Analysis of an immunoadjuvant saponin fraction from Quillaja brasiliensis leaves by electrospray ionization ion trap multiple-stage mass spectrometry

Wallace, F. Morgan; Bennadji, Zohra; Ferreira, Fernando; Olivaro, Cristina

doi:10.1016/j.phytol.2017.04.020

Cited by 19 publications

(30 citation statements)

References 24 publications

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“…Fraction B from the leaves was obtained by fractionation of an aqueous extract on a C18 SPE column as described in our previous work …”

Section: Methodsmentioning

confidence: 99%

“…The bark was dried in a ventilated oven (Marconi, model MA037) and grounded in a hammer mill (Marconi, model MA340, serial 9304176). The aqueous extract and the saponins Fraction B from the bark were obtained in the same way as that for the leaves …”

Section: Methodsmentioning

confidence: 99%

“…The parameters of the source ESI (DI and LC) and the chromatographic method were detailed in our previous work . MS analysis was conducted in the negative ionisation mode.…”

Section: Methodsmentioning

confidence: 99%

“…In our previous investigation, 27 triterpenic saponins were identified from the immunoadjuvant Fraction B, produced from Q. brasiliensis leaves . Figure shows their general structure, which shared many features with those from Q. saponaria .…”

Section: Introductionmentioning

confidence: 91%

“…It has been demonstrated that the aqueous extract and some of the purified fractions obtained from leaves of Q. brasiliensis have immunoadjuvant activity in vaccines against several viruses . One of the fractions studied is Fraction B, which was obtained by solid‐phase extraction on reverse phase C‐18 eluted with a stepwise gradient of methanol and water of aqueous extract …”

Section: Introductionmentioning

confidence: 99%

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Structural characterisation of new immunoadjuvant saponins from leaves and the first study of saponins from the bark of Quillaja brasiliensis by liquid chromatography electrospray ionisation ion trap mass spectrometry

Wallace¹,

Bennadji

Ferreira³

et al. 2019

Phytochemical Analysis

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Introduction Quillaja brasiliensis (St. A. ‐Hil. & Tul) Mart (Quillajaceae) is a species native to South America, which is rich in saponins. Saponins are used in different industries, so there is a constant demand for this type of compound. Based on the wide range of applications for the saponins found in this species, notably as immunoadjuvants, we conducted a comprehensive study of this tree and its saponins. Objective The purpose of this work is to complete the characterisation of the immunoadjuvant saponin fraction from Q. brasiliensis leaves and further study the saponin fraction obtained from Q. brasiliensis bark. Methodology Saponin fractions were studied using mass spectrometry in combination with classical methods of monosaccharide and methylation analysis. We performed direct infusion and liquid chromatography/electrospray ionisation ion trap multiple‐stage mass spectrometry (DI‐ESI‐IT‐MSn and LC‐ESI‐IT‐MS2). Results Seventy‐five saponins, 21 from leaves and 54 from bark, were tentatively identified according to their molecular mass, fragmentation pattern and chromatographic behaviour. This work represents the first investigation of saponins from the bark of Q. brasiliensis and some of them presented new structural motifs not previously reported in the genus Quillaja. Conclusion The efficiency and selectivity of the data dependent LC‐MS2 method allowed the rapid profiling of saponins from Q. brasiliensis. The results of the monosaccharide and methylation analysis performed in saponins from Q. brasiliensis fractions and Q. saponaria Molina (Quillajaceae) fraction gives further support to the structures proposed according to the mass spectral data, validating the strategy used in the present work.

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“…Fraction B from the leaves was obtained by fractionation of an aqueous extract on a C18 SPE column as described in our previous work …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…The parameters of the source ESI (DI and LC) and the chromatographic method were detailed in our previous work . MS analysis was conducted in the negative ionisation mode.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Structural characterisation of new immunoadjuvant saponins from leaves and the first study of saponins from the bark of Quillaja brasiliensis by liquid chromatography electrospray ionisation ion trap mass spectrometry

Wallace¹,

Bennadji

Ferreira³

et al. 2019

Phytochemical Analysis

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Quillaja brasiliensis (A. St.-Hil. & Tul.) Mart.

Chiesa

Wallace

Bennadji

et al. 2021

Medicinal and Aromatic Plants of the World

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ISCOM-Matrices Nanoformulation Using the Raw Aqueous Extract of Quillaja lancifolia (Q. brasiliensis)

et al. 2022

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Quillaja saponins have an intrinsic capacity to interact with membrane lipids that self-assembles in nanoparticles (immunostimulating complexes or ISCOM-matrices) with outstanding immunoadjuvant activity and low toxicity profile. However, the expensive and laborious purification processes applied to purify Quillaja saponins used to assemble ISCOM-matrices show an important drawback in the large-scale use of this vaccine adjuvant. Thus, in this study, we describe a protocol to appropriately formulate ISCOM-matrices using the raw aqueous extract (AE) of Quillaja lancifolia leaves. In the presence of lipids, AE was able to self-assemble in nanostructures that resembles immunostimulating complexes (ISCOM). These negatively charged nanoparticles of approximately 40 nm were characterized by transmission electron microscopy and dynamic light scattering. In addition, well-known saponins with remarkable immunoadjuvant activity, as QS-21, were detected into nanoparticles. Thus, the easier, robust, cheaper, and environmentally friendly method developed here may be an alternative to the classical methods for ISCOM-matrices production that use high-purified saponins. Graphical abstract

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Analysis of an immunoadjuvant saponin fraction from Quillaja brasiliensis leaves by electrospray ionization ion trap multiple-stage mass spectrometry

Cited by 19 publications

References 24 publications

Structural characterisation of new immunoadjuvant saponins from leaves and the first study of saponins from the bark of Quillaja brasiliensis by liquid chromatography electrospray ionisation ion trap mass spectrometry

Structural characterisation of new immunoadjuvant saponins from leaves and the first study of saponins from the bark of Quillaja brasiliensis by liquid chromatography electrospray ionisation ion trap mass spectrometry

Quillaja brasiliensis (A. St.-Hil. & Tul.) Mart.

ISCOM-Matrices Nanoformulation Using the Raw Aqueous Extract of Quillaja lancifolia (Q. brasiliensis)

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