopropane in complex structures (5b-d). Conversely,t he diazoalkanes 2p and 2r afforded the cyclopropanes 5a and 5e,r espectively,i n moderate yields and as amixture of diastereomers.…”

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confidence: 99%

Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology

et al. 2018

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Die Hintergrundinformationen zu dieser Zuschrift enthalten eine inkorrekte Struktur für Verbindung 3k,erhalten nach [3þ2]-Cycloaddition von 2k mit Acetylendicarbonsäuredimethylester.Ursprünglich wurde das Pyrazolenin abgebildet, in diesem Beispiel wurde allerdings das Pyrazol 3k erhalten. Diese Struktur ist in den revidierten Hintergrundinformationen korrigiert, die online mit dieser Berichtigung verçffentlicht werden. Darüber hinaus enthält die Reaktionsgleichung in Tabelle 1einen Fehler,der in der hier abgebildeten Fassung korrigiert ist.Schwerer wiegt aber,dass die Verbindungen 5a bis 5d inkorrekt als Cyclopropane beschrieben wurden. Während die Autoren zunächst davon ausgingen, dass die 1-Pyrazoline aus den [3þ2]-Cycloadditionen mit Alkenen sich spontan in die gewünschten Cyclopropane umwandeln (Gasentwicklung wurde beobachtet), wurden nach der Aufreinigung tatsächlich die 1-Pyrazoline als Produkte isoliert. Diese Verbindungen kçnnen durch UV-C-Bestrahlung (l = 254 nm) in die ursprünglich gezeigten Cyclopropane überführt werden. [1] Die entsprechenden Strukturen und Ausbeuten sind in der hier gezeigten Fassung von Schema 5und in den revidierten Hintergrundinformationen korrigiert. Alle Autoren entschuldigen sich fürdiese Fehlinterpretation der Charakterisierungsdaten und alle daraus folgenden Unannehmlichkeiten. Während das Cyclopropan 5e in 53 %Ausbeute (2.1:1 dr) isoliert wurde, ließ sich das entsprechende 1-Pyrazolin interessanterweise auch im 1 H-NMR-Spektrum der Reaktionsmischung nachweisen (> 15 %). Da alle in der Zuschrift beschriebenen Reaktionen ohne besondere Maßnahmen zum Lichtausschluss ausgeführt wurden, wurde diese Umsetzung mit einem strikt lichtgeschützten Auffanggefäßwiederholt. Dabei nahm die Menge an Pyrazolin im 1 H-NMR-Spektrum der Reaktionsmischung deutlich zu (~50 %), was darauf hindeutet, dass sichtbares Licht die Stickstoffabspaltung und Bildung der gewünschten Cyclopropane in bestimmten Fällen induzieren kann. Die Autoren bitten, diese Fehler zu entschuldigen. Sie danken Professor Szymon Buda (Jagiellonen-Universität) fürd en Hinweis sowie Professor Christopher Moody (University of Nottingham), der sie auf die falsche Strukturformel für 3k aufmerksam machte.

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“…Sesquiterpenoids are known for their herbal and spicy odorous notes and biological activities [9,16,22]. Terpenoids are also an important component in the essential oil of other medicinal Araliaceae species including Panax ginseng, Schefflera spp., and Eleutherococcus spp.…”

Section: Resultsmentioning

confidence: 99%

Volatile Compounds and Antiproliferative Effects of Dendropanax morbifera on HepG2 Cells

Yang¹,

Garcia²,

Lee³

2017

Journal of Life Science

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Dendropanax morbifera Lev. is known in Korea for its golden sap and medicinal properties. The many biological activities of the leaf and stem extracts suggest that this tree could be a valuable source of medicinal compounds for the treatment of various ailments such as dermatitis, migraines, dysmenorrhea, muscle pain, and infectious diseases. However, there is little information on the composition and biological activity of the volatile fraction of D. morbifera. Therefore, in this study, the volatile compounds in leaves, stems, and sap of D. morbifera were isolated using solvent and supercritical fluid extraction (SFE), and analyzed by gas chromatography/mass spectrometry to reveal their chemical composition and identify potential compounds of interest. Fifteen compounds were identified in the leaf extracts, whereas 29 and 3 compounds were identified in the stem and sap extracts, respectively. The volatile profiles obtained using solvent and SFE differed. Esters and aromatic hydrocarbons predominated in the solvent extract of leaves and SFE extract of stems, whereas the solvent extract of stems and SFE extract of leaves contained terpenoids. Limonene, α-pinene, and β-myrcene were identified in the volatile extract of sap, with limonene representing 96.30% of the total peak area. In addition, the antiproliferative effects of the solvent extracts of leaves and stems were evaluated, revealing that these solvent extracts were particularly effective in decreasing the proliferation of HepG2 cells.

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Biological activity of natural sesquiterpenoids containing a gem-dimethylcyclopropane unit

Abstract: The biological activity of sesquiterpenes containing the gem-dimethylcyclopropane unit is described.

Cited by 63 publications

References 113 publications

Centaurea rupestris L.: Cytogenetics, Essential Oil Chemistry and Biological Activity

Centaurea rupestris L.: Cytogenetics, Essential Oil Chemistry and Biological Activity

Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology

Volatile Compounds and Antiproliferative Effects of Dendropanax morbifera on HepG2 Cells

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