Senna alata leaves are a good source of propelargonidins

Proanthocyanidins (PA) in Senna alata leaves were investigated by thiolysis with benzyl mercaptan, LC–MS and NMR and consisted of almost pure propelargonidins with <6% procyanidins, had B-type linkages and a mean degree of polymerisation of three. Epiafzelechin was the major flavan-3-ol subunit (>94%) and epicatechin a minor constituent (6.4%) in residual PA and mainly detected as an extension unit.

Sodium hydroxide enhances extractability and analysis of proanthocyanidins in ensiled sainfoin (onobrychis viciifolia)

Little information exists on the effects of ensiling on condensed tannins or proanthocyanidins. The acetone–butanol–HCl assay is suitable for measuring proanthocyanidin contents in a wide range of samples, silages included, but provides limited information on proanthocyanidin composition, which is of interest for deciphering the relationships between tannins and their bioactivities in terms of animal nutrition or health. Degradation with benzyl mercaptan (thiolysis) provides information on proanthocyanidin composition, but proanthocyanidins in several sainfoin silages have proved resistant to thiolysis. We now report that a pretreatment step with sodium hydroxide prior to thiolysis was needed to enable their analysis. This alkaline treatment increased their extractability from ensiled sainfoin and facilitated especially the release of larger proanthocyanidins. Ensiling reduced assayable proanthocyanidins by 29%, but the composition of the remaining proanthocyanidins in silage resembled that of the fresh plants.

Efficient access to conjugated 4,4’-bipyridinium oligomers using the Zincke reaction: synthesis, spectroscopic and electrochemical properties

The cyclocondensation reaction between rigid, electron-rich aromatic diamines and 1,1′-bis(2,4-dinitrophenyl)-4,4′-bipyridinium (Zincke) salts has been harnessed to produce a series of conjugated oligomers containing up to twelve aromatic/heterocyclic residues. These oligomers exhibit discrete, multiple redox processes accompanied by dramatic changes in electronic absorption spectra.

Galloylated proanthocyanidins from shea (Vitellaria paradoxa) meal have potent anthelmintic activity against Ascaris suum

Proanthocyanidins (PA) from shea (Vitellaria paradoxa) meal were investigated by thiolytic degradation with benzyl mercaptan and the reaction products were analysed by high performance liquid chromatography–mass spectrometry. These PA were galloylated (≈40%), contained only B-type linkages and had a high proportion of prodelphinidins (>70%). The mean degree of polymerisation was 8 (i.e. average molecular size was 2384 Da) and epigallocatechin gallate (EGCg) was the major flavan-3-ol subunit in PA. Shea meal also proved to be a potentially valuable source for extracting free flavan-3-ol-O-gallates, especially EGCg (575 mg/kg meal), which is known for its health and anti-parasitic benefits. Proanthocyanidins were isolated and tested for bioactivity against Ascaris suum, which is an important parasite of pigs. Migration and motility tests revealed that these PA have potent activity against this parasitic nematode.

Proanthocyanidins from Averrhoa bilimbi fruits and leaves

Proanthocyanidins from Averrhoa bilimbi fruits and leaves were analysed by thiolysis with benzyl mercaptan and high performance liquid chromatography–mass spectrometry and consisted of pure B-type procyanidins. These tannins consisted of almost pure homopolymers, with epicatechin accounting for most of the monomeric subunits in fruits (97%) and leaves (99%). Leaves contained more procyanidins (4.5 vs 2.2 g/100 g dry weight) with a higher mean degree of polymerisation (9 vs 6) than fruits. This study thus contributes information on the proanthocyanidins of a traditional food that can make an important contribution to the intake of compounds with antioxidant and health benefits. The fruits are prized for culinary purposes and the leaves are used in traditional medicine.