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The total ethanolic extract, different fractions and crude polysaccharides of leaves of Abutilon hirtum (Lam.) Sweet, were evaluated for their antimicrobial and antiparasitic activities. The antimicrobial activity was determined using the disc diffusion method against Staphylococcus aureus (Gram-positive, Facultative anaerobic bacteria), Escherichia coli, Klebsiella pneumonia, Pseudomonas aeruginosa (Gram-negative, Facultative anaerobic bacteria), Candida albicans, C. krusei (Diploid fungi) and C. glabrata (haploid fungus). The antimalarial activity was examined on chloroquine-sensitive (D6, Sierra Leone) strain of Plasmodium falciparum protozoan and the antileishmanial activity was tested against Leishmania donovani. The results of the present study showed that the total extract exhibited the lowest MIC (11.8 μg/ml) against P. aeruginosa. While, the chloroform fraction showed low MIC (59.03, 181.72 and 364.03 μg/ml) against S. aureus, K. pneumoniae and P. aeruginosa, respectively. The petroleum ether fraction exhibited the lowest MIC value (3.00 μg/ml) against C. albicans, while the total extract showed the lowest MIC (33.11 μg/ml) against C. glabrata. A. hirtum leaves extract and fractions showed a weak antimalarial activity. On the other hand, the chloroform fraction of A. hirtum leaves exhibited a potent antileishmanial activity with the highest percentage of inhibition (78%) against Leishmania donovani AMASTTHP_Pinh.

A total methanolic extract and its sub-extracts of Orobanche crenata (Forssk.) aerial parts were subjected to acute toxicity, anti-inflammatory, and hepatoprotective investigations. The methanolic extract was safe upto 3 g/kg on mice. The EtOAc fraction reduced the carrageenan-induced rat paw edema better than indomethacin. It also demonstrated a drop in the elevated ALT, AST, and TB at 300 mg/kg, better than silymarin. Histopathological examination of liver cells of rats given the EtOAc fraction showed a complete absence of the CCl4-induced cloudy swelling. A phytochemical investigation of the n-hexane and EtOAc fractions yielded 11 compounds [indole-3-carboxylic acid (1), n-butyl palmitate (2), tyrosol (3), L-rhamnonic acid-1,4-lactone (4), β-sitosterol/stigmasterol mixture (5/5'), β-sitosterol/stigmasterol glycosides mixture (6/6'), chrysoeriol (7), luteolin (8), apigenin (9), crenatoside (10), and verbascoside (11)] as identified by UV, 1D & 2D NMR and ESIMS techniques. Their reported biological actions were in relation to and supported our herein detected pharmacological findings.

Lotus corniculatus L. (Fabaceae) is widely grown in Egypt. It has a great history of folkloric medicinal uses. All fractions of aerial parts of L. corniculatus L. showed significant antioxidant and...

Previous phytochemical investigations have revealed the presence of a variety of compounds such as pyrrolidine derivatives, flavonoids, and megastigmanes in Egyptian plants. Onopordum alexandrinum has been traditionally used by the natives for treatment of skin cancers and leprosy. In this paper the isolation of four new sesquiterpene-amino acid conjugates, onopornoids A-D (1-4), i.e., three elemanes and one germacrane, and a new acylated flavonoid glucoside (5) along with nine known compounds (6-14) from the whole aerial parts of the title plant is discussed. The structures were elucidated based on chemical and spectroscopic/spectrometric data.

The present study evaluates the chemical composition of Zinnia elegans and Gazania rigens based on their metabolomic profiles using liquid chromatography coupled with high-resolution mass spectrometry (LC-HR-MS), alongside with the anti-infective activities of their ethanol extracts, as well as, different fractions. A significant difference was observed between the LC-MS profiles of the two plants such as, coumarins, sesquiterpene lactones and phenylethanoids which were characteristic for Z. elegans, while amides and phenolic acid derivatives were characteristic for G. rigens. These results highlight the chemical potential of Z. elegans and G. rigens. Furthermore, the ethyl acetate fraction of Z. elegans showed a significant antimalarial activity with IC50 values of 21.03 and 13.72 µg/mL against Plasmodium falciparum D6 and P. falciparum W2, respectively.

The chemical study of Cannabis sativa roots led to the isolation and identification of 10 compounds. Their chemical structures were unambiguously established on the basis of 1D and 2D NMR spectroscopy and mass spectrometry as friedelan-3-one (1), epifriedelanol (2), β-sitosterol (3), ergost-5-en-3-ol (4), methyl hexadecanoate (5), pentadecanoic acid (6), 10E-hexadecenoic acid (7), 4-hydroxy-3-methoxybenzaldehyde (8), β-sitosterol-β-D-glucoside (9) and p-coumaroyltyramine (10). Compounds 5–9 were reported for the first time from C. sativa roots. All the isolated compounds were tested for their antimicrobial activity. Compound 4 showed modest activity against Cryptococcus neoformans with an IC50 value of 13.7 μg/mL, while compound 10 displayed potent activity against Escherichia coli with an IC50 value of 0.8 μg/mL. A high-performance liquid chromatography method was developed and validated for the detection and quantification of p-coumaroyltyramine (10) in the extracts of different varieties of C. sativa roots.

Purpose: To isolate new antimicrobial agents from the leaves of Markhamia platycalyx (Baker) Sprague and assess their phytochemical characteristics and antimicrobial activity. Methods: Different chromatographic and spectroscopic techniques (NMR and ESI-MS) were applied for the identification of antimicrobial compounds. Agar-well diffusion technique was used for determination of antimicrobial activity. Anti-HCV effects were investigated using VITROS Anti-HCV assay. Results: Eighteen compounds were isolated for the first time from this genus. These were phytol, noctacosanoic acid (OCTA), tormentic acid and β-sitosterol-3-O-(6'-O-heptadecanoyl)-β-Dglucopyranoside. The other compounds were β-sitosterol, ursolic acid (URSA), oleanolic acids, pomolic acid (POMA), 2-epi-tormentic and β-sitosterol-3-O-β-D-glucopyranoside. However, stigmasterol and acteoside, which were seen in previous studies, were also present. Total ethanol extract (TEE) was the most effective against Escherichia coli, with the lowest minimum inhibitory concentration (MIC) of 1.0 μg/mL. Acteoside, URSA and 2-epi-tormentic acid showed the highest antibacterial effect on Pseudomonas aeruginosa while 2-epi-tormentic acid and acteoside produced the least MIC on Candida glabrata. These effects were superior to those produced by standard antibiotics. However, 2-epitormentic acid and β-sitosterol-3-O-β-D-glucopyranoside had no anti-HCV effects. Conclusion: Due to the good antimicrobial properties of Markhamia platycalyx, it is a potential source of new antimicrobial drugs.

Bignoniaceae Juss. (Bignonia family) includes many genera of high economic and medicinal values. It comprises 104 genera and 860 species. Markhamia genus is traditionally used in the treatment of several diseases. Literature survey showed few chemical works on the Markhamia platycalyx and nothing could be found about the antimicrobial study. This provoked us to carry out an extensive study of this plant including GC/MS for saponifiable matter and volatile oil. The main recognized fatty acids were linolenic (44.66%), followed by palmitic (30.63%) of the saponifiable matter composition. While, E-phytol was the major identified compound of the volatile oil composition (12.95%). Moreover, this study included the antimicrobial activity of the volatile oil. It exhibited a potent antibacterial effect against E. coli with MIC 7.48 μg/ml compared to the standard antibiotics MICs, amikacin (28.96 μg/ml) and gentamycin (26.44 μg/ml).

A total methanolic extract and its sub-extracts of

Two series of novel 1,2,4-triazol-3-yl-thioacetamide 3a-b and 4a-b and 5-pyrazin-2-yl-3H-[1,3,4]oxadiazole-2-thiones 9a-h were designed and synthesized. The compounds prepared have been identified using 1H NMR, 13C NMR and elemental analyses. The synthesized compounds 3a, 3b, 4a, 4b, 9a, 9b, 9d-e and 9f have been evaluated with α-difluoromethylornithine (DFMO) as a control drug for their in vitro antitrypanosomal activity against Trypanosoma brucei. Results showed that 3b was the most active compound in general and also more potent than control DFMO. 3b was 8 folds more potent than the reference with IC50 of 0.79 μM and IC90 of 1.35 μM, respectively compared to DFMO (IC50 = 6.10 μM and IC90 of 8.66 μM). The tested compounds showed moderate cytotoxicity with selectivity indices ranging from 12 (9d) to 102 (3b) against L6 cells. Docking study was performed into ten of T. brucei enzymes which have been identified as potential/valid targets for most of the antitrypanosomal agents. The results of the docking study revealed high binding scores toward many of the selected enzymes. A good correlation was observed only between log (IC50) of antitrypanosomal activity of the new compounds and their calculated Ki values against TryR enzyme (R2 = 0.726). Compound 3b, the most active as antitrypanosomal agents exhibited similar binding orientation and interaction to those of WP6 against TryR enzyme. However, in a next round of work, a complementary studies will be carried out to clarify the mechanism of action of these compounds.

The in vitro antidiabetic and antihyperlipidemic activities of an alcoholic extract of Trigonella stellata were evaluated in terms of the activation of PPARα and PPARγ in human hepatoma (HepG2) cells. The extract was investigated phytochemically, aiming at the isolation of the most active compounds to be used as a platform for drug discovery. Three new isoflavans, (3S,4R)-4,2′,4′-trihydroxy)-7-methoxyisoflavan (1), (3R,4S)-4,2′,4′-trihydroxy-7-methoxy-4′-O-β-d-glucopyranosylisoflavan (2), and (2S,3R,4R)-4,2′,4′-trihydroxy-2,7-dimethoxyisoflavan (3), were isolated and characterized along with the five known compounds p-hydroxybenzoic acid (4), 7,4′-dihydroxyflavone (5), dihydromelilotoside (6), quercetin-3,7-O-α-l-dirhamnoside (7), and soyasaponin I (8). The structures of 1–3 were elucidated using various spectroscopic techniques including HRESIMS and 1D and 2D NMR. The absolute stereochemistry of the new isoflavans (1–3) was determined using both experimental and calculated electronic circular dichroism a...

Four new ceramides (1–4) were isolated from the sponge Monanchora clathrata, along with four epidioxysterols (5–8), two sterols (9, 10), uracil (11), and three triglycerides (12–14). All compounds were isolated for the first time from the genus Monanchora, also this is the first time for isolation and identification of compounds 5–8, and the ceramide moieties from the family Crambeidae. Acetylation of compounds (5–8) yielded two new chemically modified compounds (15, 16), in addition to the known 17, 18. Their chemical structures were elucidated using a combination of spectroscopic methods, including extensive 1D and 2D NMR, IR, HRESIMS, and GC/MS. The configuration of compounds 1–4 were assigned as 2S,3S,4R,2′R based on the modified Mosher’s reaction, optical rotation measurements and spectroscopic data comparison. The compounds were evaluated for their, cytotoxic, antiprotozoal, antimicrobial, and antimalarial potentials. Compound 1 showed remarkable cytotoxicity against MES-SA, MCF-7, and HK-2 cell lines with IC50 values of 3.29, 17.95 and 4.45 μM, respectively.

Cannabinoids are a group of terpenophenolic compounds in the medicinal plant Cannabis sativa (Cannabaceae family). Cannabigerolic acid, Δ9-tetrahydrocannabinolic acid A, cannabidiolic acid, Δ9-tetrahydrocannabinol, cannabigerol, cannabidiol, cannabichromene, and tetrahydrocannabivarin are major metabolites in the classification of different strains of C. sativa. Degradation or artifact cannabinoids cannabinol, cannabicyclol, and Δ8-tetrahydrocannabinol are formed under the influence of heat and light during processing and storage of the plant sample. An ultrahigh-performance liquid chromatographic method coupled with photodiode array and single quadruple mass spectrometry detectors was developed and validated for quantitative determination of 11 cannabinoids in different C. sativa samples. Compounds 1 – 11 were baseline separated with an acetonitrile (with 0.05% formic acid) and water (with 0.05% formic acid) gradient at a flow rate of 0.25 mL/min on a Waters Cortec UPLC C18 column (100 mm × 2.1 mm I. D., 1.6 µm). The limits of detection and limits of quantitation of the 11 cannabinoids were below 0.2 and 0.5 µg/mL, respectively. The relative standard deviation for the precision test was below 2.4%. A mixture of acetonitrile and methanol (80 : 20, v/v) was proven to be the best solvent system for the sample preparation. The recovery of all analytes was in the range of 97 – 105%. A total of 32 Cannabis samples including hashish, leaves, and flower buds were analyzed.

Two new iridoid glycosides, named 6 β - O -methyl-unedoside ( 1 ) and 6 β - O -methyl-5-deoxythunbergioside ( 2 ) along with two known phenyl propanoid glucoside compounds dolichandroside A ( 3 ) and verbascoside ( 4 ) were isolated from the aerial parts of Odontonema cuspidatum (Nees) Kuntze (Acanthaceae). Structure elucidation of the new compounds was established by interpretation of their 1D and 2D-NMR spectral data by comparing with literatures, HRESIMS and optical activity measurement. The isolated compounds were tested for their in vitro antimicrobial and antimalarial activities. Compound 4 showed a moderate antimicrobial activity against E. coli with IC 50 value of 17.5 μM in comparing with Vancomycin and Cefotaxime.

Achillea fragrantissima (Forssk) Sch. Bip. (Asteraceae) is one of the most important medicinal plant species in Egypt. Phytochemical investigation of the methanolic extract of A. fragrantissima led to the isolation of two phenolic compounds Piceol (1) and Veratric acid (2), which are reported for the first time from this plant. In addition, four known flavonoid compounds; Eupatilin 7-methyl ether (3), Chrysosplenol D (4), Cirsiliol (5), and Cirsimaritin (6) were isolated. Structure elucidation was achieved using spectroscopic techniques, including one-dimensional and two-dimensional nuclear magnetic resonance. Potential cytotoxic activities of the isolated compounds were measured by the sulphorhodamine B assay. Compounds 1, 2, 3, 4, 5, and 6 displayed cytotoxic activity against (MCF7) with IC50 values of 18.2, 15.7, 9.5, 8.33, 3.23, and 3.83 µg/ml, respectively, and against (HepG2) with IC50 values of 19.4, 41.2, 28.3, 20.8, 23.8, and 23.8 µg/ml, respectively. Also there was moderate cytotoxic activity against (A549) with IC50 values of 17.8, 13.6, 3.98, and 10.3 µg/ml for the compounds 1, 2, 4 and 5, respectively, and against (HeLa) with IC50 values of 10.1, 10.4, 4.88, and 3.98 µg/ml for the compounds 3, 4, 5, and 6, respectively. In addition, compounds 4 and 5 showed cytotoxic activity against (PC3) with IC50 values of 3.83 and 3.98 µg/ml, respectively. An in silico study was performed, where cirsiliol (5) and piceol (1) were docked into the active sites of the crystal structures of PI3K and Akt, two protein kinases which are involved in prostate and breast cancer proliferation and survival.

Two new α- Pyrone derivatives (1,2) have been isolated from the endophytic fungus Embellisia sp. The isolated compounds were chemically identified as 5-(3-S-hydroxybutyl)-4-methoxy-6-methyl-2H-pyran-2-one (1) and 4-(4-methoxy-6-methyl-2-oxo-2H-pyran-5-yl)butanoic acid (2). The chemical structures of 1 and 2 were determined based on one and two dimensional NMR spectroscopy and high resolution mass spectrometry. Absolute configuration of compound 1 was determined using modified mosher ester reaction. In vitro antileishmanial, antifungal, antibacterial and antimalarial activities of 1 and 2 were examined but they didn’t show promising activities.

Twenty compounds were determined in the tar of cigarette smoke. The tar was obtained using tobacco filters and then analyzed by liquid chromatography-mass spectrometry (LC-MS). Tobacco tar expressed marked decrease in the susceptibility of Staphylococcus aureus to penicillin, tetracycline and amoxicillin/clavulanic antibiotics and showed marked decrease in susceptibility of Candida albicans to the tested antifungals except for clotrimazole and ketoconazole. Tobacco tar decreased the permeability of the tested organisms to ethidium bromide in the presence of antimicrobials, after 2 h for both S. aureus (17.8-20%) and C. albicans (13.3-16.3%) and decreased the adherence of the tested microorganisms at concentrations above Minimal Inhibitory Concentration (MIC). Tobacco tar showed a marked increase in the hydrophobicity of the tested microorganisms by 2.5 to 7 fold. Tobacco tar increased or upregulated ALS1 and HWP1 genes that play an important role in adhesion, hyphae formation and biofilm formation of C. albicans and increased the expression of ica A gene that regulate biofilm formation of S. aureus. Key words: Tobacco tar, Staphylococcus aureus, Candida albicans, antimicrobial susceptibility, ethidium bromide, biofilm formation.

In our natural products screening program for mosquitoes, carrot seed essential oil showed high repellency. The gas chromatography (GC)/flame ionization detector and GC/mass spectrometry analysis of the essential oil revealed the presence of 47 compounds. Carotol was more than 75% w/w, followed by muurolene (4.86%), (Z)-β-farnesene (2.9%), and diepicedrene (1.1%). Systematic bioassay-guided fractionation of the essential oil was performed to identify active repellent compounds. In both Klun and Debboun (K&D) and Ali and Khan (A&K) bioassays, carotol showed biting deterrent activity similar to N,N-Diethyl-3-methylbenzamide (deet) and carrot seed essential oil against both Aedes aegypti and Anopheles quadrimaculatus, while in in vivo cloth patch bioassay, the minimum effective dose (MED) of deet was lower (12.5 μg/cm2) than the essential oil and carotol (25 μg/cm2) against Ae. aegypti. In the A&K bioassay, the MED values were similar, whereas the values of the mixtures of deet with essential oil and carotol was lower (6.25 + 6.25 = 12.5 μg/cm2) than their individual treatments (25 μg/cm2). In direct skin application bioassay, both the essential oil and carotol provided good repellency. The mixtures of deet and essential oil or carotol significantly increased the residual activity, indicating synergism. Mosquito repellency of the essential oil and carotol is reported for the 1st time. These data indicate the potential of these natural products to be developed as commercial repellents.

Terpenes are the major components of the essential oils present in various Cannabis sativa L. varieties. These compounds are responsible for the distinctive aromas and flavors. Besides the quantification of the cannabinoids, determination of the terpenes in C. sativa strains could be of importance for the plant selection process. At the University of Mississippi, a GC-MS method has been developed and validated for the quantification of terpenes in cannabis plant material, viz., α-pinene, β-pinene, β-myrcene, limonene, terpinolene, linalool, α-terpineol, β-caryophyllene, α-humulene, and caryophyllene oxide. The method was optimized and fully validated according to AOAC (Association of Official Analytical Chemists) guidelines against reference standards of selected terpenes. Samples were prepared by extraction of the plant material with ethyl acetate containing n-tridecane solution (100 µg/mL) as the internal standard. The concentration-response relationship for all analyzed terpenes using the developed method was linear with r2 values > 0.99. The average recoveries for all terpenes in spiked indoor cultivated samples were between 95.0 – 105.7%, with the exception of terpinolene (67 – 70%). The measured repeatability and intermediate precisions (% relative standard deviation) in all varieties ranged from 0.32 to 8.47%. The limit of detection and limit of quantitation for all targeted terpenes were determined to be 0.25 and 0.75 µg/mL, respectively. The proposed method is highly selective, reliable, and accurate and has been applied to the simultaneous determination of these major terpenes in the C. sativa biomass produced by our facility at the University of Mississippi as well as in confiscated marijuana samples.

The chemical constituents of

A series of new 1,6-dihydropyrimidin-2-thiol derivatives (scaffold A) as VEGFR-2 inhibitors has been designed and synthesized. Compounds 3a, 3b, 3e and 4b have been selected for in vitro anticancer screening by the National Cancer Institute. Compound 3e showed remarkable anticancer activity against most of the cell lines tested, where a complete cell death against leukemia, non-small cell lung cancer, colon, CNS, melanoma, and breast cancer cell lines was observed. In vitro five dose tests showed that compound 3e had high activity against most of the tested cell lines with GI50 ranging from 19 to 100 μM and selectivity ratios ranging between 0.75 and 1.71 at the GI50 level. VEGFR-2-kinase was tested against 3a, 3b, 3e, 4b and sorafenib was used as a reference. Compounds 3a and 3e were the most potent analogues with IC50 values of 386.4 nM and 198.7 nM against VEGFR-2, respectively, in comparison to sorafenib (IC50 = 0.17 nM). The results of the docking study showed a good fitting of the new compounds to the active site of VEGFR-2 with binding free energies in the range of −9.80 to −11.25 kcal/mol compared to −12.12 kcal/mol for sorafenib. Compounds 4a-e with the hydroxyimino group had a higher affinity to VEGFR-2 than their parent derivatives 3a-e.

In this study, an ultra-performance liquid chromatography (UPLC)/photodiode array method was developed for the simultaneous determination of trigonellan glucoside (1), isotrigonellan (2), and methoxy-isotrigonellan (3) in Trigonella stellata extract using an external standard method. The extract was prepared using a standardized method by maceration of the dried plant material in ethanol. The 3 isoflavans (1-3) were separated on an Acquity UPLC C18 column using gradient elution with a mobile phase consisting of 0.1% (v/v) formic acid aqueous solution and 0.1% (v/v) formic acid in acetonitrile, and ultraviolet detection. The method provides a linear correlation for all analytes over the investigated ranges with all correlation coefficients greater than 0.998. The validated lower limits of quantitation were 53, 127, and 5 μg/mL for isoflavans 1, 2, and 3, respectively. Intraday and interday precisions (percent relative SD [RSD%]) were less than 8.3% and accuracy (RE%) ranged from 90% to 100%. The method’s capability to remain unaffected by small, but deliberate variations in method parameters (method’s reliability during normal usage) described by the robustness showed RSD% less than 4.6% measured by varying 3 different parameters. The validated method was successfully applied to simultaneously determine the concentration of the 3 new isoflavans having anti-inflammatory and antidiabetic activities. The results revealed that the validated method can be used for quality control of herbal preparations containing these or similar isoflavans that are marketed for the prevention of inflammation and as antidiabetics.

WOS: 000534529000001, The volatile oils of fresh and air-dried buds of 3 different varieties of Cannabis, namely, high cannabidiol (CBD) chemotype, inter- mediate CBD/tetrahydrocannabinol chemotype, and high THC chemotype were prepared by hydrodistillation. Gas chro- matography analysis of the volatile oils resulted in the identification of 71 compounds, of which 33 were monoterpenes and 38 were sesquiterpenes. the volatile oil obtained from the THC chemotype showed an increase in the ratio of the sesquiterpenes to monoterpenes content. the content of terpinolene was dramatically decreased upon drying of THC chemotype. Moderate increase in beta-caryophyllene and caryophyllene oxide was observed. However, there was no detectable change in the percentage of monoterpenes and sesquiterpenes content in both the intermediate type and CBD chemotype upon drying. the insecticidal activity of the volatile oils was evaluated. the oil obtained from the fresh and dried high CBD cannabis showed good biting deterrent activity at 10 ug/cm(2) compared with N,N-diethyl-meta-toluamide at 4.78 mu g/cm(2), and good larvicidal activity., National Institute on Drug AbuseUnited States Department of Health & Human ServicesNational Institutes of Health (NIH) - USANIH National Institute on Drug Abuse (NIDA) [N01DA-15-7793], The author(s) disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: this work was supported in part by the National Institute on Drug Abuse, contract #N01DA-15-7793.

Bioassay-guided fractionation of the marine sponge Lendenfeldia dendyi and the soft coral Sinularia dura resulted in the isolation of five polybrominated diphenyl ethers (1–5). The structures of the isolated compounds were determined using spectroscopic methods (1D and 2D NMR) and HRMS analyses. The absolute structures of compounds 1 and 2 were confirmed by X-ray analysis. Antimicrobial testing of the isolated compounds along with the acetylated derivative of compound 2 (2a) indicated that they displayed a significant and selective activity against methicillin-resistant Staphylococcus aureus (MRSa) with IC50 values of

Three aromatic glycosides (1-3), two sulfur and nitrogen-containing compound glucosides (4, 5), and one flavonoid glycoside (6) were isolated from the leaves of Ixora undulata. Their structures were established by extensive 1D, 2D NMR, and HRESIMS experiments, and structure 4 was further confirmed by single crystal X-ray diffraction analysis. Of the assayed compounds, 7, 11 and 12 showed strong inhibitory activity toward advanced glycation end-products formation with IC50 values of 86.0 μM, 76.6 μM and 98.6 μM, respectively.

Alcea rosea L. is widely cultivated in gardens of Egypt as an ornamental plant and it has a great history of folkloric medicinal uses. In the present work, phytochemical investigation of the alcoholic extract of the flowers of A. rosea L. led to the isolation of six flavonoids (1–6). Dihydrokaempferol-4′-O-β-d-glucopyranoside (1), dihydrokaempferol (2), kaempferol-3-O-[6″-(E-coumaroyl)]-β-d-glucopyranoside (3), kaempferol-3-O-β-d-glucopyranoside (4), Apigenin (5) and kaempferol-3-O-α-l-rhamnopyranosyl-(1′″→6″)-β-d-glucopyranoside (6). Four of the isolated compounds were evaluated for their antioxidant, immunostimulant and cytotoxic activities against HepG-2 cell line. Compound (3) showed potent cytotoxic activity against HepG-2 cell line with high selectivity towards hepatocellular carcinoma in vitro (with IC50 = 3.8 μg/mL). Compounds 1 and 2 exhibited significant antioxidant activity and compound 4 showed a significant immune stimulant activity. Compound 1 is isolated for the first time from genus Alcea and this is the first report for its biological investigation.

Cannabis has gained a lot of popularity in last few years not only because of its use as illicit drug but due to its use as food, fiber and medicine. It is a complex mixture of constituents which contain a unique class of secondary metabolites called phytocannabinoids. In general, so far a total of 565 constituents including 120 phytocannabinoids have been reported in Cannabis sativa. This chapter discusses the chemistry of phytocannabinoids in the plant with particular emphasis on the Δ9-THC type of cannabinoids and different analytical methods available for cannabinoids analysis in cannabis plant and cannabis products.

Extracts of aerial parts of Lotus corniculatus L. exhibited significant antioxidant, immunostimulant and anticancer activities [1]. Bioactivity-guided fractionation of the aerial parts of L. corniculatus led to the isolation of seven known compounds (1-7). The structure elucidation of the isolated compounds was achieved using spectroscopic techniques, including 1D and 2D NMR. Their chemical structures were identified as: 7,2'-dihydroxy-4'-methoxyisoflavan (vestitol) (1), kaempferol-3-O-rhamnoside (afzelin) (2), kaempferol-3,7-O-dirhamnoside (kaempferitin) (3), kaempferol-3-O-(2"-xylopyranosyl) galactopyranoside (4), soyasapogenol-β-3-O-glucopyranoside (5), soyasapogenol-β-3-O-[α-L-rhamnopyranosyl-(1'''→2'')-β-D-galactopyranosyl-(1''→2')-β-D-glucuronopyranoside] (soyasaponin I) (6) and methyl -O-β-D-glucopyranoside (7). Compounds 4 and 5 are reported for the first time from the genus Lotus. References: [1] Alqasoumi, S.I.; Al-Rehaily, A.J.; Abdel-Kader, M.S. "Two isoflavans and a 3-aryl coumarin from the roots of Lotus lalambensis growing in Saudi Arabia", Revistalatinoamericana de Quimica, 41 (1):61 (2013).

Ultra-high-performance supercritical fluid chromatography (UHPSFC) is an efficient analytical technique and has not been fully employed for the analysis of cannabis. Here, a novel method was developed for the analysis of 30 cannabis plant extracts and preparations using UHPSFC/PDA-MS. Nine of the most abundant cannabinoids, viz. CBD, ∆8 -THC, THCV, ∆9 -THC, CBN, CBG, THCA-A, CBDA, and CBGA, were quantitatively determined (RSDs < 6.9%). Unlike GC methods, no derivatization or decarboxylation was required prior to UHPSFC analysis. The UHPSFC chromatographic separation of cannabinoids displayed an inverse elution order compared to UHPLC. Combining with PDA-MS, this orthogonality is valuable for discrimination of cannabinoids in complex matrices. The developed method was validated, and the quantification results were compared with a standard UHPLC method. The RSDs of these two methods were within ±13.0%. Finally, chemometric analysis including principal component analysis (PCA) and partial least squares-discriminant analysis (PLS-DA) were used to differentiate between cannabis samples.

An HPLC single-laboratory validation was performed for the detection and quantification of the 11 major cannabinoids in most cannabis varieties, namely, cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabidiol (CBD), tetrahydrocannabivarin (THCV), cannabinol (CBN), Δ9-trans-tetrahydrocannabinol (Δ9-THC), Δ8- trans-tetrahydrocannabinol (Δ8-THC), cannabicyclol (CBL), cannabichromene (CBC), and Δ9-tetrahydrocannabinolic acid-A (THCAA). The analysis was carried out on the biomass and extracts of these varieties. Methanol–chloroform (9:1, v/v) was used for extraction, 4-androstene-3,17-dione was used as the internal standard, and separation was achieved in 22.2 min on a C18 column using a two- step gradient elution. The method was validated for the 11 cannabinoids. The concentration-response relationship of the method indicated a linear relationship between the concentration and peak area with r2 values of >0.99 for all 11 cannabinoids. Method accuracy was determined through a spike study, and recovery ranged from 89.7 to 105.5% with an RSD of 0.19 to 6.32% for CBDA, CBD, THCV, CBN, Δ9-THC, CBL, CBC, and THCAA; recovery was 84.7, 84.2, and 67.7% for the minor constituents, CBGA, CBG, and Δ8-THC, respectively, with an RSD of 2.58 to 4.96%. The validated method is simple, sensitive, and reproducible and is therefore suitable for the detection and quantification of these cannabinoids in different types of cannabis plant materials.

From the EtOAc and 1-BuOH fractions, three new ursane-type and four new lupane-type triterpenes, along with nine known glycosides and glycosyl esters of lupane-type were isolated from the leaves of Schefflera actinophylla. All the isolated compounds were obtained for the first time from this plant. The structures of the new triterpenes were determined through a combination of spectroscopic and chemical analyses.

The cannabis plant is one of the oldest plants known in medicine, with many reported medicinal uses for > 5,000 years. However, the chemistry of the plant was not fully investigated till the chemical structure of the active component was determined in 1964. Since then, over 10,000 scientific citations could be found on cannabis and the cannabinoids. The legal status of cannabis in the United States has been in a state of controversy. Although the drug in classified as a Schedule I Controlled Substance, therefore, illegal to possess without appropriate Drug Enforcement Administration (DEA) Registration, 23 states and the District of Columbia have passed laws allowing the medical use of cannabis. Furthermore, Colorado and Washington State have passed legislations allowing recreational use of the drug as well. Over the past few years there has been a tremendous public interest in cannabis and cannabis oil, with many growers sprouting in all states with legal medical use. The medical community and the end users have also shown much interest in knowing the composition of the materials on the market. Several laboratories have reported on methods to determine the chemical composition of the cannabis products, particularly the Δ9-THC and the CBD levels, along with a few other cannabinoids. This report is directed toward an ultra-high performance liquid chromatographic method (UHPLC) with UV detection for the quantitation of eleven different cannabinoids with base line separation namely cannabidiolic acid, cannabigerolic acid, cannabigerol, cannabidiol, tetrahydrocannabivarin, cannabinol, Δ9-tetrahydrocannabinol, Δ8-tetrahydrocannabinol, cannabicyclol, cannabichromene, and Δ9-tetrahydrocannabinolic acid A. The method was validated and applied to the analysis and profiling of different varieties of cannabis produced at the UM Medicinal Plants Garden, as well as for the analysis of several confiscated cannabis preparations. The LOD, LOQ and linearity of the method were 0.2 – 0.4 µg/mL, 0.5 – 1.0 µg/mL and 1.0 – 200 µg/mL respectively, for all eleven cannabinoids.