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Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica

Abstract : Eight new acylated triterpenoid saponins were isolated from the stem bark of Harpullia austro-caledonica along with the known harpuloside (9). Their structures were established using 1D and 2D NMR and mass spectrometry as 3-O-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloylbarringtogenol C (1), 3-O-α-l-rhamnopyranosyl-(1 → 3)-[β-d-galactopyranosyl-(1 → 2)]-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloyl barringtogenol C (2), 3-O-α-l-arabinofuranosyl-(1 → 3)-[β-d-galactopyranosyl-(1 → 2)]-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloylbarringtogenol C (3), 3-O-α-l-arabinofuranosyl-(1 → 2)-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloylprotoaescigenin (4), 3-O-α-l-arabinofuranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 2)]-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloyl protoaescigenin (5), 3-O-α-l-arabinofuranosyl-(1 → 3)-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloylprotoaescigenin (6), 3-O-α-l-arabinofuranosyl-(1 → 3)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloylprotoaescigenin (7), 3-O-β-d-xylopyranosyl-(1 → 2)-β-d-glucuronopyranosyl-21β, 22α-di-O-angeloylprotoaescigenin (8). The EtOH extract of the stem bark showed in vitro cytotoxic activity against KB cells (90% at 10 μg/ml). At a concentration of 5 μg/ml, the saponin mixture showed haemolytic activity and caused 100% haemolysis of a 10% suspension of sheep erythrocytes.
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https://hal.univ-reims.fr/hal-03351444
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Submitted on : Wednesday, September 22, 2021 - 12:48:18 PM
Last modification on : Friday, August 5, 2022 - 11:22:46 AM
Long-term archiving on: : Thursday, December 23, 2021 - 6:38:28 PM

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Laurence Voutquenne, Pauline Guinot, Clément Froissard, Odile Thoison, Marc Litaudon, et al.. Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica. Phytochemistry, 2005, 66 (7), pp.825-835. ⟨10.1016/j.phytochem.2005.02.009⟩. ⟨hal-03351444⟩

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