Steroid Sapogenins VII. Identification and Origin of 25D-Spirosta-3,5-diene Among the Fenugreek Sapogenins

Bedour, M. S.; Elmunajjed, Dalal T.; Fayez, M. B. E.; Girgis, A. N.

doi:10.1002/jps.2600531042

Cited by 17 publications

(4 citation statements)

References 8 publications

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“…Steroidal sapogenins have been obtained by acid hydrolysis of plant material, followed by extraction with an organic solvent such as chloroform or petroleum ether (Fazli and Hardman, 1968). Extraction of steroidal saponins with a water-miscible organic solvent has been done first, followed by acid hydrolysis (Bedour et al, 1964). In the present investigation, the steroidal saponins were isolated by extraction with 80% ethanol, and then the concentrated extracts were hydrolyzed with hydrochloric acid.…”

Section: Resultsmentioning

confidence: 99%

“…Diosgenin and yamogenin have been shown to undergo dehydration reactions in the presence of hydrochloric acid to give 3,5-spirostadienes (M + 396 amu) as artifacts (Bedour et al, 1964;Fazli and Hardman, 1971). Four components of this molecular weight, with retention times of 13.5, 13.6, 13.8, and 13.9 min, were found in hydrolyzed extracts from seed and foliage (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

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Analysis of Steroidal Sapogenins from Amber Fenugreek (Trigonella foenum-graecum) by Capillary Gas Chromatography and Combined Gas Chromatography/Mass Spectrometry

Taylor

Zaman

Mir

et al. 1997

J. Agric. Food Chem.

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Mixtures of steroidal sapogenins isolated from the seed and combined aerial parts (foliage) of fenugreek (cultivar Amber) have been examined by capillary column gas chromatography with mass spectral and flame ionization detectors. Diosgenin [(25R)-spirost-5-en-3β-ol] was the major component in seed and foliage extracts hydrolyzed with hydrochloric acid. Yamogenin also appeared to be present. Tigogenin, neotigogenin, smilagenin, and sarsasapogenin were identified in the extracts. Dihydroxy steroidal sapogenins, tentatively identified as yuccagenin, gitogenin, and neogitogenin, were detected as minor components in hydrolyzed extracts from seed. A gas chromatographic method based on the use of an internal standard and a column of HP-5MS was developed to determine diosgenin in Amber fenugreek. Expressed on a dry weight basis, mean levels of diosgenin in seed were 0.54%. In field-grown foliage sampled during a season at 9, 15, and 19 weeks postseeding, diosgenin levels were 0.16, 0.07, and 0.07%, respectively. Keywords: Steroidal sapogenins; spirostanols; fenugreek; diosgenin; quantitation; seed; foliage

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Analysis of Steroidal Sapogenins from Amber Fenugreek (Trigonella foenum-graecum) by Capillary Gas Chromatography and Combined Gas Chromatography/Mass Spectrometry

Taylor

Zaman

Mir

et al. 1997

J. Agric. Food Chem.

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“…Two spirostadienes were also identified and they accounted for only around 5% of the total sapogenin profile of the HFE. These last compounds are artefacts generated by dehydration reactions of diosgenin and yamogenin in presence of hydrochloric acid [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

Chemical Characterization and Bioaccessibility of Bioactive Compounds from Saponin-Rich Extracts and Their Acid-Hydrolysates Obtained from Fenugreek and Quinoa

Hierro

Reglero

Martín

2020

Foods

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Saponin-rich extracts from edible seeds have gained increasing interest and their hydrolysis to sapogenin-rich extracts may be an effective strategy to enhance their potential bioactivity. However, it remains necessary to study the resulting chemical modifications of the extracts after hydrolysis as well as their impact on the subsequent bioaccessibility of bioactive compounds. The chemical composition of non-hydrolyzed and hydrolyzed extracts from fenugreek (FE, HFE) and quinoa (QE, HQE), and the bioaccessibility of saponins, sapogenins and other bioactive compounds after an in vitro gastrointestinal digestion was assessed. In general, FE mainly contained saponins (31%), amino acids (6%) and glycerides (5.9%), followed by carbohydrates (3.4%), fatty acids (FFA) (2.3%), phytosterols (0.8%), tocols (0.1%) and phenolics (0.05%). HFE consisted of FFA (35%), sapogenins (8%) and partial glycerides (7%), and were richer in phytosterols (1.9%) and tocols (0.3%). QE mainly contained glycerides (33%), FFA (19%), carbohydrates (16%) and saponins (7.9%), and to a lesser extent alkylresorcinols (1.8%), phytosterols (1.5%), amino acids (1.1%), tocols (0.5%) and phenolics (0.5%). HQE mainly consisted of FFA (57%), partial glycerides (23%) and sapogenins (5.4%), were richer in phytosterols (2.4%), phenolics (1.2%) and tocols (0.7%) but poorer in alkylresorcinols (1%). After in vitro digestion, saponins from FE and QE were fully bioaccessible, sapogenins from HFE displayed a good bioaccessibility (76%) and the sapogenin from HQE was moderately bioaccesible (38%). Digestion of saponin and sapogenin standards suggested that other components of the extracts were enhancing the bioaccessibility. Other minor bioactive compounds (phytosterols, alkylresorcinols, tocols and some phenolics) also displayed optimal bioaccessibility values (70–100%).

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“…Dioscorea and Trigonella species are rich sources of sapogenins. These include T. foenuns-graecum L. [1][2][3][4][5][6][7], T. corniculata [1,8,9] and T. occulta [10], but there is no report of their presence in T. polycerata1, hence the present investigation was taken up. Seeds collected from the field in the month of April were powdered, refluxed in 2N HC1 for two hours, neutralized with sodium bicarbonate and washed 2-3 times with distilled water [11] those of the standards were collected separately from about 200 preparative (0.4 to 0.5 mm thick) silica gel plates, eluted in chloroform, filtered, dried in vacuo and crystallised at low temperature in methanol and acetone.…”

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confidence: 99%

Sapogenins fromTrigonella polycerata

Sharma¹,

Kamal²

1981

Planta Med

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Steroid Sapogenins VII. Identification and Origin of 25D-Spirosta-3,5-diene Among the Fenugreek Sapogenins

Cited by 17 publications

References 8 publications

Analysis of Steroidal Sapogenins from Amber Fenugreek (Trigonella foenum-graecum) by Capillary Gas Chromatography and Combined Gas Chromatography/Mass Spectrometry

Analysis of Steroidal Sapogenins from Amber Fenugreek (Trigonella foenum-graecum) by Capillary Gas Chromatography and Combined Gas Chromatography/Mass Spectrometry

Chemical Characterization and Bioaccessibility of Bioactive Compounds from Saponin-Rich Extracts and Their Acid-Hydrolysates Obtained from Fenugreek and Quinoa

Sapogenins fromTrigonella polycerata

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