Identification of saponins from sugar beet (Beta vulgaris) by low and high-resolution HPLC-MS/MS.

We profiled triterpene saponins from the roots of sugar beet Beta vulgaris L. cultivars Huzar and Boryna using reversed-phase liquid chromatography combined with negative-ion electrospray ionization quadrupole mass spectrometry. We tentatively identified 26 triterpene saponins, including 17 that had not been detected previously in this plant species and 7 saponins that were tentatively identified as new compounds. All observed compounds were glycosides of five different aglycones, of which gypsogenin and norhederagenin are reported for the first time in sugar beet. Thirteen of the saponins detected in sugar beet roots were substituted with dioxolane-type (4 saponins) or acetal-type (9 saponins) dicarboxylic acids. Among the 26 detected saponins, we identified 2 groups of isomers distinguished using high-resolution mass measurements that were detected only in the Huzar cultivar of sugar beet.

[1]  H. Matsuda,et al.  Medicial Foodstuffs. XV. Sugar Beet. (2) : Structures of Betavulgarosides V, VI, VII, VIII, IX and X from the Roots and Leaves of Sugar Beet (Beta vulgaris L., Chenopodiaceae) , 1998 .

[2]  M. Melzig,et al.  Saponins as tool for improved targeted tumor therapies. , 2009, Current drug targets.

[3]  B. Domon,et al.  A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates , 1988, Glycoconjugate Journal.

[4]  H. Sunada,et al.  Measurement of the Adhesive Force between Particles and a Substrate by Means of the Impact Separation Method. Effect of the Surface Roughness and Type of Material of the Substrate , 1993 .

[5]  H. Kuang,et al.  A strategy for characterization of triterpene saponins in Caulophyllum robustum hairy roots by liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry. , 2014, Journal of pharmaceutical and biomedical analysis.

[6]  Yan-jing Li,et al.  Characterization and identification of saponins in Achyranthes bidentata by rapid-resolution liquid chromatography with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. , 2010, Rapid communications in mass spectrometry : RCM.

[7]  Jørgen Holst Christensen,et al.  Engineering traditional monolignols out of lignin by concomitant up-regulation of F5H1 and down-regulation of COMT in Arabidopsis. , 2010, The Plant journal : for cell and molecular biology.

[8]  L. Kenne,et al.  Oligosaccharide sequences in Quillaja saponins by electrospray ionization ion trap multiple-stage mass spectrometry. , 2004, Journal of mass spectrometry : JMS.

[9]  C. Lapierre,et al.  Isolation from Sugar Beet Cell Walls of Arabinan Oligosaccharides Esterified by Two Ferulic Acid Monomers1 , 2004, Plant Physiology.

[10]  K. Morreel,et al.  Metabolite profiling of triterpene saponins in Medicago truncatula hairy roots by liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry. , 2011, Journal of natural products.

[11]  S. Mahato,et al.  Advances in triterpenoid research, 1990-1994. , 1997, Phytochemistry.

[12]  M. Ralet,et al.  Evidence for linkage position determination in known feruloylated mono- and disaccharides using electrospray ion trap mass spectrometry. , 2004, Journal of mass spectrometry : JMS.

[13]  H. Matsuda,et al.  Medicinal Foodstuffs. XVI. Sugar Beet. (3). Absolute Stereostructures of Betavulgarosides II and IV, Hypoglycemic Saponins Having a Unique Substituent, from the Roots of Beta vulgaris L. , 1999 .

[14]  F. Song,et al.  Structural analysis of saponins from medicinal herbs using electrospray ionization tandem mass spectrometry , 2004, Journal of the American Society for Mass Spectrometry.

[15]  N. Murakami,et al.  Medicinal foodstuff. III. Sugar beet. (1): Hypoglycemic oleanolic acid oligoglycosides, betavulgarosides I, II, III, and IV, from the root of Beta vulgaris L. (Chenopodiaceae). , 1996, Chemical & pharmaceutical bulletin.

[16]  D. Couteau,et al.  Fixed-bed purification of ferulic acid from sugar-beet pulp using activated carbon: Optimization studies , 1998 .

[17]  I. Kapusta,et al.  Triterpene saponin content in the roots of red beet (Beta vulgaris L.) cultivars. , 2012, Journal of agricultural and food chemistry.

[18]  Agnieszka Galanty,et al.  Saponins as cytotoxic agents: a review , 2010, Phytochemistry Reviews.

[19]  N. Murakami,et al.  Betavulgarosides I, II, III, IV, and V, hypoglycemic glucuronide saponins from the roots and leaves of Beta vulgaris L. (Sugar beet) , 1995 .

[20]  Nicholas M. H. Khong,et al.  Antioxidant activity of phenolics–saponins rich fraction prepared from defatted kenaf seed meal , 2014 .

[21]  Mingshun Chen,et al.  Optimisation of ultrasonic-assisted extraction of phenolic compounds, antioxidants, and anthocyanins from sugar beet molasses. , 2015, Food chemistry.

[22]  P. Kachlicki,et al.  Characterisation and identification of triterpene saponins in the roots of red beets (Beta vulgaris L.) using two HPLC-MS systems. , 2016, Food chemistry.

[23]  S. Mahato,et al.  Review article number 67Triterpenoids , 1992 .