Comparative Fatty Acid Analysis of Telekia Speciosa

Fatty acids in petroleum-ether extracts prepared from the flower, stem, and leaf of Telekia speciosa (Schreb.) Baung. were studied by capillary gas chromatography-mass spectrometry (GC-MS). The flower and leaf extracts were found to contain similar fatty acids, namely palmitic, linoleic, and oleic acids, whereas the stem extract contained only caproic acid.     

Amberinone,a new guaianolide from Amberboa ramosa

The Amberboa is a medicinally important genus present in the family Asteraceae; members of this genus are mainly distributed in Pakistan and India. It has been used in different systems of traditional medicines for different diseases. Amberinone (1), a new sesquiterpene lactone, has been isolated from the ethyl acetate (EtOAc) soluble fraction of Amberboa ramosa together with chrysin (2), quercitine (3), eriodictyol (4) and keamferol (5). This is the first report of these compounds from this species. The structures of the isolated compounds have been elucidated by 1D and 2D ¹H ¹³C NMR spectroscopy.     

A new lanostane-type triterpene and sesquiterpene lactones from Vernonia leopoldii and their in vitro cytotoxicity

Investigation of the aerial parts of Vernonia leopoldii (Sch. Bip.) Vatke afforded a new lanostane-type triterpene along with known hirsutinolide-type sesquiterpene lactones and flavonoid glycosides, all are identified for the first time in this species. The new compound was identified as lanost-3β, 23S-dihydroxy-22(31)-ene. The structures of the isolated compounds were elucidated based on spectroscopic evidence. The hirsutinolides and the triterpene were evaluated for their cytotoxicity against four human cancer cell lines using MTT assay.     

Anti-infective assessment of Senecio smithioides (Asteraceae) and isolation of 9-oxoeuryopsin,a furanoeremophilane-type sesquiterpene with antiplasmodial activity

The search for anti-infective activity in the antipyretic plant Senecio smithioides was conducted. Petroleum ether (PE), dichloromethane (CH₂Cl₂), ethyl acetate (EtOAc) and hydroethanolic (96% EtOH) extracts, and compounds 9-oxoeuryopsin (1), epoxydecompostin (2) and senecionine (3) were obtained from the aerial parts. All extracts and 1 were tested against chloroquine-resistant strain of Plasmodium falciparum (ref. chloroquine), Trypanosoma cruzi (ref. nifurtimox), Leishmania braziliensis, Leishmania amazonensis and Leishmania donovani (ref. pentamidine), Staphylococcus aureus and Escherichia coli (ref. gentamicin) and, Neurospora crassa and Candida albicans (ref. ketoconazole). The PE extract exhibited the strongest in vitro activity against Plasmodium falciparum IC₅₀ < 1.0 μg/mL. 1 was established as a potent antiplasmodial compound with an IC₅₀ = 1.2 μg/mL, 5.2 μM. Other antiparasitic activities were recorded for all extracts and 1. Antibacterial and antifungal activity was negligible.     

Phytochemical Profile,Antioxidant Activity,and Cytotoxicity Assessment of Tagetes erecta L. Flowers

Tagetes erecta L. is a popular ornamental plant of the Asteraceae family, which is widely cultivated not only for its decorative use, but also for the extraction of lutein. Besides carotenoid representatives, which have been extensively studied, other important classes of secondary metabolites present in the plant, such as polyphenols, could exhibit important biological activities. The phytochemical analysis of a methanolic extract obtained from T. erecta inflorescences was achieved using liquid chromatography–mass spectrometry (LC-MS) techniques. The extract was further subjected to a multistep purification process, which allowed the separation of different fractions. The total extract and its fractions contain several polyphenolic compounds, such as hydroxybenzoic and hydroxycinnamic acid derivatives, flavonols (especially quercetagetin glycosides), and several aglycons (e.g., quercetin, patuletin). One of the fractions, containing mostly quercetagitrin, was subjected to two different antioxidant assays (metal chelating activity and lipoxygenase inhibition) and to in vitro cytotoxicity assessment. Generally, the biological assays showed promising results for the investigated fraction compared to the initial extract. Given the encouraging outcome of the in vitro assays, further purification and structural analysis of compounds from T. erecta extracts, as well as further in vivo investigations are justified.     

In Vitro Anti-Inflammatory Activity of Cotula anthemoides Essential Oil and In Silico Molecular Docking of Its Bioactives

The genus Cotula (Asteraceae) comprises about 80 species, amongst them Cotula anthemoides L. It is a wild plant growing in Egypt that possesses many traditional uses as a headache, colic, and chest cold remedy. In our study, the chemical composition of C. anthemoides essential oils was analyzed using GC-MS spectroscopy. Sixteen components of leave and stem oils and thirteen components of flower oils were characterized. The main components in both essential oil parts were camphor (88.79% and 86.45%) and trans-thujone (5.14% and 10.40%) in the leaves and stems and the flowers, respectively. The anti-inflammatory activity of the oils in lipopolysaccharide-stimulated RAW 264.7 macrophage cells was evaluated. The flower oil showed its predominant effect in the amelioration of proinflammatory cytokines and tumor necrosis factor-α, as well as cyclooxygenase-2. The bornyl acetate showed the highest affinity for the cyclooxygenase-2 receptor, while compound cis-p-menth-2-ene-1-ol had the best affinity for the tumor necrosis factor receptor, according to the results of molecular docking. In addition, the molecule cis-β-farnesene showed promising dual affinity for both studied receptors. Our findings show that essential oils from C. anthemoides have anti-inflammatory properties through their control over the generation of inflammatory mediators. These findings suggest that C. anthemoides essential oils could lead to the discovery of novel sources of anti-inflammatory treatments.     

Four new compounds from Ligularia virgaurea: isolation of eremophilane and noreremophilane sesquiterpenoids and the absolute configuration of 2α-hydroxyeremophil-11-en-9-one by CD spectrum and DFT calculation

Four new compounds, rearranged noreremophilan-8,6-olide, rearranged dinoreremophilanone, epoxy γ-lactone, and 2α-hydroxyermophil-11-en-9-one, along with eremophilenolides related to ligularol and other known terpenoids, were isolated from Ligularia virgaurea (ligularol type) collected from the northern Sichuan Province of China. Three of the new compounds had degraded and unique structures. The absolute configuration of 2α-hydroxyermophil-11-en-9-one was determined on the basis of density functional theory calculation. The back octant rule cannot be applied to this compound because of the contribution of the hydroxy group to the front octant.     

ESSENTIAL OIL COMPOSITION OF THREE SPECIES OF Achillea FROM KAZAKHSTAN

The chemical composition of essential oils ofAchillea millefoliumL.,A. NobilisL. from Kazakhstan flora andA. GrandifloraBieb introduced in culture at the Karaganda Botanic garden were determined by GC/MS. The main component in the essential oil ofA. MillefoliumL. andA. NobilisL. was found to be camphor, while it was -pinene for A. grandiflora.     

Phytochemical,antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1β,2α,3β,19α,23-pentahydroxy-urs-12-en-28-oic acid

Abstract

Phytochemical study of the aerial part of Pulicaria undulata L. led to the isolation of nine compounds. The structure of 1β,2α,3β,19α,23-pentahydroxy-urs-12-en-28-oic acid (4) was revised and confirmation of the stereochemical configuration of the hydroxyl groups was established using NOESY and selective decoupling experiments. The other compounds were identified as 1,2-dehydro-1,10α-dihydropseudoivalin (1), axillarin (2), grandifloric acid-15-β-glucoside (3), myrianthic acid (5), caffeic acid (6), quercetin (7), paniculoside IV (8) and caffeic anhydride (9). The structures were characterized by 1?D, 2?D NMR spectroscopy and confirmed with HRMS. Antimicrobial and antiquorum-sensing activities of the different extracts and isolated compounds of the plant were investigated. Generally, the phenolic rather than the terpenoidal compounds exhibited remarkable antimicrobial and antiquorum-sensing activity.

     

Minor Alicyclic Diterpene Acidsfrom Conyza incana

Summary.  The reinvestigation of the CH₂Cl₂ extract of the aerial parts of Conyza incana led to the isolation of three minor alicyclic diterpene acids. The structures of the new compounds were established by a combination of spectroscopic methods. Received February 20, 2001. Accepted (revised) March 27, 2001