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Int. J. Mol. Sci. 2017, 18(11), 2358; https://doi.org/10.3390/ijms18112358

Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

1
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
2
Research Institute of Odontology, Meikai University, 1-1 Keyaki-dai, Sakado, Saitama 350-0283, Japan
*
Author to whom correspondence should be addressed.
Received: 13 September 2017 / Revised: 1 November 2017 / Accepted: 2 November 2017 / Published: 7 November 2017
(This article belongs to the Section Bioactives and Nutraceuticals)
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Abstract

Phytochemical examination of Convallaria majalis (Liliaceae) whole plants yielded 15 steroidal glycosides (115), including nine new compounds (46, 1015) 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. View Full-Text
Keywords: Convallaria majalis; Liliaceae; steroidal glycoside; apoptosis; necrosis; A549; HL-60; HSC-4; HSC-2 Convallaria majalis; Liliaceae; steroidal glycoside; apoptosis; necrosis; A549; HL-60; HSC-4; HSC-2
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Matsuo, Y.; Shinoda, D.; Nakamaru, A.; Kamohara, K.; Sakagami, H.; Mimaki, Y. Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity. Int. J. Mol. Sci. 2017, 18, 2358.

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