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1.
Molecules ; 29(12)2024 Jun 08.
Article in English | MEDLINE | ID: mdl-38930796

ABSTRACT

The current study was designed to uncover the chemistry and bioactivity potentials of Bupleurum lancifolium growing wild in Jordan. In this context, the fresh aerial parts obtained from the plant material were subjected to hydrodistillation followed by GC/MS analysis. The main components of the HDEO were γ-patchoulene (23.79%), ß-dihydro agarofuran (23.50%), α-guaiene (14.11%), and valencene (13.28%). Moreover, the crude thanolic extract was partitioned to afford two main major fractions, the aqueous methanol (BLM) and butanol (BLB). Phytochemical investigation of both fractions, using conventional chromatographic techniques followed by careful inspection of the spectral data for the isolated compounds (NMR, IR, and UV-Vis), resulted in the characterization of five known compounds, including α-spinasteryl (M1), ethyl arachidate (M2), ethyl myristate (M3), quercetin-3-O-ß-d-glucopyranosyl-(1-4")-α-L-rhamnopyranosyl (B1), and isorhamnetin-3-O-ß-d-glucopyranosyl-(1-4")-α-L-rhamnopyranosyl (B2). The TPC, TFC, and antioxidant activity testing of both fractions and HDEO revealed an interesting ABTS scavenging potential of the BLB fraction compared to the employed positive controls, which is in total agreement with its high TP and TF contents. Cytotoxic evaluation tests revealed that BLM had interesting cytotoxic effects on the normal breast cell line MDA-MB-231 (ATCC-HTB-26) and the normal dermal fibroblast (ATCC® PCS-201-012) and normal African green monkey kidney Vero (ATCC-CCL-81) cell lines. Despite both the BLB and BLM fractions showing interesting AChE inhibition activities (IC50 = 217.9 ± 5.3 µg/mL and 139.1 ± 5.6 µg/mL, respectively), the HDEO revealed an interestingly high AChE inhibition power (43.8 ± 2.7 µg/mL) that far exceeds the one observed for galanthamine (91.4 ± 5.2 µg/mL). The HDEO, BLM, and BLB exhbitied no interesting antimicrobial activity against Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, or Pseudomonas aeruginosa.


Subject(s)
Antioxidants , Bupleurum , Plant Extracts , Jordan , Plant Extracts/chemistry , Plant Extracts/pharmacology , Antioxidants/pharmacology , Antioxidants/chemistry , Animals , Bupleurum/chemistry , Humans , Vero Cells , Phytochemicals/chemistry , Phytochemicals/pharmacology , Chlorocebus aethiops , Cell Line, Tumor , Plant Components, Aerial/chemistry , Gas Chromatography-Mass Spectrometry , Cell Survival/drug effects , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry
2.
Life (Basel) ; 13(6)2023 Jun 16.
Article in English | MEDLINE | ID: mdl-37374186

ABSTRACT

The genus Scrophularia is one of the largest genera belonging to the Scrophulariaceae family. Different members of the genus exhibit an interesting, wide spectrum of bioactivities. Accordingly, the current study aimed to investigate, for the first time, the chemical composition of the essential oil of Scrophularia peyronii Post. from Jordan. Additionally, extracts obtained from the aerial parts with solvents of different polarities were assayed for their phytochemical constituents and in vitro antioxidant activities. The major constituents detected in the essential oil, as revealed by GC/MS analysis, contained mainly Z,Z-farnesyl acetone (11.04%), ß-elemene (6.36%), n-octanal (5.98%), and spathulenol (4.58%). Each of the aqueous methanol (Sp-M) and butanol (Sp-B) extracts contained flavonoids, saponins, anthraquinone, and glycosides. Both extracts were evaluated for their total phenolic content (TPC), total flavonoid content (TFC), and their in vitro antioxidant activity, which were assayed using the DPPH radical scavenging activity and ABTS radical scavenging methods. Additionally, the two extracts were then subjected to LC-ESI-MS/MS for the qualitative determination of their secondary metabolite content, especially in flavonoids and phenolic compounds. The results showed that the Sp-B extract of S. peyronii had the highest contents of both phenolic compounds and flavonoids and showed high radical scavenging activity, as determined by the two assay methods, when compared with the Sp-M extract. The LC-ESI-MS/MS analysis resulted in the detection of 21 compounds, including 8 flavonoids, 6 phenolic acids, 6 iridoids, and 2 acids. Although the majority of compounds were detected in both extracts, it was noticed that scropolioside B, 6'-O-cinnamoylharpagide, isoferulic acid, and 6-O-methylcatapol were only detected in the Sp-M fraction.

3.
Molecules ; 27(3)2022 Jan 27.
Article in English | MEDLINE | ID: mdl-35164120

ABSTRACT

This study aimed to evaluate the antioxidant activity and total phenolic content (TPC) and total flavonoid content (TFC) of crude extracts obtained from three Asclepiadaceae species, namely, Calotropis procera L., Peruglaria tomentosa L., and Pentatropis spiralis (Forsk.) Decne. Both butanol and aq. methanol extracts of the three species showed the highest amount of phenol and flavonoid contents, which exhibited the greatest antioxidant activity in the scavenging of 2,2-diphenyl-2-picrylhydrazyl free radical (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radical cation (ABTS), ferrous chelating effect (FIC), and hydroxyl radical (HDR) assays. Phytochemical screening of the extracts revealed the presence of alkaloids, tannins, sponins, flavonoids, terpenoids, and glycosides. LC-MS analysis was carried out to identify the major compounds from each crude extract. A total of 12 phenolic compounds in the extracts of the 3 species were identified and quantified, including 9 flavonoids, 2 hydroxybenzoic acids, and 3 hydroxycinnamic acids. The current study also revealed a good correlation between total phenolic contents and the observed antioxidant activity of the crude extracts.


Subject(s)
Antioxidants/analysis , Apocynaceae/chemistry , Flavonoids/analysis , Plant Extracts/chemistry , Plant Leaves/chemistry , Apocynaceae/growth & development , Chromatography, Liquid , Jordan , Plant Leaves/growth & development , Species Specificity , Tandem Mass Spectrometry
4.
Saudi Pharm J ; 30(12): 1773-1780, 2022 Dec.
Article in English | MEDLINE | ID: mdl-36601509

ABSTRACT

Objective: The study aimed to identify the current practice carried out by community pharmacists to dispose of expired medications in their workplace and assess any practical steps utilized to reduce medication waste. Method: A cross-sectional study was conducted among community pharmacists in the United Arab Emirates (UAE). The participants were asked about their routine practice in disposing of different expired medications and the current actions taken to reduce the number of disposed medicines. Results: The study included (n = 418) community pharmacists. More than a third of expired liquid, solid, and semi-solid dosage forms were collected by licensed contractors. In addition, more than a third of the pharmacists disposed of different dosage forms via unauthorized methods (general garbage, sink and toilet). Most expired drugs were skin and hair products, antibiotics and analgesics. The majority of pharmacists (68.4 %, n = 286) agreed that expired pharmaceutical and non-pharmaceutical products, other than those disposed of via contractor, should be done through a specialized centre. This opinion was found to be strongly associated with years of practice as community pharmacists (P < 0.05). Conclusion: Part of the existing disposal practices for expired pharmaceutical products in the UAE is carried out by contractors licensed by health authorities. However, concern remains regarding some pharmaceutical and non-pharmaceutical products that have not been disposed of correctly. Additionally, there is a need for a specialized center for medication disposal (p < 0.05). A stock limitation is the best practice for managing medication quantities in stock (p < 0.05).

5.
J Org Chem ; 82(7): 4001-4005, 2017 04 07.
Article in English | MEDLINE | ID: mdl-28318256

ABSTRACT

Cationic 1-aza-2-azoniaallene salts react with structurally constrained alkenes in intramolecular reactions by C-H insertion at the allylic position, or by (2+1)-cycloaddition with the alkene followed by ring opening. The latter reaction gives further evidence of the nitrenium-like character of 1-aza-2-azoniaallene salts. DFT calculations show that alkene addition is intrinsically more favorable, but that predistortion can lead to C-H insertion.


Subject(s)
Alkenes/chemistry , Azo Compounds/chemistry , Cycloaddition Reaction , Carbon-13 Magnetic Resonance Spectroscopy , Molecular Structure , Proton Magnetic Resonance Spectroscopy , Salts/chemistry , Spectrometry, Mass, Electrospray Ionization
6.
J Am Chem Soc ; 137(28): 9100-7, 2015 Jul 22.
Article in English | MEDLINE | ID: mdl-26151292

ABSTRACT

The 1-aza-2-azoniaallene salts, generated from α-chloroazo compounds by treatment with halophilic Lewis acids, undergo intramolecular C-H amination reactions to form pyrazolines in good to excellent yields. This intramolecular amination occurs readily at both benzylic and tertiary aliphatic positions and proceeds at an enantioenriched chiral center with retention of stereochemistry. Competition experiments show that insertion occurs more readily at an electron-rich benzylic position than it does at an electron-deficient one. The C-H amination reaction occurs only with certain tethers connecting the heteroallene cation and the pendant aryl groups. With a longer tether or when the reaction is intermolecular, electrophilic aromatic substitution occurs instead of C-H amination. The mechanism and origins of stereospecificity and chemoselectivity were explored with density functional theory (B3LYP and M06-2X). The 1-aza-2-azoniaallene cation undergoes C-H amination through a hydride transfer transition state to form the N-H bond, and the subsequent C-N bond formation occurs spontaneously to generate the heterocyclic product. This concerted two-stage mechanism was shown by IRC and quasi-classical molecular dynamics trajectory studies.


Subject(s)
Alkadienes/chemistry , Aza Compounds/chemistry , Salts/chemistry , Amination , Benzyl Compounds/chemistry , Models, Molecular , Pyrazoles/chemistry , Stereoisomerism
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