Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic <i>Pittosporum tenuifolium</i> (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-<i>O</i>-β-<...
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| Autores principales: | , , , , , , |
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| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
MDPI AG
2021
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| Materias: | |
| Acceso en línea: | https://doaj.org/article/0c029106e3fe468299dd855ebb3b8913 |
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| Sumario: | Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic <i>Pittosporum tenuifolium</i> (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-[α-<span style="font-variant: small-caps;">l-</span>arabinopyranosyl-(1→3)]-β-<span style="font-variant: small-caps;">d</span>-glucuronopyranosyl-21-<i>O</i>-angeloyl-28-<i>O</i>-acetylbarringtogenol C, 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-galactopyranosyl-(1→2)-[α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→3)]-β-<span style="font-variant: small-caps;">d-</span>glucuronopyranosyl-21-<i>O</i>-angeloyl-28-<i>O</i>-acetylbarringtogenol C, and the known 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-[α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→3)]-β-<span style="font-variant: small-caps;">d</span>-glucuronopyranosyl-21-<i>O</i>-angeloyl-28-<i>O</i>-acetylbarringtogenol C (Eryngioside L). From the roots, the known 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-β-<span style="font-variant: small-caps;">d</span>-galactopyranosyl-(1→2)-β-<span style="font-variant: small-caps;">d</span>-glucuronopyranosyloleanolic acid (Sandrosaponin X) was identified. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR experiments and mass spectrometry (ESI-MS). According to their structural similarities with gymnemic acids, the inhibitory activities on the sweet taste TAS1R2/TAS1R3 receptor of an aqueous ethanolic extract of the leaves and roots, a crude saponin mixture, 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-(1→2)-[α-<span style="font-variant: small-caps;">l</span>-arabinopyranosyl-(1→3)]-β-<span style="font-variant: small-caps;">d</span>-glucuronopyranosyl-21-<i>O</i>-angeloyl-28-<i>O</i>-acetylbarringtogenol C, and Eryngioside L were evaluated. |
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