Quillaja saponaria Molina represents the main source of saponins for industrial applications. Q. saponaria triterpenoids have been studied for more than four decades and their relevance is due to their biological activities, especially as a vaccine adjuvant and immunostimulant, which have led to important research in the field of vaccine development. These saponins, alone or incorporated into immunostimulating complexes (ISCOMs), are able to modulate immunity by increasing antigen uptake, stimulating cytotoxic T lymphocyte production (Th1) and cytokines (Th2) in response to different antigens. Furthermore, antiviral, antifungal, antibacterial, antiparasitic, and antitumor activities are also reported as important biological properties of Quillaja triterpenoids. Recently, other saponins from Q. brasiliensis (A. St.-Hill. & Tul.) Mart. were successfully tested and showed similar chemical and biological properties to those of Q. saponaria barks. The aim of this manuscript is to summarize the current advances in phytochemical and pharmacological knowledge of saponins from Quillaja plants, including the particular chemical characteristics of these triterpenoids. The potential applications of Quillaja saponins to stimulate further drug discovery research will be provided.

An immunoadjuvant preparation (named Fraction B) was obtained from the aqueous extract of Quillaja brasiliensis leaves, and further fractionated by consecutive separations with silica flash MPLC and reverse phase HPLC. Two compounds were isolated, and their structures elucidated using a combination of NMR spectroscopy and mass spectrometry. One of these compounds is a previously undescribed triterpene saponin (Qb1), which is an isomer of QS-21, the unique adjuvant saponin employed in human vaccines. The other compound is a triterpene saponin previously isolated from Quillaja saponaria bark, known as S13. The structure of Qb1 consists of a quillaic acid residue substituted with a β-d-Galp-(1→2)-[β-d-Xylp-(1→3)]-β-d-GlcpA trisaccharide at C3, and a β-d-Xylp-(1→4)-α-l-Rhap-(1→2)-[α-l-Arap-(1→3)]-β-d-Fucp moiety at C28. The oligosaccharide at C28 was further substituted at O4 of the fucosyl residue with an acyl group capped with a β-d-Xylp residue.

The effect on color of the initial pH employed in dulce de leche (DL) production was evaluated through physicochemical and spectroscopical characterization of the melanoidins formed in the process. Melanoidins originated at pH values of 6.5, 7.0, and 7.5, and they were released by the enzymatic hydrolysis of the protein backbone and purified by gel filtration. They showed a significant degree of polydispersity, in general, with molecular weights (MWs) below 1,800 Da. DL produced at a higher pH released melanoidins with higher average MW after the enzymatic hydrolysis. They also presented darker colors (dE^*ab, C^*), more closely resembling those typical of the commercial product. Analysis of the fractions isolated by gel filtration using HPLC-DAD and multinuclear NMR showed an heterogeneous and complex composition. Even though structurally related, the 1H NMR spectra of melanoidins showed a higher degree of aromaticity at higher pH values. In conclusion, the pH employed in DL production affects the amount and structure of the colored products originated by MR reactions, and thus the color of the final product.

Free (epi) catechin, quercetin, (epi) gallocatechin, flavonol glycosides and condensed tannins were identified according to their molecular mass, characteristic product ions and retention times in extracts obtained from leaves and branches of Maytenus ilicifolia (Congorosa) by mass spectrometry. The in vitro anthelmintic activity against cattle gastrointestinal nematodes of Congorosa extract was determined using the Egg Hatch Inhibition Assay. Additionally, commercial quercetin, gallocatechin and epicatechin were evaluated. Although total phenolics, total tannins and condensed tannins contents were lower in branches extract than in leaves extract, the EC₅₀ were 0.065 mg/mL and 0.890 mg/mL for branches and leaves extract, respectively. Moreover, the use of polyvinylpyrrolidone as a blocking agent of tannins, did not change significantly the EC₅₀ for branches extract, but significantly changed for leaves extract. Quercetin and gallocatechin EC₅₀ values were in the range 0.03–0.05 mg/mL and epicatechin showed 100% inhibition of the egg hatching process at 0.004 mg/mL. Graphical Abstract