Anti-inflammatory potential of some eudesmanolide and guaianolide sesquiterpenes.

Ten sesquiterpene lactones isolated from Anvillea garcinii (Burm.f.) DC ethanolic extract were assessed for their anti-inflammatory potential by myeloperoxidase (MPO) activity assignment, and mice paw swelling model. 3α,4α-10ß-trihydroxy-8α-acetyloxyguaian-12,6α-olide (1), epi-vulgarin (3), 9a-hydroxyparthenolide (4), garcinamine C (7), garcinamine D (8), garcinamine E (9), and 4, 9-dihydroxyguaian-10(14)-en-12-olide (10) showed explicit anti-inflammatory activity in rodent paw edema and MPO assignment. The findings of this study showed that the α-methylene γ-lactone moiety does not always guarantee an anti-inflammatory effect, but the presence of proline at the C3 of the lactone ring improves the binding of sesquiterpene lactones with MPO isoenzymes, resulting in a more potent inhibition.

Bioassay Directed Isolation, Biological Evaluation and in Silico Studies of New Isolates from Pteris cretica L.

Members of genus Pteris have their established role in the traditional herbal medicine system. In the pursuit to identify its biologically active constituents, the specie Pteris cretica L. (P. cretica) was selected for the bioassay-guided isolation. Two new maleates (F9 and CB18) were identified from the chloroform extract and the structures of the isolates were elucidated through their spectroscopic data. The putative targets, that potentially interact with both of these isolates, were identified through reverse docking by using in silico tools PharmMapper and ReverseScreen3D. On the basis of reverse docking results, both isolates were screened for their antioxidant, acetylcholinesterase (AChE) inhibition, α-glucosidase (GluE) inhibition and antibacterial activities. Both isolates depicted moderate potential for the selected activities. Furthermore, docking studies of both isolates were also studied to investigate the binding mode with respective targets followed by molecular dynamics simulations and binding free energies. Thereby, the current study embodies the poly-pharmacological potential of P. cretica.

Biological Evaluation of Different Extracts of Aerial Parts of Nepeta deflersiana and Standardization of Active Extracts Using 8-Epi-7-Deoxyloganic Acid and Ursolic Acid by Validated HPTLC Method.

Nepeta deflersiana (Lamiaceae) is a well-known medicinal plant that grows in Saudi Arabia. This plant is used in Saudi and Yemeni folk medicine as an anti-inflammatory, carminative, and antirheumatic agent. In order to prove its use in folk medicine, four different extracts from the aerial parts of the plant: petroleum ether, chloroform, ethyl acetate, and n-butanol extracts were subjected to biological assays to screen PPARα and PPAR ϒ agnostic, antioxidant, anti-inflammatory, and cytotoxic activities. Ethyl acetate and n-butanol extracts of N. deflersiana NDEE and NDBE, respectively, showed a decrease in oxidative stress and inhibition of both NF-kB and iNOS activities with no cytotoxic effects on four human cancer cell lines. Both active extracts were standardized using two bioactive metabolites which were isolated from the aerial parts of the same plant [8-epi-7-deoxyloganic acid (compound 1) and Ursolic acid (compound 2)] by developing a validated HPTLC method. It was found to provide a sharp and compact band of compound 1 at Rf = 0.07 and Rf = 0.57 for compound 2, using chloroform, methanol, and formic acid (8.9:0.8:0.3, v/v/v) as mobile phase at 550 nm. Compounds 1 and 2 were found in NDEE by 9.59 %, w/w, and 84.63 %, w/w, respectively, and by 11.97 %, w/w, and 21.26 %, w/w, respectively, in NDBE.

Trichosides A and B, new withanolide glucosides from Tricholepis eburnea.

Trichosides A (1) and B (2), new withanolide glucosides, have been isolated from the n-butanolic fraction of the 75% methanolic extract of aerial parts of Tricholepis eburnea. Their structures were elucidated through spectroscopic analysis including ESI-MS, 2D NMR and acid hydrolysis.

Evaluation of Antiulcer and Cytotoxic Potential of the Leaf, Flower, and Fruit Extracts of Calotropis procera and Isolation of a New Lignan Glycoside.

Calotropis procera is traditionally used for treating many diseases including ulcers and tumors. It was thus deemed of interest to investigate and compare the antiulcer and cytotoxic activities of C. procera leaf, flower, and fruit extracts in an attempt to verify its traditional uses. Phytochemical studies on the fruits, flowers, and leaves of C. procera, collected from the desert of Saudi Arabia, led to the isolation of one new lignan 7'-methoxy-3'-O-demethyl-tanegool-9-O-ß-d-glucopyranoside and five known compounds from the flowers, four compounds from leaves, and a flavonoid glycoside and a lignan glycoside from the fruits. The structures of compounds were determined by spectroscopic techniques. Ethanol extracts of the three parts of C. procera were evaluated for their antiulcer activity and we found that the leaf extract possessed a powerful antiulcer activity which could be considered as a promising drug candidate. All the extracts and the isolated compounds were evaluated for their cytotoxic activity against MCF-7, HCT-116, HepG-2, and A-549 human cancer cell lines. Compound 2 was highly active on all the cell lines, whereas compounds 5 and 11 were more selective on colon and liver cell lines. Compound 10 demonstrated a significant activity on liver and lung cancer cell lines.

New anthrarobin acyl derivatives as butyrylcholinesterase inhibitors: synthesis, in vitro and in silico studies.

To treat Alzheimer's disease (AD), the available candidates are effective only against mild AD or have side effects. So, a study was planned to synthesis new candidates that may have good potential to treat AD. A series of new anthrarobin acyl derivatives (2-8) were synthesized by the reaction of anthrarobin (1) and acetic anhydride/acyl chlorides. The product were characterized by 1H NMR and EI-MS, and evaluated for butyrylcholinesterase (BuChE) inhibition activity. Compounds 5 and 4 showed notable BuChE inhibitory potential with IC50 5.3 ± 1.23 and 17.2 ± 0.47 µM, respectively when compared with the standard eserine (IC50 7.8 ± 0.27 µM), compound 5 showed potent BuChE inhibition potential than the standard eserine. The active compounds 5 and 4 have acyl groups at 2-OH and 10-OH positions which may be responsible for inhibitory potential as this orientation is absent in other products. In silico studies of 5 and 4 products revealed the high inhibitory potential due to stable binding of ligand with the BuChE active sites with docking energy score -18.8779 kcal/mol and -23.1159 kcal/mol, respectively. Subsequently, compound 5 that have potent BuChE inhibitory activity could be the potential candidate for drug development for Alzheimer's disease.

Eburneolins A and B, new withanolide glucosides from Tricholepis eburnea.

Eburneolins A (1) and B (2), new withanolide glucosides, have been isolated from the n-butanolic fraction of the 75% methanolic extract of aerial parts of Tricholepis eburnea. Their structures were elucidated through spectroscopic analysis including ESI-MS, 2D NMR and acid hydrolysis.

New ellagic acid derivative from the fruits of heat-tolerant plant Conocarpus lancifolius Engl. and their anti-inflammatory, cytotoxic, PPAR agonistic activities.

Conocarpus lancifolius (Combretaceae), is distributed in Riyadh, Saudi Arabia. It is a heat-tolerant Saudi medicinal plant, demonstrates prominent antidiabetic potential and the fruit extract fruits showed cytotoxicity against MRC-5 cancer cell line, as well as prominent antiprotozoal and antibacterial activities. The objective of this study is to isolate the compounds and evaluate the anti-inflammatory, cytotoxic, PPAR agonistic and antioxidant activities of extracts and pure constituents from C. lancifolius. A new trimethoxyellagic acid derivative 1 and two compounds, kaempferol 3-O-rutinoside 2 and ß-sitosterol glucoside 3 were isolated from the fruits of Conocarpus lancifolius, a heat-tolerant plant. Compound 2 showed strong dual activation for PPARα and PPARγ with 2.6 fold increment in PPARα activity, while 2.2 fold increment in PPARγ at 25µ/ml. This is first report on isolation and screening of different biological activities of extract and pure constituents from fruits of C. lancifolius.

Ailanthus altissima (Miller) Swingle fruit - new acyl ß-sitosteryl glucoside and in vitro pharmacological evaluation.

ß-Sitosterol-3-O-(6'-O-13"-octadecenoyl)-ß-D-glucoside (1), a new acyl ß-sitosteryl glucoside, along with three known compounds ß-sitosterol-3-O-ß-D-glucoside (2), ß-sitosterol (3) and methyl gallate (4) have been isolated from the ethyl acetate soluble fraction of methanolic extract of Ailanthus altissima fruits. Their structures were elucidated through spectroscopic data including 2D NMR, ESI-MS, methanolysis and oxidative cleavage of double bond. Antibacterial, antifungal, cytotoxic, phytotoxic and insecticidal activities were evaluated of compound 1, crude extract and its fractions so far for the first time. Pharmacological activities results showed that n-butanol fraction was good active against Pseudomonas aeruginosa and Salmonella typhi bacteria, and moderate active against Microsporum canis fungus. Crude extract, n-butanol and aqueous fractions showed good cytotoxicity. Moreover, compound 1, extract and all fractions showed notable phytotoxicity at higher concentrations, whereas all inactive against assayed insects.

Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase.

A series of thiazole derivatives 1-21 were prepared, characterized by EI-MS and (1)H NMR and evaluated for α-glucosidase inhibitory potential. All twenty one derivatives showed good α-glucosidase inhibitory activity with IC50 value ranging between 18.23±0.03 and 424.41±0.94µM when compared with the standard acarbose (IC50, 38.25±0.12µM). Compound (8) (IC50, 18.23±0.03µM) and compound (7) (IC50=36.75±0.05µM) exhibited outstanding inhibitory potential much better than the standard acarbose (IC50, 38.25±0.12µM). All other analogs also showed good to moderate enzyme inhibition. Molecular docking studies were carried out in order to find the binding affinity of thiazole derivatives with enzyme. Studies showed these thiazole analogs as a new class of α-glucosidase inhibitors.

Cytotoxicity Assessment of Six Different Extracts of Abelia triflora leaves on A-549 Human Lung Adenocarcinoma Cells.

The present investigation was designed to assess the anticancer activity of six different leaf extracts (ethyl acetate, methanol, chloroform, petroleum ether, n-butanol, and water soluble) of Abelia triflora on A-549 human lung adenocarcinoma epithelial cells. A-549 cells were exposed to 10-1000 µg/ml concentrations of the leaf extracts of A. triflorafor 24 h and then percentage cell viability was assessed by 3-(4,5-dimethylthiazol-2yl)-2,5-biphenyl tetrazolium bromide (MTT) assay. The results showed that leaf extracts of A. triflora significantly reduced the viability of A-549 cells in a concentration-dependent manner. Decrease was recorded as 31% with ethyl acetate, 36% with methanol, 46% with chloroform, 54% with petroleum ether, 62% with n-butanol, and 63% with water soluble extracts at 1000 µg/ml each. Among the various plant extracts, ethyl acetate extract showed the highest decrease in the percentage cell viability, followed by methanol, chloroform, petroleum ether, n-butanol, and water soluble extracts. Our results demonstrated preliminary screening of anticancer activity of different soluble extracts of A. triflora extracts against A-549 cells, which can be further used for the development of a potential therapeutic anticancer agents.

Abeliaside, a new phenolic glucoside from Abelia triflora.

A new phenolic glucoside, abeliaside, along with four known compounds, 5,6,7,4'-tetrahydroxy flavones, caffeic acid, 4-O-caffeoylquinic acid and caffeic acid glucoside, was isolated from the leaves of Abelia triflora R. Br. (Caprifoliaceae). The structure of the new compound was elucidated by different spectroscopic techniques. Compounds 1-5 were assayed for their anticancer activities against two cancerous human cell lines, MCF-7 and PC-3 cells, and normal Vero cell line using the crystal violet staining method. From the results it could be seen that caffeic acid possessed the highest anticancer effect against MCF-7 (IC50: 17 µg/mL) and PC-3 (IC50: 20.1 µg/mL) compared to vinblastine sulphate as reference drug (IC50: 4.6, 2.8 µg/mL). The other compounds showed weak anticancer activity on both cell lines.

New flavonol glycosides from the leaves of Caragana brachyantha.

Two new flavonol glycosides, brachysides C and D, together with three known flavonol glycosides, were isolated from the leaves of Caragana brachyantha. The structures of brachysides C and D were elucidated on the basis of detailed spectroscopic analysis as quercetin 5-O-[α-L-rhamnopyranosyl-(1 → 6)-ß-D-glucopyranoside]-7-O-[α-L-rhamnopyranoside] and quercetin 5-O-[α-L-rhamnopyranosyl-(1 → 6)-ß-D-glucopyranoside]-7-O-[α-L-rhamnopyranoside]-4'-O-[α-L-rhamnopyranoside], respectively. The presence of flavonol tetra- and triglycosides bearing a sugar moiety at position 5 was the first report from this genus Caragana.

New acylated oligosaccharides from Pistacia integerrima.

Integrisides A (1) and B (2), new acylated oligosaccharides, have been isolated from the n-butanol-soluble sub-fraction of the methanolic extract collected from the aerial parts of Pistacia integerrima. Their structures were elucidated by spectroscopic techniques and hydrolysis.

Flavonoid constituents of Pistacia integerrima.

Pistacides A and B (1-2), two new flavonoid glycosides, have been isolated from the methanolic extract of the aerial parts of Pistacia integerrima, along with 2'-hydroxyisoorientin (3), echioidinin 2'-O-beta-D-(6"-O-acetyl) glucopyranoside (4), chrysoeriol (5), and diandraflavone A (6), reported for the first time from this species. Their structures were elucidated by spectroscopic analysis including 2D NMR, FAB-MS, and acidic hydrolysis.

Spiraeamide, new sphingolipid from Spiraea brahuica.

Spiraeamide, a new sphingolipid, has been isolated from the ethyl acetate-soluble fraction of the methanolic extract of the whole plant of Spiraea brahuica, along with marrubiin, 19-acetylmarrubenol, and 6-acetylmarruenol. Their structures were elucidated by ¹H and ¹³C NMR spectra, and COSY, NOESY, HMQC, HMBC, EI-MS, and FAB-MS experiments.

Vicarin, a new isoflavone from Eremostachys vicaryi.

Vicarin (1), a new isoflavone, has been isolated from the ethyl acetate-soluble fraction of the ethanolic extract of Eremostachys vicaryi, along with soforanarin B (2), luteolin 7-O-ß-D-glucopyranoside (3), and hamighriprasin (4). Their structures were elucidated on the basis of their spectral data including MS and 2D NMR.

Alliumonoate: a new cyclopentane derivative from Allium victorialis.

Alliumonoate, a new cyclopentane derivative, has been isolated from the chloroform-soluble fraction of the ethanolic extract of Allium victorialis, along with ß-amyrin acetate, ß-sitosterol acetate, 22-cyclohexyl-1-docosanol, ß-amyrin, ß-sitosterol, and ß-sitosterol 3-O-ß-D-glucopyranoside, reported for the first time from this species. Their structures were elucidated on the basis of spectral data including mass spectra and 2D NMR experiments.

Paniculacin, a new coumarin derivative from Murraya paniculata.

Paniculacin (1), a new coumarin derivative, has been isolated from the ethyl acetate soluble fraction of the ethanolic extract of Murraya paniculata along with umbelliferone, scopoletin, 4-hydroxybenzoic acid, trans-cinnamic acid, and ß-sitosterol. Their structures were elucidated on the basis of spectral data.

Structural determination of crotamides A and B, the new amides from Croton sparsiflorus.

Two new amides crotamides A and B, have been isolated from the n-hexane soluble fraction of Croton sparsiflorus in addition to salisomide and N-(4-hydroxyphenethyl)-octacosanamide reported for the first time from this species. Their structures were assigned from spectral data including 1D and 2D NMR spectroscopic data.