Isolation of a new flavonoid from Prasium majus L. with evaluation of its potential biological activities.

In line with the importance of Prasium majus L. (Lamiaciatae) in traditional medicine as a calming and sedative remedy, the present study was designed to reveal its chemical constituents and bioactivity potentials. Thus, after extraction and fractionation of the plant material, the obtained butanol fraction (BPm) was subjected to conventional chromatographic separation of its constituents in addition to LC-MS/MS evaluation versus some authentic standards. The study resulted in the isolation and characterisation of 8 compounds, including one new chrysoeriol derivative, majusiode (1). Structural elucidation of all isolated compounds was based on detailed investigation of their spectral data (NMR (1 & 2D), ESI-MS, IR and UV-Vis). HPLC-MS/MS analysis versus authentic samples lead to the detection of 31 constituents, including all 8 isolated compounds. The new compound (1) showed moderate AChE inhibition power (IC50: 163.3 ± 3.4 µg/mL) as compared to the positive control galanthamine (91.4 ± 5.2 µg/mL) and moderate DPPH•/ABTS•+ scavenging power.

Uncovering the Chemical Composition and Biological Potentials of Bupleurum lancifolium Hornem. from Jordan.

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.

Conyza canadensis from Jordan: Phytochemical Profiling, Antioxidant, and Antimicrobial Activity Evaluation.

In this investigation, the chemical composition of the hydro-distilled essential oil (HD-EO), obtained from the fresh aerial parts (inflorescence heads (Inf), leaves (L), and stems (St)) of Conyza canadensis growing wild in Jordan was determined by GC/MS. Additionally, the methanolic extract obtained from the whole aerial parts of C. canadensis (CCM) was examined for its total phenolic content (TPC), total flavonoids content (TFC), DPPH radical scavenging activity, iron chelating activity and was then analyzed with LC-MS/MS for the presence of certain selected phenolic compounds and flavonoids. The GC/MS analysis of CCHD-EOs obtained from the different aerial parts revealed the presence of (2E, 8Z)-matricaria ester as the main component, amounting to 15.4% (Inf), 60.7% (L), and 31.6% (St) of the total content. Oxygenated monoterpenes were the main class of volatile compounds detected in the Inf-CCHD-EO. However, oils obtained from the leaves and stems were rich in polyacetylene derivatives. The evaluation of the CCM extract showed a richness in phenolic content (95.59 ± 0.40 mg GAE/g extract), flavonoids contents (467.0 ± 10.5 mg QE/ g extract), moderate DPPH radical scavenging power (IC50 of 23.75 ± 0.86 µg/mL) and low iron chelating activity (IC50 = 5396.07 ± 15.05 µg/mL). The LC-MS/MS profiling of the CCM extract allowed for the detection of twenty-five phenolic compounds and flavonoids. Results revealed that the CCM extract contained high concentration levels of rosmarinic acid (1441.1 mg/kg plant), in addition to caffeic acid phenethyl ester (231.8 mg/kg plant). An antimicrobial activity assessment of the CCM extract against a set of Gram-positive and Gram-negative bacteria, in addition to two other fungal species including Candida and Cryptococcus, showed significant antibacterial activity of the extract against S. aureus with MIC value of 3.125 µg/mL. The current study is the first phytochemical screening for the essential oil and methanolic extract composition of C. canadensis growing in Jordan, its antioxidant and antimicrobial activity.

Unveiling the Impact of Drying Methods on Phytochemical Composition and Antioxidant Activity of Anthemis palestina.

Different drying techniques may alter the chemical composition of plant extracts and consequently affect their bioactivity potential. The current study was designed to reveal the effect of four different drying methods on the phytochemical composition and antioxidant activity of hydrodistilled essential oil (HD-EO) and methanolic (APM) extract obtained from the aerial part of Anthemis palestina from Jordan. Aerial parts of A. palestina in their fresh (FR) form and after drying in shade (ShD), sun (SD), oven at 40 °C (O40D) and 60 °C (O60D), in addition to microwave (MWD), were used to extract their essential oils by hydrodistillation and to prepare the different methanolic extracts (APM). GC/MS analysis of the different HD-EOs revealed qualitative and quantitative differences among the different samples. While FR, O40D, O60D, and MWD EO samples contained mainly sesquiterpene hydrocarbons (35.43%, 29.04%, 53.69%, and 59.38%, respectively), ShD sample was rich in oxygenated monoterpenes (33.57%), and SD-EO contained mainly oxygenated sesquiterpenes (40.36%). Principal component analysis (PCA) and Cluster analysis (CA) grouped the different drying methods based on their impact on the concentration of chemical constituents. SD-EO demonstrated high DPPH and ABTS antioxidant activity (1.31 ± 0.03) × 10-2; (1.66 ± 0.06) × 10-2 µg/mL, respectively). Furthermore, A. paleistina methanolic extracts (APM) obtained after subjecting the plant to different drying methods showed interesting patterns in terms of their TPC, TFC, antioxidant activity, and phytochemical profiling. Of all extracts, SD-APM extract had the highest TPC (105.37 ± 0.19 mg GA/g DE), highest TFC (305.16 ± 3.93 mg Q/g DE) and demonstrated the highest DPPH and ABTS scavenging activities ((4.42 ± 0.02) × 10-2; (3.87 ± 0.02) × 10-2 mg/mL, respectively); all were supported by correlation studies. LC-MS/MS analysis of the different extracts revealed the richness of the SD-APM extract in phenolic acids and flavonoids.

Scrophularia peyronii Post. from Jordan: Chemical Composition of Essential Oil and Phytochemical Profiling of Crude Extracts and Their In Vitro Antioxidant Activity.

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.

Exploring Echinops polyceras Boiss. from Jordan: Essential Oil Composition, COX, Protein Denaturation Inhibitory Power and Antimicrobial Activity of the Alcoholic Extract.

In this article, we present the first detailed analysis of the hydro-distilled essential oil (HDEO) of the inflorescence heads of Echinops polyceras Boiss. (Asteraceae) from the flora of Jordan, offering observations at different growth (pre-flowering, full-flowering and post-flowering) stages. Additionally, we investigated the methanolic extract obtained from the aerial parts of the plant material at the full flowering stage in order to determine its inhibitory activity in terms of COX and protein denaturation and evaluate its antimicrobial effects against S. aureus (Gram-positive) and E. coli (Gram-negative) bacteria. Performing GC/MS analysis of HDEO, obtained from the fresh inflorescence heads at the different growth stages, resulted in the identification of 192 constituents. The main class of compounds detected in these three stages comprised aliphatic hydrocarbons and their derivatives, which amounted to 50.04% (pre-flower), 40.28% (full-flower) and 41.34% (post-flower) of the total composition. The oils also contained appreciable amounts of oxygenated terpenoids, primarily sesquiterpenoids and diterpenoids. The pre-flowering stage was dominated by (2E)-hexenal (8.03%) in addition to the oxygenated diterpene (6E,10E)-pseudo phytol (7.54%). The full-flowering stage primarily contained (6E,10E)-pseudo phytol (7.84%), ß-bisabolene (7.53%, SH) and the diterpene hydrocarbon dolabradiene (5.50%). The major constituents detected in the HDEO obtained at the post-flowering stage included the oxygenated sesquiterpenoid intermedeol (5.53%), the sesquiterpene hydrocarbon (E)-caryophyllene (5.01%) and (6E,10E)-pseudo phytol (4.47%). The methanolic extract obtained from air-dried aerial parts of E. polyceras displayed more COX-2 inhibition than COX-1 inhibition at a concentration level of 200 µg/mL. The extract exhibited a capacity to inhibit protein denaturation that was comparable with respect to the activity of diclofenac sodium and displayed moderate levels of antimicrobial activity against both bacterial species. The current results demonstrate the need to perform further detailed phytochemical investigations to isolate and characterize active constituents.

A new cyclic polyketide and other constituents from Ononis spinosa growing wildly in Jordan and their antioxidant activity.

The new cyclic polyketide 7,9,11-trihydroxytetracos-2-eneoic acid δ-lactone (1), together with other eleven known compounds, were isolated from Ononis spinosa, growing wildly in Jordan. All isolated compounds were identified by thorough investigation of their spectral data including NMR and HRESIMS. Antioxidant activity testing of puerol B, specionin and the new cyclic polyketide revealed that puerol B had the highest DPPH radical scavenging activity (IC50 0.09 ± 0.006 mg/ml) as compared to α-tocopherol (IC50 0.039 ± 0.0006 mg/ml), while specionin had the highest ABTS radical scavenging power (IC50 0.013 ± 0.0008 mg/ml) as compared to α-tocopherol and ascorbic acid (IC50 0.042 ± 0.0004; 0.026 ± 0 .0007 mg/ml; respectively).

A new diterpene and other constituents of Salvia multicaulis from Jordan.

Phytochemical investigation of the aqueous methanol and butanol extracts of Salvia multicaulis from Jordan resulted in the isolation of 17 compounds including one new abietane diterpene derivative that was identified as 2,20-dihydroxyferruginol. Structural elucidation of all isolated compounds was based on extensive analysis of their spectroscopic data.[Formula: see text].

Aroma Profiles Analysis of Two Populations of Salvia palaestina Benth. Collected from Mediterranean and Irano-Turanian Zones in Jordan.

The volatile principles emitted from different aerial organs of two S. palaestina Benth. populations (Mediterranean (Med) and Irano-Turanian (IrT)) growing wild in Jordan were extracted by Solid Phase Micro-Extraction (SPME) and analysed by GC/MS technique. Sesquiterpene hydrocarbons dominated stems (59.38%, 49.67%) and leaves (93.28%, 32.39%) emissions from Med and IrT zones, respectively while monoterpene hydrocarbons had the major contribution to the aroma of pre-flowering buds (78.62%, 74.96%), opened flowers (76.12%, 59.99%) and petals (69.57%, 54.28%) and were mostly represented by sabinene (in Med zone) and ociemene isomers (Z & E) in IrT zone. Multivariate analysis classified the two populations into two different clusters based on their origin and indicated the occurrence of two ecotypes of this species. Different organs from the same collection site showed emission profiles of similar chemical composition.

HPLC profiling of selected phenolic acids and flavonoids in Salvia eigii, Salvia hierosolymitana and Salvia viridis growing wild in Jordan and their in vitro antioxidant activity.

BACKGROUND: Salvia eigii., Salvia hierosolymitana and Salvia viridis are native to the Mediterranean region, and are used in traditional medicine for the treatment of many ailments. In the current investigation, the methanolic extracts obtained from the air dried aerial parts of S. eigii, S. hierosolymitana and S. viridis from Jordan were screened for their total phenolics content (TPC), total flavonoids content (TFC) and their in vitro antioxidant activity. Additionally, the presence of four bioactive phenolic acids including gallic acid, caffeic acid, rosmarinic acid and salvianolic acid B and other seven flavonoids including luteolin-7-O-glucoside, apigenin, apigenin-7-O-glucoside, rutin, nariginin, hesperidin and quercetin was determined using Liquid chromatography-Electron Spray Ionization-Tandom Mass Spectrometry (LC-ESI-MS/MS). METHODS: Antioxidant activity of the obtained three extracts were examined via the DPPH•, ABTS• + radical scavenging methods in addition to Ferrous Ion Chelating (FIC) effect. TFC and TPC of the extracts were measured using the aluminum chloride colorimetric method and the Folin-Ciocalteau method, respectively. The presence and concentration of the selected 11 compounds was further determined through LC-ESI-MS/MS. RESULTS: The results indicated that three Salvia species had high total flavonoids content expressed in mg quercetin/g dry extract (S. heirosolymitana: 770.85 ±  5.26; S. eigii: 520.60 ±  6.24, S. viridis: 311.36 ±  4.41). S. heirosolymitana had the highest DPPH• activity (0.184 ±  1.22 × 10-2 mg/ml) and FIC effect (0.354 ±  0.018 mg/ml). S. heirosolymitana had slightly higher ABTS• + scavenging activity than S. eigii (0.176 ±  1.16 × 10-2 mg/ml; 0.183 ±  0.031 mg/ml, respectively). All 11 compounds were detected in the extracts of the three Salvia species. Luteolin-7-O-glucoside was detected in high concentration levels in the three species (1756.73, 21651.36, and 26125.14 mg/kg dry plant; S. eigii, S. hierosolyimitana and S. viridis, respectively), yet rosmarinic acid had the highest contribution to both S. hierosolymitana (27124.93 mg/kg) and S. eigii (15783.33 mg/kg). Notably, S. hierosolymitana and S. viridis contained salvianolic acid B (896.11; 890.9 mg/kg). CONCLUSIONS: The three Salvia species exhibited good antioxidant activity, especially S. heirosolymitana due to its high TPC, TFC, and the presence of high concentration levels of romarinic acid and other phenolic acids and flavonoids. This is the first phytochemical and antioxidant evaluation of S. eigii, S. hierosolymitana and S. viridis from Jordan. Prior to this investigation, no phytochemical investigation on S. eigii was reported.

Characterization of Chemical Components in Organs Emissions of Two Salvia dominica L. Populations from Jordan.

The current investigation reports the chemical composition of volatile organic compounds emitted from the different aerial organs of two populations of Salvia dominica L. from Jordan collected from Mediterranean and Irano-Turanian bio-geographical zones. Oxygenated monoterpenes dominated the emission profiles of most organs from the two populations but with variable qualitative and quantitative differences. Mediterranean samples contained higher content of oxygenated monoterpenes (stems: 88.37%, leaves 89.95%, pre-flowering buds 67.14%, fully opened flowers 79.43%, sepals 90.93% and petals 92.25%) as compared to those from Irano-Turanian origin (range 39.85% to 75.06%). trans-Sabinene hydrate dominated the emission profiles of all organs from Irano-Turanian zone (range 38.54% to 73.24%) in addition to the stem, sepal and petal samples from the Mediterranean zone (51.37% to 86.98%). The other organs from the Mediterranean zone were dominated by α-terpenyl acetate (27.66-54.87%). Cluster and Principle Component statistical analysis classified the two populations into two clusters based on their origin. The current study evidenced the different VOCs composition in the two populations, that was mainly related to climatic and environmental conditions and suggested the presence of two ecotypes of S. dominica L.in Jordan.

Phytochemical Diversity and Pharmacological Properties of Rhus coriaria.

Rhus coriaria L. (Anacardiaceae), sumac, is a common condiment, appetizer and souring agent in the Mediterranean region that has a long history in traditional medicine. R. coriaria has been prescribed for the treatment of many ailments including diarrhea, ulcer, hemorrhoids, hemorrhage, wound healing, hematemesis, and eye ailments like ophthalmia and conjunctivitis. The plant is also used as diuresis, antimicrobial, abortifacient and as a stomach tonic. Sumac is known to be rich in different classes of phytochemicals including tannins, polyphenols, flavonoids, organic acids and essential oils and continues to be a hot topic for extensive research work designed for revealing its phytochemical constituents and evaluating its bioactive properties. This review summarizes the recent phytochemical and diverse bioactivity studies on R. coriaria, especially those concerned with antitumor, antioxidant, hypoglycemic, antimicrobial, and anti-inflammatory studies.

Aroma Profile of Two Populations of Salvia verbenaca Collected from Two Bio-Geographical Zones from Jordan.

The aroma emitted from the different organs of two Salvia verbenaca L. populations from Jordan were extracted by Solid Phase Micro-Extraction (SPME) and then analyzed by GC/MS. The emission profile of the stem, leaf and sepal samples from the Mediterranean zone (Al-Salt) was dominated by monoterpene hydrocarbons (68.0 %, 33.7 %, and 42.2 %, respectively). The emission profile of flowering parts including pre-flowering buds, fully expanded flowers and petals was dominated by oxygenated monoterpenes (58.6 %, 59.3 % and 87.1 %, respectively). The major constituent detected in these organs was trans-sabinene hydrate acetate (range 14.5 %-87.0 %). On the other hand, samples collected from Irano-Turanian zone showed different emission patterns. While the stems, leaves and petal emissions were dominated by sesquiterpene hydrocarbons (54.9 %, 76.8 % and 52.6 %, respectively), monoterpene hydrocarbons dominated the emission profiles of the pre-flowering buds (75.1 %) and fully expanded flowers (73.6 %). Petals emissions were characterized by high concentrations of oxygenated monoterpenes (58.8 %). Notably, trans-sabinene hydrate dominated most organs emissions except for leaves (range 20.0 %-58.8 %). Principle Component Analysis (PCA) and Cluster Analysis (CA) revealed two different clusters related to the two different geographical zones. The current investigation revealed two ecotypes of S. verbenaca that could result in two different chemotypes. Trans-sabinene hydrate acetate and trans-sabinene hydrate are suggested compounds for identifying these two chemotypes.

Chemical constituents of the aerial parts of Salvia judaica Boiss. from Jordan.

Investigation of the chemical constituents of Salvia judaica growing wild in Jordan led to the isolation and identification of 15 known compounds. These included: luteolin-3'-methyl ether (1), indole-3-carboxyaldehyde (2), p-hydroxybenzaldehyde (3), tricin (4), apigenin (5), methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (6), methyl rosmarinate (7), rosmarinic acid (8), salvigenin (9), ß-sitosterol (10), 3ß, 28-dihydroxyurs-12-ene (11), cirsilineol (12), 2,3-dihydroxyurs-12-en-28-oic acid (13), ß-sitosteryl glucoside (14), and tormentic acid (15). Compounds 6 and 7 exhibited strong radical scavenging and chelating activities as compared to α-tocopherol and ascorbic acid, compound 7 showed a 2-fold greater antioxidant activity as compared to compound 6. Furthermore, low doses of compounds 6 and 7 were able to inhibit the growth of leukemic (HL-60, Jurkat, K562 and CCRF-SB) and solid tumor cells (MCF-7, MDA-MB-231 and Caco-2). Compound 7 showed a ca. 3-4-fold stronger cytotoxicity against the tested cells as compared to compound 6.

Composition, Antioxidant, and Cytotoxic Activities of the Essential Oils from Fresh and Air-Dried Aerial Parts of Pallenis spinosa.

This study was performed to determine the chemical composition, antioxidant and cytotoxic effects of essential oils extracted from the aerial parts of fresh (F-PSEO) and air-dried (D-PSEO) Pallenis spinosa. The composition of the oils was analyzed by gas chromatography (GC) and GC/mass spectrometry, the antioxidant activity by free radical scavenging and metal chelating assays, and their cytotoxicity by a flow cytometry analysis. The primary components in both oils were sesquiterpene hydrocarbons and oxygentated sesquiterpenes. F-PSEO contained 36 different compounds; α-cadinol (16.48%), germacra-1(10),5-diene-3,4-diol (14.45%), γ-cadinene (12.03%), and α-muurolol (9.89%) were the principal components. D-PSEO contained 53 molecules; α-cadinol (19.26%), δ-cadinene (13.93%), α-muurolol (12.88%), and germacra-1(10),5-diene-3,4-diol (8.41%) constituted the highest percentages. Although both oils exhibited a weak radical scavenging and chelating activity, compared to α-tocopherol and ascorbic acid, D-PSEO showed a 2-fold greater antioxidant activity than F-PSEO. Furthermore, low doses of F-PSEO were able to inhibit the growth of leukemic (HL-60, K562, and Jurkat) and solid tumor cells (MCF-7, HepG2, HT-1080, and Caco-2) with an IC50 range of 0.25 - 0.66 µg/ml and 0.50 - 2.35 µg/ml, respectively. F-PSEO showed a ca. 2 - 3-fold stronger cytotoxicity against the tested cells than D-PSEO. The potent growth inhibitory effect of the plant essential oil encourages further studies to characterize the molecular mechanisms of its cytotoxicity.

New flavonol glycoside from Scabiosa prolifera L. aerial parts with in vitro antioxidant and cytotoxic activities.

Phytochemical investigation of the chemical constituents of the aerial parts of Scabiosa prolifera L. led to the isolation of one new flavonol glycoside, kaempferol-3-O-(4″,6″-di-E-p-coumaroyl)-ß-D-galactopyranoside (1), along with ten other known compounds including luteolin-7-O-(2″-O-ethyl-ß-glucopyranoside), ß-sitosterol, ß-sitosterylglucoside, ursolic acid, corosolic acid, ursolic acid 3-O-ß-D-arabinopyranoside, apigenin, methyl-α-D-glucopyranoside, luteolin-7-O-ß-glucopyranoside and isoorientin. The structures of all isolated compounds were established using chemical methods and spectroscopic methods including IR, UV, NMR (1D and 2D) and HRESIMS. All compounds were isolated for the first time from the plant. The antioxidant and cytotoxic activities of compounds 1 and 2 were also investigated.

New aristolochic acid and other chemical constituents of Aristolochia maurorum growing wild in Jordan.

Investigation of the chemical constituents of Aristolochia maurorum growing wild in Jordan resulted in the isolation and characterisation of one new compound in addition to 19 known compounds. The new compound was identified as aristolochic acid II alanine amide (14). The other known compounds were the following: palmitic acid (1), ß-sitosterol (2), E-ethyl-p-coumarate (3), Z-ethyl-p-coumarate (4), aristolochic acid IV methyl ester (5), aristolactam I (6), loliolide (7), (+)-dehydrovomifoliol (8), glycerol-1-palmitate (9), aristolochic acid I (10), E-p-coumaric acid (11), E-N-coumaroyltyramine (12), ß-sitosteryl glucoside (13), aristolochic acid IV (15), aristolochic acid III (16), esculetin (17), uracil (18), shepherdine (19) and adenosine (20). The isolated compounds were characterised by different spectroscopic methods including NMR (1D and 2D), UV, IR and HRESIMS.

Composition and Biological Activity of Volatile Oil from Salviajudaica and S. multicaulis from Jordan.

The aim of this work was to determine the composition of the hydro-distilled essential oil of Salvia judaica Boiss. and S. multicaulis Vahl. (Lamiaceae) from Jordan by GC and GC-MS and to report the actual composition of their fresh leaves and flowers using SPME (Solid Phase Micro-Extraction).Their dual alpha-amylase/alpha glucosidase and pancreatic lipase inhibitory activities as well as their anti-proliferative potential were screened. The aroma profile of the leaves, flowers, and flowers at pre-flowering stages of S. judaica, obtained through SPME was composed of sesquiterpene hydrocarbons (87.7 %, 71.8 %, and 86.2 %, respectively) while the hydro-distilled oil of the dry leaves was rich in oxygenated sesquiterpenes (50.8%). Fresh leaves of S. multicaulis were rich in oxygenated monoterpenes (58.1%), while monoterpene hydrocarbons dominated the blooming flowers (57.2%) and the flowers at the pre-flowering stage (64.7%). The hydro-distilled oil of the dry leaves was rich in oxygenated monoterpenes (77.6%). With doxorubicin as a positive control, no anti-proliferative activity was observed against colorectal cancer cell lines HT29, HCT116, and SW620 using SRB assay for either Salvia spp. In vitro enzymatic starch digestion was evaluated with Acarbose (IC50: 0.2 ± 0.0 µg /mL) as the reference drug. The respective IC50 (mg/mL) values of S. judaica and S. multicaulis aqueous extracts were 4.9 ± 0.4 and 10.3 ± 0.9. Modulation of pancreatic lipase activity (PL) was determined by colorimetry and compared with Orlistat (IC50 : 0.11 ± 0.0 µg/mL). PL-IC50 values (µg/mL) obtained for S. judaica and S. multicaulis were 108.5±6.4 and 31.8 ± 0.8, respectively.

New isoflavones from Gynandriris sisyrinchium and their antioxidant and cytotoxic activities.

Chemical investigation of Gynandriris sisyrinchium (L.) Parl growing in Jordan resulted in the isolation and characterization of a total of twelve compounds two of which are reported here for the first time in nature. These new compounds included the isoflavones; 3'-methyl tenuifone (2) and gynandrinone (5). In addition, ten known compounds including; ß-sitosterol (1), 7,3'-dimethoxy-5,6,4'-trihydroxyisoflavone (3), iristectorigenin (4), hispidulin (6), galangustin (7), 6-hydroxybiochanin A (8), ursolic acid (9), ladanetin (10), 4'-O-methylgenistein (11) and ß-sitosterol glucoside (12) are also reported here for the first time from G. sisyrinchium. The isolated compounds were characterized by different spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRESIMS and EIMS). The antioxidant and cytotoxic activities of isoflavones 2, 3 and 5 were investigated. Compound 3 showed the highest antioxidant activity (IC50=17.3µg/mL), as compared to compounds 5 and 2 (IC50=26.7 and 51.7µg/mL, respectively). The cytotoxic activity against the human promyelocytic leukemia HL-60 cells revealed that compound 2 was the most active (40µM). The results indicate that the cytotoxicity of compound 2 is mediated by apoptosis.

Flavonoid and phenolic compounds from Salvia palaestina L. growing wild in Jordan and their antioxidant activities.

Investigation of the butanol fraction of Salvia palaestina Benth. from Jordanian origin resulted in the isolation and characterization of nine compounds, three of which are reported here for the first time in Nature. These compounds included the two phenolics: salpalaestinin (1), methyl 3-O-methylrosmarinate (3) and the flavonoid luteolin 7-O-(2″-p-hydroxybenzoyl)-ß-glucuronide) (8). In addition, 3,4-dihydroxyphenyl caffeate (2), diosmetin (4), apigenin-7-O-(6″-butyryl-ß-glucopyranoside) (5), luteolin-3'-O-methyl-7-O-(6″-butyryl-ß-glucopyranoside) (6) and clinopodic acid B (7) were also obtained from the butanol fraction of the plant. The structures of the isolated compounds were elucidated by different spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRESIMS and EIMS). The DPPH radical scavenging activity for compounds 1, 3, 5, 6 &8 was evaluated. Compound 3 had the highest antioxidant activity (91.9±1.30% inhibition) with an IC50 value of 1.0±0.23(µg/mL).