Synthesis of amidocrownophanes with 27‐ and 28‐membered rings and their molecular recognition toward urea and its derivatives

Novel crownophanes with 27‐ and 28‐membered rings having two hydroxyl groups, two amide groups, and aromatic moieties such as naphthalene, pyridine, and phenyl rings were successfully synthesized by a one‐step reaction from the corresponding macrocyclic polyethers via “tandem Claisen rearrengement” in moderate yields. They can solubilize urea and its derivatives into chloroform solution, while the corresponding macrocyclic polyethers do not solubilize them. According to NMR studies, crownophanes 1 and 2 interact with urea and its derivatives forming 1:1 complexes.     

Structure determination of bioactive galloyl derivatives by NMR spectroscopy

The investigation of the chemical constituents of Symplocos racemosa Roxb led to the isolation of two new glycosides, symcomoside A (1) and symcomoside B (2), together with one known glycoside, tortoside C (3), which is reported for the first time from this plant. The structures of the new compounds were determined by 1D and 2D homonuclear and heteronuclear NMR spectroscopy, from chemical evidence and by comparison with published data for closely related compounds. Symcomoside B (2) showed potent inhibitory activity against alpha-glucosidase in a concentration-dependent fashion with an IC50 value of 0.733 +/- 0.033 mM whereas symcomoside A (1) showed very weak inhibitory activity against alpha-glucosidase (9.90% in 0.70 mM).     

Graphene and Carbon Nanotube-based Electrochemical Sensing Platforms for Dopamine

Dopamine (DA) is an important neurotransmitter, which is created and released from the central nervous system. It plays a crucial role in human activities, like cognition, emotions, and response to anything. Maladjustment of DA in human blood serum results in different neural diseases, like Parkinson's and Schizophrenia. Consequently, researchers have started working on DA detection in blood serum, which is undoubtedly a hot research area. Electrochemical sensing techniques are more promising to detect DA in real samples. However, utilizing conventional electrodes for selective determination of DA encounters numerous problems due to the coexistence of other materials, such as uric acid and ascorbic acid, which have an oxidation potential close to DA. To overcome such problems, researchers have put their focus on the modification of bare electrodes. The aim of this review is to present recent advances in modifications of most used bare electrodes with carbonaceous materials, especially graphene, its derivatives, and carbon nanotubes, for electrochemical detection of DA. A brief discussion about the mechanistic phenomena at the electrode interface has also been included in this review.     

Alpha-glucosidase inhibitors from Millettia conraui

A new geranylated isoflavone, 7-O-geranyl-6-methoxypseudobaptigenin (1) was isolated from the stem barks of Millettia conraui, along with known compounds 5-methoxydurmillone (2), conrauinone A (3), beta-amyrine (4), sitosterol (5), 3-O-beta-D-glucopyranosyl sitosterol (6) and n-docosanol (7). Compounds 1 and 4 showed a significant alpha-glucosidase inhibitory activity. The structures of the compounds were determined by analysis of their spectroscopic data.     

Alpha-glucosidase inhibitory constituents from Duranta repens

Three C-alkylated flavonoids 7-O-alpha-D-glucopyranosyl-3,5-dihydroxy-3'-(4"-acetoxyl-3"-methylbutyl)-6,4'-dimethoxyflavone (1), 7-O-alpha-D-glucopyranosyl-3,4'-dihydroxy-3'-(4"-acetoxyl-3"-methylbutyl)-5,6-dimethoxyflavone (2), 3,7,4'-trihydroxy-3'-(8"-acetoxy-7"-methyloctyl)-5,6-dimethoxyflavone (3) and a trans-clerodane type diterpenoid (-)-6beta-hydroxy-5beta,8beta,9beta,10alpha-cleroda-3,13-dien-16,15-olid-18-oic acid (4) are reported from Duranta repens along with (+)-hardwickiic acid (5) and (+)-3,13-clerodadien-16,15-olid-18-oic acid (6), isolated for the first time from this species. Their structures were established on the basis of the spectral methods, especially two dimensional (2D) NMR spectroscopy.     

Microbial transformation of oleanolic acid by Fusarium lini and alpha-glucosidase inhibitory activity of its transformed products

The biotransformation of a pentacyclic triterpene, oleanolic acid (1), with Fusarium lini afforded two oxidative metabolites, 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (2), and 2alpha,3beta,11beta-trihydroxyolean-12-en-28-oic acid (3). Metabolite 3 was found to be a new compound. The structures were characterized on the basis of spectroscopic studies. These metabolites exhibited a potent inhibition of alpha-glucosidase enzyme.     

Alpha-glucosidase inhibitors ellagic acid derivatives with immunoinhibitory properties from Terminalia superba

Fractionation of stem barks of Terminalia superba yielded two new ellagic acid derivatives, 3,4'-di-O-methylellagic acid 3'-O-beta-D-xylopyranoside (1) and 4'-O-galloy-3,3'-di-O-methylellagic acid 4-O-beta-D-xylopyranoside (2) together with known 3,3'-di-O-methylellagic acid, ellagic acid and 3,3'-di-O-methylellagic acid 4'-O-beta-D-xylopyranoside. Compounds (1) and (2) showed significant alpha-glucosidase inhibition activity and possessed significant immunoinhibitory activities with no cytotoxic effects.     

Duboscic acid: a potent α-glucosidase inhibitor with an unprecedented triterpenoidal carbon skeleton from Duboscia macrocarpa

Duboscic acid (1), a triterpenoid with a unique carbon backbone, was isolated from Duboscia macrocarpa Bocq. It is the first member of a new class of triterpenoids, for which the name "dubosane" is proposed. Duboscic acid has a potent α-glucosidase inhibition, and its structure was unambiguously deduced by a single-crystal X-ray diffraction study.     

Alpha-glucosidase inhibitory and antioxidant acridone alkaloids from the stem bark of Oriciopsis glaberrima ENGL. (Rutaceae)

The CH2Cl2/MeOH extract of the stem bark of Oriciopsis glaberrima ENGL. afforded four new acridone alkaloids namely oriciacridone C, D, E and F along with six known compounds: atalaphyllidine, oleanolic acid, butulinic acid, beta-sitosterol, stigmasterol, glucoside of stigmasterol and one synthetically known acridone: 1,3,5-trihydroxy-4-prenylacridone. The structures were established on the basis of MS, 1D and 2D NMR experiments. The acridones 1, 4 and 5 showed potent activity against alpha-glucosidase, while the acridones 1-5 showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH).     

High-temperature stable transition aluminas nanoparticles recovered from sol–gel processed chitosan-AlO<Subscript>x</Subscript> organic–inorganic hybrid films

Five and ten weight percent-alumina-containing chitosan-AlO_x films were prepared via sol–gel processing. The films were AlO_x-agglomerate-free. These organic–inorganic films were degraded by heating at 500?°C. The solid powder residues were found by means of thermogravimetry, X-ray diffractometry, infrared spectroscopy, and electron microscopy to consist of alumina (Al₂O₃) nanoparticles entraping volatile components, whose thermal removal encouraged ambient oxygen uptake. The surface microstructure and morphology of the recovered alumina nanoparticle were inspected by high-resolution transmission and scanning electron microscopy. Also, the surface chemistry and texture were evaluated by X-ray photoelectron spectroscopy and N₂ sorptiometry. Coalescences of globular nanoparticles of γ-/η-Al₂O₃ were the dominant composition of the 800?°C calcination product of the recovered alumina, irrespective of the alumina-content of the film. Upon increasing the calcination temperature up to 1100?°C, an enhanced polymorphic transition into agglomerated nanoparticles of the seldom encountered Iota-(ι-)Al₂O₃ took place. The high thermal stability of the otherwise unstable transition aluminas (at ≥950?°C) may suggestively owe to its polymorphic interdependence and/or persistent nanoscopic nature (average particle size?=?ca. 3–4?nm; specific surface area?=?ca. 80–60?m²/g). The surface chemical composition for the recovered transition aluminas nanopowders promises versatile acid–base properties for catalysis applications. Accordingly, the highly abundant bio-waste, chitosan, was successfully utilized as a novel synthesis medium for catalytic-grade alumina nanoparticles.

Open image in new window

The highly abundant bio-waste material, chitosan, is successfully employed as a synthetic medium for catalytic-grade alumina nanoparticles. This novel sol–gel synthesis process resulted in nearly 100%-recovery of nanoparticle transition γ-/η- and ι-Al₂O₃ and may be utilized in fabricating other materials/metal oxides