Phenolic profile of Centaurea aegyptiaca L. growing in Egypt and its cytotoxic and antiviral activities

Background: Centaurea aegyptiaca L (Asteraceae), is one of the most attractive plants growing wildly in Sinai, and is not well investigated for its phytochemical constituents. This study represents the first in-depth characterization of the phenolic profile of the aerial parts of C. aegyptiaca methanolic extract utilizing liquid chromatography (LC) combined with electrospray ionization (ESI) tandem mass spectrometry (MS/MS).Material and Methods: Phenolic profile was researched utilizing LC-HRESI-MS-MS. Assessment of cytotoxic activity against four human cancer cell lines (Hep-G2; hepatocellular carcinoma cells, MCF-7; breast adenocarcinoma cells, and HCT-116; colon carcinoma and HELA; cervical carcinoma cells) was performed using 3-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay. Antiviral activity was surveyed utilizing cytopathic effect inhibition assay.Results: A total of sixty-one compounds were tentatively distinguished (twenty-one phenolic acids and their derivatives, thirty-one flavonols and nine flavones) in the negative and positive modes. Centaurea aegyptiaca demonstrated outstanding results against Hep-G2, MCF-7, HCT-116 and HELA cell lines with IC50 of 12.1, 30.9, 11.7 and 19.5 μg/mL respectively compared and doxorubicin as a reference drug. Weak antiviral activity was seen against hepatitis A virus (HAV) and no impact against herpes simplex virus type 1 (HSV 1).Conclusion: This study provides a better understanding of the chemistry of C. aegyptiaca that announces itself as a promising cytotoxic agent.Keywords: Centaurea aegyptiaca, Cytotoxicity, MTT assay, flavonoi

PHENOLIC PROFILE OF Centaurea aegyptiaca L. GROWING IN EGYPT AND ITS CYTOTOXIC AND ANTIVIRAL ACTIVITIES

Background: Centaurea aegyptiaca L (Asteraceae), is one of the most attractive plants growing wildly in Sinai, and is not well investigated for its phytochemical constituents. This study represents the first in-depth characterization of the phenolic profile of the aerial parts of C. aegyptiaca methanolic extract utilizing liquid chromatography (LC) combined with electrospray ionization (ESI) tandem mass spectrometry (MS/MS). Material and Methods: Phenolic profile was researched utilizing LC-HRESI-MS-MS. Assessment of cytotoxic activity against four human cancer cell lines (Hep-G2; hepatocellular carcinoma cells, MCF-7; breast adenocarcinoma cells, and HCT-116; colon carcinoma and HELA; cervical carcinoma cells) was performed using 3-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay. Antiviral activity was surveyed utilizing cytopathic effect inhibition assay. Results: A total of sixty-one compounds were tentatively distinguished (twenty-one phenolic acids and their derivatives, thirty-one flavonols and nine flavones) in the negative and positive modes. Centaurea aegyptiaca demonstrated outstanding results against Hep-G2, MCF-7, HCT-116 and HELA cell lines with IC50 of 12.1, 30.9, 11.7 and 19.5 μg/mL respectively compared and doxorubicin as a reference drug. Weak antiviral activity was seen against hepatitis A virus (HAV) and no impact against herpes simplex virus type 1 (HSV 1). Conclusion: This study provides a better understanding of the chemistry of C. aegyptiaca that announces itself as a promising cytotoxic agent

Kemijski sastav endemske biljke Centaurea austro-anatolica i ispitivanje antimikrobnog djelovanja protiv multi-rezistentnih bakterija

Hexane, chloroform, ethyl acetate and ethanolic extracts of the aerial parts of C. austro-anatolica Hub.-Mor. (Asteraceae) were evaluated against microorganisms, including multi-resistant bacteria, using a paper disc diffusion method. The chloroform extract exhibited significant antibacterial activity toward all bacteria tested. The chemical composition of the chloroform extract was determined by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The major compounds of the extract were caryophyllene oxide (21.32 %), spathulenol (10.86 %), n-tricosanol (9.58 %) and geranyl isovalerate (8.71 %).Heksanski, kloroformski, etil-acetatni i etanolni ekstrakti vršnih dijelova biljke C. austro-anatolica Hub.-Mor. (Asteraceae) ispitivani su na antimikrobno djelovanje protiv multi-rezistentnih bakterija, koristeći difuzijsku metodu na papirnom disku. Kloroformski ekstrakt pokazao je značajno antibakterijsko djelovanje protiv svih testiranih bakterija. Kemijski sastav tog ekstrakta određivan je plinskom kromatografijom (GC) i plinskom kromatografijom-spektrometrijom masa (GC-MS). Najvažniji sastojci ekstrakta bili su kariofilen oksid (21,32 %), spatulenol (10,86 %), n-trikozanol (9,58 %) i geranil izovalerat (8,71 %)

VolSurf analysis of pharmacokinetic properties for several antifungal sesquiterpene lactones isolated from Greek Centaurea sp.

Sesquiterpene lactones are terpenoid compounds characteristic of the Asteraceae (Compositae) possessing a variety of biological activities, such as cytotoxic, antitumor, antibacterial, and antifungal. The prediction of the pharmacokinetic profile of several antifungal sesquiterpene lactones, isolated from Greek taxa of Centaurea sp., was undertaken in this study using the VolSurf procedure. The molecules were projected on the following pre-calculated ADME models: Caco-2 cell permeability, plasma protein affinity, blood-brain barrier permeation and thermodynamic solubility. The in silico projection revealed a non optimal pharmacokinetic profile for the studied compounds. ADME in silico screening of a semi-synthetic derivatives virtual library has been performed in order to optimize the pharmacokinetic properties. A number of derivatives were proposed as it was predicted to have higher Caco-2 cell permeability, while the pharmacokinetic behaviour regarding BBB penetration, protein binding and solubility was mainly preserved. © Springer Science+Business Media, Inc. 2005

Secondary metabolites from the aerial parts of Centaurea pannonica (Heuffel) Simonkai (Asteraceae) and Origanum scabrum Boiss. & Heldr. (Lamiaceae) and their antimicrobial activities

Predmet doktorske disertacije je izolovanje i identifikacija sekundarnih metabolita iz ekstrakata nadzemnih delova biljaka Centaurea pannonica (Heuffel) Simonkai (Asteraceae) i Origanum scabrum Boiss. & Heldr. (Lamiacea), kao i ispitivanje obima njihove antimikrobne aktivnosti i hemotaksonomski značaj. Takođe, predmet ispitivanja je hemijski sastav etarskog ulja Centaurea pannonica i antimikrobna aktivnost. Primenom hromatografskih metoda izolovanja jedinjenja i spektroskopskih metoda identifikacije struktura, iz nepolarnog ekstrakta biljke Centaurea pannonica sa područja Srbije, izolovano je i identifikovano 25 jedinjenja: 14 seskviterpenskih laktona, 7 flavonoida, 3 lignana i 1 fenilpropanoid glukozid. Navedena jedinjenja po prvi put su izolovana iz navedene biljke dok su germakranolid 2α-hidroksi 8- dehidroksi-15-Ο-metakrilat salonitenolid i gvajanolidi: 2α,8α-dihidroksi dehidrokostunolid lakton i panonin novi prirodni proizvodi, prvi put izolovani iz prirodnog resursa. Ispitivanjem esencijalnog ulja navedene biljke, identifikovano je ukupno 45 jedinjenja, što je 82,2% ukupnog sastava esencijanog ulja. Kvantitativno najzastupljenije grupe jedinjenja čine višemasne kiseline sa 43,7% i kiseonični derivati seskviterpena 18,7%.In the present thesis, the secondary metabolites of two different plant species, namely Centaurea pannonica (Heuffel) Simonkai (Asteraceae) growing wild in Serbia and Origanum scabrum Boiss. & Heldr. (Lamiaceae) growing wild in Greece, were isolated and identified. Moreover, the antimicrobial activities of the total plant extracts and the isolates were evaluated. In addition, the chemical composition and the antimicrobial activity of the essential oil of C. pannonica were investigated. The chemical composition of the plant extracts was investigated by means of standard chromatographic (VLC, MPLC, HPLC, CC, TLC) and spectroscopic methods (UV, IR, HREIMS and 1D & 2D NMR). The lipophilic extract of C. pannonica afforded twenty-five compounds including fourteen sesquiterpene lactones, seven flavonoids, three lignans and one phenylpropanoid glycoside. All compounds were isolated for the first time from C. pannonica. Among them, one germacranolide, 2α-hydroxy, 8-dehydroxy 15-Ο-methacrylate salonitenolide and two guaianolides, i.e. 2α, 8α-dihydroxy-dehydrocostus lactone and pannonin are new natural products. Forty-five compounds were identified, representing 82.2% of the total C. pannonica essential oil. Unsaturated and aliphatic acids (43.7%) and oxygenated sesquiterpenes (18.7%) are the major groups of components