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Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’

‘Globemaster’ is an ornamental hybrid cultivar whose parent plants are Allium cristophii and A. macleanii. The chemical constituents of ‘Globemaster’ bulbs have not yet been examined; thus, a systematic phytochemical investigation was undertaken herein. A series of chromatographic separations of the...

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Autores principales: Shimazaki, Tamami, Iguchi, Tomoki, Takahashi, Yuna, Yamamoto, Kie, Takahashi, Naoki, Mimaki, Yoshihiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10488941/
https://www.ncbi.nlm.nih.gov/pubmed/37687077
http://dx.doi.org/10.3390/molecules28176248
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author Shimazaki, Tamami
Iguchi, Tomoki
Takahashi, Yuna
Yamamoto, Kie
Takahashi, Naoki
Mimaki, Yoshihiro
author_facet Shimazaki, Tamami
Iguchi, Tomoki
Takahashi, Yuna
Yamamoto, Kie
Takahashi, Naoki
Mimaki, Yoshihiro
author_sort Shimazaki, Tamami
collection PubMed
description ‘Globemaster’ is an ornamental hybrid cultivar whose parent plants are Allium cristophii and A. macleanii. The chemical constituents of ‘Globemaster’ bulbs have not yet been examined; thus, a systematic phytochemical investigation was undertaken herein. A series of chromatographic separations of the MeOH extract of ‘Globemaster’ bulbs afforded 27 steroidal glycosides (1–27), which are classified into 23 spirostanol glycosides (1–8 and 11–25), two furostanol glycosides (9 and 26), a pregnane glycoside (10), and a cholestane glycoside (27). The structures of the hitherto undescribed compounds (1–10) were determined from the two-dimensional NMR spectroscopic data and hydrolysis. The cytotoxicity of the isolated compounds (1–27) toward HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells was evaluated. Compounds 8, 22, 23, 24, and 26 exhibited cytotoxicity toward all cell lines in a dose-dependent manner, with IC(50) values in the 1.3–49 µM range.
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spelling pubmed-104889412023-09-09 Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’ Shimazaki, Tamami Iguchi, Tomoki Takahashi, Yuna Yamamoto, Kie Takahashi, Naoki Mimaki, Yoshihiro Molecules Article ‘Globemaster’ is an ornamental hybrid cultivar whose parent plants are Allium cristophii and A. macleanii. The chemical constituents of ‘Globemaster’ bulbs have not yet been examined; thus, a systematic phytochemical investigation was undertaken herein. A series of chromatographic separations of the MeOH extract of ‘Globemaster’ bulbs afforded 27 steroidal glycosides (1–27), which are classified into 23 spirostanol glycosides (1–8 and 11–25), two furostanol glycosides (9 and 26), a pregnane glycoside (10), and a cholestane glycoside (27). The structures of the hitherto undescribed compounds (1–10) were determined from the two-dimensional NMR spectroscopic data and hydrolysis. The cytotoxicity of the isolated compounds (1–27) toward HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells was evaluated. Compounds 8, 22, 23, 24, and 26 exhibited cytotoxicity toward all cell lines in a dose-dependent manner, with IC(50) values in the 1.3–49 µM range. MDPI 2023-08-25 /pmc/articles/PMC10488941/ /pubmed/37687077 http://dx.doi.org/10.3390/molecules28176248 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shimazaki, Tamami
Iguchi, Tomoki
Takahashi, Yuna
Yamamoto, Kie
Takahashi, Naoki
Mimaki, Yoshihiro
Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
title Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
title_full Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
title_fullStr Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
title_full_unstemmed Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
title_short Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii × A. macleanii ‘Globemaster’
title_sort determination of structure and cytotoxicity of ten undescribed steroidal glycosides from allium cristophii × a. macleanii ‘globemaster’
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10488941/
https://www.ncbi.nlm.nih.gov/pubmed/37687077
http://dx.doi.org/10.3390/molecules28176248
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