Chemical Profile and Biological Activities of Fungal Strains Isolated from Piper nigrum Roots: Experimental and Computational Approaches.

The current report describes the chemical investigation and biological activity of extracts produced by three fungal strains Fusarium oxysporum, Penicillium simplicissimum, and Fusarium proliferatum isolated from the roots of Piper nigrum L. growing in Vietnam. These fungi were namely determined by morphological and DNA analyses. GC/MS identification revealed that the EtOAc extracts of these fungi were associated with the presence of saturated and unsaturated fatty acids. These EtOAc extracts showed cytotoxicity towards cancer cell lines HepG2, inhibited various microbacterial organisms, especially fungus Aspergillus niger and yeast Candida albicans (the MIC values of 50-100 µg/mL). In α-glucosidase inhibitory assay, they induced the IC50 values of 1.00-2.53 µg/mL were better than positive control acarbose (169.80 µg/mL). The EtOAc extract of F. oxysporum also showed strong anti-inflammatory activity against NO production and PGE-2 level. Four major compounds linoleic acid (37.346 %), oleic acid (27.520 %), palmitic acid (25.547 %), and stearic acid (7.030 %) from the EtOAc extract of F. oxysporum were selective in molecular docking study, by which linoleic and oleic acids showed higher binding affinity towards α-glucosidase than palmitic and stearic acids. In subsequent docking assay with inducible nitric oxide synthase (iNOS), palmitic acid, oleic acid and linoleic acid could be moderate inhibitors.

Antioxidative and α-glucosidase inhibitory constituents of Polyscias guilfoylei: experimental and computational assessments.

Searching for bioactive agents from medicinal plants, eleven constituents were isolated from Polyscias guilfoylei stem for the first time, including a nucleoside uracil (1), two sterols ß-sitosterol (2) and daucosterol (3), a saponin androseptoside A (4), two lignans (+)-pinoresinol (5) and (+)-syringaresinol (6), four phenolic acids protocatechuic acid (7), methyl protocatechuate (8), caffeic acid (9), and 5-O-caffeoylquinic acid (10), and a flavonoid quercitrin (11). Metabolites 1, 4, and 6-11 have never been observed in genus Polyscias before. Phenolic compounds 7 and 9 possessed the respective IC50 values of 21.33 and 13.88 µg/mL in DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidative assay, as compared with that of the positive control resveratrol (IC50 = 13.21 µg/mL). From density functional theory (DFT) calculated approach, the DPPH free radical scavenging capacity of two compounds 7 and 9 can be explained by the role of OH groups at carbons C-3 and C-4. Antioxidative actions of these two potential agents are followed HAT (H atom transfer) mechanism by OH bond disruption in gas, but SPLET (sequential proton loss electron transfer) mechanism in solvents water and methanol. Compared to 4-OH group, 3-OH group showed better bond disruption enthalpies and better kinetic energies since it reacted with HOO• and DPPH radicals. Sterols 2-3 and flavonoid 11 induced the IC50 values of < 2.0 µg/mL better than the positive control acarbose (IC50 = 184.0 µg/mL) in α-glucosidase inhibitory assay. Their interactions with human intestinal C- and N-terminal domains of α-glucosidase were explored using molecular docking study. The obtained results proved that compounds 2, 3, and 11 bind relatively stronger with the C-terminal domain than to the N-terminal domain through pivotal residues in the binding site and could be hypothesized as mixed inhibitors.

New nor-lignans from the leaves of styrax annamensis guillaumin.

Phytochemical study of the leaves of Styrax annamensis Guillaumin resulted in the isolation of a new natural product egonol-3''-sulphate (1), and two new derivatives egonol-3-methyl-D-galactopyranoside (2) and 7-methoxy-2-(3',4'-methylenedioxyphenyl)-benzofuran-5-carboxamide (3). Their chemical structures were -elucidated by spectroscopic data. Compounds 1 and 3 significantly established a great role for the chemotaxonomic aspect. Compound 1 showed cytotoxicity against four cancer cell lines KB, HepG2, Lu, and MCF7 with the IC50 values of 84.90-101.69 µg/mL, and exhibited acetylcholinesterase (AChE) inhibitory activity with the IC50 value of 97.08 µg/mL.

Garcicowanones C-E, three new hydrated-geranylated xanthones from the roots of Garcinia cowa Roxb. ex Choisy, and their α-glucosidase inhibition activities.

Three new xanthones, garcicowanones C-E (1 - 3), and six known xanthones (4 - 9) were isolated from the roots of Garcinia cowa Roxb. ex Choisy. Their chemical structures were determined using spectroscopic technics, including HR-ESI-MS and 2 D NMR. All isolated compounds were evaluated for in vitro α-glucosidase inhibition. Cowanol (6) and norcowanin (8) had the most potent α-glucosidase inhibitory activity, with respective IC50 values of 33.5 ± 0.8 and 17.2 ± 0.3 µM, compared with the positive control, acarbose (IC50 257.3 ± 4.8 µM).

Garcimckeans A-C, three new xanthones from the stems of Garcinia mckeaniana, and their cytotoxic activity.

Three new xanthones, garcimckeans A-C (1-3) were isolated from the methanol extract of the stems of Garcinia mckeaniana (Clusiaceae). Their structures were established by extensive spectroscopic analysis (HR-ESI-MS and 1 D and 2 D NMR) and by comparison of the spectral data with those reported in the literature. Compounds 1-3 displayed weak cytotoxic activity toward KB, Lu, HepG2, and MCF7 cell lines using the MTT assay with IC50 values ranging from 71.03 ± 2.93 to 90.40 ± 7.13 µM compared to that of the positive control compound, ellipticine (IC50: 1.22 ± 0.10 ∼ 2.44 ± 0.2 µM).

A new cytotoxic compound from the leaves of Styrax annamensis Guillaumin.

New propene derivative 1-(3',4'-methylenedioxyphenyl)-2-(2''-hydroxy-5-(3'''-hydroxypropyl)-3''-methoxyphenyl)prop-2-en-1-one (1), along with three known triterpenoids ursolic acid (2), pomolic acid (3), and maslinic acid (4) were isolated from the leaves of Styrax annamensis species. All structures were assigned by spectroscopic analysis. Compound 1 showed potent cytotoxicity against four cancer cell lines (KB, HepG2, Lu, and MCF7) with the IC50 values of 3.19, 2.87, 2.33, and 2.44 µM, respectively.

Medicinal Plant Centipeda Minima: A Resource of Bioactive Compounds.

BACKGROUND: Centipeda minima (the family Asteraceae) is an annual herbaceous plant native to the tropical regions, especially in eastern tropical Asia. C. minima is well-known in the list of medicinal plants with capacities in treatment of whooping cough, nasal allergy, malaria, and asthma. More than sixty reports on phytochemical and pharmacological aspects of this plant are now available, but a supportive review is insufficient. OBJECTIVE: The current review aims to make a compilation of almost all of the isolated compounds from the title plant, together with their pharmacological activities. METHODOLOGY: Centipeda minima is a meaningful keyword to search for previous references, while the reliable databases, such as Sci-Finder, Google Scholar, Pub Med, Science Direct, the Web of Science, Scopus, Bentham science, Taylor Francis, Springer, IOP Science were utilized at most. CONCLUSION: More than one hundred secondary metabolites, classifying as terpenoids, flavonoids, mono-phenols, fatty acids, amides, and other types, were isolated from this plant. Among them, sesquiterpene lactones are dominant in either C. minima species or numerous plants of genus Centipeda. These phytochemical groups also possessed various biological results like anti-cancer, anti-bacteria, anti-allergy, anti-virus, anti-inflammation, and hepatoprotective activities. With many kinds of bioactive results such as anti-cancer and anti-inflammation, the use of C. minima plant extracts and isolated compounds for drug development seems to be a futuristic strategy.

Biologically Active Constituents from Plants of the Genus Xanthium.

Herbaceous annual plants of the genus Xanthium are widely distributed throughout the world and have been employed medicinally for millennia. This contribution aims to provide a systematic overview of the diverse structural classes of Xanthium secondary metabolites, as well as their pharmacological potential. On searching in various reference databases with a combination of three keywords "Xanthium", "Phytochemistry", and "Pharmacology", relevant publications have been obtained subsequently. From the 1950s to the present, phytochemical investigations have focused mainly on 15 Xanthium species, from which 300 compounds have been isolated and structurally resolved, primarily using NMR spectroscopic methodology. Xanthium constituents represent several secondary metabolite types, including simple phenols, sulfur and nitrogen-containing compounds, lignans, sterols, flavonoids, quinones, coumarins, and fatty acids, with terpenoids being the most common of these. Among the 174 terpenoids characterized, xanthanolide sesquiterpenoids are abundant, and most of the compounds isolated containing sulfur were found to be new in Nature. The ethnomedical uses of Xanthium crude extracts are supported by the in vitro and in vivo effects of their constituents, such as cytotoxicity, antioxidant, antibacterial, antifungal, antidiabetes, and hepatoprotective activities. Toxicological results suggest that Xanthium plant extracts are generally safe for use. In the future, additional phytochemical investigations, along with further assessments of the biological profiles and mechanism of action studies of the components of Xanthium species, are to be expected.