Analysis of variations in the contents of steroidal saponins in Fructus Tribuli during stir‐frying treatment

Just as natural saponins transform into aglycones, secondary glycosides and their derivatives using biotransformation technology, steroidal saponins may also undergo similar transformation after stir-frying. The purpose of this study was to elucidate the variations and the reasons for these variations in the contents of steroidal saponins in Fructus Tribuli (FT) during a stir-frying treatment. Stir-fried FT was processed in different time-temperature conditions. An UHPLC-MS/MS method was established and fully validated for quantitative analysis. In addition, the simulation processing products of tribuluside A, terrestroside B, terrestrosin K, terrestrosin D and 25R-tribulosin were determined by qualitative analysis using UHPLC-Q-TOF-MS. The established UHPLC-MS/MS method provides a rapid, flexible, and reliable method for the quality assessment of FT. The present study revealed that furostanol saponins with a C22-OH group could transform into corresponding furostanol saponins with a C-20-C-22 double bond (FSDB) via dehydroxylation. Additionally, FSDB could be successively converted into its secondary glycosides via a deglycosylation reaction. The transformation of spirostanol saponins into corresponding aglycones via deglycosylation led to a decrease in spirostanol saponins and an increase in aglycones. The results of this research provided scientific evidence of variation and structural transformation among steroidal saponins. These findings might be helpful for elucidating the processing mechanism of FT.

[1]  Yinmao Dong,et al.  A review of traditional pharmacological uses, phytochemistry, and pharmacological activities of Tribulus terrestris , 2017, Chemistry Central Journal.

[2]  V. Neychev,et al.  Pro-sexual and androgen enhancing effects of Tribulus terrestris L.: Fact or Fiction. , 2016, Journal of ethnopharmacology.

[3]  Yuehua Jiang,et al.  Aqueous extracts of Tribulus terrestris protects against oxidized low-density lipoprotein-induced endothelial dysfunction , 2016, Chinese Journal of Integrative Medicine.

[4]  Ming-cang Chen,et al.  Anti-depressive activities and biotransformation of timosaponin B-III and its derivatives , 2014, Natural product research.

[5]  Natesh M Prabhu,et al.  Effect of Tribulus Terrestris on Learning And Memory in Wistar Rats , 2014 .

[6]  Y. Guan,et al.  Cellular and Molecular Mechanisms in Vascular Smooth Muscle Cells by which Total Saponin Extracted from Tribulus Terrestris Protects Against Artherosclerosis , 2013, Cellular Physiology and Biochemistry.

[7]  Qiong-lin Liang,et al.  Steaming-induced chemical transformations and holistic quality assessment of red ginseng derived from Panax ginseng by means of HPLC-ESI-MS/MS(n)-based multicomponent quantification fingerprint. , 2012, Journal of agricultural and food chemistry.

[8]  Tian Guo-fang Study on simulation processing method for rhubarb pieces , 2011 .

[9]  Tonghua Liu,et al.  Furostanol Glycosides from leaves of the Chinese plant Tribulus terrestris , 2010, Chemistry of Natural Compounds.

[10]  W. Zhang,et al.  Biotransformation of Chinese Herbs and Their Ingredients , 2010 .

[11]  Jin,et al.  Separation and Bio-activities of Spirostanol Saponin from Tribulus terrestris , 2010 .

[12]  Xuyu Zu,et al.  Five furostanol saponins from fruits of Tribulus terrestris and their cytotoxic activities , 2009, Natural product research.

[13]  M. Simmonds,et al.  Chromatographic behaviour of steroidal saponins studied by high-performance liquid chromatography-mass spectrometry. , 2007, Journal of chromatography. A.

[14]  I. Kostova,et al.  Saponins in Tribulus terrestris – Chemistry and Bioactivity , 2005, Phytochemistry Reviews.

[15]  Da-yuan Zhu,et al.  Terrestrinins A and B, two new steroid saponins from Tribulus terrestris , 2003, Journal of Asian natural products research.

[16]  D. Prashanth,et al.  Tribulosin and beta-sitosterol-D-glucoside, the anthelmintic principles of Tribulus terrestris. , 2002, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[17]  I. Khan,et al.  New steroidal glycosides from the fruits of Tribulus terrestris. , 2000, Journal of natural products.

[18]  Hai-sheng Chen,et al.  Three new saponins from Tribulus terrestris. , 2000, Planta medica.

[19]  H. Chen,et al.  Two sapogenins from tribulus terrestris , 1998 .

[20]  R. Kasai,et al.  Steroidal saponins from fruits of Tribulus terrestris. , 1997, Phytochemistry.

[21]  F. Jiang,et al.  Steroidal glycosides from Tribulus terrestris. , 1996, Phytochemistry.

[22]  J. Nishikawa,et al.  Carbon-13 nmr spectra of 5β-steroidal sapogenins. Reassignment of the F-ring carbon signals of (25)-spirostans , 1981 .