The nature and characteristics of the CH/π interaction are discussed by comparison with other weak molecular forces such as the CH/O and OH/π interaction. The CH/π interaction is a kind of hydrogen bond operating between a soft acid CH and a soft base π-system (double and triple bonds, C6 and C5 aromatic rings, heteroaromatics, convex surfaces of fullerenes and nanotubes). The consequences of CH/π hydrogen bonds in supramolecular chemistry are reviewed on grounds of recent crystallographic findings and database analyses. The topics include intramolecular interactions, crystal packing (organic and organometallic compounds), host/guest complexes (cavity-type inclusion compounds of cyclodextrins and synthetic macrocyclic hosts such as calixarenes, catenanes, rotaxanes and pseudorotaxanes), lattice-inclusion type clathrates (including liquid crystals, porphyrin derivatives, cyclopentadienyl compounds and C60 fullerenes), enantioselective clathrate formation, catalytic enantioface discriminating reactions and solid-state photoreaction. The implications of the CH/π concept for crystal engineering and drug design are evident.

CH/π hydrogen bonds in crystals

This review provides an updated overview of the most important applications of supercritical fluids in the extraction of bioactive compounds from plant matrices The main factors influencing the extraction yields, solubility, and manufacturing costs are described Aspects concerning the operational processing in the extraction and fractionation are also discussed The data compiled herein are focused on the extraction of essential oils, phenolic compounds, carotenoids, tocopherols, and tocotrienols

Supercritical Fluid Extraction of Bioactive Compounds: Fundamentals, Applications and Economic Perspectives

Non-thermal stabilization mechanisms of anthocyanins in model and food systems—An overview

Antibacterial mode of action of Cudrania tricuspidata fruit essential oil, affecting membrane permeability and surface characteristics of food-borne pathogens

Natural products as a source of Alzheimer's drug leads

Characterisation of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis

Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata.

The most abundant polyphenol of soy leaves, coumestrol, displays potent α-glucosidase inhibitory activity

The antioxidative properties of five prenylated flavonoids, including new flavanone (2), from the root bark of Cudrania tricuspidata were examined against the ABTS, DPPH, and hydroxyl radicals. In most of the assays to determine their antioxidative properties, the ABTS activity was strongly correlated with DPPH because both methods are responsible for the same chemical property of hydrogen- or electron-donation to the antioxidant. On the other hand, the prenylated flavonoids (1-5) acted differently with both methods; namely, all the prenylated flavonoids strongly scavenged the ABTS radical (IC(50) 300 microM). Even though isolated 5,7,2',4',-tetrahydroxy-6,5'-diprenylflavanone (3) showed weak reducing power (746 mV) by cyclic voltammetry when compared to quercetin (394 mV), both had similar ABTS activity (IC(50) < 5 microM).

https://www.tandfonline.com/doi/pdf/10.1271/bbb.70.427

Selective ABTS Radical-Scavenging Activity of Prenylated Flavonoids from Cudrania tricuspidata

The methanolic root extract of Glycine max (L.) Merr. was chromatographed, which yielded 10 flavonoids, including three isoflavones 1−3, five pterocarpans 4−8, one flavonol 9, and one anthocyanidin 10. All isolated compounds were examined for LDL-antioxidant activities using four different assay systems on the basis of Cu2+-mediated oxidation. Among them, seven compounds showed potent LDL-antioxidant activities in the thiobarbituric acid reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. Three pterocarpans 4, 6, and 7, never reported as LDL-antioxidant, showed potent activities with IC50 values of 19.8, 0.9, 45.0 μM, respectively, in comparison with probucol (IC50 = 5.6 μM) as positive control. Interestingly, coumestrol 6 (IC50 = 0.9 μM) showed 20 times more activity in the TBARS assay than genistein (IC50 = 30.1 μM) and daidzein (IC50 = 21.6 μM), representative antioxidants...

Jin Hwan Lee

Papers

Characterisation of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis

Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata.

The most abundant polyphenol of soy leaves, coumestrol, displays potent α-glucosidase inhibitory activity

Selective ABTS Radical-Scavenging Activity of Prenylated Flavonoids from Cudrania tricuspidata

LDL-Antioxidant Pterocarpans from Roots of Glycine max (L.) Merr.