This review focuses on the methodology used for the construction of tetrahydropyran (THP) rings in the synthesis of natural products over the last seven years. While methods like cyclisation onto oxocarbenium ions, reduction of cyclic hemi-ketals, Michael reactions, hetero-Diels-Alder cycloadditions and cyclisations onto epoxides continue to find application, several other strategies including metal-mediated cyclisations, ring-closing metathesis, radical cyclisations and carbocation cyclisations have also found use. This review is intended to provide an overview of the area for those who are unfamiliar, and to refresh and remind those who do work in the area of the exciting developments in the field.

No abstract

Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and reaction conditions.

The Maitland-Japp reaction has been extended to the synthesis of highly functionalised dihydropyran-4-ones. These dihydropyran-4-ones can in turn be converted stereoselectively into tetrahydropyran-4-ones with tertiary and quaternary stereocentres via the one-pot addition of hydride or carbon nucleophiles and trapping with carbon electrophiles. The utility of this method is demonstrated by providing access to the functionalised tetrahydropyran units present in a component of the Civet fragrance and the anticancer polyketide lasonolide A.

The air-dried powdered stem bark of Calophyllum nodusum (Guttiferea) collected from Sandakan (Sabah, Malaysia), was extracted sequentially with hexane, chloroform and methanol. The solvents were removed by rotary evaporator to give dark viscous extracts. Detailed and repeated chromatographic separation of the extracts lead to isolation of two new xanthones, identified as nodusuxanthone (1a) and trapezifolixanthone A (2). Other common terpenoids such as betulinic acid, lupeol, stigmasterol and friedelin were also isolated from the extracts and identified. The structures of the compounds were established by detailed spectral analysis and comparison with previously reported data.

Oil palm (Elaeis guineensis Jacq.) leaflets (OPLs) are one of the major agricultural by-products generated from the massive cultivation of Malaysian palm oil. This biomass is also reported to be of potential value based on its health-improving effects. By employing proton nuclear magnetic resonance (1H-NMR) spectroscopy combined with multivariate data analysis (MVDA), the metabolite profile of OPLs was characterized and correlated with their antioxidant and wound healing properties. Principal component analysis (PCA) classified four varieties of extracts, prepared using solvents ranging from polar to medium polarity, into three distinct clusters. Cumulatively, six flavonoids, eight organic acids, four carbohydrates, and an amine were identified from the solvent extracts. The more polar extracts, such as, the ethyl acetate-methanol, absolute methanol, and methanol-water, were richer in phytochemicals. Based on partial least square (PLS) analysis, the constituents in these extracts, such as (+)-catechin, (−)-epicatechin, orientin, isoorientin, vitexin, and isovitexin, were strongly correlated with the measured antioxidant activities, comprising ferric reducing antioxidant power (FRAP), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and nitric oxide (NO) free radical scavenging activities, as well as with cell proliferation and migration activities. This study has provided crucial evidence on the importance of these natural antioxidant compounds on the wound healing properties of OPL.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Curculigo is a potent plant with a variety of traditional uses, such as anti-oxidant, anti-diabetic, anti-tumor, anti-bacterial, anti-cancer, anti-osteoporosis, and wound-healing. The comprehensive profiling of the Curculigolatifolia metabolome was carried out by generating a molecular network (MN) from Liquid Chromatography–Tandem Mass Spectrometry (LC-MS/MS) data to profile the methanol extract and correlating them with their antioxidant (2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), total phenolic contents (TPC), and β-carotene) and antimicrobial (disk-diffusion agar method, minimum inhibitory concentration (MIC), and minimum bactericidal concentration (MBC)) properties. The antioxidant capacity was observed to be significantly higher in the rhizome crude extract, with 18.10 ± 0.91 µg/mL DPPH activity, and a β-carotene bleaching result of 35.20%. For the antimicrobial activity, the leaf crude extract exhibited a strong Staphylococcus aureus and Salmonella choleraesuis (8–15 ± 3.0 mm) inhibition in the disk-diffusion agar. The leaf extract also exhibited maximum antibacterial activity against S. aureus (MIC = ±0.25 mg/mL, MBC = ±0.25 mg/mL) and S. choleraesuis (MIC = ±0.25 mg/mL, MBC = ±0.25 mg/mL). LC-MS/MS analysis and MN revealed norlignans and phenolic glycosides as major metabolites in the rhizome and leaf extracts of the negative mode (M − H)−. Fourteen known compounds were identified, and three unknown compounds were putatively identified in the rhizome extract, while ten known compounds and six unknown compounds were putatively identified in the leaf extract.