Phytochemical Investigation, In silico/In vivo Analgesic, and Anti-inflammatory Assessment of the Egyptian Cassia occidentalis L.

Cassia occidentalis L., from Fabaceae family phytochemical screening, revealed several biologically active principles mainly flavonoids and anthraquinones. GLC analysis of the lipoidal matter afforded 12 hydrocarbons: 9-dodecyl-tetradecahydro-anthracene (48.97 %), 9-dodecyl-tetradecahydro-phenanthrene (14.43 %), and 6 sterols/triterpenes: isojaspisterol (11.99%) and fatty acids were palmitic acid (50 %), and Linoleic acid (16.06%). Column chromatography led to the isolation of fifteen compounds (1-15), elucidated using spectroscopic evidence. First report of undecanoic acid (4) from the family Fabaceae, while p-dimethyl amino-benzaldehyde (15) was first time isolated from a natural origin. Eight compounds isolated for the first time from C. occidentalis L.; ß-amyrin (1), ß-sitosterol (2), stigmasterol (3), camphor (5), lupeol (6), chrysin (7), pectolinargenin (8), and 1, 2, 5-trihydroxy anthraquinone (14) besides five known compounds previously isolated; apigenin (9), kaempferol (10), chrysophanol (11), physcion (12), and aloe-emodin (13). In-vivo evaluation of anti-inflammatory and analgesic effects of C. occidentalis L. extracts where the n-butanol and total extracts showed the highest activities. The percentage of the inhibitory effect of the n-butanol extract was 29.7 at a dose of 400 mg/Kg. Furthermore, identified phytoconstituents were docked into the active sites of enzymes nAChRs, COX-1, and COX-2 to evaluate binding affinity. Phyto-compounds Physcion, aloe-emodin, and chrysophanol were found to have a good affinity for targeted receptors compared to co-crystalized inhibitors, validating the analgesic and anti-inflammatory effects of the phytochemicals.

In silico and in vitro studies of isolated constituents from Callistemon citrinus leaves: Anti-microbial potential and inhibition of iNOS activity.

Phytochemical investigation of Callistemon citrinus (Curtis) Skeels (syn. Callistemon lanceolatus (Sm.) Sweet and Melaleuca citrina (Curtis) Dum.Cours.) leaves resulted in the isolation of five undescribed compounds, including one acylphloroglucinol derivative and four monoterpene galloylglucosides, in addition to 29 known diverse secondary metabolites. Interestingly, this study reports chemosystematically significant isolation of the monoterpene galloylglucosides from the genus for the first time. Furthermore, exploration of the isolated compounds as inhibitors of inflammation-related molecular targets, molecular docking studies targeting human adipocyte lipid-binding protein FABP4 (3P6H) and human nitric oxide synthase (3E7G) were carried out in order with the in vitro evaluation of the isolated compounds for their anti-microbial and inhibitory of inducible nitric oxide synthase (iNOS) activities. Molecular docking studies revealed that eighteen compounds showed lower docking scores than ibuprofen, the native ligand in the crystal structure 3P6H, and nine compounds showed lower docking scores than AR-C95791, the native ligand in the binding site of 3E7G. Additionally, in vitro studies revealed that seven compounds showed moderate iNOS inhibitory activity. They also were moderately cytotoxic to HepG2, LLC-PK1 and Vero cells. Pulverulentone A showed moderate antibacterial activity against MRSA (IC50 22.2 µM) and antifungal activity against C. neoformans, while corosolic acid showed strong antibacterial activity against VRE (IC50 15.9 µM).Thus, the in silico and in vitro studies indicated that some isolated compounds hold potentials as inhibitors of iNOS activity and anti-microbial agents.

New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors.

Phytochemical investigation of Ficus pandurata Hance (Moraceae) fruits has led to the isolation of two new triterpenoids, ficupanduratin A [1ß-hydroxy-3ß-acetoxy-11α-methoxy-urs-12-ene] (11) and ficupanduratin B [21α-hydroxy-3ß-acetoxy-11α-methoxy-urs-12-ene] (17), along with 20 known compounds: α-amyrin acetate (1), α-amyrin (2), 3ß-acetoxy-20-taraxasten-22-one (3), 3ß-acetoxy-11α-methoxy-olean-12-ene (4), 3ß-acetoxy-11α-methoxy-12-ursene (5), 11-oxo-α-amyrin acetate (6), 11-oxo-ß-amyrin acetate (7), palmitic acid (8), stigmast-4,22-diene-3,6-dione (9), stigmast-4-ene-3,6-dione (10), stigmasterol (12), ß-sitosterol (13), stigmast-22-ene-3,6-dione (14), stigmastane-3,6-dione (15), 3ß,21ß-dihydroxy-11α-methoxy-olean-12-ene (16), 3ß-hydroxy-11α-methoxyurs-12-ene (18), 6-hydroxystigmast-4,22-diene-3-one (19), 6-hydroxystigmast-4-ene-3-one (20), 11α,21α-dihydroxy-3ß-acetoxy-urs-12-ene (21), and ß-sitosterol-3-O-ß-D-glucopyranoside (22). Compound 21 is reported for the first time from a natural source. The structures of the 20 compounds were elucidated on the basis of IR, 1D ((1)H and (13)C), 2D ((1)H-(1)H COSY, HSQC, HMBC and NOESY) NMR and MS spectroscopic data, in addition to comparison with literature data. The isolated compounds were evaluated for their anti-microbial, anti-malarial, anti-leishmanial, and cytotoxic activities. In addition, their radioligand displacement affinity on opioid and cannabinoid receptors was assessed. Compounds 4, 11, and 15 exhibited good affinity towards the CB2 receptor, with displacement values of 69.7, 62.5 and 86.5 %, respectively. Furthermore, the binding mode of the active compounds in the active site of the CB2 cannabinoid receptors was investigated through molecular modelling.

Bombacaceae: a phytochemical review.

CONTEXT: Bombacaceae is a small family of the order Malvales and contains about 28 genera and 200 species. Members of this family are not only showy ornamentals but they possess significant economical and commercial reputation as well. In addition, various plant parts of several species are widely used as foods and traditional medicines in many parts of the world. OBJECTIVE: Chemical analyses of Bombacaceae species have recently yielded a number of important phytocompounds belonging to different classes. Hence, this work represents a comprehensive appraisal of the phytochemical studies conducted on Bombacaceae plants. MATERIALS AND METHODS: Searches were conducted using electronic databases (e.g., Medline, Pubmed, Academic Journals, and Springer Link); general web searches were also undertaken using Google applying some related search terms "e.g., Bombacaceae, phytochemical studies of Bombacaeae plants, and chemical investigation of Bombacaeae", journals and scientific theses. The bibliographies of papers relating to the review subject were also searched for further relevant references. RESULTS: Chemical investigations were concentrated primarily on certain species leaving fertile fields for further phytopharmacological research. CONCLUSION: The reviewed findings present Bombacaceae species as an untapped reservoir of phytocompounds which may play a supportive role in the pharmaceutical field and will be of high chemotaxonomic value within this recently separated family.