Triterpenoid Saponins from the Cultivar “Green Elf” of Pittosporum tenuifolium

Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic Pittosporum tenuifolium (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-O-β-<...

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Autores principales:	David Pertuit, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Christine Belloir, Loïc Briand, Marie-Aleth Lacaille-Dubois
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Pittosporum tenuifolium</i> Pittosporaceae barringtogenol C TAS1R2/TASR3 sweet taste taste inhibitor Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/0c029106e3fe468299dd855ebb3b8913
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spelling	oai:doaj.org-article:0c029106e3fe468299dd855ebb3b89132021-11-25T18:27:23ZTriterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>10.3390/molecules262268051420-3049https://doaj.org/article/0c029106e3fe468299dd855ebb3b89132021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6805https://doaj.org/toc/1420-3049Four 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.David PertuitAnne-Claire Mitaine-OfferTomofumi MiyamotoChiaki TanakaChristine BelloirLoïc BriandMarie-Aleth Lacaille-DuboisMDPI AGarticle<i>Pittosporum tenuifolium</i>Pittosporaceaebarringtogenol CTAS1R2/TASR3sweet tastetaste inhibitorOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6805, p 6805 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Pittosporum tenuifolium</i> Pittosporaceae barringtogenol C TAS1R2/TASR3 sweet taste taste inhibitor Organic chemistry QD241-441
spellingShingle	<i>Pittosporum tenuifolium</i> Pittosporaceae barringtogenol C TAS1R2/TASR3 sweet taste taste inhibitor Organic chemistry QD241-441 David Pertuit Anne-Claire Mitaine-Offer Tomofumi Miyamoto Chiaki Tanaka Christine Belloir Loïc Briand Marie-Aleth Lacaille-Dubois Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
description	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.
format	article
author	David Pertuit Anne-Claire Mitaine-Offer Tomofumi Miyamoto Chiaki Tanaka Christine Belloir Loïc Briand Marie-Aleth Lacaille-Dubois
author_facet	David Pertuit Anne-Claire Mitaine-Offer Tomofumi Miyamoto Chiaki Tanaka Christine Belloir Loïc Briand Marie-Aleth Lacaille-Dubois
author_sort	David Pertuit
title	Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
title_short	Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
title_full	Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
title_fullStr	Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
title_full_unstemmed	Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>
title_sort	triterpenoid saponins from the cultivar “green elf” of <i>pittosporum tenuifolium</i>
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/0c029106e3fe468299dd855ebb3b8913
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Triterpenoid Saponins from the Cultivar “Green Elf” of <i>Pittosporum tenuifolium</i>

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