Structure of the tetraoside jamogenin from seeds of Trigonella foenum-graecum

Bogacheva, N. G.; Шейченко, В. И.; Kogan, L. M.

doi:10.1007/bf00778022

Cited by 3 publications

(1 citation statement)

References 7 publications

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“…odoratum. On the basis of the comparison to the NMR and MS data previously reported in the literature, known compounds ( 3 – 8 ) were identified as timosaponin H1 ( 3 ), (25 S )-funkioside B ( 4 ), (25 S )-(3β,14α)-dihydroxy-spirost-5-ene-3- O -β- d -glucopyranosyl-(1→2)-[β- d -xylopyranosyl-(1→3)]-β- d -glucopyranosyl-(1→4)-β- d -galacopyranoside ( 5 ), (25 S )-(3β,14α)-dihydroxy-spirost-5-en-3- O -β- d -glucopyranosyl-(1→2)-β- d -glucopyranosyl-(1→4)-β- d -galactopyranoside ( 6 ), 3- O -β- d -glucopyranosyl-(1→2)-[β- d -xylopyranosyl-(1→3)]-β- d -glucopyranosyl-(1→4)-β- d -galacopyranosyl-yamogenin ( 7 ), and (22 S )-cholest-5-ene-1β,3β,16β,22-tetrol-1- O -α- l -rhamnopyranosyl-16- O -β- d -glucopyranoside ( 8 ) . Among them, compounds 3 and 4 were obtained from the genus of Polygonatum for the first time.…”

Section: Resultsmentioning

confidence: 92%

Isolation, Structural Elucidation, and Liquid Chromatography–Mass Spectrometry Analysis of Steroidal Glycosides from Polygonatum odoratum

Liu

Nagata

et al. 2018

J. Agric. Food Chem.

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The rhizomes of Polygonatum odoratum represent a traditional Chinese medicine and functional food. A phytochemical investigation resulted in the isolation of eight steroidal glycosides (1-8), including two new compounds, polygonatumosides F (1) and G (2). The structures were elucidated by spectroscopic data and chemical reactions. Compound 7 showed antiproliferation activity against human hepatocellular carcinoma cell line HepG2 (IC of 3.2 μM). The chemical profile and contents of steroidal glycosides of P. odoratum rhizomes collected at different dates and geographical locations were also investigated, indicating that the rational harvest of P. odoratum in spring and autumn is preferable to obtain higher levels of steroidal glycosides. Compounds 1 and 7 showed the highest contents in all P. odoratum samples and have potential to serve as chemotaxonomic and chemical markers for quality control of this important plant material. 14-Hydroxylation may be a key step for the biosynthesis of compounds 1-7.

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Section: Resultsmentioning

confidence: 92%

Isolation, Structural Elucidation, and Liquid Chromatography–Mass Spectrometry Analysis of Steroidal Glycosides from Polygonatum odoratum

Liu

Nagata

et al. 2018

J. Agric. Food Chem.

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Fenugreek: A Wonder Spice with Versatile Pharmacological Activities and Clinical Applications

Pundarikakshudu

Shah

2021

Fenugreek

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Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

Matsuo

Shinoda

Nakamaru

et al. 2017

IJMS

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Phytochemical examination of Convallaria majalis (Liliaceae) whole plants yielded 15 steroidal glycosides (1–15), including nine new compounds (4–6, 10–15) with a lycotetrose unit. The structures of the new compounds were determined using two-dimensional Nuclear magnetic resonance (NMR) analyses and chemical methods. The isolated compounds were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and HSC-4 and HSC-2 human oral squamous cell carcinoma cell lines. Of these, (25S)-spirost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (1) exhibited cytotoxic activity against HL-60, A549, HSC-4, and HSC-2 cells with IC50 values ranging from 0.96 to 3.15 μM. The corresponding furostanol glycoside of 1, (25S)-26-[(β-d-glucopyranosyl)oxy]-22α-hydroxyfurost-5-en-3β-yl O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (8), was cytotoxic to the adherent cell lines of A549, HSC-4, and HSC-2 cells with IC50 values of 2.97, 11.04, and 8.25 μM, respectively. The spirostanol lycotetroside (1) caused necrotic cell death in A549 cells in a dose-dependent manner. Alternatively, the furostanol lycotetroside (8) induced apoptotic cell death in A549 cells in a time-dependent manner, as was evident by morphological observations and flow cytometry analyses.

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Structure of the tetraoside jamogenin from seeds of Trigonella foenum-graecum

Cited by 3 publications

References 7 publications

Isolation, Structural Elucidation, and Liquid Chromatography–Mass Spectrometry Analysis of Steroidal Glycosides from Polygonatum odoratum

Isolation, Structural Elucidation, and Liquid Chromatography–Mass Spectrometry Analysis of Steroidal Glycosides from Polygonatum odoratum

Fenugreek: A Wonder Spice with Versatile Pharmacological Activities and Clinical Applications

Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

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