Phytochemical Profile, GC-MS Profiling and In Vitro Evaluation of Some Biological Applications of the Extracts of Origanum syriacum L. and Cousinia libanotica D.C.

Indigenous to Lebanon, Origanum syriacum L. and Cousinia libanotica D.C. are notable plants in the Middle East, with O. syriacum known for its aromatic qualities and C. libanotica being less explored. Both plants have a significant role in traditional medicine for treating various ailments. This study aimed to evaluate the phytochemical composition and biological properties of the extracts from these plants. The extracts were obtained through cold maceration with solvents of increasing polarity. The ethyl acetate extract of O. syriacum exhibited the highest total polyphenol content. High-performance liquid chromatography (HPLC) identified fifteen compounds in both C. libanotica and O. syriacum extracts, whereas gas chromatography-mass spectrometry (GC-MS) analysis unveiled 179 volatile compounds. Notably, the O. syriacum-MeOH extract showed moderate antioxidant activity. Both plants' methanolic extracts demonstrated significant anti-Alzheimer's potential. The O. syriacum-dichloromethane and C. libanotica-cyclohexane extracts displayed the highest cytotoxicities against the HCT-116 cell line. For anti-proliferative activity against the Caco-2 cell line, the O. syriacum-methanol and C. libanotica-cyclohexane extracts were the most effective. This study provides valuable insights into the phytochemistry and potential therapeutic applications of extracts from these two oriental plant species.

Comparative Study of Phytochemistry, Antioxidant and Biological Activities of Berberis libanotica Fruit and Leaf Extracts.

Berberis libanotica Ehrenb. ex C.K. Schneider of the Berberidaceae family is an endemic Lebanese plant and is widely used in folk medicine. This study highlights the phytochemical composition and biological activities (in vitro) of fruit and leaf extracts. The two organs were extracted by cold maceration with four solvents of increasing polarity: cyclohexane, dichloromethane, ethyl acetate and methanol. The extracts were screened for their chemical composition by HPLC-DAD to identify and quantify the phenolic compounds. Volatile compounds were detected by GC-MS. The antioxidant capacity through DPPH inhibition was tested. The anti-acetylcholinesterase, antibacterial and anti-proliferative activities were evaluated. Thirteen compounds, including 12 phenolics, were detected in the fruits, whereas 8 phenolic compounds were identified in the leaves. A total of 137 volatile compounds were identified in both organs. At 50 µg/mL, the methanolic leaf extract presented the highest antioxidant capacity, with an inhibition percentage of 54.9%. The dichloromethane fruit extract reduced the acetylcholinesterase activity by 65.3%. The cyclohexane leaf extract reduced the proliferation of the HCT-116 cells by 54.8%, while the dichloromethane fruit extract exhibited the best inhibition against the Caco-2 cells (54%). Interestingly, the minimum inhibitory concentration (MIC) value of the cyclohexane fruit extract against Salmonella enterica serovar Kentucky was 2.4 µg/mL, and the MIC value of the cyclohexane leaf extract against E. coli was 9.7 µg/mL.

Chemical Characterization and Antioxidant, Antibacterial, Antiacetylcholinesterase and Antiproliferation Properties of Salvia fruticosa Miller Extracts.

The Salvia fruticosa (Mill.) is the most medicinal plant used in Lebanon. The aim of this study is to investigate the phytochemical composition and the biological activities (in vitro) of its extracts. The plant was extracted by cold maceration with four solvents presenting an increasing polarity: cyclohexane (CHX), dichloromethane (DCM), ethyl acetate (EtOAc) and methanol (MeOH). The extracts were screened for their chemical composition by a HPLC-DAD detector for phenolic compounds identification and quantification and by GC-MS for volatile compounds detection. The antioxidant capacity (DPPH inhibition) was tested. Biological activities, mainly anti-Alzheimer activity (acetylcholinesterase inhibition), the antiproliferation of two human colon cancer cell lines (HCT-116 and Caco-2 cells) and antibacterial activity, were evaluated. Ten aromatic compounds were quantified by HPLC-DAD analysis. A total of 123 compounds were detected by GC-MS analysis. The MeOH extract showed a very interesting antioxidant activity with an inhibition percentage (IP) of 76.1% and an IC50 of 19.4 µg/mL. The EtOAc extract exhibited the strongest inhibition against the acetylcholinesterase activity (IP = 60.6%) at 50 µg/mL. It also strongly inhibited the proliferation of the HCT-116 cells (IP = 87.5%), whereas the DCM extract gave the best result with the Caco-2 cells (IP = 72.3%). The best antibacterial activity was obtained with the MeOH extract against Staphylococcus aureus (MIC = 1.2 µg/mL) and with the EtOAc extract against Escherichia coli (MIC = 2.4 µg/mL). This study highlights the chemical composition and therapeutic potential of S. fruticosa. It is important to mention that the following chemical compounds were identified for the first time in plant extracts: 2,6,11,15-tetramethyl-hexadeca-2,6,8,10,14-pentaene; 4,5,6,7-tetrahydroxy-1,8,8,9-tetramethyl-8,9-dihydrophenaleno [1,2-b]furan-3-one; podocarpa-1,8,11,13-tetraen-3-one,14-isopropyl-1,13-dimethoxy; podocarpa-8,11,13-trien-3-one,12-hydroxy-13-isopropyl-,acetate; 3',8,8'-trimethoxy-3-piperidin-1-yl-2,2'-binaphthyl-1,1',4,4'-tetrone; and 2,3-dehydroferruginol, thus underlining the originality of this study.

Astragalus species: Insights on its chemical composition toward pharmacological applications.

Astragalus L. is widely distributed throughout the temperate regions of Europe, Asia, and North America. The genus is widely used in folk medicine and in dietary supplements, as well as in cosmetics, teas, coffee, vegetable gums, and as forage for animals. The major phytoconstituents of Astragalus species with beneficial properties are saponins, flavonoids, and polysaccharides. Astragalus extracts and their isolated components exhibited promising in vitro and in vivo biological activities, including antiaging, antiinfective, cytoprotective, antiinflammatory, antioxidant, antitumor, antidiabesity, and immune-enhancing properties. Considering their proven therapeutic potential, the aim of this work is to give a comprehensive summary of the Astragalus spp. and their active components, in an attempt to provide new insight for further clinical development of these xenobiotics. This is the first review that briefly describes their ethnopharmacology, composition, biological, and toxicological properties.

Effect of geographical origin on yield and composition of cone essential oils of Cedrus libani A. Rich. growing in Lebanese protected areas and variability assessment in comparison with literature survey.

Gas chromatography-mass spectrometry analysis together with principal component analysis revealed that geographical origin influenced the yield and composition of the essential oils (EOs) extracted by hydrodistillation performed for 3 h using a Clevenger-type apparatus, from the cones of Cedrus libani A. Rich., growing wild at four Lebanese natural reserves and protected areas: Bsharri, Chouf, Ehden, and Tannourine, and from a cultivated cedar growing in Qartaba. Essential oil chemical variability established between the different studied provenances suggested the involvement of abiotic factors such as geographical conditions, cultivation conditions, soil composition, and environmental factors in the chemical polymorphism of C. libani cones EOs. α-Pinene/ß-pinene characterized Ehden (ß-pinene 35.6%/α-pinene 27.7%), Chouf (α-pinene 37.3%/ß-pinene 26.1%), Bsharri (α-pinene 27.7%/ß-pinene 21.4%), and Tannourine (α-pinene 25.1%/ß-pinene 16.0%) samples, whereas Qartaba EO was distinguished by the dominance of myrcene (30.6%), α-pinene(26%), and limonene (14.1%). Comparison with the existing literature reinforced the chemical variability of C. libani EOs. This current study helped the estimation of a best harvest location for a good EO quality production, resource optimization, and pharmacological properties evaluation, according to the market demand.

Origanum syriacum Essential Oil Chemical Polymorphism According to Soil Type.

BACKGROUND: Origanum syriacum L. is an aromatic plant growing wild in Lebanon. This species is highly used in Lebanese traditional medicine and is a staple food in Lebanese gastronomy. Due to the over-harvesting, this species has become a cultivated crop rather than being collected from the wild. This study aims to evaluate the chemical polymorphism according to soil type. METHODS: Plant samples were cultivated in different soil types including manure, potting mix, professional agriculture mixture, vegetable compost, nursery soils, and natural agricultural soil inoculated with arbuscular mycorrhizal fungi. After 16 weeks of culture, fresh shoot biomass was measured. Root colonization rate was evaluated and foliar biomasses were used for essential oil (EO) extraction. EO yield was calculated and the identification of the main chemical compounds of EO samples was performed by gas chromatography (GC) and gas chromatography⁻mass spectrometry (GC/MS). RESULTS: Our findings revealed that the soil type affects the O. syriacum chemotype. Indeed, the EO samples could be divided into two groups: thymol chemotype group including manure and vegetable compost soils and non-sterilized non-inoculated EO samples, and the thymol/carvacrol chemotype including potting mix, professional agriculture mixture, nursery mixture, sterilized non-inoculated, non-sterilized inoculated, and sterilized inoculated EO samples. These results showed that manure and vegetable compost soils promoted thymol synthesis, whereas potting mix, professional agriculture mixture, and nursery mixture soils were thymol/carvacrol chemotype. Moreover, mycorrhizal inoculation increased carvacrol and reduced thymol productions in comparison to non-inoculated conditions. Additionally, mycorrhizal inoculation showed significant enhancements in mycorrhizal rates and shoot biomass production with respect to the non-sterilized soil. CONCLUSIONS: These variations confirm the influence of the edaphic conditions on the chemical components biosynthesis pathways of oregano plants. The results of this investigation could be used for determining optimal soil type, leading to a good quality herb production.

Chemical Variability of the Essential Oil of Origanum ehrenbergii Boiss. from Lebanon, Assessed by Independent Component Analysis (ICA) and Common Component and Specific Weight Analysis (CCSWA).

Origanum ehrenbergii Boiss., an endemic plant to Lebanon, is widely acknowledged in Lebanese traditional medicine. The aim of the present study was to evaluate the influence of the drying method, region, and time of harvest on yield and chemical composition of O. ehrenbergii essential oils (EOs). Plants were harvested monthly throughout 2013 and 2014, from two different regions, Aabadiye and Qartaba, then dried using two drying methods: lyophilization and shade-drying at 4 °C. EO was extracted by hydrodistillation and analyzed by GC/MS. GC-MS data, combined with independent component analysis (ICA) and common component and specific weight analysis (CCSWA), showed that drying techniques, region of harvest, and soil composition have no effect on the chemical composition of O. ehrenbergii EOs. Of the factors analyzed, only harvesting time affected the EO composition of this species. High and stable amounts of carvacrol, associated with reliable antimicrobial activities, were detected in material harvested between March and October. EOs obtained from plants harvested in Aabadiye in January and February showed high amounts of thymoquinone, related to anti-inflammatory and cytotoxic effects. The use of ICA and CCSWA was proven to be efficient, and allowed the development of a discriminant model for the classification of O. ehrenbergii chemotype and the determination of the best harvesting time.

Hirtellina lobelii DC. essential oil, its constituents, its combination with antimicrobial drugs and its mode of action.

With the goal of unravelling antimicrobial agents and mixtures inspired by plant defences, we investigated the antibacterial and antifungal efficacy of Hirtellina lobelii DC. essential oil (EO), both alone and in combination with antimicrobial drugs. Hirtellina lobelii DC. EO was analysed by GC, GC-MS and partial fractionation/NMR. It was essentially composed of oxygenated sesquiterpenes (75.2%), with α-bisabolol (34.5%), fokienol (12.0%) and T-muurolol (6.8%) serving as the main components. Microbial susceptibility was determined by the broth microdilution method and was expressed as minimum inhibitory concentration (MIC) and minimum bactericidal or fungicidal concentration (MBC or MFC). This EO was found to possess remarkable bactericidal (MBC/MIC = 2) and fungicidal (MFC/MIC = 1-4) potential, particularly against the Gram (+) bacteria Staphylococcus aureus, including its methicillin-resistant forms, the yeast Cryptococcus neoformans and dermatophytes from the genus Trichophyton (MICs 8-128 µg/ml). The examination of the combined effects of the EO with antimicrobial drugs revealed synergisms of the EO with vancomycin against S. aureus and of the EO with fluconazole and griseofulvin against dermatophytic fungi (FICI 0.2-0.5). The effect of H. lobelii EO on the morphologies of fungal hyphae and bacteria, as determined by scanning electronic microscopy (SEM), showed fungal hyphae swelling and bulging. These results suggest that H. lobelii EO and its major constituent, α-bisabolol, have remarkable antimicrobial potential. Combination therapies of this EO with antifungal drugs could offer a promising alternative for treatment of human mycoses caused by filamentous dermatophytic fungi.

Phytochemical screening and antityrosinase activity of carvacrol, thymoquinone, and four essential oils of Lebanese plants.

OBJECTIVE: In our study, we aim to explore the ability of four essential oils (EO) of Lebanese plants to inhibit the tyrosinase activity and to correlate their efficiency level to their phytochemical compositions. METHODS: The EO have been extracted by hydrodistillation using a Clevenger apparatus and have been studied by GC-MS analysis. Active compounds of Origanum species were identified and antityrosinase activities of EO and active molecules (carvacrol and thymoquinone) have been tested in tubo. RESULTS: Antityrosinase activities were obtained as follows: EO of Origanum syriacum (80.41% ± 2.00%), EO of Origanum ehrenbergii (45.33% ± 2.20%), EO of Salvia fruticosa (14.62% ± 2.30%), EO of Calamintha origanifolia (16.51% ± 5.80%), Carvacrol (56.55% ± 3.10%), and Thymoquinone (19.49% ± 1.50%). CONCLUSION: Origanum essential oils resulted in the highest antityrosinase activity due to their high content in carvacrol. However, when present together with carvacrol, thymoquinone decreases the efficiency of carvacrol, which is the case of O. ehrenbergii essential oil. Thus, for improved antityrosinase activity, O. syriacum and O. ehrenbergii should be harvested during flowering stage where carvacrol is present at its highest dosage and thymoquinone at its lowest.

Phytochemical composition and antioxidant activity of Tunisian Laurus nobilis.

We study the composition of Tunisian laurel leaves essential oil (EO), the fatty acid composition of laurel seed fixed oil and the total phenolics, flavonoids and tannins of laurel leaves methanolic extract. We also evaluated its free radical scavenging activity by the DPPH test. The predominant chemical class in Tunisian Laurus nobilis leaves EO was represented by oxygenated monoterpenes accounting for 64.29% of whole EO with the major compound was 1,8-cineole (46.8%). The predominant fatty acid was oleic acid (C18: 1) with an amount of 42.0%. Total polyphenols were present in the methanolic extract of Laurusnobilis leaves at an amount of 174.1 mg GAE.g-1dry matter. Total flavonoids and total tannins accounted respectively for 149.2mg CE.g-1 dry matter and 24.9mg CEg-1 dry matter. Furthermore, concerning free radical scavenging activity, Laurus nobilis leaves methanolic extract presented a significant IC50 (3mg/mL).

Chemical Composition and Antimicrobial Activity of Satureja, Thymus, and Thymbra Species Grown in Lebanon.

The essential oils were extracted by hydrodistillation from Satureja cuneifolia, Satureja thymbra, Coridothymus capitatus, Thymus syriacus, and Thymbra spicata growing wild in Lebanon. Their phytochemical analysis performed by GC/MS showed that the aforementioned species are characterized either by carvacrol (60.9%) or thymol (54.3%) or by a more or less equal amounts of these two phenols. Assessment of their in vitro antimicrobial activity against Candida albicans and six pathogenic bacteria using the broth dilution method revealed that the tested oils have a broad activity spectrum with minimum inhibitory concentration ranging from 0.1 to 0.8 mg/ml. Among the tested species, S. thymbra EO showed the highest antimicrobial potential whereas T. syriacus showed the lowest inhibitory activity. These results give scientific evidence for the use of those species in the Lebanese folk medicine and lend support to implement them as natural alternatives for synthetic antimicrobials.

Report on the Medicinal Use of Eleven Lamiaceae Species in Lebanon and Rationalization of Their Antimicrobial Potential by Examination of the Chemical Composition and Antimicrobial Activity of Their Essential Oils.

Many Lamiaceae species are consumed in the Lebanese cuisine as food or condiment and are largely used in the traditional medicine of Lebanon to treat various diseases, including microbial infections. In this article we report the traditional medicinal uses of eleven Lamiaceae species: Coridothymus capitatus L., Lavandula stoechas L., Lavandula angustifolia Mill., Mentha spicata L. subsp. condensata, Origanum syriacum L., Rosmarinus officinalis, Salvia fruticosa Miller., Satureja cuneifolia Ten., Satureja thymbra L., Thymbra spicata L., and Vitex agnus-castus L. and study the chemical composition and antimicrobial activity of their essential oils (EOs). Our survey showed that Lamiaceae species are mainly used against gastrointestinal disorders and microbial infections. Chemical analysis of the EOs obtained from these plants allowed us to identify seventy-five compounds describing more than 90% of the relative composition of each EO. Essential oils with high amounts of thymol and carvacrol possessed the strongest antimicrobial activity. As expected, these two compounds demonstrated an interesting antifungal efficacy against the filamentous fungus T. rubrum. Our results confirmed that some of the Lamiaceae species used in Lebanon ethnopharmacological practices as antimicrobial agents do possess antibacterial and antifungal potential consistent with their use in alternative or complementary medicine.

Plants used as remedies antirheumatic and antineuralgic in the traditional medicine of Lebanon.

AIM OF THE STUDY: In the present investigation, ethnobotanical and ethnopharmacological research of the traditional use of plants to cure antirheumatic and antineuralgic diseases was carried out in Lebanon. MATERIALS AND METHODS: The information was collected from different cities and villages of the twenty-six districts "aqdya or qadaa" of the six governorates "mohaafazah" of Lebanon. The knowledge on the medicinal use of plants has been recorded directly on the basis of a detailed survey on herbalists "Attarin or dabbous", folk healers, on older experienced people and midwives "daye". This research was carried out for 5 years (2002-2007). RESULTS AND CONCLUSIONS: In this survey, 231 species of which 5 are endemic, distributed in 79 botanical families, currently used as antirheumatic herbal remedies, were collected and identified. Among them 53.3% are indigenous, 19.2% are cultivated and 17.5% are imported. Their latin names, local names, local medicinal uses, the used parts of the plant and the preparations and the ways of administration are described. The anti-inflammatory properties due to the plant compounds have been demonstrated and discussed.