New acylated saponins from Polygala myrtifolia

Mohamed Haddad, Tomofumi Miyamoto, Clément Delaude, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The ten new acylated presenegenin (=(2β,3β,4α )-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid) glycosides 1-10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, i.e., myrtifoliosides A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6), D1/D2 (7/8), and E1/E2 (9/10). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-β-D-apio-β -D-furanosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-arabinopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl] ester (1) and its cis-isomer 2, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-[D-apio-β-D-furanosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (5) and its cis-isomer 6, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-D-apio-β -D-furanosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (7) and its cis-isomer 8, and 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α -L-arabinopyranosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4methoxycinnamoyl)-β-D-fucopyranosyl} ester (9) and its cis-isomer 10.

Original languageEnglish
Pages (from-to)3055-3065
Number of pages11
JournalHelvetica Chimica Acta
Volume86
Issue number9
DOIs
Publication statusPublished - Oct 22 2003

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Polygala
Saponins
Isomers
esters
Esters
isomers
Glycosides
glucosides
varespladib methyl
Nuclear magnetic resonance
presenegenin
Derivatives
nuclear magnetic resonance
acids
Acids

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Haddad, M., Miyamoto, T., Delaude, C., & Lacaille-Dubois, M. A. (2003). New acylated saponins from Polygala myrtifolia. Helvetica Chimica Acta, 86(9), 3055-3065. https://doi.org/10.1002/hlca.200390247

New acylated saponins from Polygala myrtifolia. / Haddad, Mohamed; Miyamoto, Tomofumi; Delaude, Clément; Lacaille-Dubois, Marie Aleth.

In: Helvetica Chimica Acta, Vol. 86, No. 9, 22.10.2003, p. 3055-3065.

Research output: Contribution to journalArticle

Haddad, M, Miyamoto, T, Delaude, C & Lacaille-Dubois, MA 2003, 'New acylated saponins from Polygala myrtifolia', Helvetica Chimica Acta, vol. 86, no. 9, pp. 3055-3065. https://doi.org/10.1002/hlca.200390247
Haddad, Mohamed ; Miyamoto, Tomofumi ; Delaude, Clément ; Lacaille-Dubois, Marie Aleth. / New acylated saponins from Polygala myrtifolia. In: Helvetica Chimica Acta. 2003 ; Vol. 86, No. 9. pp. 3055-3065.
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abstract = "The ten new acylated presenegenin (=(2β,3β,4α )-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid) glycosides 1-10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, i.e., myrtifoliosides A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6), D1/D2 (7/8), and E1/E2 (9/10). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-β-D-apio-β -D-furanosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-arabinopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl] ester (1) and its cis-isomer 2, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-[D-apio-β-D-furanosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (5) and its cis-isomer 6, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-D-apio-β -D-furanosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (7) and its cis-isomer 8, and 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α -L-arabinopyranosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4methoxycinnamoyl)-β-D-fucopyranosyl} ester (9) and its cis-isomer 10.",
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TY - JOUR

T1 - New acylated saponins from Polygala myrtifolia

AU - Haddad, Mohamed

AU - Miyamoto, Tomofumi

AU - Delaude, Clément

AU - Lacaille-Dubois, Marie Aleth

PY - 2003/10/22

Y1 - 2003/10/22

N2 - The ten new acylated presenegenin (=(2β,3β,4α )-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid) glycosides 1-10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, i.e., myrtifoliosides A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6), D1/D2 (7/8), and E1/E2 (9/10). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-β-D-apio-β -D-furanosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-arabinopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl] ester (1) and its cis-isomer 2, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-[D-apio-β-D-furanosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (5) and its cis-isomer 6, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-D-apio-β -D-furanosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (7) and its cis-isomer 8, and 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α -L-arabinopyranosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4methoxycinnamoyl)-β-D-fucopyranosyl} ester (9) and its cis-isomer 10.

AB - The ten new acylated presenegenin (=(2β,3β,4α )-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid) glycosides 1-10 have been isolated by successive MPLC from the roots of Polygala myrtifolia L. as five inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, i.e., myrtifoliosides A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6), D1/D2 (7/8), and E1/E2 (9/10). Their structures were elucidated mainly by extensive spectroscopic experiments, including 2D NMR techniques, as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-β-D-apio-β -D-furanosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-arabinopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl] ester (1) and its cis-isomer 2, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-[D-apio-β-D-furanosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-β -D-galactopyranosyl-(1 → 3)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (5) and its cis-isomer 6, 3-O-β-D-glucopyranosyl)presenegenin 28-{O-D-apio-β -D-furanosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (7) and its cis-isomer 8, and 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α -L-arabinopyranosyl-(1 → 3)-O-[β-D-xylopyranosyl-(1 → 4)]-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-(trans-4methoxycinnamoyl)-β-D-fucopyranosyl} ester (9) and its cis-isomer 10.

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