Fintiamin: A diketopiperazine from the marine sponge-derived fungus Eurotium sp.

The fungus Eurotium sp., derived from the marine sponge Ircinia variabilis, was found to produce a diketopiperazine-indole alkaloid that we named fintiamin (1). Structural elucidation of 1 was achieved by extensive spectroscopic analysis including nuclear magnetic resonance spectroscopy and mass spectrometry. Compound 1 is a lipophilic terpenoid-dipeptide hybrid molecule that shows affinity for the cannabinoid CB1 receptor at low micromolar concentrations. Docking studies based on previous X-ray structures provide a plausible binding pose for compound 1 in the orthosteric binding site of the CB1 receptor.

Natural Phenolics as Inhibitors of the Human Neutrophil Elastase (HNE) Release: An Overview of Natural Anti-inflammatory Discoveries during Recent Years.

Serine protease, Human Neutrophil Elastase (HNE), has been shown to be useful in medical science, however, its over production and malfunctioning may produce devastating effects and cause serious damage to the host. Unfortunately, the present approved drug, sivelestat, only alleviates the symptoms of the diseases caused by malfunction of HNE but not the disease progression. Therefore, there is a crucial need to search potent and safer molecules as elastase inhibitors and to develop better anti-inflammatory drugs in future. In addition, nature is the best architect that may provide a safer future drug candidate as HNEproduction/ activity inhibitor. Since phenolic natural products are already known as antiinflammatory compounds, either by acting as antioxidants or by any other mechanism, thus, this review article summarizes the discovery and elastase inhibitory activity of ∼180 phenolics isolated from diverse natural sources during more than one decade, i.e. 2005-2017.

Metabolome based classification of artichoke leaf: A prospect for phyto-equivalency of its different leaf origins and commercial preparations.

The growing interest in assuring phytomedicines efficacy and moreover the increase in requirements for its safety drive the development of analytical methods for its quality control assurance. Herein, we present a nuclear magnetic resonance (NMR) fingerprinting approach of artichoke leaf material from different origins and in its commercial preparations. Under optimized conditions, we were able to simultaneously identify 23 metabolites including sugars, amino and organic acids, sesquiterpene lactones, flavones, cinnamates, inulin, fatty acids and nitrogenous bases. Principal component analysis (PCA) was used to reveal for differences among artichoke specimens. PCA score plot derived from the aromatic region (5-10 ppm) provided better classification model than that of full scan (0-10 ppm), and revealing for enrichment of wild Egyptian and Tanzanian artichoke in sesquiterpene viz. aguerin B versus O-caffeoylquinic acid and luteolin abundance in cultivated leaf. PCA analysis of 3 commercial artichoke preparations showed discrimination of a silymarin-containing capsule suggesting that NMR can distinguish liver-aid herbal preparations based on its different chemical composition. Quantitative 1H NMR (qHNMR) was further employed to assess major metabolites levels and revealing for the enrichment of cultivated plants in cinnamates viz. (E)-cinnamaldehyde (1.1 mg/g) and O-caffeoyl quinic acid (15.09 mg/g,). To the best of our knowledge, this study provides the first approach utilizing NMR fingerprinting to assess for phytoequivalency among artichoke leaf and in its preparations.

Cytotoxic constituents of Alocasia macrorrhiza.

An indole alkaloid, 2-(5-hydroxy-1H-indol-3-yl)-2-oxo-acetic acid (1) isolated for the first time from nature, in addition to the nine known compounds 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (2), alocasin B (3), hyrtiosin B (4), α-monopalmitin (5), 1-O-ß-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (6), 3-epi-betulinic acid (7), 3-epi-ursolic acid (8), ß-sitosterol (9) and ß-sitosterol 3-O-ß-D-glucoside (10) were isolated from the rhizomes of Alocasia macrorrhiza (Araceae). Their structures were elucidated by 1D and 2D NMR spectroscopic data. Of these compounds, 6 exhibited the strongest cytotoxicity against the four tested human cancer cell lines (IC50 of about 10 µM against Hep-2 larynx cancer cells).

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent.

The different pharmacologic properties of plants-containing cynaropicrin, especially artichokes, have been known for many centuries. More recently, cynaropicrin exhibited a potential activity against all genotypes of hepatitis C virus (HCV). Cynaropicrin has also shown a wide range of other pharmacologic properties such as anti-hyperlipidemic, anti-trypanosomal, anti-malarial, antifeedant, antispasmodic, anti-photoaging, and anti-tumor action, as well as activation of bitter sensory receptors, and anti-inflammatory properties (e.g., associated with the suppression of the key pro-inflammatory NF-κB pathway). These pharmacological effects are very supportive factors to its outstanding activity against HCV. Structurally, cynaropicrin might be considered as a potential drug candidate, since it has no violations for the rule of five and its water-solubility could allow formulation as therapeutic injections. Moreover, cynaropicrin is a small molecule that can be easily synthesized and as the major constituent of the edible plant artichoke, which has a history of safe dietary use. In summary, cynaropicrin is a promising bioactive natural product that, with minor hit-to-lead optimization, might be developed as a drug for HCV.

Fungal phenalenones: chemistry, biology, biosynthesis and phylogeny.

Covering up to the end of August 2013. Phenalenones are members of a unique class of natural polyketides exhibiting diverse biological potential. This is a comprehensive review of 72 phenalenones with diverse structural features originating from fungal sources. Their bioactive potential and structure elucidation are discussed along with a review of their biosynthetic pathways and the taxonomical relationship between the fungi producing these natural products.