Spirostanol Saponins Derivated from the Seeds of<i>Trigonella foenum-graecum</i>by<i>β</i>-Glucosidase Hydrolysis and Their Inhibitory Effects on Rat Platelet Aggregation

Pang, Xu; Cong, Yu‐Sheng; Yu, Heshui; Kang, Liping; Feng, Bing; Han, Bing-Xing; Zhao, Yang; Cai, Xiong; Tan, Dali; Song, Wei; Liu, Bin; Cong, Yang; B, Ma

doi:10.1055/s-0031-1280373

Cited by 19 publications

(13 citation statements)

References 14 publications

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“…9, 15, 17), being the main source of diosgenin released during acid hydrolysis. It has been reported that 25S and 25R sapogenins mutually epimerize (5,27,28); therefore, under acidic conditions, yamogenin may be converted to diosgenin.…”

Section: Hplc-elsd-esi-ms Separationmentioning

confidence: 99%

“…Fenugreek (Trigonella foenum-graecum, Fabaceae) is an annual, herbaceous plant, originating from the Mediterranean region and cultivated all over Europe. Fenugreek seeds are known to contain several groups of secondary metabolites, of which, besides flavones (1,2), isoflavones (1) and polysaccharides (3), the most abundant are steroidal saponins (2,(4)(5)(6)(7)(8)(9)(10)(11)(12). The complex of steroidal saponins in fenugreek seeds is composed of different spirostanol and furostanol saponins with straight or branched sugar chains (2,(4)(5)(6)(7)(8)(9)(10)(11)(12).…”

mentioning

confidence: 99%

“…The main aglycones are diosgenin and its 25-epimer yamogenin (6). Research on saponins occurring in Trigonella foenum-graecum seeds was the subject of many independent studies (2,(4)(5)(6)(7)(8)(9)(10)(11)(12) and, as a result, different common names have been given to compounds of the same chemical structure, e.g., protodioscin/compound C, protoneodioscin/trigonelloside C (2, 4, 6-9, 11, 13-16).…”

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Qualitative and quantitative HPLC-ELSD-ESI-MS analysis of steroidal saponins in fenugreek seed

2019

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Fenugreek seeds are known as a source of various compounds, the most common of which are steroidal saponins. However, despite the growing interest in this plant material as a healing agent, spice and dietary supplement ingredient, the composition of Polish fenugreek seeds remains unknown. Therefore, the steroidal saponin complex in the seeds of T. foenum-graecum cultivated in Poland was qualitatively and quantitatively analyzed by the HPLC-ELSDESI-MS method. Two C-18 columns connected in series were used for the first time in analysis of fenugreek saponins and ELS detector parameters were optimized. A total of 26 furostanol saponins were revealed, of which 24 were tentatively identified. The HPLC-ELSD method developed for quantitative analysis was preliminarily validated and the determined amount of steroidal saponins in Polish fenugreek seeds was 0.14 %.

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Section: Hplc-elsd-esi-ms Separationmentioning

confidence: 99%

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Qualitative and quantitative HPLC-ELSD-ESI-MS analysis of steroidal saponins in fenugreek seed

2019

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“…Detailed extraction and isolation of the 25 (R/S)-spirostanol saponin diastereomers was described elsewhere [9]. The structures of the six 25 R/S diastereomers used in this study are shown in Fig.…”

Section: Sample Preparationmentioning

confidence: 99%

Analytical and semipreparative separation of 25 (R/S)‐spirostanol saponin diastereomers using supercritical fluid chromatography

Zhao

McCauley

Pang

et al. 2013

J of Separation Science

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Spirostanol saponins are a class of steroidal saponins with many pharmacological activities. The structural complexity of the spirostanol saponins presents a daunting challenge in separating their 25 R/S diastereomers. Using two CHIRALPAK IC columns coupled in series, six 25 (R/S)-spirostanol saponin diastereomers from the Trigonella foenum-graecum L. seed were successfully separated using supercritical fluid chromatography (SFC) for the first time. In addition, three 25 (R/S)-spirostanol saponin diastereomers were isolated into their respective individual isomers. The structures of the isolated isomers were unambiguously confirmed by NMR analysis. The SFC method development strategy and its associated underlying principles presented in this paper are generally applicable. SFC is a viable addition to the natural product research toolbox, especially for stereoselective analysis and purification.

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“…Also, a purified fraction prepared from Fenugreek seeds which contained more than 90% steroid saponins enhanced food consumption and induced hypercholesterolaemia in experimental rats [19]. Recently [27], spirostanol saponin aglycones, obtained from Fenugreek seed by enzymatic hydrolysis, were shown to inhibit platelet aggregation in rats. The potential of plant (and animal) steroids as antiviral agents was reviewed elsewhere [28].…”

Section: Introductionmentioning

confidence: 99%

Variability in the Content of 25α- and 25β-Steroidal Sapogenins among Thirty Morphologically Different Sudanese Seed Accessions of Fenugreek

Osman¹,

Elhussein²,

Albalawi³

2014

JLS

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Abstract:Seeds of Fenugreek (Trigonellafoenum-graecum L.), an international spice commodity, are much consumed in Sudan as a food, for flavoring and as a folk-remedy for several ailments, together with local beliefs in nutraceutical benefits. The authors have noted an immense variability in colour and other morphological characters of Fenugreek seeds offered in local Sudanese markets and wondered whether this variability is extended to their chemical composition. Steroidal sapogenins are important chemical constituents of Fenugreek seeds in view of their potential as precursors for the commercial synthesis of steroid drugs and their continually revealed beneficial biological activities. In this study, thirty Sudanese Fenugreek seed accessions collected from different geographical regions in Sudan were analyzed for their 25α-, 25β-and total sapogenin content using a simple and specific infra-red spectroscopic method. The seed accessions exhibited much morphological variability particularly in outer seed coat color and size. Preparative TLC followed by gravimetric analysis showed that steroidal sapogenins, mostly diosgenin and yamogenin, represented more than 70% of the steroids of Fenugreek seeds. Infra-red spectroscopic analysis showed that total 25α-sapogenins (calculated as diosgenin) varied from 0.65% to 1.68%. Total 25β-sapogenin (calculated as yamogenin) varied from 0.38% to 2.03%. The content of total sapogenins (α + β epimeric forms) varied between 1.24% and 3.0% of the oven-dry weight of seeds. β-sapogenins (mostly yamogenin) were dominant over α-sapogenins (diosgenin) in most Sudanese Fenugreek seed accessions.

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Spirostanol Saponins Derivated from the Seeds ofTrigonella foenum-graecumbyβ-Glucosidase Hydrolysis and Their Inhibitory Effects on Rat Platelet Aggregation

Cited by 19 publications

References 14 publications

Qualitative and quantitative HPLC-ELSD-ESI-MS analysis of steroidal saponins in fenugreek seed

Qualitative and quantitative HPLC-ELSD-ESI-MS analysis of steroidal saponins in fenugreek seed

Analytical and semipreparative separation of 25 (R/S)‐spirostanol saponin diastereomers using supercritical fluid chromatography

Variability in the Content of 25α- and 25β-Steroidal Sapogenins among Thirty Morphologically Different Sudanese Seed Accessions of Fenugreek

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