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Review
. 2021 Jan;32(1):38-61.
doi: 10.1002/pca.2946. Epub 2020 Jun 8.

Features in the NMR spectra of the aglycones of Agave spp. saponins. HMBC method for aglycone identification (HMAI)

Ana M Simonet  1 , Alexandra G Durán  1 , Andy J Pérez  2 , Francisco A Macías  1
Affiliations
Review

Features in the NMR spectra of the aglycones of Agave spp. saponins. HMBC method for aglycone identification (HMAI)

Ana M Simonet et al. Phytochem Anal. 2021 Jan.

Abstract

Introduction: The analysis and detection of steroidal saponins is mainly performed using chromatographic techniques coupled with mass spectrometry. However, nuclear magnetic resonance (NMR) spectroscopy is a potential tool that can be combined with these techniques to obtain unambiguous structural characterisation.

Objective: This work provides a review of the carbon-13 (13 C)- and proton (1 H)-NMR spectroscopic data of aglycones from Agave saponins reported in the literature and also the development of an easy identification method for these natural products.

Methods: The database Scifinder was used for spectroscopic data collection in addition to data obtained from the Cadiz Allelopathy research group. The keywords used were Agave, spirostanic, furostanic, and saponin.

Results: The shielding variations produced by functional groups on the aglycone core and the structural features of the most representative aglycones from Agave species are described. The effects are additive for up to four long-range connectivities. A method for the identification of aglycones (HMAI) is proposed to classify aglycones from Agave spp. through the use of 1 H-NMR and heteronuclear multiple bond correlation (HMBC) experiments.

Conclusions: The HMBC spectrum is representative of the structural features of aglycones from Agave spp. The HMBC method for aglycone identification (HMAI) method allowed the identification of pure saponins or mixtures thereof and this method can be used in combination with chromatographic techniques coupled with mass spectrometry to provide a more thorough analysis of Agave samples that contain aglycones.

Keywords: 13C-NMR; 1H-NMR; Agave; HMAI; HMBC; aglycone; identification; saponin.

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References

REFERENCES

    1. Osbourn A. Saponins and plant defence - a soap story. Trends Plant Sci. 1996;1:4-9.
    1. Hussain M, Debnath B, Qasim M, et al. Role of saponins in plant defense against specialist herbivores. Molecules. 2019;24:2067-2087.
    1. Faizal A, Geelen D. Saponins and their role in biological processes in plants. Phytochem Rev. 2013;12:877-893.
    1. Yang Y, Laval S, Yu B. Chemical synthesis of saponins. In: Horton D, ed. Advances in Carbohydrate Chemistry and Biochemistry, First edition. London: Elsevier; 2014:137-226.
    1. Oleszek W, Bialy Z. Chromatographic determination of plant saponins-an update (2002-2005). J Chromatogr A. 2006;1112:78-91.

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