Records of Natural Products Articles

Leishmaniasis is widely ignored in discussion s on the priorities of tropical diseases, and the already-existing drugs present high toxicity or teratogenicity, as well as reduced efficacy due to the emergence of resistant strains. Marine natural products have received increasing attention over the last few decades because of the isolation of metabolites found in many products , with structural pattern not available in terrestrial organisms. Several molecules of marine origin have been investigated in respect of their effects on different species of parasites that cause leishmaniasis . In this study, we review the pharmacological information obtained from the in vitro and in vivo assays on such metabolites.

This study aimed to assess the chemical compositions of essential oils (EOs) extracted through microwave-assisted hydrodistillation from aerial parts of 11 Artemisia species growing wild in different regions in Northern, Eastern, Western, and Central parts of Iran. The EOs were subsequently analyzed via GC and GC-MS. The percentage yields of the EOs varied over the range of 0.21-0.50 (w/w%). On the basis of these characterizations and spectral assignments, natural compounds including camphor, 1,8-cineole, camphene, α-pinene, β-pinene, β-thujone, and sabinene were the most abundant and frequent constituents among all studied chemical profiles. Accordingly, oxygenated monoterpenes, monoterpene hydrocarbons, and non-terpene hydrocarbons were the dominant groups of natural compounds in the chemical profiles of 13, 4, and 2 samples, respectively. Moreover, five chemotypes were identified using statistical analyses: camphene, α-pinene and β-pinene; 1,8-cineole; camphore and 1,8-cineole; camphore and camphore and β-thujone.

Two new biflavonoids, (8-hydroxy-3'-β-D-galactosyl-isoflavone)-2'-8''-(4'''-hydroxy-flavone)-biflavone (2); 2',3',5-trihydroxy-5''-methoxy-3''-O- α-glucosyl-3-4'"-O-biflavone (3) and along with apigenin (1) and quercetin-3-O-β-glucoside (4) were isolated by activity guided fractionation from the whole plant of Solanum nigrum L.. The structures were established on the basis of UV, IR, 1D, 2D NMR and HRESI-MS spectroscopic methods. The anticholinesterase activity was performed against acetylcholinesterase and butyrylcholinesterase – the chief enzymes of Alzheimers’ disease – using the Ellman method. The tyrosinase inhibitory activity was performed according to L -DOPA method. Since the ethyl acetate (IC 50: 90.6±0.3 µg/mL) and n-butanol (IC 50: 140.6±1.7 µg/mL) extracts exhibited good butyrylcholinesterase inhibitory activity, both were fractionated and the active fractions were used for isolation of the compounds. These both extracts were also exhibited better tyrosinase inhibitory activity (IC 50: 76.0±0.6, and 156.8±1.9 µg/mL, respectively). Tested enzyme inhibitory activities of S. nigrum were presented in this study for the first time.

The phytochemical investigation of the aerial parts of Commicarpus grandiflorus ( Standl.) resulted in the isolation of two new flavonol 3-O-glucosides, commicarpiflavonol glucoside A (1) and commicarpiflavonol glucoside B (2), along with the known compounds β-sitosterol (3) and betulinic acid (4). The structures of the isolated compounds have been elucidated by extensive 1D ( 1H, 13C) and 2D (COSY, HSQC, HMBC) NMR spectral data analysis, as well as high-resolution mass determinations.

The chemical composition of the essential oils obtained by hydrodistillation from the different parts of Daucus aristidis Coss. (syn. Ammiopsis aristidis Batt.) (Apiaceae) from two locations (Ghoufi and Bousaada) in East of Algeria, was investigated for the first time by GC and GC-MS and evaluated for their in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity, the enzymes linked to Alzheimer’s disease, by a spectrophotometric method of Ellman using ELISA microplate reader at 100 µg/mL. The main components of D. aristidis oils from Ghoufi and Bousaada were α-pinene (74.1%- 49%) and β-pinene (11.9% - 19.2%). This suggests that β-pinene was the main component from Bousaada. The oils exhibited a moderate inhibitory activity (over 50%) against both of the enzymes.

Aroma is one of the essential parameters for the evaluation of fruit quality and consumer acceptance, with volatile components being determinant for this characteristic. During this work, the volatile profile of fresh fruits (pulp and peel) and leaves of Tunisian Ficus carica L. white (‘‘Bither Abiadh”, ‘‘Bidi”) and dark (‘‘Bither Kholi”, ‘‘Himri”, ‘‘Kholi” and ‘‘Tchich Asal”) varieties were characterised by GC and GC-MS. The major components detected among the volatiles of leaves were cedrol (38.9%), manoyl oxide (24.8%), α-terpineol acetate (21.7%), abietatriene (11.8%), γ-muurolene (7.4%), α-pinene (6.1%), pentadecanal (5.2%) and nonadecanal (2.3%). The major components detected in the volatiles of the fruits were cedrol (43.8%), α-terpinyl acetate (22.5%), manoyl oxide (12.9%), α-pinene (9.3%), abietadiene (8.1%),trans-calamenene (3.9%) and n-heneicosane (3.5%).The results suggest that the varieties could be distinguished on the basis of their volatile fractions composition.

A new phenolic compound, named 3-geranyl-2,5-dihydroxy-benzaldehyde (1), together with seven known chalone derivatives (2–8) has been isolated from the seeds of Celosia cristata L. Their chemical structures have been elucidated by spectroscopic analysis. All these compounds (1–8) were isolated from C. cristata for the first time.

The extracted oil of Argania spinosa (L.) was investigated in regard to its fatty acid composition and polyphenols by Gas Chromatography-Mass Spectrometry (GC–MS) and Ultra-high Performance Liquid Chromatography-Electro Spray Ionization-Quadruple Time Of Flight-Mass Spectrometry (UPLC-ESI-QTOF-MS), respectively. The reduction rate of topical inflammation of extracted oil was calculated using a mouse model. The skin toxicity of argan oil on intact and damaged skin was assessed using a rabbit model. The findings revealed a rich content of monounsaturated and polyunsaturated fatty acids and presence of phenolic acids. The oil exhibited a reduction of inflammation and facilitated a healing process without any irritation. The experimental study revealed that A. spinosa seed oil displays remarkable wound-healing and anti-inflammatory activities related to its chemical composition. Argan oil has positive potential for skin medicinal application.

Glucosinolates are secondary metabolites of almost all plants of the order Brassicales, and have been known to control nematode populations. In this study, 14 glucosinolates were identified, quantified, and compared in several varieties and cultivars of cruciferous plants including Brassica campestris ssp. pekinensis (Chinese cabbage), Brassica juncea var. crispifolia L. H. Bailey (mustard), Brassica juncea L. Czern. var. juncea (leaf mustard), Brassica oleracea L. var. acephala (kale), Raphanus sativus L. (radish), and Brassica campestris L. ssp. oleifera (winter turnip rape). The most abundant glucosinolate in mustard, leaf mustard, kale, and radish was sinigrin. In leaf mustard, the sinigrin content ranged from 193.05 μmol/g to 215.52 μmol/g, and in mustard, the sinigrin contents of blue mustard and red mustard were 219.08 μmol/g and 215.73 μmol/g, respectively. Kale and radish contained 137.79 μmol/g and 120.25 μmol/g, respectively, of sinigrin. Gluconapin was the most abundant glucosinolate in winter turnip rape, at 121.17 μmol/g. Chinese cabbage contained mostly glucocochlearin (79.88 μmol/g). These results will be useful in the development of environmentally friendly plant-based pesticides by allowing for proper control of glucosinolates based on those present in the chosen plant species.

The essential oils obtained from hydrodistillation of  Ocimum basilicum L. harvested at four different growth stages during spring-summer and rain-autumn cropping seasons , were characterized using GC and GC-MS. The e ssential oil yield was found to vary from 0.28–0.32% and 0.40–0.52% during spring-summer and rain-autumn cropping season, respectively with its maximal at full bloom stage. Altogether , forty constituents, comprising 94.9–98.3% were identified represented by ( E )-methyl cinnamate (36.6 – 66.4%), linalool (11.2 – 43.8%), and (Z )-methyl cinnamate (5.4-7.6%) as main constituents. Results showed that growth stages strongly influenced the chemical composition of the essential oil in two cropping seasons, particularly concerning to the content of ( E )-methyl cinnamate and linalool. Seed setting stage was optimized for harvesting ( E )-methyl cinnamate rich oil (66.4%) in rain-winter cropping season. The antimicrobial potential of the essential oil was tested againist eight pathogenic bacteria and three fungal strains. Antimicrobial assay showed that the essential oil possessed good antibacterial activity against Streptococcus mutans, Staphylococcus epidermidis, Escherichia coli , and antifungal activity against Candida kefyr and Candida albicans.

The extracts of powdered root and nutgall of Iraqian Aleppo oak (Q. infectoria) were obtained by using three different solvents along with two extraction methods. Liquid chromatography and tandem mass spectrometry (LC-MS/MS) was implemented to identify phytochemicals in the extracts. Antioxidant activity was determined by DPPH radical scavenging activity. Also, for measurement of antibacterial activity, disc diffusion and microdilution assays were used. Specifically, the nutgall extracts were found to have higher concentration of phenolic acid contents, and to some extent flavonoids and greater antioxidant and antimicrobial activities in comparison with the root extracts. Furthermore, microwave extraction technique was proven to be much more effective than conventional one in view of extraction yield for both plant parts used here.

This paper represents the phytochemical properties of Lebanese Papaver rhoeas, from which five protopine alkaloids are isolated, namely; stylopine (1), canadine (2), sinactine (3), berberine (4), and epiberberine (5). This is the first report for the isolation of epiberberine (5) from the genus Papaver and canadine (2) from Papaver rhoeas, suggesting a new chemotype of Papaver rhoeas growing in Lebanon. The cytotoxic activity of the total ethanolic extract and the isolated alkaloids were determined by MTT assay on human colon cancer cells (HCT116), breast cancer cells (MCF7), human keratinocyte cell line (HaCaT), and non-cancerous colon cells (NCM460). The compounds showed dose-dependent inhibitory effect with highest activity for compound 4 against all cell lines. The activity of the alkaloids varied between the various cell lines indicating cell type specificity and suggesting different cell-compound interactions. IC 50 values on normal cells was higher than cancer cell lines (>200 µM), indicating the selectivity of these compounds to cancer cells. It was noticed that the presence of methylenedioxy group at positions C-2 and C-3 rather than at position C-9 and C-10 potentiated the compound’s cytotoxic activity. Further studies are underway to explore the activity of these compounds at the molecular level.

ngelica sinensis contains a large amount of essential oil (angelica oil), which is rich in phthalide derivatives with a lot of bioactivities. In vitro activity screening of angelica oil from the roots of A. sinensis found that it had concentration-dependent effect on glutamate-induced injury in PC12 cells. Further phytochemical investigation on this angelica oil led to the isolation of nine butylphthalides (1 –9) including two new compounds (1 and 2). Their structures were elucidated by extensive spectroscopic analyses. It is noteworthy that most of the isolated butylphthalides also displayed protective activity at low concentrations and cytotoxicity at high concentrations. These results imply that angelica oil and its main chemical components have protective effect for injured neurons only in appropriate concentration range.

Ethyl acetate layer of the methanolic extract of Seriphidium quettense was subjected to silica gel column chromatography to isolate one new; seriphiloid (1), and four known compounds; ilicic acid (2), 6 a -hydroxy-8(10)-oplopen-14-one (3), 2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one (4) and 2-(3,4-dihydroxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one (5). The chemical structure of the new isolate was established with the help of 1D, 2D NMR techniques and high resolution mass spectrometry. Known compounds were identified because of 1D NMR and mass spectrometric analysis and in comparison with the literature values. Compounds 1-5 were evaluated for their acetylcholinesterase, butyrylcholinesterase, a -glucosidase and urease inhibitory activities. Most of the metabolites were found inactive; however, compounds 2 and 3 showed good antiurease activity with IC 50 value 21.5±0.1 and 20.8±0.1 µg/mL, respectively.

Phytochemical investigation of the aerial parts of Eryngium caeruleum led to the isolation of two new source flavone glycosides (1 and 2). The structures of these compounds were determined with the help of one- and two-dimensional (1D- and 2D-) NMR techniques including 1H-NMR, 13C-NMR, HMQC, HMBC, 1H- 1H COSY, and NOESY experiments. The compounds were studied for their in vitro aldose reductase (ALR1 and ALR2) and glucosidase (α and β) inhibitory activities, and antiglycation potential. Both the compounds showed higher inhibition potential against ALR1 than ALR2. Compound 2 showed three fold higher potency against ALR2 than the reference drug Sorbinil. In silico studies were performed to understand the binding mechanism of these compounds to aldose reductase .