Steroidal glycosides from Ornithogalum dubium Houtt

Nampoina Andriamisaina, Anne Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Thomas Paululat, Frédéric Lirussi, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside. Their cytotoxic activities against two human cells, a lung carcinoma A-549 and a promyelocytic leukemia HL-60 cell lines, were evaluated by using the XTT method. The results showed no significant cytotoxicity on the tested cells. The influence of the potentiation of cisplatin cytotoxicity in A-549 cells was also investigated and a slight effect was observed only for the (25R) spirostane-type derivative.

Original languageEnglish
Pages (from-to)78-84
Number of pages7
JournalPhytochemistry
Volume160
DOIs
Publication statusPublished - Apr 1 2019

Fingerprint

Ornithogalum
Cytotoxicity
glycosides
Cells
cytotoxicity
Phytochemicals
Glycosides
Cisplatin
Mass spectrometry
Asparagaceae
cisplatin
HL-60 Cells
Nuclear magnetic resonance
cells
Derivatives
leukemia
phytopharmaceuticals
carcinoma
Mass Spectrometry
Leukemia

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Andriamisaina, N., Mitaine-Offer, A. C., Miyamoto, T., Tanaka, C., Paululat, T., Lirussi, F., & Lacaille-Dubois, M. A. (2019). Steroidal glycosides from Ornithogalum dubium Houtt. Phytochemistry, 160, 78-84. https://doi.org/10.1016/j.phytochem.2019.01.013

Steroidal glycosides from Ornithogalum dubium Houtt. / Andriamisaina, Nampoina; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Paululat, Thomas; Lirussi, Frédéric; Lacaille-Dubois, Marie Aleth.

In: Phytochemistry, Vol. 160, 01.04.2019, p. 78-84.

Research output: Contribution to journalArticle

Andriamisaina, N, Mitaine-Offer, AC, Miyamoto, T, Tanaka, C, Paululat, T, Lirussi, F & Lacaille-Dubois, MA 2019, 'Steroidal glycosides from Ornithogalum dubium Houtt', Phytochemistry, vol. 160, pp. 78-84. https://doi.org/10.1016/j.phytochem.2019.01.013
Andriamisaina N, Mitaine-Offer AC, Miyamoto T, Tanaka C, Paululat T, Lirussi F et al. Steroidal glycosides from Ornithogalum dubium Houtt. Phytochemistry. 2019 Apr 1;160:78-84. https://doi.org/10.1016/j.phytochem.2019.01.013
Andriamisaina, Nampoina ; Mitaine-Offer, Anne Claire ; Miyamoto, Tomofumi ; Tanaka, Chiaki ; Paululat, Thomas ; Lirussi, Frédéric ; Lacaille-Dubois, Marie Aleth. / Steroidal glycosides from Ornithogalum dubium Houtt. In: Phytochemistry. 2019 ; Vol. 160. pp. 78-84.
@article{754221c210bd4b2e940b3e343fea564c,
title = "Steroidal glycosides from Ornithogalum dubium Houtt",
abstract = "The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside. Their cytotoxic activities against two human cells, a lung carcinoma A-549 and a promyelocytic leukemia HL-60 cell lines, were evaluated by using the XTT method. The results showed no significant cytotoxicity on the tested cells. The influence of the potentiation of cisplatin cytotoxicity in A-549 cells was also investigated and a slight effect was observed only for the (25R) spirostane-type derivative.",
author = "Nampoina Andriamisaina and Mitaine-Offer, {Anne Claire} and Tomofumi Miyamoto and Chiaki Tanaka and Thomas Paululat and Fr{\'e}d{\'e}ric Lirussi and Lacaille-Dubois, {Marie Aleth}",
year = "2019",
month = "4",
day = "1",
doi = "10.1016/j.phytochem.2019.01.013",
language = "English",
volume = "160",
pages = "78--84",
journal = "Phytochemistry",
issn = "0031-9422",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Steroidal glycosides from Ornithogalum dubium Houtt

AU - Andriamisaina, Nampoina

AU - Mitaine-Offer, Anne Claire

AU - Miyamoto, Tomofumi

AU - Tanaka, Chiaki

AU - Paululat, Thomas

AU - Lirussi, Frédéric

AU - Lacaille-Dubois, Marie Aleth

PY - 2019/4/1

Y1 - 2019/4/1

N2 - The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside. Their cytotoxic activities against two human cells, a lung carcinoma A-549 and a promyelocytic leukemia HL-60 cell lines, were evaluated by using the XTT method. The results showed no significant cytotoxicity on the tested cells. The influence of the potentiation of cisplatin cytotoxicity in A-549 cells was also investigated and a slight effect was observed only for the (25R) spirostane-type derivative.

AB - The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside. Their cytotoxic activities against two human cells, a lung carcinoma A-549 and a promyelocytic leukemia HL-60 cell lines, were evaluated by using the XTT method. The results showed no significant cytotoxicity on the tested cells. The influence of the potentiation of cisplatin cytotoxicity in A-549 cells was also investigated and a slight effect was observed only for the (25R) spirostane-type derivative.

UR - http://www.scopus.com/inward/record.url?scp=85061666014&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85061666014&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2019.01.013

DO - 10.1016/j.phytochem.2019.01.013

M3 - Article

C2 - 30743238

AN - SCOPUS:85061666014

VL - 160

SP - 78

EP - 84

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

ER -