Revisit to 25R/25S Stereochemical Analysis of Spirostane-type Steroidal Sapogenins and Steroidal Saponins via 1H NMR Chemical Shift Data

Agrawal, Pawan K.; Burkholz, Torsten; Jacob, Claus

doi:10.1177/1934578x1200700605

Cited by 3 publications

(2 citation statements)

References 30 publications

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“…15 The 13 4,16 Moreover, the small difference in δ H values of the 2 protons at C-26 (Δ ea = δ H-26eq −δ H-26ax = 0.07) of 1 agreed with that of the (25R) form (25R: Δ ea < 0.20; 25S: Δ ea > 0.35). 17 Therefore, the R* configuration was suggested for C-25 of 1. This was further confirmed by the ROESY correlations of H 3 -27 to H 2 -24 (δ H 1.52)/H-26.…”

Section: Resultsmentioning

confidence: 99%

Aspidiata E, a New Spirostanol Saponin From Aspidistra triradiata and its Cytotoxic Activity

Anh

Nguyen

et al. 2023

Natural Product Communications

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Aspidiata E (1), a new spirostanol saponin {(22 S*,25 R*)-1 β,3 β,4 β,5 β,6 β-pentahydroxyspirostan-2 β-yl β-D-xylopyranoside), together with 2 known compounds, (22 S*,25 R*)-spirost-5-ene-3 β-yl O- α-L-rhamnopyranosyl-(1→2)- O-[ O- α-L-rhamnopyranosyl-(1→5)- α-L-arabinofuranosyl-(1→4)]- β-D-glucopyranoside (2), and (22 S*)-16-[( β-D -glucopyranosyl)oxy]-1 β,3 β,22-trihydroxycholest-5-en-1 β-yl α-L-rhamnopyranoside (3), were isolated from Aspidistra triradiata. Their structures were determined by NMR spectroscopic and high resolution electrospray ionisation mass spectrometry analysis and by comparison with published data. Compound 2 revealed strong cytotoxic potential against MCF7, HepG2, SK-LU-1, and HT-29 cancer cell lines with IC50 values ranging from 0.28 to 0.81 µM. In contrast, compound 1 showed a weak inhibitory effect on MCF7, HepG2, and HT-29 cell lines, with IC50 values within the range of 68.85 to 84.19 µM. All compounds 1-3 were discovered for the first time in the genus Aspidistra.

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Section: Resultsmentioning

confidence: 99%

Aspidiata E, a New Spirostanol Saponin From Aspidistra triradiata and its Cytotoxic Activity

Anh

Nguyen

et al. 2023

Natural Product Communications

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“…40 Reviews covering the most characteristic 13 C signals to determine the ring fusion and spirostane/furostane skeleton have been published 35 Likewise, taking into account the 1 H-NMR chemical shift patterns of methylene C-26 of a range of saponins, the stereochemistry of C-25 could be ascertained. [41][42][43] Recently, a comprehensive review of the structural features of saponins from Agave species was published by Sidana et al 16 The . present review will focus on the influence of the main structural characteristics of 1 H and 13 C chemical shifts and will also provide an exhaustive overview of patterns and signals that could be key clues to identify the aglycone.…”

Section: Salient and Common Features In The Nmr Spectra Of Saponin mentioning

confidence: 99%

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

Simonet

Durán

Pérez

et al. 2020

Phytochemical Analysis

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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 (13C)‐ and proton (1H)‐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 1H‐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.

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Preliminary Qualitative Analysis of Plant Samples by High-performance Thin-layer Chromatography for the Presence of Steroid Sapogenins of Some Representatives of the Dioscoreacae, Fabaceae, Ranunculaceae, Melanthiaceae, Scrophulariaceae

Sukhanov,

Krylov,

Sepp

et al. 2024

Razrabotka i registraciâ lekarstvennyh sredstv

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Introduction. Results of original research carried out by means of high performance thin layer chromatography (HPTLC) of various plant samples (air-dry raw material) of Dioscoreaceae, Ranunculaceae, Fabaceae, Melanthiaceae, Scrophulariaceae families are presented in this article.Aim. To carry out preliminary qualitative analysis by HPTLC method of steroidal sapogenins composition in hydrolyzed extracts, obtained from vegetative samples of above-ground and underground organs of some Dioscoreaceae, Ranunculaceae, Fabaceae, Melanthiaceae, Scrophulariaceae families.Materials and methods. Extraction from pre-dehydrated raw materials was carried out with 50 % aqueous isopropanol (c.p.) in an ultrasonic bath, followed by acidic hydrolysis of O-glycoside bonds, evaporation and redissolution of dry residue in 99 % methanol (c.p.); purification from suspended solids by filtering through filters with 20 µm perforation diameter. HPTLC was performed on apparatus complex CAMAG (Switzerland) using HPTLC Aluminium sheets Silica gel 60 F254 plates 20 × 20 cm, which were cut to the size 20 × 10 cm.Results and discussion. After scanning densitometry at 254 nm, we found that the separation of isopropanol extracts, followed by redissolution in strong methanol in this solvent system allows a fairly acceptable separation and identification of the compounds studied. Comparison of the tracks of plant extracts was performed with standard samples of steroid sapogenins, whose methanol solutions were applied to one stain-strobe of track 1, provided that they had different Rf indices and coloration after derivatization.Conclusion. Diosgenin was identified in plant extracts of rhizomes and roots of Dioscorea nipponica and Dioscorea caucasica and in seeds of Trigonella foenum-graecum preliminarily. Sarsasapogenin was verified in extracts of fruits of Sophora japonica, tigogenin in extracts of seeds of Trigonella foenum-graecum, herb of Pulsatilla patens and herb of Veronica officinalis. Yamogenin was detected in extracts of seeds of Trigonella foenum-graecum and herb of Veronica officinalis. This work is exploratory in nature, assessing the presence of certain saponins by their sapogenins in selected extracts. We will optimize the HPLC separation procedure and choose other detection methods to unambiguously assess the co-presence of the studied sapogenins with approximately the same staining shades after derivatization and matching retention indices: there are pairs of steroidal sapogenins that have the same retention, we decided to group them in mixtures so that there would be separation within the group and subsequent comparison with the original extracts would make it possible to identify those or other sapogenins in such extracts.

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Revisit to 25R/25S Stereochemical Analysis of Spirostane-type Steroidal Sapogenins and Steroidal Saponins via ¹H NMR Chemical Shift Data

Cited by 3 publications

References 30 publications

Aspidiata E, a New Spirostanol Saponin From Aspidistra triradiata and its Cytotoxic Activity

Aspidiata E, a New Spirostanol Saponin From Aspidistra triradiata and its Cytotoxic Activity

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

Preliminary Qualitative Analysis of Plant Samples by High-performance Thin-layer Chromatography for the Presence of Steroid Sapogenins of Some Representatives of the Dioscoreacae, Fabaceae, Ranunculaceae, Melanthiaceae, Scrophulariaceae

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