Acylated triterpene saponins from Atroxima liberica STAPF

Turibio Kuiate Tabopda, Anne Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Jean François Mirjolet, Olivier Duchamp, Bonaventure Tchaleu Ngadjui, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

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Abstract

The four new acylated triterpene saponins 1-4, isolated as two pairs of isomers and named libericosides A1/A2 and B 1/B2, one pair of isomers 5/6, the (Z)-isomer libericoside C2 (5) being new, one new sucrose ester, atroximoside (7), and eight known compounds were isolated from the roots of Atroxima liberica by repeated MPLC and VLC on normal and reversed-phase silica gel. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies (1H- and 13C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3-O-β-D-glucopyranosylpresenegenin 28-{O-α-L- arabinopyranosyl-(1→3)-O-β-D-xylopyranosyl-(1→4) -O-α-L-rhamnopyranosyl-(1→2)-4-O-[(E)-3,4-dimethoxycinnamoyl] -β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-β-D- glucopyranosylpresenegenin 28-{O-α-L-arabinopyranosyl-(1→4)-O-β- D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2) -O-[O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)] -4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, 3-O-β-D-glucopyranosylpresenegenin 28-{O-β-D- xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2) -O-[6-O-acetyl-β-D-glucopyranosyl-(1→3)]-4-O-[(Z)-3, 4-dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (5), and 3-O-[(Z)-feruloyl]-β-D-fructofuranosyl α-D-glucopyranoside (7). Compounds 1-6 and the known saponins 8/9 were evaluated against the human colon cancer cells HCT 116 and HT-29 and showed moderate to weak cytotoxicity.

Original languageEnglish
Pages (from-to)2066-2076
Number of pages11
JournalHelvetica Chimica Acta
Volume94
Issue number11
DOIs
Publication statusPublished - Nov 1 2011

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Triterpenes
Saponins
Isomers
Esters
isomers
esters
HCT116 Cells
Nuclear magnetic resonance
Silica Gel
nuclear magnetic resonance
varespladib methyl
Colonic Neoplasms
sucrose
Sucrose
Silica gel
Sugar (sucrose)
silica gel
Mass Spectrometry
Cytotoxicity
Mass spectrometry

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Tabopda, T. K., Mitaine-Offer, A. C., Miyamoto, T., Tanaka, C., Mirjolet, J. F., Duchamp, O., ... Lacaille-Dubois, M. A. (2011). Acylated triterpene saponins from Atroxima liberica STAPF. Helvetica Chimica Acta, 94(11), 2066-2076. https://doi.org/10.1002/hlca.201100147

Acylated triterpene saponins from Atroxima liberica STAPF. / Tabopda, Turibio Kuiate; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Mirjolet, Jean François; Duchamp, Olivier; Ngadjui, Bonaventure Tchaleu; Lacaille-Dubois, Marie Aleth.

In: Helvetica Chimica Acta, Vol. 94, No. 11, 01.11.2011, p. 2066-2076.

Research output: Contribution to journalArticle

Tabopda, TK, Mitaine-Offer, AC, Miyamoto, T, Tanaka, C, Mirjolet, JF, Duchamp, O, Ngadjui, BT & Lacaille-Dubois, MA 2011, 'Acylated triterpene saponins from Atroxima liberica STAPF', Helvetica Chimica Acta, vol. 94, no. 11, pp. 2066-2076. https://doi.org/10.1002/hlca.201100147
Tabopda TK, Mitaine-Offer AC, Miyamoto T, Tanaka C, Mirjolet JF, Duchamp O et al. Acylated triterpene saponins from Atroxima liberica STAPF. Helvetica Chimica Acta. 2011 Nov 1;94(11):2066-2076. https://doi.org/10.1002/hlca.201100147
Tabopda, Turibio Kuiate ; Mitaine-Offer, Anne Claire ; Miyamoto, Tomofumi ; Tanaka, Chiaki ; Mirjolet, Jean François ; Duchamp, Olivier ; Ngadjui, Bonaventure Tchaleu ; Lacaille-Dubois, Marie Aleth. / Acylated triterpene saponins from Atroxima liberica STAPF. In: Helvetica Chimica Acta. 2011 ; Vol. 94, No. 11. pp. 2066-2076.
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AU - Tanaka, Chiaki

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N2 - The four new acylated triterpene saponins 1-4, isolated as two pairs of isomers and named libericosides A1/A2 and B 1/B2, one pair of isomers 5/6, the (Z)-isomer libericoside C2 (5) being new, one new sucrose ester, atroximoside (7), and eight known compounds were isolated from the roots of Atroxima liberica by repeated MPLC and VLC on normal and reversed-phase silica gel. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies (1H- and 13C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3-O-β-D-glucopyranosylpresenegenin 28-{O-α-L- arabinopyranosyl-(1→3)-O-β-D-xylopyranosyl-(1→4) -O-α-L-rhamnopyranosyl-(1→2)-4-O-[(E)-3,4-dimethoxycinnamoyl] -β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-β-D- glucopyranosylpresenegenin 28-{O-α-L-arabinopyranosyl-(1→4)-O-β- D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2) -O-[O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)] -4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, 3-O-β-D-glucopyranosylpresenegenin 28-{O-β-D- xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2) -O-[6-O-acetyl-β-D-glucopyranosyl-(1→3)]-4-O-[(Z)-3, 4-dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (5), and 3-O-[(Z)-feruloyl]-β-D-fructofuranosyl α-D-glucopyranoside (7). Compounds 1-6 and the known saponins 8/9 were evaluated against the human colon cancer cells HCT 116 and HT-29 and showed moderate to weak cytotoxicity.

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