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Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity
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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5713327/ https://www.ncbi.nlm.nih.gov/pubmed/29112119 http://dx.doi.org/10.3390/ijms18112358 |
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author | Matsuo, Yukiko Shinoda, Daisuke Nakamaru, Aina Kamohara, Kuni Sakagami, Hiroshi Mimaki, Yoshihiro |
author_facet | Matsuo, Yukiko Shinoda, Daisuke Nakamaru, Aina Kamohara, Kuni Sakagami, Hiroshi Mimaki, Yoshihiro |
author_sort | Matsuo, Yukiko |
collection | PubMed |
description | 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 IC(50) 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 IC(50) 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. |
format | Online Article Text |
id | pubmed-5713327 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-57133272017-12-07 Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity Matsuo, Yukiko Shinoda, Daisuke Nakamaru, Aina Kamohara, Kuni Sakagami, Hiroshi Mimaki, Yoshihiro Int J Mol Sci Article 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 IC(50) 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 IC(50) 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. MDPI 2017-11-07 /pmc/articles/PMC5713327/ /pubmed/29112119 http://dx.doi.org/10.3390/ijms18112358 Text en © 2017 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Matsuo, Yukiko Shinoda, Daisuke Nakamaru, Aina Kamohara, Kuni Sakagami, Hiroshi Mimaki, Yoshihiro Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity |
title | Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity |
title_full | Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity |
title_fullStr | Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity |
title_full_unstemmed | Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity |
title_short | Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity |
title_sort | steroidal glycosides from convallaria majalis whole plants and their cytotoxic activity |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5713327/ https://www.ncbi.nlm.nih.gov/pubmed/29112119 http://dx.doi.org/10.3390/ijms18112358 |
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