New acylated preatroxigenin saponins from Atroxima congolana

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

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Eight new acylated preatroxigenin saponins 1-8 were isolated as four inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, atroximasaponins A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6) and D1/D2 (7/8) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)-2,3,22,27- tetrahydroxyolean-12-ene-23,28-dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and FAB-MS as 3-O(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 4)-O-[O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (1) and its cis-isomer 2, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-(β-D-glucopyranosyl)preatroxigen-in 28-{O-β-D-xylopyranosyl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (5) and its cis-isomer 6, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl ester (7) and its cis-isomer 8.

Original languageEnglish
Pages (from-to)522-531
Number of pages10
JournalHelvetica Chimica Acta
Volume86
Issue number2
DOIs
Publication statusPublished - Apr 1 2003

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Saponins
Isomers
esters
Esters
isomers
Triterpenes
FORTRAN
varespladib methyl
Nuclear magnetic resonance
Derivatives
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

New acylated preatroxigenin saponins from Atroxima congolana. / Elbandy, Mohamed; Miyamoto, Tomofumi; Delaude, Clément; Lacaille-Dubois, Marie Aleth.

In: Helvetica Chimica Acta, Vol. 86, No. 2, 01.04.2003, p. 522-531.

Research output: Contribution to journalArticle

Elbandy, Mohamed ; Miyamoto, Tomofumi ; Delaude, Clément ; Lacaille-Dubois, Marie Aleth. / New acylated preatroxigenin saponins from Atroxima congolana. In: Helvetica Chimica Acta. 2003 ; Vol. 86, No. 2. pp. 522-531.
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abstract = "Eight new acylated preatroxigenin saponins 1-8 were isolated as four inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, atroximasaponins A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6) and D1/D2 (7/8) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)-2,3,22,27- tetrahydroxyolean-12-ene-23,28-dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and FAB-MS as 3-O(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 4)-O-[O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (1) and its cis-isomer 2, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-(β-D-glucopyranosyl)preatroxigen-in 28-{O-β-D-xylopyranosyl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (5) and its cis-isomer 6, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl ester (7) and its cis-isomer 8.",
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T1 - New acylated preatroxigenin saponins from Atroxima congolana

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AU - Miyamoto, Tomofumi

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N2 - Eight new acylated preatroxigenin saponins 1-8 were isolated as four inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, atroximasaponins A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6) and D1/D2 (7/8) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)-2,3,22,27- tetrahydroxyolean-12-ene-23,28-dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and FAB-MS as 3-O(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 4)-O-[O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (1) and its cis-isomer 2, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-(β-D-glucopyranosyl)preatroxigen-in 28-{O-β-D-xylopyranosyl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (5) and its cis-isomer 6, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl ester (7) and its cis-isomer 8.

AB - Eight new acylated preatroxigenin saponins 1-8 were isolated as four inseparable mixtures of the trans- and cis-4-methoxycinnamoyl derivatives, atroximasaponins A1/A2 (1/2), B1/B2 (3/4), C1/C2 (5/6) and D1/D2 (7/8) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)-2,3,22,27- tetrahydroxyolean-12-ene-23,28-dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and FAB-MS as 3-O(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 4)-O-[O-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (1) and its cis-isomer 2, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl} ester (3) and its cis-isomer 4, 3-O-(β-D-glucopyranosyl)preatroxigen-in 28-{O-β-D-xylopyranosyl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-6-O-acetyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranoyl} ester (5) and its cis-isomer 6, 3-O-(β-D-glucopyranosyl)preatroxigenin 28-{O-β-D-xylopyranosl-(1 → 4)-O-[β-D-apiofuranosyl-(1 → 3)]-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-4-O-(trans-4-methoxycinnamoyl)-β-D-fucopyranosyl ester (7) and its cis-isomer 8.

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