Triterpene saponins from four species of the polygalaceae family

Anne Claire Mitaine-Offer, Tomofumi Miyamoto, Claire Jolly, Clément Delaude, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Twelve triterpene saponins were isolated by successive MPLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1-5 of which 1-4 as two pairs of (E)/(Z)-isomers, together with the four known compounds tenuifoline, (E)- and (Z)-senegasaponin b, (E)- and (Z)-senegin II, and polygalasaponin XXVIII, from the genus Carpolobia, one new saponin 6 from C. alba and the known arilloside (11) from C. lutea, and another new triterpene glycoside 7 from Polygala arenaria. Their structures were established mainly by 600-MHz 2D-NMR techniques (1H, 1H-COSY, TOCSY, NOESY, HSQC, HMBC) as 3-O-(β-D-glucopyranosyl) presenegenin 28-{O-α-L-arabinopyranosyl-(1 → 4)-O-β-D- xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-[(E)-4-methoxycinnamoyl]-β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α-L- arabinopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-[(£)-3,4- dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, 3-O-(β-D-glucopyranosyl)presenegenin 28-[O-β-D-galactopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl] ester (5), 3-O-(β-D-glucopyranosyl) presenegenin 28-{O-α-L-arabinopyranosyl-(1 → 3)-O-[β3-D- galactopyranosyl-(1 → 4)]-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl} ester (6), and 3-O-(β-D- glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 4)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl} ester (7) (presenegenin = (2β,3β,4α)-2,3,27-trihydroxyolean-12-ene-23,28- dioic acid).

Original languageEnglish
Pages (from-to)2986-2995
Number of pages10
JournalHelvetica Chimica Acta
Volume88
Issue number11
DOIs
Publication statusPublished - Jan 1 2005

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Polygalaceae
Triterpenes
Saponins
esters
Esters
Isomers
Polygala
isomers
Glycosides
glucosides
Silica gel
silica gel
Silica Gel
Nuclear magnetic resonance
presenegenin
nuclear magnetic resonance
acids
Acids

All Science Journal Classification (ASJC) codes

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

Cite this

Mitaine-Offer, A. C., Miyamoto, T., Jolly, C., Delaude, C., & Lacaille-Dubois, M. A. (2005). Triterpene saponins from four species of the polygalaceae family. Helvetica Chimica Acta, 88(11), 2986-2995. https://doi.org/10.1002/hlca.200590241

Triterpene saponins from four species of the polygalaceae family. / Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Jolly, Claire; Delaude, Clément; Lacaille-Dubois, Marie Aleth.

In: Helvetica Chimica Acta, Vol. 88, No. 11, 01.01.2005, p. 2986-2995.

Research output: Contribution to journalArticle

Mitaine-Offer, AC, Miyamoto, T, Jolly, C, Delaude, C & Lacaille-Dubois, MA 2005, 'Triterpene saponins from four species of the polygalaceae family', Helvetica Chimica Acta, vol. 88, no. 11, pp. 2986-2995. https://doi.org/10.1002/hlca.200590241
Mitaine-Offer AC, Miyamoto T, Jolly C, Delaude C, Lacaille-Dubois MA. Triterpene saponins from four species of the polygalaceae family. Helvetica Chimica Acta. 2005 Jan 1;88(11):2986-2995. https://doi.org/10.1002/hlca.200590241
Mitaine-Offer, Anne Claire ; Miyamoto, Tomofumi ; Jolly, Claire ; Delaude, Clément ; Lacaille-Dubois, Marie Aleth. / Triterpene saponins from four species of the polygalaceae family. In: Helvetica Chimica Acta. 2005 ; Vol. 88, No. 11. pp. 2986-2995.
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T1 - Triterpene saponins from four species of the polygalaceae family

AU - Mitaine-Offer, Anne Claire

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AU - Jolly, Claire

AU - Delaude, Clément

AU - Lacaille-Dubois, Marie Aleth

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N2 - Twelve triterpene saponins were isolated by successive MPLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1-5 of which 1-4 as two pairs of (E)/(Z)-isomers, together with the four known compounds tenuifoline, (E)- and (Z)-senegasaponin b, (E)- and (Z)-senegin II, and polygalasaponin XXVIII, from the genus Carpolobia, one new saponin 6 from C. alba and the known arilloside (11) from C. lutea, and another new triterpene glycoside 7 from Polygala arenaria. Their structures were established mainly by 600-MHz 2D-NMR techniques (1H, 1H-COSY, TOCSY, NOESY, HSQC, HMBC) as 3-O-(β-D-glucopyranosyl) presenegenin 28-{O-α-L-arabinopyranosyl-(1 → 4)-O-β-D- xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-[(E)-4-methoxycinnamoyl]-β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α-L- arabinopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-[(£)-3,4- dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, 3-O-(β-D-glucopyranosyl)presenegenin 28-[O-β-D-galactopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl] ester (5), 3-O-(β-D-glucopyranosyl) presenegenin 28-{O-α-L-arabinopyranosyl-(1 → 3)-O-[β3-D- galactopyranosyl-(1 → 4)]-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl} ester (6), and 3-O-(β-D- glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 4)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl} ester (7) (presenegenin = (2β,3β,4α)-2,3,27-trihydroxyolean-12-ene-23,28- dioic acid).

AB - Twelve triterpene saponins were isolated by successive MPLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1-5 of which 1-4 as two pairs of (E)/(Z)-isomers, together with the four known compounds tenuifoline, (E)- and (Z)-senegasaponin b, (E)- and (Z)-senegin II, and polygalasaponin XXVIII, from the genus Carpolobia, one new saponin 6 from C. alba and the known arilloside (11) from C. lutea, and another new triterpene glycoside 7 from Polygala arenaria. Their structures were established mainly by 600-MHz 2D-NMR techniques (1H, 1H-COSY, TOCSY, NOESY, HSQC, HMBC) as 3-O-(β-D-glucopyranosyl) presenegenin 28-{O-α-L-arabinopyranosyl-(1 → 4)-O-β-D- xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-[(E)-4-methoxycinnamoyl]-β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-α-L- arabinopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-4-O-[(£)-3,4- dimethoxycinnamoyl]-β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, 3-O-(β-D-glucopyranosyl)presenegenin 28-[O-β-D-galactopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl] ester (5), 3-O-(β-D-glucopyranosyl) presenegenin 28-{O-α-L-arabinopyranosyl-(1 → 3)-O-[β3-D- galactopyranosyl-(1 → 4)]-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl} ester (6), and 3-O-(β-D- glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1 → 4)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl} ester (7) (presenegenin = (2β,3β,4α)-2,3,27-trihydroxyolean-12-ene-23,28- dioic acid).

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